CIPROFLOXACIN HYDROCHLORIDE SESQUIHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C17H18FN3O3.2ClH.3H2O
Molecular Weight	789.651
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of CIPROFLOXACIN HYDROCHLORIDE SESQUIHYDRATE

Structure Search

SMILES

O.O.O.Cl.Cl.OC(=O)C1=CN(C2CC2)C3=CC(N4CCNCC4)=C(F)C=C3C1=O.OC(=O)C5=CN(C6CC6)C7=CC(N8CCNCC8)=C(F)C=C7C5=O

InChI

InChIKey=SMFVXHJJUFAKBS-UHFFFAOYSA-N

InChI=1S/2C17H18FN3O3.2ClH.3H2O/c2*18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24;;;;;/h2*7-10,19H,1-6H2,(H,23,24);2*1H;3*1H2

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021744s016lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.drugs.com/ciprofloxacin.html | https://clinicaltrials.gov/ct2/show/NCT02598362 | https://www.ncbi.nlm.nih.gov/pubmed/25951434

Ciprofloxacin (1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid) is the synthetic antimicrobial agent for oral or intravenous administration. Ciprofloxacin is a member of the fluoroquinolone class of antibacterial agents. The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV (both Type II topoisomerases), which are required for bacterial DNA replication, transcription, repair, and recombination. Ciprofloxacin is used to treat a wide variety of infections, including infections of bones and joints, endocarditis, gastroenteritis, malignant otitis externa, respiratory tract infections, cellulitis, urinary tract infections, prostatitis, anthrax, and chancroid. In the United States, ciprofloxacin is pregnancy category C. This category includes drugs for which no adequate and well-controlled studies in human pregnancy exist, and for which animal studies have suggested the potential for harm to the fetus, but potential benefits may warrant use of the drug in pregnant women despite potential risks. Fluoroquinolones have been reported as present in a mother's milk and thus passed on to the nursing child. Oral and intravenous ciprofloxacin is approved by the FDA for use in children for only two indications due to the risk of permanent injury to the musculoskeletal system: Inhalational anthrax (postexposure) and Complicated urinary tract infections and pyelonephritis due to Escherichia coli.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase 4 subunit B 7 Target ID: CHEMBL3329081 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26119992	Inhibitor 8297
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25951434	Inhibitor 8297		150.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 205 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021744s016lbl.pdf	Curative	Approved 8429	CIPRO Approved Use Ciprofloxacin Tablets, USP are indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions and patient populations listed below. Please see DOSAGE AND ADMINISTRATION for specific recommendations. Adult Patients Urinary Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Serratia marcescens, Proteus mirabilis, Providencia rettgeri, Morganella morganii, Citrobacter diversus, Citrobacter freundii, Pseudomonas aeruginosa, methicillin-susceptible Staphylococcus epidermidis, Staphylococcus saprophyticus, or Enterococcus faecalis. Acute Uncomplicated Cystitis in females caused by Escherichia coli or Staphylococcus saprophyticus. Chronic Bacterial Prostatitis caused by Escherichia coli or Proteus mirabilis. Lower Respiratory Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Pseudomonas aeruginosa, Haemophilus influenzae, Haemophilus parainfluenzae, or penicillin-susceptible Streptococcus pneumoniae. Also, Moraxella catarrhalis for the treatment of acute exacerbations of chronic bronchitis. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the treatment of presumed or confirmed pneumonia secondary to Streptococcus pneumoniae. Acute Sinusitis caused by Haemophilus influenzae, penicillin-susceptible Streptococcus pneumoniae, or Moraxella catarrhalis. Skin and Skin Structure Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Proteus vulgaris, Providencia stuartii, Morganella morganii, Citrobacter freundii, Pseudomonas aeruginosa, methicillin susceptible Staphylococcus aureus, methicillin susceptible Staphylococcus epidermidis, or Streptococcus pyogenes. Bone and Joint Infections caused by Enterobacter cloacae, Serratia marcescens, or Pseudomonas aeruginosa. Complicated Intra-Abdominal Infections (used in combination with metronidazole) caused by Escherichia coli, Pseudomonas aeruginosa, Proteus mirabilis, Klebsiella pneumoniae, or Bacteroides fragilis. Infectious Diarrhea caused by Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, Shigella boydii † , Shigella dysenteriae, Shigella flexneri or Shigella sonnei † when antibacterial therapy is indicated. Typhoid Fever (Enteric Fever) caused by Salmonella typhi. NOTE: The efficacy of ciprofloxacin in the eradication of the chronic typhoid carrier state has not been demonstrated. Uncomplicated cervical and urethral gonorrhea due to Neisseria gonorrhoeae. Pediatric patients (1 to 17 years of age)Complicated Urinary Tract Infections and Pyelonephritis due to Escherichia coli. