NORFLOXACIN

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 Search

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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019384s052lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II beta 14 Target ID: CHEMBL3396 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2824776	Inhibitor 8504
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources:

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 207 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019384s052lbl.pdf	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
Gonorrhea 30 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019384s052lbl.pdf	Curative	Approved 8583	NOROXIN Approved Use Uncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae. Launch Date 1986
Prostatitis 25 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019384s052lbl.pdf	Curative	Approved 8583	NOROXIN Approved Use Prostatitis due to Escherichia coli Launch Date 1986
Conjunctivitis 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/19757S10lbl.pdf	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 879 CYP3A2 10 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/8894516/	likely
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14738594/	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC188773/	yes [Inhibition 500 uM]
CYP3A2 13	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/8894516/	yes [Ki 2300 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/17027138/

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Norfloxacin in the treatment of uncomplicated gonococcal infections.	1987 Jun 26	3300310
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.	2000 Oct	10991859
Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity.	2001	11791885
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	11772147
The impact of norfloxacin, ciprofloxacin and ofloxacin on human gut colonization by Candida albicans.	2001	11450873
[Activity of bicozamycin against Escherichia coli O157:H7 producing Vero toxin].	2001	11431931
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.	2001	11339881
The fungus Pestalotiopsis guepini as a model for biotransformation of ciprofloxacin and norfloxacin.	2001 Aug	11549022
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].	2001 Dec	11856982
Relationship among plasmids recovered from Staphylococcus aureus, milk leukocytes, and antimicrobial resistance.	2001 Dec	11814020
Antituberculous activity of norfloxacin mannich bases with isatin derivatives.	2001 Jul-Aug	11399863
Antimicrobial resistance of Enterococci in Lebanon.	2001 Mar	11282266
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	11281018
Effect of disintegrants with different hygroscopicity on dissolution of Norfloxacin/Pharmatose DCL 11 tablets.	2001 Mar 23	11274814
[Acute pancreatitis secondary to administration or norfloxacin].	2002 Jan	11878127
Spontaneous bacterial peritonitis caused by quinolone-resistant Escherichia coli: could steroid therapy play a role?	2002 Jan	11782580

Patents

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 `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

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Name

Type

Language

NORFLOXACIN

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