Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H18FN3O3.H2O |
| Molecular Weight | 337.3461 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CCN1C=C(C(O)=O)C(=O)C2=C1C=C(N3CCNCC3)C(F)=C2
InChI
InChIKey=ITBINNOMHXTMLQ-UHFFFAOYSA-N
InChI=1S/C16H18FN3O3.H2O/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;/h7-9,18H,2-6H2,1H3,(H,22,23);1H2
| Molecular Formula | C16H18FN3O3 |
| Molecular Weight | 319.3308 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
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 plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
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 plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
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 plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1600 mg single, oral Studied dose |
healthy, 24 ± 2 years Health Status: healthy Age Group: 24 ± 2 years Sex: M 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) Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F 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 Health Status: unhealthy Age Group: 46.0 years Sex: M+F 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) Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F 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) Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F 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 Health Status: unhealthy Age Group: 46.0 years Sex: M+F 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 |
|
| Resistance to antibiotics in injured coliforms isolated from drinking water. | 2001 |
|
| The impact of norfloxacin, ciprofloxacin and ofloxacin on human gut colonization by Candida albicans. | 2001 |
|
| Comparison of ofloxacin and norfloxacin concentration in prostatic tissues in patients undergoing transurethral resection of the prostate. | 2001 Aug |
|
| Influence of ruminal distribution on norfloxacin pharmacokinetics in adult sheep. | 2001 Aug |
|
| The fungus Pestalotiopsis guepini as a model for biotransformation of ciprofloxacin and norfloxacin. | 2001 Aug |
|
| Characterization of sparfloxacin-resistant mutants of Staphylococcus aureus obtained in vitro. | 2001 Aug |
|
| Multiresidue analysis of fluoroquinolone antibiotics in chicken tissue using automated microdialysis-liquid chromatography. | 2001 Aug |
|
| Trace determination of fluoroquinolone antibacterial agents in urban wastewater by solid-phase extraction and liquid chromatography with fluorescence detection. | 2001 Aug 1 |
|
| [In vitro activity of six fluoroquinolones and penicillin against 101 viridans group streptococci characterized by their susceptibility to erythromycin]. | 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 |
|
| In vitro method for prediction of the phototoxic potentials of fluoroquinolones. | 2001 Dec |
|
| [Observations of properties of the L-form of M. tuberculosis induced by the antituberculosis drugs]. | 2001 Jan |
|
| Interaction between biofilms formed by Staphylococcus epidermidis and quinolones. | 2001 Jul |
|
| 2D molecular square grid with strong blue fluorescent emission: a complex of norfloxacin with zinc(II). | 2001 Jul 30 |
|
| [A study on the resistance of Staphylococcus aureus and the mechanisms of its resistance to fluoroquinolone]. | 2001 Mar |
|
| Natural antibiotic susceptibility of recently established coryneform bacteria. | 2001 May |
|
| 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 |
|
| 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 |
|
| Plasmid-mediated dimethoate degradation in Pseudomonas aeruginosa MCMB-427. | 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 |
|
| [Multidrug-resistant and fluoroquinolone-resistant Salmonella enterica serotype Typhimurium definitive phage type 12 isolated from infantile diarrhea]. | 2001 Sep |
|
| Na+-driven multidrug efflux pump VcmA from Vibrio cholerae non-O1, a non-halophilic bacterium. | 2001 Sep 25 |
|
| Utilization of quinolone drugs as monomers: characterization of the synthesis reaction products for poly(norfloxacin diisocyanatododecane polycaprolactone). | 2001 Spring |
|
| 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 |
|
| [Acute pancreatitis secondary to administration or norfloxacin]. | 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 |
|
| 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
| Substance Class |
Chemical
Created
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Edited
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by
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| Record UNII |
YUF620IF4G
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| Record Status |
Validated (UNII)
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| Record Version |
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19829980
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YUF620IF4G
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DTXSID10197298
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478082-34-7
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ANHYDROUS->SOLVATE |
