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Details

Stereochemistry ACHIRAL
Molecular Formula C16H18FN3O3
Molecular Weight 319.3314
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORFLOXACIN

SMILES

CCn1cc(c(=O)c2cc(c(cc21)N3CCNCC3)F)C(=O)O

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

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

5.31014386E11
Curative
NOROXIN

Approved Use

Uncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae.

Launch Date

5.31014386E11
Curative
NOROXIN

Approved Use

Prostatitis due to Escherichia coli

Launch Date

5.31014386E11
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

6.770304E11
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 unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
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 unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
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 unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
1600 mg single, oral
Studied dose
Dose: 1600 mg
Route: oral
Route: single
Dose: 1600 mg
Sources:
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)
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
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

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)
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids.
1980 Dec
World-wide clinical experience with norfloxacin: efficacy and safety.
1986
Norfloxacin versus co-trimoxazole in the treatment of recurring urinary tract infections in men.
1986
Norfloxacin in the treatment of uncomplicated gonococcal infections.
1987 Jun 26
Effect of fluoroquinolone concentration on selection of resistant mutants of Mycobacterium bovis BCG and Staphylococcus aureus.
1999 Jul
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.
2000 Oct
An outbreak of Salmonella enteritidis infection in pygmy hogs (Sus salvanius).
2001 Apr
Stability of norfloxacin in an extemporaneously prepared oral liquid.
2001 Apr 1
Comparison of ofloxacin and norfloxacin concentration in prostatic tissues in patients undergoing transurethral resection of the prostate.
2001 Aug
[In vitro activity of six fluoroquinolones and penicillin against 101 viridans group streptococci characterized by their susceptibility to erythromycin].
2001 Dec
[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
Epidemiology of hospital-acquired infections in cirrhotic patients: effect of carriage of methicillin-resistant Staphylococcus aureus and influence of previous antibiotic therapy and norfloxacin prophylaxis.
2001 Dec
Removal of bowel aerobic gram-negative bacteria is more effective than immunosuppression with cyclophosphamide and steroids to decrease natural alpha-galactosyl IgG antibodies.
2001 Feb
Tendon disorders attributed to fluoroquinolones: a study on 42 spontaneous reports in the period 1988 to 1998.
2001 Jun
Malignant hyperthermia susceptibility revealed by myalgia and rhabdomyolysis during fluoroquinolone treatment.
2001 Jun
Synthesis and activities of pyoverdin-quinolone adducts: a prospective approach to a specific Therapy against Pseudomonas aeruginosa.
2001 Jun 21
Antimicrobial resistance of Enterococci in Lebanon.
2001 Mar
Selective separation and simultaneous determination of trace levels of five types of fluorinated quinolone drugs by thin-layer chromatography/fluorescence densitometry.
2001 May-Jun
Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs.
2001 May-Jun
Enantioselective binding of ofloxacin to B form DNA.
2001 Nov 1
Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones.
2001 Nov-Dec
Fluoroquinolone adverse effects and drug interactions.
2001 Oct
Treatment of malignant biliary stenosis: which stent to use?
2001 Oct-Dec
Comparison of aztreonam against other antibiotics used in urinary tract infections.
2001 Oct-Dec
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.
2001 Sep
Comparative in vitro activities of five quinolone antibiotics, including gemifloxacin, against clinical isolates.
2001 Sep
Antimicrobial susceptibilities of Campylobacter strains isolated from broilers in the southern part of Japan from 1995 to 1999.
2001 Sep
[Multidrug-resistant and fluoroquinolone-resistant Salmonella enterica serotype Typhimurium definitive phage type 12 isolated from infantile diarrhea].
2001 Sep
Comparison of the in vitro activities of BMS-284756 and four fluoroquinolones against Streptococcus pneumoniae.
2001 Sep
Antimicrobial resistance and plasmid profiles of Campylobacter jejuni and Campylobacter coli from human and animal sources.
2002
Ignoring pharmacokinetics may lead to isoboles misinterpretation: illustration with the norfloxacin-theophylline convulsant interaction in rats.
2002 Feb
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.
2002 Feb
Activation of phagocytic cell NADPH oxidase by norfloxacin: a potential mechanism to explain its bactericidal action.
2002 Feb
[Acute pancreatitis secondary to administration or norfloxacin].
2002 Jan
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.
2002 Jan
[Urinary infections without complications: comparison of a treatment with norfloxacin for 7 days versus norfloxacin for 3 days].
2002 Jan
Resistance of Klebsiella pneumoniae strains producing and not producing ESBL (extended-spectrum beta-lactamase) type enzymes to selected non-beta-lactam antibiotics.
2002 Mar
Rapid antimicrobial susceptibility testing of urinary tract isolates and samples by flow cytometry.
2002 Mar
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.
Name Type Language
NORFLOXACIN
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NORFLOXACIN [MI]
Common Name English
NORFLOXACIN [VANDF]
Common Name English
NSC-757250
Code English
NORFLOXACIN [EP MONOGRAPH]
Common Name English
NORFLOXACIN [USP]
Common Name English
NORFLOXACIN [WHO-DD]
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
CHIBROXIN
Brand Name English
3-QUINOLINECARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-
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
Classification Tree Code System Code
WHO-VATC QS01AE02
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
LIVERTOX 697
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
NDF-RT N0000007606
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
WHO-VATC QJ01MA06
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
WHO-ATC S01AE02
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
WHO-ATC J01RA13
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
WHO-ATC J01MA06
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
NDF-RT N0000175937
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
NCI_THESAURUS C795
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
WHO-ATC S01AX12
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C47638
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
DRUG BANK
DB01059
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL9
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
PRIMARY
MESH
D009643
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
FDA UNII
N0F8P22L1P
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
RXCUI
7517
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
1967
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
PRIMARY
EVMPD
SUB09365MIG
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
PRIMARY
LACTMED
Norfloxacin
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
274-614-4
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
WIKIPEDIA
NORFLOXACIN
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
MERCK INDEX
M8059
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY Merck Index
INN
5105
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
HSDB
8029
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
EPA CompTox
70458-96-7
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
PUBCHEM
4539
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY
USP_CATALOG
1471506
Created by admin on Fri Jun 25 21:13:31 UTC 2021 , Edited by admin on Fri Jun 25 21:13:31 UTC 2021
PRIMARY USP-RS
CAS
70458-96-7
Created by admin on Fri Jun 25 21:13:30 UTC 2021 , Edited by admin on Fri Jun 25 21:13:30 UTC 2021
PRIMARY