Enoxacin

HCID 3229CAS 74011-58-8

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Basic information

Standard SMILES: CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)nc21
InChIKey: IDYZIJYBMGIQMJ-UHFFFAOYSA-N
Molecular formula: C15H17FN4O3
Average molar mass: 320.32 g/mol
Monoisotopic mass: 320.12846862

Overview

Enoxacin is a 1,8-naphthyridine derivative that is 1,4-dihydro-1,8-naphthyridine with an ethyl group at the 1 position, a carboxy group at the 3-position, an oxo sustituent at the 4-position, a fluoro substituent at the 5-position and a piperazin-1-yl group at the 7 position. An antibacterial, it is used in the treatment of urinary-tract infections and gonorrhoea. It has a role as an antibacterial drug and a DNA synthesis inhibitor. It is a monocarboxylic acid, an amino acid, a N-arylpiperazine, a 1,8-naphthyridine derivative, a quinolone antibiotic and a fluoroquinolone antibiotic.

Names & identifiers

Preferred name: Enoxacin
IUPAC: 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid

Names & synonyms

enoxacin74011-58-8PenetrexEnoxacine1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acidFlumarkComprecinEnoxacinoAT-2266EnoxacinumCI-9191-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Show more names

PD 1077791-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acidPD-107779CI 919DTXSID5022984NSC-629661NSC-758416CHEBI:157175

Database identifiers

CAS: 74011-58-8
PubChem CID: 3229
DTXSID: DTXSID5022984
ChEMBL: CHEMBL826
ChEBI: CHEBI:157175
UNII: 325OGW249P
EC Number: 961-175-5
Nikkaji: J20.568K

Properties

Computed structural properties

XLogP: -0.2
Topological polar surface area: 85.8 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 8
Rotatable bonds: 3
Heavy atoms: 23
Formal charge: 0
Complexity: 521

Experimental & physicochemical properties

Drugs · 4 items

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use

LogP2.3

Solubility1.09e+00 g/L

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones

FDA approved drugs -> Active ingredient

Melting Point · 2 items

220-224 °C

220 - 224 °C

Physical DescriptionSolid

Safety & regulation

GHS classification

GHS ClassificationNot Classified

Hazard information

Hazard Classes and CategoriesNot Classified

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemistry & industry

Pharmacology

ATC Code · 2 items

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingEnoxacin is approximately 40% bound to plasma proteins in healthy subjects and is approximately 14% bound to plasma proteins in patients with impaired renal function.

Pharmacodynamics · 1 item

Enoxacin is a quinolone/fluoroquinolone antibiotic. Enoxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Enoxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. Enoxacin may be active against pathogens resistant to drugs that act by different mechanisms.

Mechanism of ActionEnoxacin exerts its bactericidal action via the inhibition of the essential bacterial enzyme DNA gyrase (DNA Topoisomerase II).

Biological Half-LifePlasma half-life is 3 to 6 hours.

Metabolism/MetabolitesHepatic. Some isozymes of the cytochrome P-450 hepatic microsomal enzyme system are inhibited by enoxacin. After a single dose, greater than 40% was recovered in urine by 48 hours as unchanged drug.