U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of NORFLOXACIN

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)

HIDE SMILES / InChI

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

Description
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

Curator's Comment: Has limited CNS penetration in rats. Human data unknown.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2363076
Sources: 
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
NOROXIN

Approved Use

Uncomplicated 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 Date

1986
Curative
NOROXIN

Approved Use

Uncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae.

Launch Date

1986
Curative
NOROXIN

Approved Use

Prostatitis due to Escherichia coli

Launch Date

1986
Curative
CHIBROXIN

Approved Use

CHIBROXIN 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 Date

1991
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
1600 mg single, oral
Studied dose
Dose: 1600 mg
Route: oral
Route: single
Dose: 1600 mg
Sources:
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)
Rash (2 patients)
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, 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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Norfloxacin in the treatment of uncomplicated gonococcal infections.
1987 Jun 26
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.
2000 Oct
Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity.
2001
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
The impact of norfloxacin, ciprofloxacin and ofloxacin on human gut colonization by Candida albicans.
2001
[Activity of bicozamycin against Escherichia coli O157:H7 producing Vero toxin].
2001
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.
2001
The fungus Pestalotiopsis guepini as a model for biotransformation of ciprofloxacin and norfloxacin.
2001 Aug
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].
2001 Dec
Relationship among plasmids recovered from Staphylococcus aureus, milk leukocytes, and antimicrobial resistance.
2001 Dec
Antituberculous activity of norfloxacin mannich bases with isatin derivatives.
2001 Jul-Aug
Antimicrobial resistance of Enterococci in Lebanon.
2001 Mar
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
Effect of disintegrants with different hygroscopicity on dissolution of Norfloxacin/Pharmatose DCL 11 tablets.
2001 Mar 23
[Acute pancreatitis secondary to administration or norfloxacin].
2002 Jan
Spontaneous bacterial peritonitis caused by quinolone-resistant Escherichia coli: could steroid therapy play a role?
2002 Jan
Patents

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
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 Mon Mar 31 17:34:47 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:47 GMT 2025
Record UNII
N0F8P22L1P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORFLOXACIN
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
CHIBROXIN
Preferred Name English
NORFLOXACIN [USP IMPURITY]
Common Name English
NORFLOXACIN [MI]
Common Name English
NORFLOXACIN [VANDF]
Common Name English
NSC-757250
Code English
NORFLOXACIN [EP MONOGRAPH]
Common Name English
NORFLOXACIN [USP-RS]
Common Name English
MK-366
Code English
NOROXIN
Brand Name English
NORFLOXACIN [USAN]
Common Name English
norfloxacin [INN]
Common Name English
NORFLOXACIN [MART.]
Common Name English
3-QUINOLINECARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-
Common Name English
Norfloxacin [WHO-DD]
Common Name English
NORFLOXACIN [ORANGE BOOK]
Common Name English
1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINE CARBOXYLIC ACID
Systematic Name English
NORFLOXACIN [JAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QS01AE02
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
LIVERTOX NBK547850
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
NDF-RT N0000007606
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
WHO-VATC QJ01MA06
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
WHO-ATC S01AE02
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
WHO-ATC J01RA13
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
WHO-ATC J01MA06
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
NDF-RT N0000175937
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
NCI_THESAURUS C795
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
WHO-ATC S01AX12
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C47638
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
CHEBI
100246
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
DRUG BANK
DB01059
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
ChEMBL
CHEMBL9
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
MESH
D009643
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
FDA UNII
N0F8P22L1P
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
RXCUI
7517
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
1967
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
EVMPD
SUB09365MIG
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
LACTMED
Norfloxacin
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
274-614-4
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
WIKIPEDIA
NORFLOXACIN
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
NSC
757250
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
MERCK INDEX
m8059
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY Merck Index
INN
5105
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
HSDB
8029
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
RS_ITEM_NUM
1471506
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID7037680
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
PUBCHEM
4539
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
SMS_ID
100000091076
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
CAS
70458-96-7
Created by admin on Mon Mar 31 17:34:47 GMT 2025 , Edited by admin on Mon Mar 31 17:34:47 GMT 2025
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC