基本情報
- CAS
112811-59-3- 標準SMILES
COc1c(N2CC[NH2+]C(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
- 375.15943435
概要
Gatifloxacin is an antibiotic agent and a member of the fourth-generation fluoroquinolone family. It works by inhibiting the bacterial enzymes DNA gyrase and topoisomerase IV. It was first introduced by Bristol-Myers Squibb in 1999 under the brand name Tequin® for the treatment of respiratory tract infections. Gatifloxacin is available as tablets and in various aqueous solutions for intravenous therapy. It is also available as eye drops under the brand name Zymar® marketed by Allergan. The FDA withdrew its approval for the use of non-ophthalmic drug products containing gatifloxacin due to the high prevalence of gatifloxacin-associated dysglycemia adverse event reports and the high incidence of hyperglycemic and hypoglycemic episodes in patients taking gatifloxacin compared to those on macrolide antibiotics.
名称と識別子
- 優先名称
- 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
- IUPAC
- 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate
- 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
Spectrum3_000999Spectrum5_001468SCHEMBL22591HMS3259P06RKL10068AKOS016340697CS-1841NC00702160738-57-8STL048947AKOS0057022861-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
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
物性
構造計算による物性
- XLogP
- -0.6
- 極性表面積
- 89.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 7
- 回転可能結合数
- 3
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 647
実験および物理化学的性質
DrugsPharmaceuticals
LogP2.6
Solubility6.31e-01 g/L
Melting Point
182-185 °C
182 - 185 °C
Physical DescriptionSolid
物理化学的性質
- 融点
- 162 °C · 162°C
- 沸点
- 607.8 · 607.8±55.0 °C(Predicted)
- 比重(密度)
- 1.386 · 1.386±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- クロロホルム（微熱）、メタノール（微熱）
- 酸解離定数(Pka)
- 6.43 · 6.43±0.50(Predicted)
- 外見
- 白色から黄色の結晶性粉末。
- 色
- ホワイトからオフホワイト
- 主な用途
- 医薬品（低分子化合物）
- InChI
- InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)
- InChIKey
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。
安全データ
- wgk
- WGK 1
- hs_code
- 29335990
- risk_code
- 20/21/22
- hazard_code
- Xn
- safety_code
- 36/37
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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/MetabolitesGatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites
Absorption, Distribution and ExcretionWell absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%
Cellular LocationsCytoplasm
応用分野
説明Gatifloxacin belongs to a class of drugs known as quinolone antibiotics and is used to treat acute sinus, lung, or urinary tract infections and sexually transmitted bacterial infection.This drug may be taken orally, in tablet form, or by injection.Common side effects associated with gatifloxacin include nausea, vaginitis(irritation or inflammation of the vagina)，diarrhea, headache, dizziness, and irregular heart beats. In general, gatifloxacin is used in people who are unresponsive to other AOM therapies.In one study, gatifloxacin was compared with amoxicillin/clavulanate in the treatment of recurrent otitis media (OM) and AOM in treatment failures in children.Three hundred fifty-four infants and children with recurrent OM or AOM failure received gatifloxacin or amoxicillin/clavulanate.Results showed that both drugs were well tolerated; the most common side effect was diarrhea.Researchers concluded that treatment with gatifloxacin once daily was as effective as amoxicillin/clavulanate twice daily.In other medical literature, gatifloxacin has been noted as a third-line treatment option in AOM.
関連反応
0 件
現在のフィルター条件では反応記録がありません。
化合物ノート
読み込み中…