Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H18FN3O3 |
Molecular Weight | 319.3308 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCNCC3
InChI
InChIKey=OGJPXUAPXNRGGI-UHFFFAOYSA-N
InChI=1S/C16H18FN3O3/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)
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 |
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: |
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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 |
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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 |
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Norfloxacin versus co-trimoxazole in the treatment of recurring urinary tract infections in men. | 1986 |
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Norfloxacin in the treatment of uncomplicated gonococcal infections. | 1987 Jun 26 |
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Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity. | 2001 |
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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 |
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Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions. | 2001 |
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Fewer bacterial relapses after oral treatment with norfloxacin than with ceftibuten in acute pyelonephritis initially treated with intravenous cefuroxime. | 2001 |
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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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[In vitro activity of six fluoroquinolones and penicillin against 101 viridans group streptococci characterized by their susceptibility to erythromycin]. | 2001 Dec |
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[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii]. | 2001 Dec |
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Antibiotic failure in the treatment of urinary tract infections in young women. | 2001 Dec |
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Accumulation of five fluoroquinolones by Mycobacterium tuberculosis H37Rv. | 2001 Dec |
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In vitro method for prediction of the phototoxic potentials of fluoroquinolones. | 2001 Dec |
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Quinolones and false-positive urine screening for opiates by immunoassay technology. | 2001 Dec 26 |
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[Observations of properties of the L-form of M. tuberculosis induced by the antituberculosis drugs]. | 2001 Jan |
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Epidemic of Vibrio cholerae serogroup O139 in Berhampur, Orissa. | 2001 Jul |
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Tendon disorders attributed to fluoroquinolones: a study on 42 spontaneous reports in the period 1988 to 1998. | 2001 Jun |
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[A study on the resistance of Staphylococcus aureus and the mechanisms of its resistance to fluoroquinolone]. | 2001 Mar |
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Antimicrobial resistance of Shigella sonnei in Korea during the last two decades. | 2001 Mar |
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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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Fluorescence characteristic study of the ternary complex of fluoroquinolone antibiotics and cobalt (II) with ATP. | 2001 May |
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Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs. | 2001 May-Jun |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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[Bilateral serous retinal detachments in acute posterior multifocal placoid pigmentous epitheliopathy]. | 2001 Nov |
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Enantioselective binding of ofloxacin to B form DNA. | 2001 Nov 1 |
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New pyridoquinoline derivatives as potential inhibitors of the fluoroquinolone efflux pump in resistant Enterobacter aerogenes strains. | 2001 Nov 8 |
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Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones. | 2001 Nov-Dec |
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Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients. | 2001 Oct |
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Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98. | 2001 Oct |
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Treatment of malignant biliary stenosis: which stent to use? | 2001 Oct-Dec |
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Comparison of aztreonam against other antibiotics used in urinary tract infections. | 2001 Oct-Dec |
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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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[Multidrug-resistant and fluoroquinolone-resistant Salmonella enterica serotype Typhimurium definitive phage type 12 isolated from infantile diarrhea]. | 2001 Sep |
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Comparison of the in vitro activities of BMS-284756 and four fluoroquinolones against Streptococcus pneumoniae. | 2001 Sep |
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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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Antimicrobial resistance and plasmid profiles of Campylobacter jejuni and Campylobacter coli from human and animal sources. | 2002 |
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Ignoring pharmacokinetics may lead to isoboles misinterpretation: illustration with the norfloxacin-theophylline convulsant interaction in rats. | 2002 Feb |
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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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Activation of phagocytic cell NADPH oxidase by norfloxacin: a potential mechanism to explain its bactericidal action. | 2002 Feb |
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Functional cloning and characterization of a plant efflux carrier for multidrug and heavy metal detoxification. | 2002 Feb 15 |
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[Acute pancreatitis secondary to administration or norfloxacin]. | 2002 Jan |
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Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae. | 2002 Jan |
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[Urinary infections without complications: comparison of a treatment with norfloxacin for 7 days versus norfloxacin for 3 days]. | 2002 Jan |
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Treatment of acute bacterial conjunctivitis with topical netilmicin. | 2002 Jan |
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Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis. | 2002 Jan |
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Spontaneous bacterial peritonitis caused by quinolone-resistant Escherichia coli: could steroid therapy play a role? | 2002 Jan |
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Bactericidal mechanism of gatifloxacin compared with other quinolones. | 2002 Jan |
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Resistance of Klebsiella pneumoniae strains producing and not producing ESBL (extended-spectrum beta-lactamase) type enzymes to selected non-beta-lactam antibiotics. | 2002 Mar |
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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
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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admin
on
Edited
Fri Dec 15 15:00:15 GMT 2023
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on
Fri Dec 15 15:00:15 GMT 2023
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Record UNII |
N0F8P22L1P
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QS01AE02
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LIVERTOX |
NBK547850
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NDF-RT |
N0000007606
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WHO-VATC |
QJ01MA06
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WHO-ATC |
S01AE02
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WHO-ATC |
J01RA13
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WHO-ATC |
J01MA06
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NDF-RT |
N0000175937
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NCI_THESAURUS |
C795
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WHO-ATC |
S01AX12
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C47638
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100246
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DB01059
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CHEMBL9
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D009643
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N0F8P22L1P
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7517
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1967
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SUB09365MIG
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Norfloxacin
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274-614-4
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NORFLOXACIN
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757250
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m8059
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5105
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8029
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1471506
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DTXSID7037680
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4539
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100000091076
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70458-96-7
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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