Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C16H18FN3O3.C3H6O3 |
| Molecular Weight | 409.4088 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)C(O)=O.CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCNCC3
InChI
InChIKey=AYEXIHJJZPTXSS-UHFFFAOYSA-N
InChI=1S/C16H18FN3O3.C3H6O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20;1-2(4)3(5)6/h7-9,18H,2-6H2,1H3,(H,22,23);2,4H,1H3,(H,5,6)
DescriptionCurator's Comment: description was created based on several sources, including
https://davisplus.fadavis.com/3976/meddeck/pdf/norfloxacin.pdf
Curator's Comment: description was created based on several sources, including
https://davisplus.fadavis.com/3976/meddeck/pdf/norfloxacin.pdf
Norfloxacin is an antibacterial agent, It inhibits inhibits DNA synthesis by inhibiting DNA gyrase enzyme. Norfloxacin was approved in 1986 for treatment of urinary tract infections, gynecological infections, prostatitis, gonorhhea and bladder infections. In ophtalmology, norfloxacin is used for treatment of conjunctivitus.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3396 |
|||
Target ID: CHEMBL2363076 Sources: |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | NOROXIN Approved UseUncomplicated urinary tract infections (including cystitis) due to Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, Staphylococcus saprophyticus, Citrobacter freundii, Enterobacter aerogenes, Enterobacter cloacae, Proteus vulgaris, Staphylococcus aureus, or Streptococcus agalactiae. Complicated urinary tract infections due to Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, or Serratia marcescens. Launch Date1986 |
|||
| Curative | NOROXIN Approved UseUncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae. Launch Date1986 |
|||
| Curative | NOROXIN Approved UseProstatitis due to Escherichia coli Launch Date1986 |
|||
| Curative | CHIBROXIN Approved UseCHIBROXIN Ophthalmic Solution is indicated for the treatment of conjunctivitis when caused by susceptible strains of the following bacteria: Acinetobacter calcoaceticus, Aeromonas hydrophila, Haemophilus influenzae, Proteus mirabilis, Pseudomonas aeruginosa, Serratia marcescens, Staphylococcus aureus Staphylococcus epidermidis, Staphylococcus warnerii, Streptococcus pneumoniae. Appropriate monitoring of bacterial response to topical antibiotic therapy should accompany the use of CHIBROXIN Ophthalmic Solution. Launch Date1991 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.02 μg/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORFLOXACIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9.8 μg × h/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORFLOXACIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4 h |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORFLOXACIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
85% |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
NORFLOXACIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1600 mg single, oral Studied dose |
healthy, 24 ± 2 years n = 14 Health Status: healthy Age Group: 24 ± 2 years Sex: M Population Size: 14 Sources: |
|
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: |
unhealthy, 32 years (range: 18-96 years) n = 357 Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F Population Size: 357 Sources: |
Disc. AE: Nausea, Rash... AEs leading to discontinuation/dose reduction: Nausea (1 patient) Sources: Rash (2 patients) |
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: |
unhealthy, 46.0 years n = 190 Health Status: unhealthy Age Group: 46.0 years Sex: M+F Population Size: 190 Sources: |
Disc. AE: Abdominal cramps... AEs leading to discontinuation/dose reduction: Abdominal cramps (1 patient) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nausea | 1 patient Disc. AE |
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: |
unhealthy, 32 years (range: 18-96 years) n = 357 Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F Population Size: 357 Sources: |
| Rash | 2 patients Disc. AE |
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: |
unhealthy, 32 years (range: 18-96 years) n = 357 Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F Population Size: 357 Sources: |
| Abdominal cramps | 1 patient Disc. AE |
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: |
unhealthy, 46.0 years n = 190 Health Status: unhealthy Age Group: 46.0 years Sex: M+F Population Size: 190 Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| likely | ||||
| no | ||||
| yes [Inhibition 500 uM] | ||||
| yes [Ki 2300 uM] |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids. | 1980 Dec |
|
| World-wide clinical experience with norfloxacin: efficacy and safety. | 1986 |
|
| Norfloxacin versus co-trimoxazole in the treatment of recurring urinary tract infections in men. | 1986 |
|
| Norfloxacin in the treatment of uncomplicated gonococcal infections. | 1987 Jun 26 |
|
| Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity. | 2001 |
|
| Profiles of hepatic and dysrhythmic cardiovascular events following use of fluoroquinolone antibacterials: experience from large cohorts from the Drug Safety Research Unit Prescription-Event Monitoring database. | 2001 |
|
| Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions. | 2001 |
|
| Comparison of ofloxacin and norfloxacin concentration in prostatic tissues in patients undergoing transurethral resection of the prostate. | 2001 Aug |
|
| [In vitro activity of six fluoroquinolones and penicillin against 101 viridans group streptococci characterized by their susceptibility to erythromycin]. | 2001 Dec |
