グレパフロキサシン

Grepafloxacin

HCID 72474

ノート反応

部分構造検索類似構造を探す

基本情報

CAS: 119914-60-2
標準SMILES: Cc1c(F)c(N2CCNC(C)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1
InChIKey: AIJTTZAVMXIJGM-UHFFFAOYSA-N
分子式: C19H22FN3O3
平均分子量: 359.4 g/mol
単同位体質量: 359.16451978

概要

Grepafloxacin is a member of quinolines, a quinolone antibiotic and a fluoroquinolone antibiotic.

名称と識別子

優先名称: Grepafloxacin
IUPAC: 1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
現地名: グレパフロキサシン
英語名: Grepafloxacin
分子式: C19H22FN3O3
分子量: 359.39

名称と別名

Grepafloxacin119914-60-21-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidGrepafloxacineGrepafloxacino1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidL1M1U2HC313-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-OPC-17116DTXSID2048321grepafloxacinumRefChem:922501

名称をさらに表示

グレパフロキサシンrac-1-シクロプロピル-6-フルオロ-1,4-ジヒドロ-5-メチル-7-(3α*-メチル-1-ピペラジニル)-4-オキソ-3-キノリンカルボン酸dl-GrepafloxacinGrepafloxacin USP/EP/BPGrepafloxacin/OPC-17116/dl-Grepafloxacin1-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

DTXCID0028296J01MA11(+--)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid(RS)-1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid631-454-3Raxar146863-02-7dl-Grepafloxacin Hydrochloride

データベース識別子

CAS: 119914-60-2
PubChem CID: 72474
DTXSID: DTXSID2048321
ChEMBL: CHEMBL583
ChEBI: CHEBI:5543
UNII: L1M1U2HC31
EC Number: 631-454-3
Nikkaji: J384.494C

物性

構造計算による物性

XLogP: -0.2
極性表面積: 72.9 Å²
水素結合供与体数: 2
水素結合受容体数: 7
回転可能結合数: 3
重原子数: 26
形式電荷: 0
複雑度: 636

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Antibiotics

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

LogP2.9

Solubility6.32e-01 g/L

Human DrugsPharmaceuticals

Physical DescriptionSolid

物理化学的性質

融点: 189 · 189-192 ºC
沸点: 610 · 610.0±55.0 °C(Predicted)
比重(密度): 1.366 · 1.366
貯蔵温度: 2 · under inert gas (nitrogen or Argon) at 2–8 °C
溶解性: DMSO（微量）、メタノール（微量）
外見: 個体
酸解離定数(Pka): 6.44 · 6.44±0.50(Predicted)
色: ペールベージュからペールイエロー
安定性: Hygroscopic
CAS データベース: 119914 · 119914-60-2(CAS DataBase Reference)

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (100%)

安全データ

注意喚起語: 危険
危険有害性情報: コード危険有害性情報危険有害性クラス区分注意喚起語シンボル P コード H301

化学と産業

薬理情報

ATC Code · 2 件

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding50%

PharmacodynamicsGrepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms.

Mechanism of ActionGrepafloxacin exerts its antibacterial activity by inhibiting bacterial topoisomerase II (DNA gyrase) and topoisomerase IV, essential enzymes for duplication, transcription, and repair of bacterial DNA.

Biological Half-Life15 ± 3 hours

Metabolism/Metabolites · 1 件

Primarily hepatic via CYP1A2 and CYP3A4. The major metabolite is a glucuronide conjugate; minor metabolites include sulfate conjugates and oxidative metabolites. The oxidative metabolites are formed mainly by the cytochrome P450 enzyme CYP1A2, while the cytochrome P450 enzyme CYP3A4 plays a minor role. The nonconjugated metabolites have little antimicrobial activity compared with the parent drug, and the conjugated metabolites have no antimicrobial activity