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the pediatric population due to an increased incidence of adverse events compared to controls, including events related to joints and/or surrounding tissues. (See WARNINGS, PRECAUTIONS, Pediatric Use , ADVERSE REACTIONS and CLINICAL STUDIES .) Ciprofloxacin, like other fluoroquinolones, is associated with arthropathy and histopathological changes in weight-bearing joints of juvenile animals. (See ANIMAL PHARMACOLOGY .) Adult and Pediatric PatientsInhalational anthrax (post-exposure): To reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. Ciprofloxacin serum concentrations achieved in humans served as a surrogate endpoint reasonably likely to predict clinical benefit and provided the initial basis for approval of this indication.5 Supportive clinical information for ciprofloxacin for anthrax post-exposure prophylaxis was obtained during the anthrax bioterror attacks of October 2001. (See also, INHALATIONAL ANTHRAX – ADDITIONAL INFORMATION ). †Although treatment of infections due to this organism in this organ system demonstrated a clinically significant outcome, efficacy was studied in fewer than 10 patients. If anaerobic organisms are suspected of contributing to the infection, appropriate therapy should be administered. Appropriate culture and susceptibility tests should be performed before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to ciprofloxacin. Therapy with Ciprofloxacin Tablets may be initiated before results of these tests are known; once results become available appropriate therapy should be continued. As with other drugs, some strains of Pseudomonas aeruginosa may develop resistance fairly rapidly during treatment with ciprofloxacin. Culture and susceptibility testing performed periodically during therapy will provide information not only on the therapeutic effect of the antimicrobial agent but also on the possible emergence of bacterial resistance. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Ciprofloxacin Tablets and other antibacterial drugs, Ciprofloxacin Tablets should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1990
Infectious diarrhea 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s085,020780s042lbl.pdf	Curative	Approved 8429	CIPRO Approved Use Ciprofloxacin Tablets, USP are indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions and patient populations listed below. Please see DOSAGE AND ADMINISTRATION for specific recommendations. Adult Patients Urinary Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Serratia marcescens, Proteus mirabilis, Providencia rettgeri, Morganella morganii, Citrobacter diversus, Citrobacter freundii, Pseudomonas aeruginosa, methicillin-susceptible Staphylococcus epidermidis, Staphylococcus saprophyticus, or Enterococcus faecalis. Acute Uncomplicated Cystitis in females caused by Escherichia coli or Staphylococcus saprophyticus. Chronic Bacterial Prostatitis caused by Escherichia coli or Proteus mirabilis. Lower Respiratory Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Pseudomonas aeruginosa, Haemophilus influenzae, Haemophilus parainfluenzae, or penicillin-susceptible Streptococcus pneumoniae. Also, Moraxella catarrhalis for the treatment of acute exacerbations of chronic bronchitis. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the treatment of presumed or confirmed pneumonia secondary to Streptococcus pneumoniae. Acute Sinusitis caused by Haemophilus influenzae, penicillin-susceptible Streptococcus pneumoniae, or Moraxella catarrhalis. Skin and Skin Structure Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Proteus vulgaris, Providencia stuartii, Morganella morganii, Citrobacter freundii, Pseudomonas aeruginosa, methicillin susceptible Staphylococcus aureus, methicillin susceptible Staphylococcus epidermidis, or Streptococcus pyogenes. Bone and Joint Infections caused by Enterobacter cloacae, Serratia marcescens, or Pseudomonas aeruginosa. Complicated Intra-Abdominal Infections (used in combination with metronidazole) caused by Escherichia coli, Pseudomonas aeruginosa, Proteus mirabilis, Klebsiella pneumoniae, or Bacteroides fragilis. Infectious Diarrhea caused by Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, Shigella boydii † , Shigella dysenteriae, Shigella flexneri or Shigella sonnei † when antibacterial therapy is indicated. Typhoid Fever (Enteric Fever) caused by Salmonella typhi. NOTE: The efficacy of ciprofloxacin in the eradication of the chronic typhoid carrier state has not been demonstrated. Uncomplicated cervical and urethral gonorrhea due to Neisseria gonorrhoeae. Pediatric patients (1 to 17 years of age)Complicated Urinary Tract Infections and Pyelonephritis due to Escherichia coli. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the pediatric population due to an increased incidence of adverse events compared to controls, including events related to joints and/or surrounding tissues. (See WARNINGS, PRECAUTIONS, Pediatric Use , ADVERSE REACTIONS and CLINICAL STUDIES .) Ciprofloxacin, like other fluoroquinolones, is associated with arthropathy and histopathological changes in weight-bearing joints of juvenile animals. (See ANIMAL PHARMACOLOGY .) Adult and Pediatric PatientsInhalational anthrax (post-exposure): To reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. Ciprofloxacin serum concentrations achieved in humans served as a surrogate endpoint reasonably likely to predict clinical benefit and provided the initial basis for approval of this indication.5 Supportive clinical information for ciprofloxacin for anthrax post-exposure prophylaxis was obtained during the anthrax bioterror attacks of October 2001. (See also, INHALATIONAL ANTHRAX – ADDITIONAL INFORMATION ). †Although treatment of infections due to this organism in this organ system demonstrated a clinically significant outcome, efficacy was studied in fewer than 10 patients. If anaerobic organisms are suspected of contributing to the infection, appropriate therapy should be administered. Appropriate culture and susceptibility tests should be performed before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to ciprofloxacin. Therapy with Ciprofloxacin Tablets may be initiated before results of these tests are known; once results become available appropriate therapy should be continued. As with other drugs, some strains of Pseudomonas aeruginosa may develop resistance fairly rapidly during treatment with ciprofloxacin. Culture and susceptibility testing performed periodically during therapy will provide information not only on the therapeutic effect of the antimicrobial agent but also on the possible emergence of bacterial resistance. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Ciprofloxacin Tablets and other antibacterial drugs, Ciprofloxacin Tablets should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1990
