ガチフロキサシン
Gatifloxacin
基本情報
- CAS
112811-59-3- 標準SMILES
COc1c(N2CCNC(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12- InChIKey
XUBOMFCQGDBHNK-UHFFFAOYSA-N- 分子式
- C19H22FN3O4
- 平均分子量
- 375.4 g/mol
- 単同位体質量
- 375.1594344
概要
Gatifloxacin is a monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes. It has a role as an antimicrobial agent, an antiinfective agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a quinolone, a quinolinemonocarboxylic acid, an organofluorine compound, a N-arylpiperazine and a quinolone antibiotic.
名称と識別子
- 優先名称
- Gatifloxacin
- IUPAC
- 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
- 現地名
- ガチフロキサシン
- 英語名
- Gatifloxacin
- 分子式
- C19H22FN3O4
- 分子量
- 375.39
名称と別名
Gatifloxacin112811-59-3TequinGatifloZymarAM-1155GatifloxacineZymaxidZymergatifloxacin anhydrousAM 11553-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-
名称をさらに表示
ガチフロキサシン1,4-ジヒドロ-1-シクロプロピル-4-オキソ-6-フルオロ-8-メトキシ-7-(3-メチルピペラジン-1-イル)キノリン-3-カルボン酸1-シクロプロピル-6-フルオロ-8-メトキシ-7-(3-メチルピペラジン-1-イル)-4-オキソ-1,4-ジヒドロキノリン-3-カルボン酸1,4-ジヒドロ-1-シクロプロピル-6-フルオロ-8-メトキシ-7-(3-メチル-1-ピペラジニル)-4-オキソキノリン-3-カルボン酸1-シクロプロピル-4-オキソ-6-フルオロ-7-(3-メチル-1-ピペラジニル)-8-メトキシ-1,4-ジヒドロ-3-キノリンカルボン酸ガチフロキシン1-シクロプロピル-6-フルオロ-8-メトキシ-7-(3-メチル-1-ピペラジニル)-4-オキソ-1,4-ジヒドロ-3-キノリンカルボン酸1-シクロプロピル-4-オキソ-6-フルオロ-7-(3-メチルピペラジノ)-8-メトキシ-1,4-ジヒドロキノリン-3-カルボン酸1-シクロプロピル-6-フルオロ-1,4-ジヒドロ-8-メトキシ-7-(3-メチルピペラジノ)-4-オキソ-3-キノリンカルボン酸1,4-ジヒドロ-1-シクロプロピル-4-オキソ-6-フルオロ-7-(3-メチルピペラジノ)-8-メトキシキノリン-3-カルボン酸チメールCG5501S)-AHPCGatiquin
物性
構造計算による物性
- XLogP
- -0.7
- 極性表面積
- 82.1 Ų
- 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
- 4
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 653
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
LogP2.6
Solubility6.31e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
182-185 °C
182 - 185 °C
Physical DescriptionSolid
Dissociation Constants
8.74
6
6
9.4
Collision Cross Section
189.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
189.03 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (97.5%)
毒性情報
Treatment
In the event of acute oral overdose, the stomach should be emptied by inducing vomiting or by gastric lavage. The patient should be carefully observed (including ECG monitoring) and given symptomatic and supportive treatment. Adequate hydration should be maintained. (L1712)
Health EffectsAntibiotic resistance
Exposure RoutesOphthalmic. Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%
Toxicity SummaryThe bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Signs and SymptomsThe most common side effects from antibiotics are diarrhea, nausea, vomiting. Fungal infections of the mouth, digestive tract and vagina can also occur with antibiotics
Carcinogen Classification
化学と産業
薬理情報
ATC Code
S - Sensory organs
J - Antiinfectives for systemic use
QS - Sensory organs
QJ - Antiinfectives for systemic use
Protein Binding20%
Pharmacodynamics
Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. 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. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.
Mechanism of ActionThe bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Biological Half-Life7-14 hours
Metabolism/Metabolites
Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites
Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites Half Life: 7-14 hours
FDA Pharmacological Classification
81485Y3A9A
GATIFLOXACIN ANHYDROUS
Established Pharmacologic Class [EPC] - Quinolone Antimicrobial
Chemical Structure [CS] - Quinolones
Gatifloxacin anhydrous is a Quinolone Antimicrobial.
GATIFLOXACIN
関連反応
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