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Details

Stereochemistry ACHIRAL
Molecular Formula C16H18FN3O3
Molecular Weight 319.3308
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORFLOXACIN

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

Description

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids.
1980 Dec
Norfloxacin versus co-trimoxazole in the treatment of recurring urinary tract infections in men.
1986
Norfloxacin-induced acute cholestatic hepatitis in a patient with alcoholic liver cirrhosis.
1999 Aug
Effect of fluoroquinolone concentration on selection of resistant mutants of Mycobacterium bovis BCG and Staphylococcus aureus.
1999 Jul
Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin mannich bases.
2000 Feb
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
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
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
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
Comparison of ofloxacin and norfloxacin concentration in prostatic tissues in patients undergoing transurethral resection of the prostate.
2001 Aug
[In vitro activity of six fluoroquinolones and penicillin against 101 viridans group streptococci characterized by their susceptibility to erythromycin].
2001 Dec
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
Antimicrobial use and susceptibility rates in isolates from intensive care unit and other nosocomial inpatient and outpatient areas.
2001 Jan
Antituberculous activity of norfloxacin mannich bases with isatin derivatives.
2001 Jul-Aug
Dental health and viridans streptococcal bacteremia in allogeneic hematopoietic stem cell transplant recipients.
2001 Mar
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
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
Determination of Norfloxacin by square-wave adsorptive voltammetry on a glassy carbon electrode.
2001 May
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
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
[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
Biphenylacetic acid enhances the antagonistic action of fluoroquinolones on the GABA(A)-mediated responses of the isolated guinea-pig ileum.
2001 Sep
[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
[Urinary infections without complications: comparison of a treatment with norfloxacin for 7 days versus norfloxacin for 3 days].
2002 Jan
Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis.
2002 Jan
Resistance of Klebsiella pneumoniae strains producing and not producing ESBL (extended-spectrum beta-lactamase) type enzymes to selected non-beta-lactam antibiotics.
2002 Mar
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: oral; topical
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.
Name Type Language
NORFLOXACIN
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NORFLOXACIN [MI]
Common Name English
NORFLOXACIN [VANDF]
Common Name English
NORFLOXACIN [USP]
Common Name English
NORFLOXACIN [WHO-DD]
Common Name English
NORFLOXACIN [USP-RS]
Common Name English
NORFLOXACIN [EP]
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 [ORANGE BOOK]
Common Name English
1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINE CARBOXYLIC ACID
Systematic Name English
Classification Tree Code System Code
WHO-VATC QS01AE02
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
LIVERTOX 697
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
NDF-RT N0000007606
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
WHO-VATC QJ01MA06
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
WHO-ATC S01AE02
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
WHO-ATC J01RA13
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
WHO-ATC J01MA06
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
NDF-RT N0000175937
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
NCI_THESAURUS C795
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
WHO-ATC S01AX12
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C47638
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
DRUG BANK
DB01059
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
ChEMBL
CHEMBL9
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
MESH
D009643
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
RXCUI
7517
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY RxNorm
EVMPD
SUB09365MIG
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
ECHA (EC/EINECS)
274-614-4
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
WIKIPEDIA
NORFLOXACIN
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
LactMed
70458-96-7
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
MERCK INDEX
M8059
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY Merck Index
INN
5105
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
HSDB
70458-96-7
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
EPA CompTox
70458-96-7
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY
CAS
70458-96-7
Created by admin on Mon Oct 21 19:47:57 UTC 2019 , Edited by admin on Mon Oct 21 19:47:57 UTC 2019
PRIMARY