U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H17FN4O3
Molecular Weight 320.3189
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOXACIN

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1N=C(N3CCNCC3)C(F)=C2

InChI

InChIKey=IDYZIJYBMGIQMJ-UHFFFAOYSA-N
InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)

HIDE SMILES / InChI

Molecular Formula C15H17FN4O3
Molecular Weight 320.3189
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://www.ncbi.nlm.nih.gov/pubmed/6226242 | https://www.ncbi.nlm.nih.gov/pubmed/8429114 | https://www.ncbi.nlm.nih.gov/pubmed/8494374

Enoxacin is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Enoxacin is bactericidal drugs, eradicating bacteria by interfering with DNA replication. Like other fluoroquinolones, enoxacin functions by inhibiting bacterial DNA gyrase and topoisomerase IV. The inhibition of these enzymes prevents bacterial DNA replication, transcription, repair and recombination. Enoxacin is active against many Gram-positive bacteria. After oral administration enoxacin is rapidly and well absorbed from the gastrointestinal tract. The antibiotic is widely distributed throughout the body and in the different biological tissues. Tissue concentrations often exceed serum concentrations. The binding of enoxacin to serum proteins is 35 to 40%. The serum elimination half-life, in subjects with normal renal function, is approximately 6 hours. Approximately 60% of an orally administered dose is excreted in the urine as unchanged drug within 24 hours. Enoxacin, like other fluoroquinolones, is known to trigger seizures or lower the seizure threshold. The compound should not be administered to patients with epilepsy or a personal history of previous convulsive attacks as may promote the onset of these disorders.

Originator

Curator's Comment: Enoxacin is a new pyridonecarboxylic acid derivative synthesized by Matsumoto et al.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PENETREX

Approved Use

INDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae.

Launch Date

1991
Curative
PENETREX

Approved Use

INDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae.

Launch Date

1991
Curative
PENETREX

Approved Use

INDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae.

Launch Date

1991
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.83 mg/L
200 mg single, intravenous
dose: 200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.58 mg/L
800 mg single, intravenous
dose: 800 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.02 mg/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.8 mg/L
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.8 mg/L
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
0.7 mg/L
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
4-OXO-ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
7.4 mg/L
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
7.4 mg/L
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
4-OXO-ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5.35 mg × h/L
200 mg single, intravenous
dose: 200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
29.08 mg × h/L
800 mg single, intravenous
dose: 800 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.67 mg × h/L
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
25.75 mg × h/L
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.2 h
200 mg single, intravenous
dose: 200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.9 h
800 mg single, intravenous
dose: 800 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.2 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.9 h
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.5 h
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
6 h
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
6 h
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
4-OXO-ENOXACIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
unhealthy, 41.9 years
Health Status: unhealthy
Age Group: 41.9 years
Sex: M+F
Sources:
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources:
unhealthy, 43.8 years
Health Status: unhealthy
Age Group: 43.8 years
Sex: M+F
Sources:
600 mg 3 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Other AEs: Gastrointestinal disorders, Epidermal and dermal conditions...
Other AEs:
Gastrointestinal disorders (1.3%)
Epidermal and dermal conditions (0.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Epidermal and dermal conditions 0.4%
600 mg 3 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Gastrointestinal disorders 1.3%
600 mg 3 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Induction of keratinocyte apoptosis by photosensitizing chemicals plus UVA.
2007-02
A new approach to quantitative NMR: fluoroquinolones analysis by evaluating the chemical shift displacements.
2006-10-11
Quinolones for uncomplicated acute cystitis in women.
2006-07-19
A batch chemiluminescence determination of enoxacin using a tris-(1,10-phenanthroline)ruthenium(II)-cerium(IV) system.
2006-07
Electrochemiluminescence of terbium (III)-two fluoroquinolones-sodium sulfite system in aqueous solution.
2006-05-01
Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA).
2006-04-19
Effect of fluoroquinolones on plasma glucose levels in fasted and glucose-loaded mice.
2006-04
Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101.
2006-04
[Study on interaction of caffeine and theophylline with bovine serum albumins].
2006-03
Genotoxic potential of quinolone antimicrobials in the in vitro comet assay and micronucleus test.
2006-02-28
Antimicrobial drug resistance, regulation, and research.
2006-02
Radiation-induced in vitro phototoxic potential of some fluoroquinolones.
2006-01
Effects of Transcutol P on the corneal permeability of drugs and evaluation of its ocular irritation of rabbit eyes.
2006-01
T cell-mediated hypersensitivity to quinolones: mechanisms and cross-reactivity.
2006-01
Selective action of fluoroquinolones against intracellular amastigotes of Leishmania (Viannia) panamensis in vitro.
2005-12
Validation of a novel HPLC sorbent material for the determination of ten quinolones in human and veterinary pharmaceutical formulations.
2005-12
Preparation and evaluation of sustained ophthalmic gel of enoxacin.
2005-12
Separation and determination of seven fluoroquinolones by pressurized capillary electrochromatography.
2005-11
Bench-to-bedside review: antimicrobial utilization strategies aimed at preventing the emergence of bacterial resistance in the intensive care unit.
2005-10-05
[Determination of enoxacin in urine by synchronous fluorimetry].
2005-10
Flow-injection electrogenerated chemiluminescence determination of fluoroquinolones based on its sensitizing effect.
2005-09-01
Photophysics and photochemistry of nalidixic acid.
2005-08-19
HPLC determination of enoxacin, ciprofloxacin, norfloxacin and ofloxacin with photoinduced fluorimetric (PIF) detection and multiemission scanning: application to urine and serum.
2005-08-05
Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation.
2005-07-04
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
Interaction study between enoxacin and fluvoxamine.
2005-06
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.
2005-05
Fluoroquinolone-resistant Campylobacter isolates from conventional and antibiotic-free chicken products.
2005-05
Susceptibility and resistance genes to fluoroquinolones in methicillin-resistant Staphylococcus aureus isolated in 2002.
2005-05
Vibrational spectroscopic characterization of fluoroquinolones.
2005-05
Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods.
2005-04-04
Determination of fluoroquinolones in edible animal tissue samples by high performance liquid chromatography after solid phase extraction.
2005-04
Direct determination of five fluoroquinolones in chicken whole blood and in veterinary drugs by HPLC.
2005-03
Antibacterial studies, DNA oxidative cleavage, and crystal structures of Cu(II) and Co(II) complexes with two quinolone family members, ciprofloxacin and enoxacin.
2005-03
Induced and photoinduced DNA damage by quinolones: ciprofloxacin, ofloxacin and nalidixic acid determined by comet assay.
2005-02-05
Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice.
2005-01-10
A novel approach to estimate in vitro antibacterial potency of Chinese medicine using a concentration-killing curve method.
2005
Spectroscopic properties of various quinolone antibiotics in aqueous-organic solvent mixtures.
2004-12-30
Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin.
2004-12
Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux.
2004-11-16
[Simultaneous determination of quinolones in foods by LC/MS/MS].
2004-10
Comparative evaluation of antiproliferative activity and induction of apoptosis by some fluoroquinolones with a human non-small cell lung cancer cell line in culture.
2004-07-13
Enoxacin trihydrate.
2004-04
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
2004-04
Sensitivity and spectrum of bacterial isolates in infectious otitis externa.
2004-03
[The history of the development and changes of quinolone antibacterial agents].
2003
Enoxacin acute liver injury.
1992-05
Interaction of the new quinolone antibacterial agent levofloxacin with fenbufen in mice.
1992-03
Assessment of temafloxacin neurotoxicity in rodents.
1991-12-30
Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs.
1991-06
Patents