Lower respiratory tract infections 51 Sources: https://www.drugs.com/pro/cipro-iv.html	Curative	Approved 8429	CIPRO Approved Use Ciprofloxacin Tablets, USP are indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions and patient populations listed below. Please see DOSAGE AND ADMINISTRATION for specific recommendations. Adult Patients Urinary Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Serratia marcescens, Proteus mirabilis, Providencia rettgeri, Morganella morganii, Citrobacter diversus, Citrobacter freundii, Pseudomonas aeruginosa, methicillin-susceptible Staphylococcus epidermidis, Staphylococcus saprophyticus, or Enterococcus faecalis. Acute Uncomplicated Cystitis in females caused by Escherichia coli or Staphylococcus saprophyticus. Chronic Bacterial Prostatitis caused by Escherichia coli or Proteus mirabilis. Lower Respiratory Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Pseudomonas aeruginosa, Haemophilus influenzae, Haemophilus parainfluenzae, or penicillin-susceptible Streptococcus pneumoniae. Also, Moraxella catarrhalis for the treatment of acute exacerbations of chronic bronchitis. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the treatment of presumed or confirmed pneumonia secondary to Streptococcus pneumoniae. Acute Sinusitis caused by Haemophilus influenzae, penicillin-susceptible Streptococcus pneumoniae, or Moraxella catarrhalis. Skin and Skin Structure Infections caused by Escherichia coli, Klebsiella pneumoniae, Enterobacter cloacae, Proteus mirabilis, Proteus vulgaris, Providencia stuartii, Morganella morganii, Citrobacter freundii, Pseudomonas aeruginosa, methicillin susceptible Staphylococcus aureus, methicillin susceptible Staphylococcus epidermidis, or Streptococcus pyogenes. Bone and Joint Infections caused by Enterobacter cloacae, Serratia marcescens, or Pseudomonas aeruginosa. Complicated Intra-Abdominal Infections (used in combination with metronidazole) caused by Escherichia coli, Pseudomonas aeruginosa, Proteus mirabilis, Klebsiella pneumoniae, or Bacteroides fragilis. Infectious Diarrhea caused by Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, Shigella boydii † , Shigella dysenteriae, Shigella flexneri or Shigella sonnei † when antibacterial therapy is indicated. Typhoid Fever (Enteric Fever) caused by Salmonella typhi. NOTE: The efficacy of ciprofloxacin in the eradication of the chronic typhoid carrier state has not been demonstrated. Uncomplicated cervical and urethral gonorrhea due to Neisseria gonorrhoeae. Pediatric patients (1 to 17 years of age)Complicated Urinary Tract Infections and Pyelonephritis due to Escherichia coli. NOTE: Although effective in clinical trials, ciprofloxacin is not a drug of first choice in the pediatric population due to an increased incidence of adverse events compared to controls, including events related to joints and/or surrounding tissues. (See WARNINGS, PRECAUTIONS, Pediatric Use , ADVERSE REACTIONS and CLINICAL STUDIES .) Ciprofloxacin, like other fluoroquinolones, is associated with arthropathy and histopathological changes in weight-bearing joints of juvenile animals. (See ANIMAL PHARMACOLOGY .) Adult and Pediatric PatientsInhalational anthrax (post-exposure): To reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. Ciprofloxacin serum concentrations achieved in humans served as a surrogate endpoint reasonably likely to predict clinical benefit and provided the initial basis for approval of this indication.5 Supportive clinical information for ciprofloxacin for anthrax post-exposure prophylaxis was obtained during the anthrax bioterror attacks of October 2001. (See also, INHALATIONAL ANTHRAX – ADDITIONAL INFORMATION ). †Although treatment of infections due to this organism in this organ system demonstrated a clinically significant outcome, efficacy was studied in fewer than 10 patients. If anaerobic organisms are suspected of contributing to the infection, appropriate therapy should be administered. Appropriate culture and susceptibility tests should be performed before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to ciprofloxacin. Therapy with Ciprofloxacin Tablets may be initiated before results of these tests are known; once results become available appropriate therapy should be continued. As with other drugs, some strains of Pseudomonas aeruginosa may develop resistance fairly rapidly during treatment with ciprofloxacin. Culture and susceptibility testing performed periodically during therapy will provide information not only on the therapeutic effect of the antimicrobial agent but also on the possible emergence of bacterial resistance. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Ciprofloxacin Tablets and other antibacterial drugs, Ciprofloxacin Tablets should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1990

