基本情報
- CAS
189279-58-1- 標準SMILES
Nc1nc(-n2cc(C(=O)O)c(=O)c3cc(F)c(N4CC(O)C4)c(Cl)c32)c(F)cc1F- InChIKey
DYDCPNMLZGFQTM-UHFFFAOYSA-N- 分子式
- C18H12ClF3N4O4
- 平均分子量
- 440.8 g/mol
- 単同位体質量
- 440.0499171
概要
Delafloxacin is a fluoroquinolone antibiotic which has been used in trials studying the treatment and basic science of Gonorrhea, Hepatic Impairment, Bacterial Skin Diseases, Skin Structure Infections, and Community Acquired Pneumonia, among others. It was approved in June 2017 under the trade name Baxdela for use in the treatment of acute bacterial skin and skin structure infections.
名称と識別子
- 優先名称
- Delafloxacin
- IUPAC
- 1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid
- 現地名
- デラフロキサシン
- 英語名
- ABT-492
- 分子式
- C18H12ClF3N4O4
- 分子量
- 440.76
名称と別名
Delafloxacin189279-58-11-(6-AMINO-3,5-DIFLUOROPYRIDIN-2-YL)-8-CHLORO-6-FLUORO-7-(3-HYDROXYAZETIDIN-1-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACIDWQ-3034RX-3341ABT492delafloxacinedelafloxacinoDelafloxacinum1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid3-Quinolinecarboxylic acid, 1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxy-1-azetidinyl)-4-oxo-DTXSID40172331
名称をさらに表示
デラフロキサシン1,4-ジヒドロ-4-オキソ-6-フルオロ-8-クロロ-7-(3-ヒドロキシアゼチジン-1-イル)-1-(3,5-ジフルオロ-6-アミノピリジン-2-イル)キノリン-3-カルボン酸1-(6-アミノ-3,5-ジフルオロ-2-ピリジル)-6-フルオロ-8-クロロ-7-(3-ヒドロキシ-1-アゼチジニル)-4-オキソ-1,4-ジヒドロキノリン-3-カルボン酸1-(6-アミノ-3,5-ジフルオロピリジン-2-イル)-8-クロロ-6-フルオロ-7-(3-ヒドロキシアゼチジン-1-イル)-4-オキソ-1,4-ジヒドロキノリン-3-カルボン酸Delafloxacin ImpurityWQ3034CS-711CS-2335ABT492/ABT-492
6315412YVFWQ 3034J01MA23RefChem:57796DTXCID9094822ABT-492BaxdelaAbt 492
物性
構造計算による物性
- XLogP
- 2.7
- 極性表面積
- 120 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 11
- 回転可能結合数
- 3
- 重原子数
- 30
- 形式電荷
- 0
- 複雑度
- 755
実験および物理化学的性質
Drugs
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
Pharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Milk, Human; Fluoroquinolones; Quinolones
EMA approved medicines: Human medicine
物理化学的性質
- 融点
- 238 · 238-241℃
- 沸点
- 698.5 · 698.5±55.0 °C(Predicted)
- 比重(密度)
- 1.796 · 1.796
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- DMSO (わずかに)、メタノール (ごくわずか、加熱、超音波処理)
- 酸解離定数(Pka)
- 5.49 · 5.49±0.50(Predicted)
- 外見
- 粉
- 色
- 白からベージュ
- InChI
- InChI=1S/C18H12ClF3N4O4/c19-12-13-7(1-9(20)14(12)25-3-6(27)4-25)15(28)8(18(29)30)5-26(13)17-11(22)2-10(21)16(23)24-17/h1-2,5-6,27H,3-4H2,(H2,23,24)(H,29,30)
- InChIKey
- DYDCPNMLZGFQTM-UHFFFAOYSA-N
- SMILES
- N1(C2=NC(N)=C(F)C=C2F)C2=C(C=C(F)C(N3CC(O)C3)=C2Cl)C(=O)C(C(O)=O)=C1
- CAS データベース
- 189279 · 189279-58-1
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。
毒性情報
Hepatotoxicity
Delafloxacin, like other fluoroquinolones, is associated with a low rate (3% to 4%) of serum enzyme elevations during therapy. These abnormalities are generally mild, asymptomatic and transient, resolving even with continuation of therapy. ALT elevations above 5 times the upper limit of normal occur in 1% or less of subjects. Although delafloxacin may not have been clearly linked to cases of clinically apparent liver injury, the other fluoroquinolones, such as ciprofloxacin, levofloxacin and moxifloxacin, rank among the 25 most common causes of drug induced liver injury in many case series. Estimates of the frequency of liver injury from fluoroquinolones have been 1:15,000 to 1:25,000 exposed persons. Delafloxacin has been in clinical use for a short time only, but is likely to have a similar frequency and pattern of liver injury as the other fluoroquinolones.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- wgk
- WGK 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingDelafloxacin is 84% bound to human plasma proteins. It primarily binds to serum albumin.
PharmacodynamicsDelafloxacin is a fluoroquinolone antibacterial drug which kills bacterial cells.
Mechanism of Action
Delafloxacin inhibits the activity of bacterial DNA topoisomerase IV and DNA gyrase (topoisomerase II). This interferes with bacterial DNA replication by preventing the relaxation of positive supercoils introduced as part of the elongation process. The resultant strain inhibits further elongation. Delafloxacin exerts concentration-dependent bacteriocidal activity.
Biological Half-LifeThe mean half life of elimination of Delafloxacin is 3.7 hours after a single intravenous administration. The mean half life of elimination for multple oral administrations is 4.2-8.5 hours.
Metabolism/MetabolitesDelafoxacin is primarily metabolized via glucuronidation mediated by UDP glucuronosyltransferase 1-1, UDP-glucuronosyltransferase 1-3, and UDP-glucuronosyltransferase 2B15. Less than 1% is metabolized via oxidation.
FDA Pharmacological Classification
6315412YVF
DELAFLOXACIN
Established Pharmacologic Class [EPC] - Fluoroquinolone Antibacterial
Chemical Structure [CS] - Fluoroquinolones
Delafloxacin is a Fluoroquinolone Antibacterial.
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Absorption, Distribution and Excretion
関連反応
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化合物ノート
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