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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
World-wide clinical experience with norfloxacin: efficacy and safety.
1986
Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin mannich bases.
2000 Feb
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000 Oct
Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity.
2001
Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions.
2001
The impact of norfloxacin, ciprofloxacin and ofloxacin on human gut colonization by Candida albicans.
2001
In vitro activity of levofloxacin against coagulase-positive and -negative staphylococci.
2001
[Activity of bicozamycin against Escherichia coli O157:H7 producing Vero toxin].
2001
Fluoroquinolones: place in ocular therapy.
2001
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.
2001
Long-Term treatment with cisapride and antibiotics in liver cirrhosis: effect on small intestinal motility, bacterial overgrowth, and liver function.
2001 Apr
Stability of norfloxacin in an extemporaneously prepared oral liquid.
2001 Apr 1
Characterization of sparfloxacin-resistant mutants of Staphylococcus aureus obtained in vitro.
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
2D molecular square grid with strong blue fluorescent emission: a complex of norfloxacin with zinc(II).
2001 Jul 30
Synthesis and antibacterial evaluation of certain quinolone derivatives.
2001 Jul 5
Antituberculous activity of norfloxacin mannich bases with isatin derivatives.
2001 Jul-Aug
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
Dental health and viridans streptococcal bacteremia in allogeneic hematopoietic stem cell transplant recipients.
2001 Mar
Development of an indirect competitive ELISA for ciprofloxacin residues in food animal edible tissues.
2001 Mar
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
Novel presentation and approach to management of hepatopulmonary syndrome with use of antimicrobial agents.
2001 May 15
Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs.
2001 May-Jun
Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones.
2001 Nov-Dec
Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients.
2001 Oct
Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98.
2001 Oct
Comparison of aztreonam against other antibiotics used in urinary tract infections.
2001 Oct-Dec
[Acute cystitis in women. Current microbial sensitivity in our setting].
2001 Sep
Antimicrobial susceptibilities of Campylobacter strains isolated from broilers in the southern part of Japan from 1995 to 1999.
2001 Sep
Antimicrobial resistance and plasmid profiles of Campylobacter jejuni and Campylobacter coli from human and animal sources.
2002
Activation of phagocytic cell NADPH oxidase by norfloxacin: a potential mechanism to explain its bactericidal action.
2002 Feb
Functional cloning and characterization of a plant efflux carrier for multidrug and heavy metal detoxification.
2002 Feb 15
[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
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
  • Download
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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