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 |
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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 Date5.31014386E11 |
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Curative | NOROXIN Approved UseUncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae. Launch Date5.31014386E11 |
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Curative | NOROXIN Approved UseProstatitis due to Escherichia coli Launch Date5.31014386E11 |
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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 Date6.770304E11 |
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 |
---|---|---|
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 |
---|---|---|
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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Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions. | 2001 |
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Resistance to antibiotics in injured coliforms isolated from drinking water. | 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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[Activity of bicozamycin against Escherichia coli O157:H7 producing Vero toxin]. | 2001 |
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The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age. | 2001 |
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Quinolone interactions with DNA and DNA gyrase. | 2001 |
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Long-Term treatment with cisapride and antibiotics in liver cirrhosis: effect on small intestinal motility, bacterial overgrowth, and liver function. | 2001 Apr |
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Characterization of sparfloxacin-resistant mutants of Staphylococcus aureus obtained in vitro. | 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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Antibiotic failure in the treatment of urinary tract infections in young women. | 2001 Dec |
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In vitro method for prediction of the phototoxic potentials of fluoroquinolones. | 2001 Dec |
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[Effect of subinhibitory levels of aminoglycosides and fluoroquinolines on hydrophobicity and motility of Serratia marcescens]. | 2001 Feb |
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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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Dental health and viridans streptococcal bacteremia in allogeneic hematopoietic stem cell transplant recipients. | 2001 Mar |
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Antimicrobial resistance of Enterococci in Lebanon. | 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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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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[Bilateral serous retinal detachments in acute posterior multifocal placoid pigmentous epitheliopathy]. | 2001 Nov |
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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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Studies on the uptake and release of fluoroquinolones by disposable contact lenses. | 2001 Oct |
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Treatment of malignant biliary stenosis: which stent to use? | 2001 Oct-Dec |
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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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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 |
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
by
admin
on
Edited
Wed Jul 05 22:32:18 UTC 2023
by
admin
on
Wed Jul 05 22:32:18 UTC 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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PRIMARY | RxNorm | ||
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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)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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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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