C_max

Value	Dose	Analyte	Population
4.56 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	400 mg 2 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.97 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.3 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
5.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
3.59 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg 2 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.07 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	400 mg 3 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
1.2 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
12.7 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	400 mg 2 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
13.7 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
11.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
20.2 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
30.8 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
31.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg 2 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
32.9 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	400 mg 3 times / day steady-state, intravenous dose: 400 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.8 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
30% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CIPROFLOXACIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
15 mg/kg 2 times / day steady, oral (median) Recommended Dose: 15 mg/kg, 2 times / day Route: oral Route: steady Dose: 15 mg/kg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	unhealthy, 1 - 17 years n = 335 Health Status: unhealthy Condition: Infection Age Group: 1 - 17 years Sex: unknown Population Size: 335 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	Disc. AE: Reaction gastrointestinal... Other AEs: Musculoskeletal disorder NOS... AEs leading to discontinuation/dose reduction: Reaction gastrointestinal (3%) Other AEs: Musculoskeletal disorder NOS (9.3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf
7.5 g single, oral Overdose Dose: 7.5 g Route: oral Route: single Dose: 7.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/9531191/	unhealthy, 15 years n = 1 Health Status: unhealthy Condition: depression and posttraumatic stress disorder Age Group: 15 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9531191/	Disc. AE: Renal tubular necrosis acute... AEs leading to discontinuation/dose reduction: Renal tubular necrosis acute (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/9531191/
12 g single, oral Overdose Dose: 12 g Route: oral Route: single Dose: 12 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, 16 years n = 1 Health Status: healthy Age Group: 16 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	Disc. AE: Pain epigastric... AEs leading to discontinuation/dose reduction: Pain epigastric (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
20 mg/kg single, oral Recommended Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16182896/	unhealthy, 2-15 years n = 90 Health Status: unhealthy Condition: childhood cholera Age Group: 2-15 years Sex: M+F Population Size: 90 Sources: https://pubmed.ncbi.nlm.nih.gov/16182896/	Other AEs: Vomited... Other AEs: Vomited (58%) Sources: https://pubmed.ncbi.nlm.nih.gov/16182896/
28 g single, oral Overdose Dose: 28 g Route: oral Route: single Dose: 28 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, 29 years n = 1 Health Status: healthy Age Group: 29 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	Disc. AE: Acute renal failure... AEs leading to discontinuation/dose reduction: Acute renal failure (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
750 mg 2 times / day steady, oral Highest studied dose Dose: 750 mg, 2 times / day Route: oral Route: steady Dose: 750 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17660035/	unhealthy, > 70 years n = 2 Health Status: unhealthy Condition: Infection Age Group: > 70 years Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/17660035/	Disc. AE: Acute renal failure... AEs leading to discontinuation/dose reduction: Acute renal failure (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17660035/
3 g single, oral Overdose Dose: 3 g Route: oral Route: single Dose: 3 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, adult n = 2 Health Status: healthy Age Group: adult Sex: unknown Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	Disc. AE: Nausea and vomiting... AEs leading to discontinuation/dose reduction: Nausea and vomiting (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
228 mg 2 times / day steady, intravenous (mean) Recommended Dose: 228 mg, 2 times / day Route: intravenous Route: steady Dose: 228 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/	unhealthy, mean 50 years n = 1869 Health Status: unhealthy Condition: Infection Age Group: mean 50 years Sex: M+F Population Size: 1869 Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/	Other AEs: Infusion site reactions, Gastrointestinal disorder (NOS)... Other AEs: Infusion site reactions (4.4%) Gastrointestinal disorder (NOS) (3%) Central nervous system disorder NOS (1.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/
10 mg/kg 2 times / day steady, intravenous Recommended Dose: 10 mg/kg, 2 times / day Route: intravenous Route: steady Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15523125/	unhealthy, preterm neonates n = 24 Health Status: unhealthy Condition: neonatal sepsis Age Group: preterm neonates Sex: unknown Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/15523125/	Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/15523125/
500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	unhealthy, ≥18 years n = 122 Health Status: unhealthy Condition: acute pyelonephritis Age Group: ≥18 years Sex: F Population Size: 122 Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	Disc. AE: Exanthema... AEs leading to discontinuation/dose reduction: Exanthema (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/
500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	unhealthy, ≥18 years n = 126 Health Status: unhealthy Condition: acute pyelonephritis Age Group: ≥18 years Sex: F Population Size: 126 Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	Disc. AE: Myalgia... AEs leading to discontinuation/dose reduction: Myalgia (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/
500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	Other AEs: Acute kidney injury, Clostridium difficile infection... Other AEs: Acute kidney injury (serious, 8 patients) Clostridium difficile infection (serious, 1 patient) Chest pain (serious, 1 patient) Dysuria (serious, 1 patient) Epistaxis (serious, 1 patient) GI bleed (serious, 1 patient) Hematuria (serious, 1 patient) Hyperkalemia (serious, 1 patient) Hypertension malignant (serious, 1 patient) Myocardial infarction (serious, 1 patient) Nausea (serious, 1 patient) Nephrolithiasis (serious, 1 patient) Neutropenia (serious, 1 patient) Pain (serious, 1 patient) Nephrostomy complication (serious, 1 patient) Radial nerve palsy (serious, 1 patient) Sepsis (serious, 2 patients) Small bowel obstruction (serious, 1 patient) Thrombocytopenia (serious, 1 patient) Urinary incontinence (serious, 1 patient) Urinary retention (serious, 3 patients) Vomiting (serious, 2 patients) Venous thromboembolism (serious, 5 patients) Wound complication (serious, 3 patients) Constipation (below serious, 12 patients) Headache (below serious, 7 patients) Hypomagnesemia (below serious, 8 patients) Insomnia (below serious, 8 patients) Osteopenia (below serious, 19 patients) Proteinuria (below serious, 12 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
500 mg 2 times / day steady, oral Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00609973	unhealthy n = 17 Health Status: unhealthy Condition: Crohn's Disease Population Size: 17 Sources: https://clinicaltrials.gov/ct2/show/NCT00609973	Other AEs: Diarrhea, Abdominal pain... Other AEs: Diarrhea (below serious, 2 patients) Abdominal pain (below serious, 2 patients) Headache (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00609973
500 mg 2 times / day steady, oral Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT02068846	unhealthy n = 9 Health Status: unhealthy Condition: BK Virus Infection Population Size: 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02068846	Other AEs: Rash... Other AEs: Rash (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT02068846

