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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18FN3O3.C5H9NO4
Molecular Weight 466.4601
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORFLOXACIN GLUTAMATE

SMILES

N[C@@H](CCC(O)=O)C(O)=O.CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCNCC3

InChI

InChIKey=BIAAXZAPCCKBJW-HVDRVSQOSA-N
InChI=1S/C16H18FN3O3.C5H9NO4/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;6-3(5(9)10)1-2-4(7)8/h7-9,18H,2-6H2,1H3,(H,22,23);3H,1-2,6H2,(H,7,8)(H,9,10)/t;3-/m.0/s1

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
Molecular Formula C5H9NO4
Molecular Weight 147.1293
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
2554
Curator's Comment: Has limited CNS penetration in rats. Human data unknown.

Originator

Approval Year

1986
103
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Topoisomerase IV
62
Target ID: CHEMBL2363076
Sources: 
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
Curative
Approved
8429
NOROXIN

Approved Use

Uncomplicated urethral and cervical gonorrhea due to Neisseria gonorrhoeae.

Launch Date

1986
Curative
Approved
8429
NOROXIN

Approved Use

Prostatitis due to Escherichia coli

Launch Date

1986
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
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 unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
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 unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
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 unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
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 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:
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

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)
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

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2A6
707

CYP3A2
10

CYP1A2
1524
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1925
 likely
CYP2A6
739
 no
CYP1A2
1692
 yes [Inhibition 500 uM]
CYP3A2
13
 yes [Ki 2300 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
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
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

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
World-wide clinical experience with norfloxacin: efficacy and safety.
1986
Norfloxacin in the treatment of uncomplicated gonococcal infections.
1987 Jun 26
Norfloxacin-induced eosinophilic necrotizing granulomatous hepatitis.
2000 Dec
Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin mannich bases.
2000 Feb
Norfloxacin-induced acute interstitial nephritis.
2000 Oct
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
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
Long-Term treatment with cisapride and antibiotics in liver cirrhosis: effect on small intestinal motility, bacterial overgrowth, and liver function.
2001 Apr
Characterization of sparfloxacin-resistant mutants of Staphylococcus aureus obtained in vitro.
2001 Aug
Multiresidue analysis of fluoroquinolone antibiotics in chicken tissue using automated microdialysis-liquid chromatography.
2001 Aug
Trace determination of fluoroquinolone antibacterial agents in urban wastewater by solid-phase extraction and liquid chromatography with fluorescence detection.
2001 Aug 1
Relationship among plasmids recovered from Staphylococcus aureus, milk leukocytes, and antimicrobial resistance.
2001 Dec
Quinolones and false-positive urine screening for opiates by immunoassay technology.
2001 Dec 26
[Effect of subinhibitory levels of aminoglycosides and fluoroquinolines on hydrophobicity and motility of Serratia marcescens].
2001 Feb
Removal of bowel aerobic gram-negative bacteria is more effective than immunosuppression with cyclophosphamide and steroids to decrease natural alpha-galactosyl IgG antibodies.
2001 Feb
[Small intestine bacterial overgrowth: six case reports and literature review].
2001 Jan
Antimicrobial use and susceptibility rates in isolates from intensive care unit and other nosocomial inpatient and outpatient areas.
2001 Jan
Interaction between biofilms formed by Staphylococcus epidermidis and quinolones.
2001 Jul
Malignant hyperthermia susceptibility revealed by myalgia and rhabdomyolysis during fluoroquinolone treatment.
2001 Jun
[A study on the resistance of Staphylococcus aureus and the mechanisms of its resistance to fluoroquinolone].
2001 Mar
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
Novel presentation and approach to management of hepatopulmonary syndrome with use of antimicrobial agents.
2001 May 15
[Bilateral serous retinal detachments in acute posterior multifocal placoid pigmentous epitheliopathy].
2001 Nov
[The activity of four fluoroquinolones against strains of Pseudomonas aeruginosa with a different sensitivity pattern to ceftazidime and imipenem].
2001 Nov
Enantioselective binding of ofloxacin to B form DNA.
2001 Nov 1
Fluoroquinolone adverse effects and drug interactions.
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
Biphenylacetic acid enhances the antagonistic action of fluoroquinolones on the GABA(A)-mediated responses of the isolated guinea-pig ileum.
2001 Sep
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
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
Rapid antimicrobial susceptibility testing of urinary tract isolates and samples by flow cytometry.
2002 Mar
Patents

Patents

04472579
22
05051505
10
05162523
6
06492373
6
JP2007537168A
10
JP2009018993A
10
JP2009501065A
33
JP2011528275A
455
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 Sat Dec 16 19:09:55 GMT 2023
Edited
by admin
on Sat Dec 16 19:09:55 GMT 2023
Record UNII
E97LKC77WL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORFLOXACIN GLUTAMATE
Common Name English
L-GLUTAMIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINECARBOXYLATE (1:1)
Systematic Name English
L-GLUTAMIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINECARBOXYLATE
Systematic Name English
Norfloxacin glutamate [WHO-DD]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID40234362
Created by admin on Sat Dec 16 19:09:55 GMT 2023 , Edited by admin on Sat Dec 16 19:09:55 GMT 2023
PRIMARY
PUBCHEM
21123686
Created by admin on Sat Dec 16 19:09:55 GMT 2023 , Edited by admin on Sat Dec 16 19:09:55 GMT 2023
PRIMARY
FDA UNII
E97LKC77WL
Created by admin on Sat Dec 16 19:09:55 GMT 2023 , Edited by admin on Sat Dec 16 19:09:55 GMT 2023
PRIMARY
CAS
85181-48-2
Created by admin on Sat Dec 16 19:09:55 GMT 2023 , Edited by admin on Sat Dec 16 19:09:55 GMT 2023
PRIMARY
Related Record Type Details
Structure of NORFLOXACIN
PARENT -> SALT/SOLVATE
NIH
NCATS
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