CIPROFLOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H18FN3O3
Molecular Weight	331.3415
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CN(C2CC2)C3=CC(N4CCNCC4)=C(F)C=C3C1=O

InChI

InChIKey=MYSWGUAQZAJSOK-UHFFFAOYSA-N

InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)

HIDE SMILES / InChI

Molecular Formula	C17H18FN3O3
Molecular Weight	331.3415
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8228
Bacterial DNA gyrase 64 Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25951434	Inhibitor 8228		150.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 204 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021744s016lbl.pdf	Curative	Approved 8360	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 6.6216958E11
Infectious diarrhea 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019537s085,020780s042lbl.pdf	Curative	Approved 8360	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 6.6216958E11
Lower respiratory tract infections 51 Sources: https://www.drugs.com/pro/cipro-iv.html	Curative	Approved 8360	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 6.6216958E11

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 1579	inhibitor 1752	inhibitor 1837	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2E1 876 CYP4A1 8 CYP2B6 799 CYP2C8 901 OAT1 595 OAT3 636 OATP1B1 781 OATP1B3 700 BSEP 401 MRP2 367 MRP3 157 MRP4 203 CYP2A6 704 CYP2C19 1463 ALDH1 40 P-gp 1437	P-gp 1527 BCRP 555 OAT1 320

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
ALDH1 40	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	inconclusive [Activation 10 uM]
BSEP 402	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
CYP2A6 736	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no [IC50 >10 uM]
CYP2C19 1537	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no [IC50 >10 uM]
CYP2D6 1875	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMOCJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2E1 964	inhibitor 3240 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 459	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
MRP3 208	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
MRP4 237	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >10 uM]
CYP2B6 985	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2C8 955	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	no
CYP4A1 25	inhibitor 3240 Sources: https://gut.bmj.com/content/44/3/347.short	no
OAT1 599	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/18381565/	no
OATP1B1 796	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	no
OATP1B3 709	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	no
P-gp 1626	inhibitor 3240 Sources: https://pubs.acs.org/doi/10.1021/tx010125x, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	no
CYP2C9 1803	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDgifX0%3D	yes [Activation 12.5893 uM]
CYP1A2 1673	inhibitor 3240 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 1909	inhibitor 3240 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 638	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/18381565/	yes

Drug as victim

Target	Modality	Activity
P-gp 1527	substrate 3326 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1038/sj.bjp.0704560	no
BCRP 555	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18200507/	yes
OAT1 320	substrate 3326 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 1632	inhibitor 1613 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
Effect of fluoroquinolone concentration on selection of resistant mutants of Mycobacterium bovis BCG and Staphylococcus aureus.	1999 Jul	10390236
Agitated sleepwalking with fluoroquinolone therapy.	1999 May	10353533
Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae.	1999 Oct	10588315
Purification and inhibition by quinolones of DNA gyrases from Mycobacterium avium, Mycobacterium smegmatis and Mycobacterium fortuitum bv. peregrinum.	1999 Sep	10517605
Activity of moxifloxacin against mycobacteria.	1999 Sep	10511409
Bilateral hydronephrosis from ciprofloxacin induced crystalluria and stone formation.	2000 Aug	10893604
Antibacterial spectrum of a novel des-fluoro(6) quinolone, BMS-284756.	2000 Dec	11083639
Comparative antimicrobial activities of the newly synthesized quinolone WQ-3034, levofloxacin, sparfloxacin, and ciprofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex.	2000 Feb	10639351
In vitro susceptibilities of rapidly growing mycobacteria to telithromycin (HMR 3647) and seven other antimicrobials.	2000 Jan	10602744
Quinolones and tendon ruptures.	2000 May	10832946
Intracellular targets of moxifloxacin: a comparison with other fluoroquinolones.	2000 May	10797078
Ciprofloxacin increases serum clozapine and N-desmethylclozapine: a study in patients with schizophrenia.	2000 Nov	11151749
Ciprofloxacin affects pregnancy loss in CBA/JxDBA/2J mice possibly via elevation of interleukin-3 and granulocyte macrophage-colony stimulating factor production.	2000 Nov	11125792
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.	2000 Oct	10991859
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.	2000 Oct	10991858
Mutant prevention concentration as a measure of antibiotic potency: studies with clinical isolates of Mycobacterium tuberculosis.	2000 Sep	10952625
The role of fluoroquinolones in tuberculosis today.	2001	11217874
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
Treatment of cat-scratch disease.	2001 Feb	11176245
In vitro activity of new quinolones against Clostridium difficile.	2001 Feb	11157906
Evaluation of the Mastalex latex agglutination test for methicillin resistance in Staphylococcus aureus grown on different screening media.	2001 Feb	11157904
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
Efficacy of ofloxacin and other otic preparations for otitis externa.	2001 Jan	11176588
In vitro Gram-positive antimicrobial activity of evernimicin (SCH 27899), a novel oligosaccharide, compared with other antimicrobials: a multicentre international trial.	2001 Jan	11152427
Interactions of a series of fluoroquinolone antibacterial drugs with the human cardiac K+ channel HERG.	2001 Jan	11125032
[Acute pyelonephritis. Randomized multicenter double-blind study comparing ciprofloxacin with combined ciprofloxacin and tobramycin].	2001 Jan 13	11210578
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
In vitro susceptibilities to topical antibiotics of bacteria isolated from the surface of clinically symptomatic eyes.	2001 Mar-Apr	11244359
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli.	2001 Mar-Apr	11173810
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.

Substance Class	Chemical Created by `admin` on `Thu Jul 06 10:59:41 UTC 2023` Edited by `admin` on `Thu Jul 06 10:59:41 UTC 2023`
Record UNII	5E8K9I0O4U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIPROFLOXACIN

Official Name

English

CIPROFLOXACIN [MART.]

Common Name

English

CIPROFLOXACIN [MI]

Common Name

English

BAY-Q-3939

Code

English

CIPROFLOXACIN [WHO-IP]

Common Name

English

CIPROFLOXACINUM [WHO-IP LATIN]

Common Name

English

CIPROFLOXACIN [USAN]

Common Name

English

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

Systematic Name

English

BAY Q 3939

Code

English

CIPROFLOXACIN [JAN]

Common Name

English

ciprofloxacin [INN]

Common Name

English

CIPRODEX COMPONENT CIPROFLOXACIN

Common Name

English

CIPROFLOXACIN [USP MONOGRAPH]

Common Name

English

CIPROFLOXACIN [USP-RS]

Common Name

English

BAY O 9867 FREE BASE

Code

English

1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINE-CARBOXYLIC ACID

Systematic Name

English

CIPROFLOXACIN [EP MONOGRAPH]

Common Name

English

CIPROFLOXACIN [VANDF]

Common Name

English

BAY-O-9867 FREE BASE

Code

English

CIPROFLOXACIN COMPONENT OF CIPRODEX

Common Name

English

ENROFLOXACIN FOR VETERINARY USE IMPURITY B [EP IMPURITY]

Common Name

English

CIPROFLOXACIN [HSDB]

Common Name

English

OTIPRIO

Brand Name

English

NSC-758467

Code

English

BAYQ3939

Code

English

CIPROFLOXACIN [ORANGE BOOK]

Common Name

English

Ciprofloxacin [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

422314