|
| [Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii]. | 2001 Dec |
|
| Relationship among plasmids recovered from Staphylococcus aureus, milk leukocytes, and antimicrobial resistance. | 2001 Dec |
|
| Epidemiology of hospital-acquired infections in cirrhotic patients: effect of carriage of methicillin-resistant Staphylococcus aureus and influence of previous antibiotic therapy and norfloxacin prophylaxis. | 2001 Dec |
|
| Antibiotic failure in the treatment of urinary tract infections in young women. | 2001 Dec |
|
| Accumulation of five fluoroquinolones by Mycobacterium tuberculosis H37Rv. | 2001 Dec |
|
| In vitro method for prediction of the phototoxic potentials of fluoroquinolones. | 2001 Dec |
|
| Quinolones and false-positive urine screening for opiates by immunoassay technology. | 2001 Dec 26 |
|
| [Observations of properties of the L-form of M. tuberculosis induced by the antituberculosis drugs]. | 2001 Jan |
|
| Epidemic of Vibrio cholerae serogroup O139 in Berhampur, Orissa. | 2001 Jul |
|
| [A study on the resistance of Staphylococcus aureus and the mechanisms of its resistance to fluoroquinolone]. | 2001 Mar |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
| [Bilateral serous retinal detachments in acute posterior multifocal placoid pigmentous epitheliopathy]. | 2001 Nov |
|
| [The activity of four fluoroquinolones against strains of Pseudomonas aeruginosa with a different sensitivity pattern to ceftazidime and imipenem]. | 2001 Nov |
|
| Enantioselective binding of ofloxacin to B form DNA. | 2001 Nov 1 |
|
| New pyridoquinoline derivatives as potential inhibitors of the fluoroquinolone efflux pump in resistant Enterobacter aerogenes strains. | 2001 Nov 8 |
|
| Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones. | 2001 Nov-Dec |
|
| Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients. | 2001 Oct |
|
| Studies on the uptake and release of fluoroquinolones by disposable contact lenses. | 2001 Oct |
|
| Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98. | 2001 Oct |
|
| Fluoroquinolone adverse effects and drug interactions. | 2001 Oct |
|
| Treatment of malignant biliary stenosis: which stent to use? | 2001 Oct-Dec |
|
| Comparison of aztreonam against other antibiotics used in urinary tract infections. | 2001 Oct-Dec |
|
| Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus. | 2001 Sep |
|
| [Acute cystitis in women. Current microbial sensitivity in our setting]. | 2001 Sep |
|
| Comparative in vitro activities of five quinolone antibiotics, including gemifloxacin, against clinical isolates. | 2001 Sep |
|
| Antimicrobial susceptibilities of Campylobacter strains isolated from broilers in the southern part of Japan from 1995 to 1999. | 2001 Sep |
|
| Utilization of quinolone drugs as monomers: characterization of the synthesis reaction products for poly(norfloxacin diisocyanatododecane polycaprolactone). | 2001 Spring |
|
| Antimicrobial resistance and plasmid profiles of Campylobacter jejuni and Campylobacter coli from human and animal sources. | 2002 |
|
| Ignoring pharmacokinetics may lead to isoboles misinterpretation: illustration with the norfloxacin-theophylline convulsant interaction in rats. | 2002 Feb |
|
| In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine. | 2002 Feb |
|
| Activation of phagocytic cell NADPH oxidase by norfloxacin: a potential mechanism to explain its bactericidal action. | 2002 Feb |
|
| Functional cloning and characterization of a plant efflux carrier for multidrug and heavy metal detoxification. | 2002 Feb 15 |
|
| [Acute pancreatitis secondary to administration or norfloxacin]. | 2002 Jan |
|
| Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae. | 2002 Jan |
|
| [Urinary infections without complications: comparison of a treatment with norfloxacin for 7 days versus norfloxacin for 3 days]. | 2002 Jan |
|
| Treatment of acute bacterial conjunctivitis with topical netilmicin. | 2002 Jan |
|
| Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis. | 2002 Jan |
|
| Spontaneous bacterial peritonitis caused by quinolone-resistant Escherichia coli: could steroid therapy play a role? | 2002 Jan |
|
| Bactericidal mechanism of gatifloxacin compared with other quinolones. | 2002 Jan |
|
| Resistance of Klebsiella pneumoniae strains producing and not producing ESBL (extended-spectrum beta-lactamase) type enzymes to selected non-beta-lactam antibiotics. | 2002 Mar |
|
| Rapid antimicrobial susceptibility testing of urinary tract isolates and samples by flow cytometry. | 2002 Mar |
Sample Use Guides
Norfloxacin tablets is administered orally with a glass of water at least 1 hour before or at least 2 hours after a meal or dairy products (e.g., milk, yogurt). Patients receiving norfloxacin should be well hydrated and should be instructed to drink fluids liberally. The maximal oral dose is 400 mg. For treatment of conjunctivitus, norfloxacin should be instilled at 1 or 2 drops to the affected eye(s) 4 times daily for up to 7 days.
Route of Administration:
Other
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
97867-34-0
Created by
admin on Sat Dec 16 13:32:06 GMT 2023 , Edited by admin on Sat Dec 16 13:32:06 GMT 2023
|
PRIMARY | |||
|
53398698
Created by
admin on Sat Dec 16 13:32:06 GMT 2023 , Edited by admin on Sat Dec 16 13:32:06 GMT 2023
|
PRIMARY | |||
|
GU3OE7CPD0
Created by
admin on Sat Dec 16 13:32:06 GMT 2023 , Edited by admin on Sat Dec 16 13:32:06 GMT 2023
|
PRIMARY |
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
