Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H18FN3O3.C5H9NO4 |
Molecular Weight | 466.4601 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CCC(O)=O)C(O)=O.CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCNCC3
InChI
InChIKey=BIAAXZAPCCKBJW-HVDRVSQOSA-N
InChI=1S/C16H18FN3O3.C5H9NO4/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;6-3(5(9)10)1-2-4(7)8/h7-9,18H,2-6H2,1H3,(H,22,23);3H,1-2,6H2,(H,7,8)(H,9,10)/t;3-/m.0/s1
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 | C5H9NO4 |
Molecular Weight | 147.1293 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14603491
Curator's Comment: Has limited CNS penetration in rats. Human data unknown.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3396 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2824776 |
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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 |
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Curative | NOROXIN Approved UseUncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae. Launch Date1986 |
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Curative | NOROXIN Approved UseProstatitis due to Escherichia coli Launch Date1986 |
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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 |
---|---|---|
World-wide clinical experience with norfloxacin: efficacy and safety. | 1986 |
|
Norfloxacin in the treatment of uncomplicated gonococcal infections. | 1987 Jun 26 |
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Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques. | 2000 Oct |
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Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening. | 2000 Oct |
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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 |
|
Resistance to antibiotics in injured coliforms isolated from drinking water. | 2001 |
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The impact of norfloxacin, ciprofloxacin and ofloxacin on human gut colonization by Candida albicans. | 2001 |
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Stability of norfloxacin in an extemporaneously prepared oral liquid. | 2001 Apr 1 |
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Influence of ruminal distribution on norfloxacin pharmacokinetics in adult sheep. | 2001 Aug |
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The fungus Pestalotiopsis guepini as a model for biotransformation of ciprofloxacin and norfloxacin. | 2001 Aug |
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Characterization of sparfloxacin-resistant mutants of Staphylococcus aureus obtained in vitro. | 2001 Aug |
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[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii]. | 2001 Dec |
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In vitro method for prediction of the phototoxic potentials of fluoroquinolones. | 2001 Dec |
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Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998). | 2001 Feb 1 |
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Development of an indirect competitive ELISA for ciprofloxacin residues in food animal edible tissues. | 2001 Mar |
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Effect of disintegrants with different hygroscopicity on dissolution of Norfloxacin/Pharmatose DCL 11 tablets. | 2001 Mar 23 |
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Derivative spectrophotometric analysis of 4-quinolone antibacterials in formulations and spiked biological fluids by their Cu(II) complexes. | 2001 Mar-Apr |
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Natural antibiotic susceptibility of recently established coryneform bacteria. | 2001 May |
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Fluorescence characteristic study of the ternary complex of fluoroquinolone antibiotics and cobalt (II) with ATP. | 2001 May |
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Novel presentation and approach to management of hepatopulmonary syndrome with use of antimicrobial agents. | 2001 May 15 |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Plasmid-mediated dimethoate degradation in Pseudomonas aeruginosa MCMB-427. | 2001 Oct |
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Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus. | 2001 Sep |
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[Acute cystitis in women. Current microbial sensitivity in our setting]. | 2001 Sep |
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Comparative in vitro activities of five quinolone antibiotics, including gemifloxacin, against clinical isolates. | 2001 Sep |
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[Multidrug-resistant and fluoroquinolone-resistant Salmonella enterica serotype Typhimurium definitive phage type 12 isolated from infantile diarrhea]. | 2001 Sep |
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Biphenylacetic acid enhances the antagonistic action of fluoroquinolones on the GABA(A)-mediated responses of the isolated guinea-pig ileum. | 2001 Sep |
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Na+-driven multidrug efflux pump VcmA from Vibrio cholerae non-O1, a non-halophilic bacterium. | 2001 Sep 25 |
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Utilization of quinolone drugs as monomers: characterization of the synthesis reaction products for poly(norfloxacin diisocyanatododecane polycaprolactone). | 2001 Spring |
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In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine. | 2002 Feb |
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Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae. | 2002 Jan |
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Bactericidal mechanism of gatifloxacin compared with other quinolones. | 2002 Jan |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7452690
Minimal inhibition concnetration of norfloxacin aganis S.aureus, E.coli and P.aeuginosa was determined using agar media by means of a standard twofold serial dilution method and comprised 0.39, 0.05 and 0.39 ug/mL correspondingly.
Substance Class |
Chemical
Created
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Edited
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Record UNII |
E97LKC77WL
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Record Status |
Validated (UNII)
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Record Version |
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