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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PENETREX
Curative
PENETREX
Curative
PENETREX

Cmax

ValueDoseCo-administeredAnalytePopulation
1.83 mg/L
200 mg single, intravenous
ENOXACIN plasma
Homo sapiens
6.58 mg/L
800 mg single, intravenous
ENOXACIN plasma
Homo sapiens
1.02 mg/L
200 mg single, oral
ENOXACIN plasma
Homo sapiens
3.8 mg/L
800 mg single, oral
ENOXACIN plasma
Homo sapiens
4.8 mg/L
400 mg 2 times / day steady-state, oral
ENOXACIN serum
Homo sapiens
0.7 mg/L
400 mg 2 times / day steady-state, oral
4-OXO-ENOXACIN serum
Homo sapiens
7.4 mg/L
600 mg 2 times / day steady-state, oral
ENOXACIN serum
Homo sapiens
7.4 mg/L
600 mg 2 times / day steady-state, oral
4-OXO-ENOXACIN serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
5.35 mg × h/L
200 mg single, intravenous
ENOXACIN plasma
Homo sapiens
29.08 mg × h/L
800 mg single, intravenous
ENOXACIN plasma
Homo sapiens
4.67 mg × h/L
200 mg single, oral
ENOXACIN plasma
Homo sapiens
25.75 mg × h/L
800 mg single, oral
ENOXACIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.2 h
200 mg single, intravenous
ENOXACIN plasma
Homo sapiens
4.9 h
800 mg single, intravenous
ENOXACIN plasma
Homo sapiens
3.2 h
200 mg single, oral
ENOXACIN plasma
Homo sapiens
4.9 h
800 mg single, oral
ENOXACIN plasma
Homo sapiens
4.5 h
400 mg 2 times / day steady-state, oral
ENOXACIN serum
Homo sapiens
6 h
600 mg 2 times / day steady-state, oral
ENOXACIN serum
Homo sapiens
6 h
600 mg 2 times / day steady-state, oral
4-OXO-ENOXACIN serum
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​

Drug as victim

PubMed

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
Substance Class Chemical
Record UNII
325OGW249P
Record Status Validated (UNII)
Record Version