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=C1C=C(N3CCNCC3)C(F)=C2
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 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 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: |
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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) 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 |
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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 |
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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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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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The impact of norfloxacin, ciprofloxacin and ofloxacin on human gut colonization by Candida albicans. | 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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The fungus Pestalotiopsis guepini as a model for biotransformation of ciprofloxacin and norfloxacin. | 2001 Aug |
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[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii]. | 2001 Dec |
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Relationship among plasmids recovered from Staphylococcus aureus, milk leukocytes, and antimicrobial resistance. | 2001 Dec |
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Antituberculous activity of norfloxacin mannich bases with isatin derivatives. | 2001 Jul-Aug |
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Antimicrobial resistance of Enterococci in Lebanon. | 2001 Mar |
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Analysis of fluoroquinolone-mediated photosensitization of 2'-deoxyguanosine, calf thymus and cellular DNA: determination of type-I, type-II and triplet-triplet energy transfer mechanism contribution. | 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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[Acute pancreatitis secondary to administration or norfloxacin]. | 2002 Jan |
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Spontaneous bacterial peritonitis caused by quinolone-resistant Escherichia coli: could steroid therapy play a role? | 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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on
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Mon Mar 31 17:34:47 GMT 2025
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Mon Mar 31 17:34:47 GMT 2025
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Record UNII |
N0F8P22L1P
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Record Status |
Validated (UNII)
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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)
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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 |
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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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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