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2E1 882 CYP4A1 8 CYP2B6 810 CYP2C8 911 OAT1 599 OAT3 642 OATP1B1 788 OATP1B3 706 BSEP 402 MRP2 383 MRP3 157 MRP4 204 CYP2A6 707 CYP2C19 1478 ALDH1 40 P-gp 1461	P-gp 1537 BCRP 561 OAT1 326

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
ALDH1 40	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	inconclusive [Activation 10 uM]
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no [IC50 >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no [IC50 >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMOCJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2E1 970	inhibitor 3277 Sources: https://gut.bmj.com/content/44/3/347.short, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no [IC50 >10 uM]
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	no
CYP4A1 25	inhibitor 3277 Sources: https://gut.bmj.com/content/44/3/347.short	no
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18381565/	no
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	no
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	no
P-gp 1650	inhibitor 3277 Sources: https://pubs.acs.org/doi/10.1021/tx010125x, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	yes [Activation 12.5893 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15058617/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=085721331, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	yes [Activation 15.84893 uM]	yes (co-administration study) Comment: Coadministration of Ciprofloxacin increased average Clozapine (CYP1A2 substrate) concentration by approximately 30% and Theophylline blood concentration and average half-life by about 20 to 30%.. Sources: https://pubmed.ncbi.nlm.nih.gov/15058617/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=085721331, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15058617/, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=085721331, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMOCJ9fQ%3D%3D	yes [IC50 >10 uM]
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18381565/	yes

Drug as victim

Target	Modality	Activity
P-gp 1537	substrate 3367 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1038/sj.bjp.0704560	no
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18200507/	yes
OAT1 326	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20190787/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjQxMzQ3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/17303420/, http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=21690, https://pubmed.ncbi.nlm.nih.gov/21443219/, https://www.sciencedirect.com/science/article/pii/S0960894X05004038, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMOCJ9fQ%3D%3D

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:100241	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:100241
ChemicalBook	CB22670034	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB22670034
ChemicalBook	CB52630301	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB52630301
MolPort	MolPort-000-724-354	https://www.molport.com/shop/molecule-link/MolPort-000-724-354
MolPort	MolPort-000-819-654	https://www.molport.com/shop/molecule-link/MolPort-000-819-654
Selleck Chemicals	ciprofloxacin-cipro	http://www.selleckchem.com/products/ciprofloxacin-cipro.html
ZINC	ZINC000000020220	http://zinc15.docking.org/substances/ZINC000000020220
eMolecules	485830	https://www.emolecules.com/cgi-bin/more?vid=485830

