Enoxacin

HCID 3229CAS 74011-58-8

基本情報

標準SMILES: CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)nc21
InChIKey: IDYZIJYBMGIQMJ-UHFFFAOYSA-N
分子式: C15H17FN4O3
平均分子量: 320.32 g/mol
単同位体質量: 320.12846862

概要

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.

名称と識別子

優先名称: Enoxacin
IUPAC: 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid

名称と別名

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

名称をさらに表示

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

データベース識別子

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

物性

構造計算による物性

XLogP: -0.2
極性表面積: 85.8 Å²
水素結合供与体数: 2
水素結合受容体数: 8
回転可能結合数: 3
重原子数: 23
形式電荷: 0
複雑度: 521

実験および物理化学的性質

Drugs · 4 件

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 件

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

FDA approved drugs -> Active ingredient

Melting Point · 2 件

220-224 °C

220 - 224 °C

Physical DescriptionSolid

安全と法規制

GHS分類

GHS ClassificationNot Classified

危険有害性情報

Hazard Classes and CategoriesNot Classified

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

化学と産業

薬理情報

ATC Code · 2 件

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 件

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.