Sample Use Guides

Enoxacin should be taken at least one hour before or at least two hours after a meal. For treatment uncomplicated urethral or cervical gonorrhea: 400 mg single dose. For treatment uncomplicated urinary tract infections 200 mg q12h for 7 days. For treatment complicated urinary tract infections: 400 mg q12h for 14 days. Dosage should be adjusted in patients with a creatinine clearance value of 30 mL/min/1.73 m 2 or less.
Route of Administration: Oral
In Vitro Use Guide
The in vitro antibacterial activity of AT-2266 (Enoxacin ) was tested by the determination of minimal bactericidal concentrations (MBCs) and the reduction of viable cells during exposure to the drug for 24 h. MIC90s of AT-2266 for P. aeruginosa resistant to gentamicin and Enterobacteriaceae resistant to nalidixic acid were 3.13 and 12.5 mkg/ml, respectively
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:59:21 GMT 2025
Edited
by admin
on Wed Apr 02 09:59:21 GMT 2025
Record UNII
325OGW249P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENETREX
Preferred Name English
ENOXACIN
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
NSC-629661
Code English
Enoxacin [WHO-DD]
Common Name English
PD 107779
Code English
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid
Systematic Name English
CI-919
Code English
1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)
Common Name English
AT-2266
Code English
ENOXACIN [MI]
Common Name English
1-ETHYL-6-FLUORO-4-OXO-7-PIPERAZIN-1-YL-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID
Systematic Name English
ENOXACIN [VANDF]
Common Name English
PD-107779
Code English
ENOXACIN [USAN]
Common Name English
NSC-758416
Code English
ENOXACIN [ORANGE BOOK]
Common Name English
enoxacin [INN]
Common Name English
ENOXACIN [MART.]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/15/1459
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
WHO-VATC QJ01MA04
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
NCI_THESAURUS C795
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
WHO-ATC J01MA04
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
Code System Code Type Description
DRUG CENTRAL
1013
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
NSC
629661
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
NSC
758416
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
SMS_ID
100000080254
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
MESH
D015365
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
CAS
74011-58-8
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
ChEMBL
CHEMBL826
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PRIMARY
INN
5351
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PRIMARY
USAN
U-65
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PRIMARY
FDA UNII
325OGW249P
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
NCI_THESAURUS
C65512
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
WIKIPEDIA
ENOXACIN
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
DRUG BANK
DB00467
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
LACTMED
Enoxacin
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
CHEBI
157175
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
IUPHAR
1157
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
PUBCHEM
3229
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
RXCUI
3925
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY RxNorm
EVMPD
SUB06540MIG
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PRIMARY
IUPHAR
316
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
EPA CompTox
DTXSID5022984
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY
MERCK INDEX
m4911
Created by admin on Wed Apr 02 09:59:21 GMT 2025 , Edited by admin on Wed Apr 02 09:59:21 GMT 2025
PRIMARY Merck Index
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY