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Details

Stereochemistry ACHIRAL
Molecular Formula C15H17FN4O3
Molecular Weight 320.3189
Optical Activity UNSPECIFIED
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

Description

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

Approval Year

Targets

Targets

Conditions
PubMed

PubMed

TitleDatePubMed
Assessment of temafloxacin neurotoxicity in rodents.
1991 Dec 30
Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs.
1991 Jun
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.
2000 Oct
[Effect of subinhibitory levels of aminoglycosides and fluoroquinolines on hydrophobicity and motility of Serratia marcescens].
2001 Feb
[Drug interactions between nonsteroidal anti-inflammatory drug and pazufloxacin mesilate, a new quinolone antibacterial agent for intravenous use: convulsions in mice after intravenous or intracerebroventricular administration].
2002 Jun
[Phototoxicity studies of pazufloxacin mesilate, a novel parenteral quinolone antimicrobial agent--in vitro and in vivo studies].
2002 Jun
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
2004 Apr
Selective action of fluoroquinolones against intracellular amastigotes of Leishmania (Viannia) panamensis in vitro.
2005 Dec
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.
2005 May
Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA).
2006 Apr 19
A batch chemiluminescence determination of enoxacin using a tris-(1,10-phenanthroline)ruthenium(II)-cerium(IV) system.
2006 Jul
Quinolones for uncomplicated acute cystitis in women.
2006 Jul 19
[Study on interaction of caffeine and theophylline with bovine serum albumins].
2006 Mar
A new approach to quantitative NMR: fluoroquinolones analysis by evaluating the chemical shift displacements.
2006 Oct 11
Patents

Sample Use Guides

In Vivo Use Guide
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
Name Type Language
ENOXACIN
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
NSC-629661
Code English
PD 107779
Code 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
PENETREX
Brand Name English
ENOXACIN [USAN]
Common Name English
ENOXACIN [ORANGE BOOK]
Common Name English
ENOXACIN [INN]
Common Name English
ENOXACIN [WHO-DD]
Common Name English
ENOXACIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01MA04
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
WHO-ATC J01MA04
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
Code System Code Type Description
MESH
D015365
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
CAS
74011-58-8
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
ChEMBL
CHEMBL826
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
INN
5351
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
NCI_THESAURUS
C65512
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
WIKIPEDIA
ENOXACIN
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
DRUG BANK
DB00467
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
IUPHAR
1157
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
PUBCHEM
3229
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY SWITZERF
RXCUI
3925
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY RxNorm
EVMPD
SUB06540MIG
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
IUPHAR
316
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
EPA CompTox
74011-58-8
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY
MERCK INDEX
M4911
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY Merck Index
LactMed
74011-58-8
Created by admin on Tue Mar 06 11:23:27 UTC 2018 , Edited by admin on Tue Mar 06 11:23:27 UTC 2018
PRIMARY