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Details

Stereochemistry ACHIRAL
Molecular Formula C16H18FN3O3.H2O
Molecular Weight 337.3461
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORFLOXACIN MONOHYDRATE

SMILES

O.CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCNCC3

InChI

InChIKey=ITBINNOMHXTMLQ-UHFFFAOYSA-N
InChI=1S/C16H18FN3O3.H2O/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);1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2363076
Sources: 
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

5.31014386E11
Curative
NOROXIN

Approved Use

Uncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae.

Launch Date

5.31014386E11
Curative
NOROXIN

Approved Use

Prostatitis due to Escherichia coli

Launch Date

5.31014386E11
Curative
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

6.770304E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.02 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
9.8 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
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

Doses

DosePopulationAdverse events​
1600 mg single, oral
Studied dose
Dose: 1600 mg
Route: oral
Route: single
Dose: 1600 mg
Sources:
healthy, 24 ± 2 years
n = 14
Health Status: healthy
Age Group: 24 ± 2 years
Sex: M
Population Size: 14
Sources:
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:
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:
Disc. AE: Nausea, Rash...
AEs leading to
discontinuation/dose reduction:
Nausea (1 patient)
Rash (2 patients)
Sources:
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:
unhealthy, 46.0 years
n = 190
Health Status: unhealthy
Age Group: 46.0 years
Sex: M+F
Population Size: 190
Sources:
Disc. AE: Abdominal cramps...
AEs leading to
discontinuation/dose reduction:
Abdominal cramps (1 patient)
Sources:
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:
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:
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:
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:
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:
unhealthy, 46.0 years
n = 190
Health Status: unhealthy
Age Group: 46.0 years
Sex: M+F
Population Size: 190
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
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 in the treatment of uncomplicated gonococcal infections.
1987 Jun 26
Effect of fluoroquinolone concentration on selection of resistant mutants of Mycobacterium bovis BCG and Staphylococcus aureus.
1999 Jul
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000 Oct
Norfloxacin-induced hallucination--an unusual CNS toxicity of 4-fluoroquinolones.
2000 Sep
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
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
Fewer bacterial relapses after oral treatment with norfloxacin than with ceftibuten in acute pyelonephritis initially treated with intravenous cefuroxime.
2001
[Activity of bicozamycin against Escherichia coli O157:H7 producing Vero toxin].
2001
Quinolone interactions with DNA and DNA gyrase.
2001
Long-Term treatment with cisapride and antibiotics in liver cirrhosis: effect on small intestinal motility, bacterial overgrowth, and liver function.
2001 Apr
Multiresidue analysis of fluoroquinolone antibiotics in chicken tissue using automated microdialysis-liquid chromatography.
2001 Aug
[Observations of properties of the L-form of M. tuberculosis induced by the antituberculosis drugs].
2001 Jan
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
Antimicrobial resistance of Shigella sonnei in Korea during the last two decades.
2001 Mar
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
Natural antibiotic susceptibility of recently established coryneform bacteria.
2001 May
Fluorescence characteristic study of the ternary complex of fluoroquinolone antibiotics and cobalt (II) with ATP.
2001 May
Selective separation and simultaneous determination of trace levels of five types of fluorinated quinolone drugs by thin-layer chromatography/fluorescence densitometry.
2001 May-Jun
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98.
2001 Oct
Treatment of malignant biliary stenosis: which stent to use?
2001 Oct-Dec
Comparison of aztreonam against other antibiotics used in urinary tract infections.
2001 Oct-Dec
Na+-driven multidrug efflux pump VcmA from Vibrio cholerae non-O1, a non-halophilic bacterium.
2001 Sep 25
Utilization of quinolone drugs as monomers: characterization of the synthesis reaction products for poly(norfloxacin diisocyanatododecane polycaprolactone).
2001 Spring
Antimicrobial resistance and plasmid profiles of Campylobacter jejuni and Campylobacter coli from human and animal sources.
2002
Functional cloning and characterization of a plant efflux carrier for multidrug and heavy metal detoxification.
2002 Feb 15
Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis.
2002 Jan
Bactericidal mechanism of gatifloxacin compared with other quinolones.
2002 Jan
Patents

Sample Use Guides

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 Thu Jul 06 09:15:16 UTC 2023
Edited
by admin
on Thu Jul 06 09:15:16 UTC 2023
Record UNII
YUF620IF4G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORFLOXACIN MONOHYDRATE
Common Name English
3-QUINOLINECARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-, MONOHYDRATE
Common Name English
NORFLOXACIN HYDRATE
Common Name English
Code System Code Type Description
PUBCHEM
19829980
Created by admin on Thu Jul 06 09:15:16 UTC 2023 , Edited by admin on Thu Jul 06 09:15:16 UTC 2023
PRIMARY
FDA UNII
YUF620IF4G
Created by admin on Thu Jul 06 09:15:16 UTC 2023 , Edited by admin on Thu Jul 06 09:15:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID10197298
Created by admin on Thu Jul 06 09:15:16 UTC 2023 , Edited by admin on Thu Jul 06 09:15:16 UTC 2023
PRIMARY
CAS
478082-34-7
Created by admin on Thu Jul 06 09:15:16 UTC 2023 , Edited by admin on Thu Jul 06 09:15:16 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE