Enoxacin

HCID 3229CAS 74011-58-8

기본 정보

표준 SMILES: CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)nc21
InChIKey: IDYZIJYBMGIQMJ-UHFFFAOYSA-N
분자식: C15H17FN4O3
평균 분자량: 320.32 g/mol
단동위원소 질량: 320.12846862

개요

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.

이름 및 식별자

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

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: -0.2
극성 표면적: 85.8 Å²
수소 결합 공여자 수: 2
수소 결합 수용자 수: 8
회전 가능 결합 수: 3
무거운 원자 수: 23
형식 전하: 0
복잡도: 521

실험 및 물리화학적 성질

Drugs · 4건

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 · 3건

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

FDA approved drugs -> Active ingredient

Melting Point · 2건

220-224 °C

220 - 224 °C

Physical DescriptionSolid

안전 및 규제

GHS 분류

GHS ClassificationNot Classified

유해성 정보

Hazard Classes and CategoriesNot Classified

독성 정보

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

화학 및 산업

약리 정보

ATC Code · 2건

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 · 1건

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.