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=CC(F)=C(C=C12)N3CCNCC3

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 8297
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources:

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 205 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019384s052lbl.pdf	Curative	Approved 8429	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 8429	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 8429	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 8429	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 unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

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

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

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

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 n = 14 Health Status: healthy Age Group: 24 ± 2 years Sex: M Population Size: 14 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) n = 357 Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F Population Size: 357 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 n = 190 Health Status: unhealthy Age Group: 46.0 years Sex: M+F Population Size: 190 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) n = 357 Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F Population Size: 357 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) n = 357 Health Status: unhealthy Age Group: 32 years (range: 18-96 years) Sex: M+F Population Size: 357 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 n = 190 Health Status: unhealthy Age Group: 46.0 years Sex: M+F Population Size: 190 Sources: https://pubmed.ncbi.nlm.nih.gov/3158272

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 707 CYP3A2 10 CYP1A2 1524

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/8894516/	likely
CYP2A6 739	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14738594/	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC188773/	yes [Inhibition 500 uM]
CYP3A2 13	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/8894516/	yes [Ki 2300 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
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
eMolecules	902214	https://www.emolecules.com/cgi-bin/more?vid=902214

PubMed

Title	Date	PubMed
Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids.	1980 Dec	7452690
World-wide clinical experience with norfloxacin: efficacy and safety.	1986	3535057
Norfloxacin versus co-trimoxazole in the treatment of recurring urinary tract infections in men.	1986	3490684
Norfloxacin in the treatment of uncomplicated gonococcal infections.	1987 Jun 26	3300310
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
Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions.	2001	11735605
Comparison of ofloxacin and norfloxacin concentration in prostatic tissues in patients undergoing transurethral resection of the prostate.	2001 Aug	11678006
[In vitro activity of six fluoroquinolones and penicillin against 101 viridans group streptococci characterized by their susceptibility to erythromycin].	2001 Dec	11856983
[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
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	11811877
Antibiotic failure in the treatment of urinary tract infections in young women.	2001 Dec	11733475
Accumulation of five fluoroquinolones by Mycobacterium tuberculosis H37Rv.	2001 Dec	11733462
In vitro method for prediction of the phototoxic potentials of fluoroquinolones.	2001 Dec	11698174
Quinolones and false-positive urine screening for opiates by immunoassay technology.	2001 Dec 26	11754677
[Observations of properties of the L-form of M. tuberculosis induced by the antituberculosis drugs].	2001 Jan	11802941
Epidemic of Vibrio cholerae serogroup O139 in Berhampur, Orissa.	2001 Jul	11762200
[A study on the resistance of Staphylococcus aureus and the mechanisms of its resistance to fluoroquinolone].	2001 Mar	11798575
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
[Bilateral serous retinal detachments in acute posterior multifocal placoid pigmentous epitheliopathy].	2001 Nov	11715108
[The activity of four fluoroquinolones against strains of Pseudomonas aeruginosa with a different sensitivity pattern to ceftazidime and imipenem].	2001 Nov	11709121
Enantioselective binding of ofloxacin to B form DNA.	2001 Nov 1	11673861
New pyridoquinoline derivatives as potential inhibitors of the fluoroquinolone efflux pump in resistant Enterobacter aerogenes strains.	2001 Nov 8	11689091
Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones.	2001 Nov-Dec	11822230
Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients.	2001 Oct	11744939
Studies on the uptake and release of fluoroquinolones by disposable contact lenses.	2001 Oct	11725985
Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98.	2001 Oct	11683796
Fluoroquinolone adverse effects and drug interactions.	2001 Oct	11642691
Treatment of malignant biliary stenosis: which stent to use?	2001 Oct-Dec	11887633
Comparison of aztreonam against other antibiotics used in urinary tract infections.	2001 Oct-Dec	11873424
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.	2001 Sep	11810583
[Acute cystitis in women. Current microbial sensitivity in our setting].	2001 Sep	11692799
Comparative in vitro activities of five quinolone antibiotics, including gemifloxacin, against clinical isolates.	2001 Sep	11678934
Antimicrobial susceptibilities of Campylobacter strains isolated from broilers in the southern part of Japan from 1995 to 1999.	2001 Sep	11642273
Utilization of quinolone drugs as monomers: characterization of the synthesis reaction products for poly(norfloxacin diisocyanatododecane polycaprolactone).	2001 Spring	11749164
Antimicrobial resistance and plasmid profiles of Campylobacter jejuni and Campylobacter coli from human and animal sources.	2002	11849513
Ignoring pharmacokinetics may lead to isoboles misinterpretation: illustration with the norfloxacin-theophylline convulsant interaction in rats.	2002 Feb	11883649
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.	2002 Feb	11858908
Activation of phagocytic cell NADPH oxidase by norfloxacin: a potential mechanism to explain its bactericidal action.	2002 Feb	11818446
Functional cloning and characterization of a plant efflux carrier for multidrug and heavy metal detoxification.	2002 Feb 15	11739388
[Acute pancreatitis secondary to administration or norfloxacin].	2002 Jan	11878127
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.	2002 Jan	11821174
[Urinary infections without complications: comparison of a treatment with norfloxacin for 7 days versus norfloxacin for 3 days].	2002 Jan	11820968
Treatment of acute bacterial conjunctivitis with topical netilmicin.	2002 Jan	11805506
Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis.	2002 Jan	11786970
Spontaneous bacterial peritonitis caused by quinolone-resistant Escherichia coli: could steroid therapy play a role?	2002 Jan	11782580
Bactericidal mechanism of gatifloxacin compared with other quinolones.	2002 Jan	11751786
Resistance of Klebsiella pneumoniae strains producing and not producing ESBL (extended-spectrum beta-lactamase) type enzymes to selected non-beta-lactam antibiotics.	2002 Mar	11889457
Rapid antimicrobial susceptibility testing of urinary tract isolates and samples by flow cytometry.	2002 Mar	11871613

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 `Fri Dec 15 15:00:15 GMT 2023` Edited by `admin` on `Fri Dec 15 15:00:15 GMT 2023`
Record UNII	N0F8P22L1P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORFLOXACIN

Official 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

CHIBROXIN

Brand 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