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Details

Stereochemistry RACEMIC
Molecular Formula C16H18FN3O3.C3H6O3
Molecular Weight 409.4088
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORFLOXACIN LACTATE

SMILES

CC(O)C(O)=O.CCN1C=C(C(O)=O)C(=O)C2=C1C=C(N3CCNCC3)C(F)=C2

InChI

InChIKey=AYEXIHJJZPTXSS-UHFFFAOYSA-N
InChI=1S/C16H18FN3O3.C3H6O3/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;1-2(4)3(5)6/h7-9,18H,2-6H2,1H3,(H,22,23);2,4H,1H3,(H,5,6)

HIDE SMILES / InChI
Molecular Formula C3H6O3
Molecular Weight 90.0779
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
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

CNS Penetrant
2588
Curator's Comment: Has limited CNS penetration in rats. Human data unknown.

Originator

Approval Year

1986
107
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Topoisomerase IV
62
Target ID: CHEMBL2363076
Sources: 
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
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
Approved
8583
NOROXIN

Approved Use

Uncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae.

Launch Date

1986
Curative
Approved
8583
NOROXIN

Approved Use

Prostatitis due to Escherichia coli

Launch Date

1986
Curative
Approved
8583
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019384s067lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019384s067lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019384s067lbl.pdf
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019384s067lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/6220672/
healthy, 24 ± 2 years
Health Status: healthy
Age Group: 24 ± 2 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6220672/
Sources:
https://pubmed.ncbi.nlm.nih.gov/6220672/
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:
https://pubmed.ncbi.nlm.nih.gov/1316075
unhealthy, 32 years (range: 18-96 years)
Health Status: unhealthy
Age Group: 32 years (range: 18-96 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/1316075
Disc. AE: Nausea, Rash...
AEs leading to
discontinuation/dose reduction:
Nausea (1 patient)
Rash (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1316075
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:
https://pubmed.ncbi.nlm.nih.gov/3158272
unhealthy, 46.0 years
Health Status: unhealthy
Age Group: 46.0 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3158272
Disc. AE: Abdominal cramps...
AEs leading to
discontinuation/dose reduction:
Abdominal cramps (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3158272
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:
https://pubmed.ncbi.nlm.nih.gov/1316075
unhealthy, 32 years (range: 18-96 years)
Health Status: unhealthy
Age Group: 32 years (range: 18-96 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/1316075
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:
https://pubmed.ncbi.nlm.nih.gov/1316075
unhealthy, 32 years (range: 18-96 years)
Health Status: unhealthy
Age Group: 32 years (range: 18-96 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/1316075
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:
https://pubmed.ncbi.nlm.nih.gov/3158272
unhealthy, 46.0 years
Health Status: unhealthy
Age Group: 46.0 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3158272
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2A6
879

CYP3A2
10

CYP1A2
2153
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
2633
 likely
CYP2A6
911
 no
CYP1A2
2333
 yes [Inhibition 500 uM]
CYP3A2
13
 yes [Ki 2300 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:100246
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:100246
ChemicalBook
CB1711035
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1711035
eMolecules
902214
https://www.emolecules.com/cgi-bin/more?vid=902214
MolPort
MolPort-001-738-625
https://www.molport.com/shop/molecule-link/MolPort-001-738-625
Selleck Chemicals
Norfloxacin(Norxacin)
http://www.selleckchem.com/products/Norfloxacin(Norxacin).html
ZINC
ZINC000000003742
http://zinc15.docking.org/substances/ZINC000000003742
PubMed