PubMed

Title	Date	PubMed
The role of fluoroquinolones in tuberculosis today.	2001	11217874
Activity and spectrum of BMS 284756, a new des-F (6) quinolone, tested against strains of ciprofloxacin-resistant Gram-positive cocci.	2001 Feb	11248528
Effect of pre-stain viability on the acid-fast staining characteristics of Mycobacterium species.	2001 Feb	11248525
Antimicrobial susceptibilities and plasmid patterns of Neisseria gonorrhoeae in Bénin.	2001 Feb	11236110
Would you get your Gonorrhoea treated in the north of England?	2001 Feb	11236101
Neisseria gonorrhoeae resistant to ciprofloxacin: first report in Cuba.	2001 Feb	11234790
Impact of gemifloxacin on the normal human intestinal microflora.	2001 Feb	11233800
[Effect of subinhibitory levels of aminoglycosides and fluoroquinolines on hydrophobicity and motility of Serratia marcescens].	2001 Feb	11233670
Epithelial infectious crystalline keratopathy.	2001 Feb	11228305
Lack of interaction between levofloxacin and oxycodone: pharmacokinetics and drug disposition.	2001 Feb	11210403
Treatment of cat-scratch disease.	2001 Feb	11176245
Nosocomial pneumonia: importance of recognition of aetiological agents to define an appropriate initial empirical therapy.	2001 Feb	11165120
Activity of gatifloxacin and ciprofloxacin in combination with other antimicrobial agents.	2001 Feb	11165113
Changes in strategies for optimal antibacterial therapy in cystic fibrosis.	2001 Feb	11165111
Emergence of high level ciprofloxacin resistant Neisseria gonorrhoeae strain in Buenos Aires, Argentina.	2001 Feb	11158704
New approach for accurate simulation of human pharmacokinetics in an in vitro pharmacodynamic model: application to ciprofloxacin.	2001 Feb	11157913
Comparative activities of isepamicin, amikacin, cefepime, and ciprofloxacin alone or in combination with other antibiotics against Stenotrophomonas maltophilia.	2001 Jan	11245333
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.	2001 Jan	11245326
Two short peptides including segments of subunit A of Escherichia coli DNA gyrase as potential probes to evaluate the antibacterial activity of quinolones.	2001 Jan	11245203
Comamonas acidovorans keratitis in a hydrogel contact lens wearer.	2001 Jan	11215608
Microbiological profile of a shipboard environment and the flora on contact lenses of seamen.	2001 Jan	11215606
Antimicrobial use and susceptibility rates in isolates from intensive care unit and other nosocomial inpatient and outpatient areas.	2001 Jan	11209842
Determination by fluorimetric titration of the ionization constants of ciprofloxacin in solution and in the presence of liposomes.	2001 Jan	11202360
Nosocomial pneumonia. Diagnostic and therapeutic considerations.	2001 Jan	11190353
Insect wing case: unusual foreign body.	2001 Jan	11188995
Efficacy of ofloxacin and other otic preparations for otitis externa.	2001 Jan	11176588
Compliance issues related to the selection of antibiotic suspensions for children.	2001 Jan	11176558
Urethral stricture associated with malacoplakia: a case report and review of the literature.	2001 Jan	11164174
[Acute pyelonephritis. Randomized multicenter double-blind study comparing ciprofloxacin with combined ciprofloxacin and tobramycin].	2001 Jan 13	11210578
Pediatric travel consultation in an integrated clinic.	2001 Jan-Feb	11182602
Radical meatoplasty in the treatment of severe chronic external otitis.	2001 Jan-Feb	11174061
Bacteriologic and clinical efficacy of ofloxacin 0.3% versus ciprofloxacin 0.3% ophthalmic solutions in the treatment of patients with culture-positive bacterial keratitis.	2001 Mar	11248824
Chryseobacterium (Flavobacterium) meningosepticum outbreak associated with colonization of water taps in a neonatal intensive care unit.	2001 Mar	11247678
A case of rhinoscleroma treated with ciprofloxacin.	2001 Mar	11244532
Chryseobacterium in burn wounds.	2001 Mar	11226658
Multi-drug resistant Pseudomonas aeruginosa outbreak in a burns unit--an infection control study.	2001 Mar	11226649
The activity of antibiotics against Legionella pneumophila: in vitro and in vivo studies.	2001 Mar	11222573
Characterization of high-level fluoroquinolone resistance in Escherichia coli O78:K80 isolated from turkeys.	2001 Mar	11222567
Factors associated with antibiotic resistance in coliform organisms from community urinary tract infection in Wales.	2001 Mar	11222563
Antimicrobial activity of fluoroquinolone photodegradation products determined by parallel-line bioassay and high performance liquid chromatography.	2001 Mar	11222559
Transepithelial intestinal excretion of ciprofloxacin in humans.	2001 Mar 1	11229852
Ciprofloxacin resistance in gonococci.	2001 Mar 10	11253997
What have we learned from pharmacokinetic and pharmacodynamic theories?	2001 Mar 15	11249828
Successful treatment of an infant with Chromobacterium violaceum sepsis.	2001 Mar 15	11247733
Treatment failure with the use of ciprofloxacin for gonorrhea correlates with the prevalence of fluoroquinolone-resistant Neisseria gonorrhoeae strains in Bangladesh.	2001 Mar 15	11247712
In vitro susceptibilities to topical antibiotics of bacteria isolated from the surface of clinically symptomatic eyes.	2001 Mar-Apr	11244359
In vitro activity of gemifloxacin against Streptococcus pneumoniae isolates in Germany.	2001 Mar-Apr	11173811
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli.	2001 Mar-Apr	11173810
Activity of moxifloxacin and twelve other antimicrobial agents against 216 clinical isolates of Streptococcus pneumoniae.	2001 Mar-Apr	11173809
Mixed pharmacokinetic population study and diffusion model to describe ciprofloxacin lung concentrations.	2001 May	11173053

