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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18FN3O3.C5H9NO4
Molecular Weight 466.4601
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORFLOXACIN GLUTAMATE

SMILES

N[C@@H](CCC(O)=O)C(O)=O.CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCNCC3

InChI

InChIKey=BIAAXZAPCCKBJW-HVDRVSQOSA-N
InChI=1S/C16H18FN3O3.C5H9NO4/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;6-3(5(9)10)1-2-4(7)8/h7-9,18H,2-6H2,1H3,(H,22,23);3H,1-2,6H2,(H,7,8)(H,9,10)/t;3-/m.0/s1

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

Molecular Formula C5H9NO4
Molecular Weight 147.1293
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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 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
World-wide clinical experience with norfloxacin: efficacy and safety.
1986
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
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000 Oct
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
Resistance to antibiotics in injured coliforms isolated from drinking water.
2001
The impact of norfloxacin, ciprofloxacin and ofloxacin on human gut colonization by Candida albicans.
2001
Stability of norfloxacin in an extemporaneously prepared oral liquid.
2001 Apr 1
Influence of ruminal distribution on norfloxacin pharmacokinetics in adult sheep.
2001 Aug
The fungus Pestalotiopsis guepini as a model for biotransformation of ciprofloxacin and norfloxacin.
2001 Aug
Characterization of sparfloxacin-resistant mutants of Staphylococcus aureus obtained in vitro.
2001 Aug
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].
2001 Dec
In vitro method for prediction of the phototoxic potentials of fluoroquinolones.
2001 Dec
Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998).
2001 Feb 1
Development of an indirect competitive ELISA for ciprofloxacin residues in food animal edible tissues.
2001 Mar
Effect of disintegrants with different hygroscopicity on dissolution of Norfloxacin/Pharmatose DCL 11 tablets.
2001 Mar 23
Derivative spectrophotometric analysis of 4-quinolone antibacterials in formulations and spiked biological fluids by their Cu(II) complexes.
2001 Mar-Apr
Natural antibiotic susceptibility of recently established coryneform bacteria.
2001 May
Fluorescence characteristic study of the ternary complex of fluoroquinolone antibiotics and cobalt (II) with ATP.
2001 May
Novel presentation and approach to management of hepatopulmonary syndrome with use of antimicrobial agents.
2001 May 15
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Plasmid-mediated dimethoate degradation in Pseudomonas aeruginosa MCMB-427.
2001 Oct
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.
2001 Sep
[Acute cystitis in women. Current microbial sensitivity in our setting].
2001 Sep
Comparative in vitro activities of five quinolone antibiotics, including gemifloxacin, against clinical isolates.
2001 Sep
[Multidrug-resistant and fluoroquinolone-resistant Salmonella enterica serotype Typhimurium definitive phage type 12 isolated from infantile diarrhea].
2001 Sep
Biphenylacetic acid enhances the antagonistic action of fluoroquinolones on the GABA(A)-mediated responses of the isolated guinea-pig ileum.
2001 Sep
Na+-driven multidrug efflux pump VcmA from Vibrio cholerae non-O1, a non-halophilic bacterium.
2001 Sep 25
Utilization of quinolone drugs as monomers: characterization of the synthesis reaction products for poly(norfloxacin diisocyanatododecane polycaprolactone).
2001 Spring
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.
2002 Feb
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.
2002 Jan
Bactericidal mechanism of gatifloxacin compared with other quinolones.
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 Sat Dec 16 19:09:55 GMT 2023
Edited
by admin
on Sat Dec 16 19:09:55 GMT 2023
Record UNII
E97LKC77WL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORFLOXACIN GLUTAMATE
Common Name English
L-GLUTAMIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINECARBOXYLATE (1:1)
Systematic Name English
L-GLUTAMIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINECARBOXYLATE
Systematic Name English
Norfloxacin glutamate [WHO-DD]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID40234362
Created by admin on Sat Dec 16 19:09:55 GMT 2023 , Edited by admin on Sat Dec 16 19:09:55 GMT 2023
PRIMARY
PUBCHEM
21123686
Created by admin on Sat Dec 16 19:09:55 GMT 2023 , Edited by admin on Sat Dec 16 19:09:55 GMT 2023
PRIMARY
FDA UNII
E97LKC77WL
Created by admin on Sat Dec 16 19:09:55 GMT 2023 , Edited by admin on Sat Dec 16 19:09:55 GMT 2023
PRIMARY
CAS
85181-48-2
Created by admin on Sat Dec 16 19:09:55 GMT 2023 , Edited by admin on Sat Dec 16 19:09:55 GMT 2023
PRIMARY
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