PubMed

TitleDatePubMed
Treatment of malignant biliary stenosis: which stent to use?
2002-03-13
Comparison of aztreonam against other antibiotics used in urinary tract infections.
2002-03-05
Resistance of Klebsiella pneumoniae strains producing and not producing ESBL (extended-spectrum beta-lactamase) type enzymes to selected non-beta-lactam antibiotics.
2002-03
Rapid antimicrobial susceptibility testing of urinary tract isolates and samples by flow cytometry.
2002-03
Functional cloning and characterization of a plant efflux carrier for multidrug and heavy metal detoxification.
2002-02-15
Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones.
2002-02-02
Ignoring pharmacokinetics may lead to isoboles misinterpretation: illustration with the norfloxacin-theophylline convulsant interaction in rats.
2002-02
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.
2002-02
Activation of phagocytic cell NADPH oxidase by norfloxacin: a potential mechanism to explain its bactericidal action.
2002-02
[Acute pancreatitis secondary to administration or norfloxacin].
2002-01
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.
2002-01
[Urinary infections without complications: comparison of a treatment with norfloxacin for 7 days versus norfloxacin for 3 days].
2002-01
Treatment of acute bacterial conjunctivitis with topical netilmicin.
2002-01
Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis.
2002-01
Spontaneous bacterial peritonitis caused by quinolone-resistant Escherichia coli: could steroid therapy play a role?
2002-01
Bactericidal mechanism of gatifloxacin compared with other quinolones.
2002-01
Antimicrobial resistance and plasmid profiles of Campylobacter jejuni and Campylobacter coli from human and animal sources.
2002
Quinolones and false-positive urine screening for opiates by immunoassay technology.
2001-12-26
[In vitro activity of six fluoroquinolones and penicillin against 101 viridans group streptococci characterized by their susceptibility to erythromycin].
2001-12
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].
2001-12
Relationship among plasmids recovered from Staphylococcus aureus, milk leukocytes, and antimicrobial resistance.
2001-12
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.
2001-12
Antibiotic failure in the treatment of urinary tract infections in young women.
2001-12
Accumulation of five fluoroquinolones by Mycobacterium tuberculosis H37Rv.
2001-12
In vitro method for prediction of the phototoxic potentials of fluoroquinolones.
2001-12
New pyridoquinoline derivatives as potential inhibitors of the fluoroquinolone efflux pump in resistant Enterobacter aerogenes strains.
2001-11-08
Enantioselective binding of ofloxacin to B form DNA.
2001-11-01
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001-11
[Bilateral serous retinal detachments in acute posterior multifocal placoid pigmentous epitheliopathy].
2001-11
[The activity of four fluoroquinolones against strains of Pseudomonas aeruginosa with a different sensitivity pattern to ceftazidime and imipenem].
2001-11
Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients.
2001-10
Studies on the uptake and release of fluoroquinolones by disposable contact lenses.
2001-10
Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98.
2001-10
Fluoroquinolone adverse effects and drug interactions.
2001-10
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.
2001-09
[Acute cystitis in women. Current microbial sensitivity in our setting].
2001-09
Comparative in vitro activities of five quinolone antibiotics, including gemifloxacin, against clinical isolates.
2001-09
Antimicrobial susceptibilities of Campylobacter strains isolated from broilers in the southern part of Japan from 1995 to 1999.
2001-09
Comparison of ofloxacin and norfloxacin concentration in prostatic tissues in patients undergoing transurethral resection of the prostate.
2001-08
Epidemic of Vibrio cholerae serogroup O139 in Berhampur, Orissa.
2001-07
[A study on the resistance of Staphylococcus aureus and the mechanisms of its resistance to fluoroquinolone].
2001-03
[Observations of properties of the L-form of M. tuberculosis induced by the antituberculosis drugs].
2001-01
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
Utilization of quinolone drugs as monomers: characterization of the synthesis reaction products for poly(norfloxacin diisocyanatododecane polycaprolactone).
2001
Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions.
2001
Norfloxacin in the treatment of uncomplicated gonococcal infections.
1987-06-26
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
Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids.
1980-12
Patents

Patents

04472579
22
05051505
10
05162523
6
06492373
6
JP2007537168A
10
JP2009018993A
10
JP2009501065A
33
JP2011528275A
456
JP4849764B2
75
JPH08193024A
6
JPS62294689A
6
JPS63190826A
6
US4146719
6

Sample Use Guides

In Vivo Use Guide
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 Tue Apr 01 20:52:57 GMT 2025
Edited
by admin
on Tue Apr 01 20:52:57 GMT 2025
Record UNII
GU3OE7CPD0
Record Status Validated (UNII)
Record Version
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Name Type Language
Norfloxacin lactate [WHO-DD]
Preferred Name English
NORFLOXACIN LACTATE
Common Name English
3-QUINOLINECARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-, COMPD. WITH 2-HYDROXYPROPANOIC ACID (1:1)
Systematic Name English
PROPANOIC ACID, 2-HYDROXY-, COMPD. WITH 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINECARBOXYLIC ACID (1:1)
Systematic Name English
3-QUINOLINECARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-, MONO(2-HYDROXYPROPANOATE)
Systematic Name English
Code System Code Type Description
CAS
97867-34-0
Created by admin on Tue Apr 01 20:52:57 GMT 2025 , Edited by admin on Tue Apr 01 20:52:57 GMT 2025
PRIMARY
PUBCHEM
53398698
Created by admin on Tue Apr 01 20:52:57 GMT 2025 , Edited by admin on Tue Apr 01 20:52:57 GMT 2025
PRIMARY
FDA UNII
GU3OE7CPD0
Created by admin on Tue Apr 01 20:52:57 GMT 2025 , Edited by admin on Tue Apr 01 20:52:57 GMT 2025
PRIMARY
Related Record Type Details
Structure of NORFLOXACIN
PARENT -> SALT/SOLVATE
NIH
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