Patents

Sample Use Guides

In Vivo Use Guide

Skin and Skin Structure 500 -750 mg every 12 hours 7 to 14 days Bone and Joint 500-750 mg every 12 hours 4 to 8 weeks Complicated Intra-Abdominal 500 mg every 12 hours 7 to 14 days Infectious Diarrhea 500 mg every 12 hours 5 to 7 days Typhoid Fever 500 mg every 12 hours 10 days Uncomplicated Gonorrhea 250 mg single dose single dose Inhalational anthrax (pos-exposure) 500 mg every 12 hours 60 days Plague 500–750 mg every 12 hours 14 days Chronic Bacterial Prostatitis 500 mg every 12 hours 28 days Lower Respiratory Tract 500 -750 mg every 12 hours 7 to 14 days Urinary Tract 250-500 mg every 12 hours 7 to 14 days Acute Uncomplicated Cystitis 250 mg every 12 hours 3 days Acute Sinusitis 500 mg every 12 hours 10 days

Route of Administration: Oral

In Vitro Use Guide

Eight hospital isolates of methicillin-resistant and two standard strains of S. epidermidis (ATCC 12228, ATCC 35984) were cultured overnight in Tryptone Soy Broth supplemented with 0.5% glucose. The solution of tested compounds in TSB-glucose medium were mixed (1:1) with the bacterial inoculums (10^7 CFU/mL) in sterile 96-well polystyrene microtiter plates (Karell - Medlab, Italy) and incubated at 37 C for 24 h. Ciprofloxacin was used as the reference antimicrobial compound; its final concentration ranged from 0.125 to 8 mkg/ml.

Name

Type

Language

CIPROFLOXACIN HYDROCHLORIDE SESQUIHYDRATE

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-, HYDROCHLORIDE, HYDRATE (2:2:3)

Common Name

English

Code System Code Type Description

PUBCHEM

76961290

Created by admin on Sat Dec 16 02:12:03 GMT 2023 , Edited by admin on Sat Dec 16 02:12:03 GMT 2023

PRIMARY

FDA UNII

G43NV09DD4

Created by admin on Sat Dec 16 02:12:03 GMT 2023 , Edited by admin on Sat Dec 16 02:12:03 GMT 2023

PRIMARY

ACTIVE MOIETY


					5E8K9I0O4U

CIPROFLOXACIN

SUBSTANCE RECORD


					G43NV09DD4

CIPROFLOXACIN HYDROCHLORIDE SESQUIHYDRATE

AE	Significance	Dose	Population
Reaction gastrointestinal	3% Disc. AE	15 mg/kg 2 times / day steady, oral (median) Recommended Dose: 15 mg/kg, 2 times / day Route: oral Route: steady Dose: 15 mg/kg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	unhealthy, 1 - 17 years n = 335 Health Status: unhealthy Condition: Infection Age Group: 1 - 17 years Sex: unknown Population Size: 335 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf
Musculoskeletal disorder NOS	9.3%	15 mg/kg 2 times / day steady, oral (median) Recommended Dose: 15 mg/kg, 2 times / day Route: oral Route: steady Dose: 15 mg/kg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf	unhealthy, 1 - 17 years n = 335 Health Status: unhealthy Condition: Infection Age Group: 1 - 17 years Sex: unknown Population Size: 335 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s086lbl.pdf
Renal tubular necrosis acute	1 patient Disc. AE	7.5 g single, oral Overdose Dose: 7.5 g Route: oral Route: single Dose: 7.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/9531191/	unhealthy, 15 years n = 1 Health Status: unhealthy Condition: depression and posttraumatic stress disorder Age Group: 15 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9531191/
Pain epigastric	1 patient Disc. AE	12 g single, oral Overdose Dose: 12 g Route: oral Route: single Dose: 12 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, 16 years n = 1 Health Status: healthy Age Group: 16 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
Vomited	58%	20 mg/kg single, oral Recommended Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16182896/	unhealthy, 2-15 years n = 90 Health Status: unhealthy Condition: childhood cholera Age Group: 2-15 years Sex: M+F Population Size: 90 Sources: https://pubmed.ncbi.nlm.nih.gov/16182896/
Acute renal failure	1 patient Disc. AE	28 g single, oral Overdose Dose: 28 g Route: oral Route: single Dose: 28 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, 29 years n = 1 Health Status: healthy Age Group: 29 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
Acute renal failure	2 patients Disc. AE	750 mg 2 times / day steady, oral Highest studied dose Dose: 750 mg, 2 times / day Route: oral Route: steady Dose: 750 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17660035/	unhealthy, > 70 years n = 2 Health Status: unhealthy Condition: Infection Age Group: > 70 years Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/17660035/
Nausea and vomiting	2 patients Disc. AE	3 g single, oral Overdose Dose: 3 g Route: oral Route: single Dose: 3 g Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/	healthy, adult n = 2 Health Status: healthy Age Group: adult Sex: unknown Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/7919575/
Central nervous system disorder NOS	1.8%	228 mg 2 times / day steady, intravenous (mean) Recommended Dose: 228 mg, 2 times / day Route: intravenous Route: steady Dose: 228 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/	unhealthy, mean 50 years n = 1869 Health Status: unhealthy Condition: Infection Age Group: mean 50 years Sex: M+F Population Size: 1869 Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/
Gastrointestinal disorder (NOS)	3%	228 mg 2 times / day steady, intravenous (mean) Recommended Dose: 228 mg, 2 times / day Route: intravenous Route: steady Dose: 228 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/	unhealthy, mean 50 years n = 1869 Health Status: unhealthy Condition: Infection Age Group: mean 50 years Sex: M+F Population Size: 1869 Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/
Infusion site reactions	4.4%	228 mg 2 times / day steady, intravenous (mean) Recommended Dose: 228 mg, 2 times / day Route: intravenous Route: steady Dose: 228 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/	unhealthy, mean 50 years n = 1869 Health Status: unhealthy Condition: Infection Age Group: mean 50 years Sex: M+F Population Size: 1869 Sources: https://pubmed.ncbi.nlm.nih.gov/2686431/
Death	grade 5, 3 patients Disc. AE	10 mg/kg 2 times / day steady, intravenous Recommended Dose: 10 mg/kg, 2 times / day Route: intravenous Route: steady Dose: 10 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15523125/	unhealthy, preterm neonates n = 24 Health Status: unhealthy Condition: neonatal sepsis Age Group: preterm neonates Sex: unknown Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/15523125/
Exanthema	2 patients Disc. AE	500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	unhealthy, ≥18 years n = 122 Health Status: unhealthy Condition: acute pyelonephritis Age Group: ≥18 years Sex: F Population Size: 122 Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/
Myalgia	2 patients Disc. AE	500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/	unhealthy, ≥18 years n = 126 Health Status: unhealthy Condition: acute pyelonephritis Age Group: ≥18 years Sex: F Population Size: 126 Sources: https://pubmed.ncbi.nlm.nih.gov/22726802/
Constipation	below serious, 12 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Proteinuria	below serious, 12 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Osteopenia	below serious, 19 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Headache	below serious, 7 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Hypomagnesemia	below serious, 8 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Insomnia	below serious, 8 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Chest pain	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Clostridium difficile infection	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Dysuria	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Epistaxis	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
GI bleed	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Hematuria	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Hyperkalemia	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Hypertension malignant	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Myocardial infarction	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Nausea	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Nephrolithiasis	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Nephrostomy complication	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Neutropenia	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Pain	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Radial nerve palsy	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Small bowel obstruction	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Thrombocytopenia	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Urinary incontinence	serious, 1 patient	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Sepsis	serious, 2 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Vomiting	serious, 2 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Urinary retention	serious, 3 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Wound complication	serious, 3 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Venous thromboembolism	serious, 5 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Acute kidney injury	serious, 8 patients	500 mg 1 times / day steady, oral Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01789203	unhealthy n = 133 Health Status: unhealthy Condition: Renal Transplant Recipients Population Size: 133 Sources: https://clinicaltrials.gov/ct2/show/NCT01789203
Abdominal pain	below serious, 2 patients	500 mg 2 times / day steady, oral Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00609973	unhealthy n = 17 Health Status: unhealthy Condition: Crohn's Disease Population Size: 17 Sources: https://clinicaltrials.gov/ct2/show/NCT00609973
Diarrhea	below serious, 2 patients	500 mg 2 times / day steady, oral Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00609973	unhealthy n = 17 Health Status: unhealthy Condition: Crohn's Disease Population Size: 17 Sources: https://clinicaltrials.gov/ct2/show/NCT00609973
Headache	below serious, 2 patients	500 mg 2 times / day steady, oral Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00609973	unhealthy n = 17 Health Status: unhealthy Condition: Crohn's Disease Population Size: 17 Sources: https://clinicaltrials.gov/ct2/show/NCT00609973
Rash	below serious, 1 patient	500 mg 2 times / day steady, oral Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT02068846	unhealthy n = 9 Health Status: unhealthy Condition: BK Virus Infection Population Size: 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02068846

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