基本情報
- CAS
192939-46-1- 標準SMILES
CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCc1ccc(C(N)=NO)cc1)C1CCCCC1- InChIKey
ZXIBCJHYVWYIKI-PZJWPPBQSA-N- 分子式
- C24H35N5O5
- 平均分子量
- 473.6 g/mol
- 単同位体質量
- 473.26381923
概要
Ximelagatran is an anticoagulant intended to become a replacement for warfarin by overcoming the dietary restrictions, drug interaction, and monitoring issues associated with the former. In 2006, its manufacturer AstraZeneca announced that it would not attempt to market ximelagatran after reports of hepatotoxicity (liver damage) during trials, and to discontinue its distribution in countries where the drug had been approved.
名称と識別子
- 優先名称
- Ximelagatran [MI]
- IUPAC
- ethyl 2-[[(1R)-1-cyclohexyl-2-[(2S)-2-[[4-(N'-hydroxycarbamimidoyl)phenyl]methylcarbamoyl]azetidin-1-yl]-2-oxoethyl]amino]acetate
- 現地名
- キシメラガトラン
- 英語名
- EXANTA
- 分子式
- C24H35N5O5
- 分子量
- 473.57
名称と別名
XIMELAGATRAN [MI]ximelagatran (oxime form)SCHEMBL4845Ximelagatran (JAN/USAN/INN)AKOS040742831NCGC00183598-02Glycine, N-[(1R)-1-cyclohexyl-2-[(2S)-2-[[[[4-[(hydroxyamino)iminomethyl]phenyl]methyl]amino]carbonyl]-1-azetidinyl]-2-oxoethyl]-, ethyl ester; Exanta; H 376/95; XimelagatranMS-28784XIMELAGATRAN [INN]XIMELAGATRAN [JAN]XIMELAGATRAN [USAN]XIMELAGATRAN [VANDF]
名称をさらに表示
キシメラガトランキシメラガトラン (JAN)EXANTAExartaCS-1834H 376/95Exanta (TN)XIMELEGATRANEXANTA/XIMELEGATRANExanta (XiMelagatran)Ximelagatran [USAN:INN]Ximelagatran (H 376/95)
XIMELAGATRAN [MART.]XIMELAGATRAN [WHO-DD]SCHEMBL8039753SCHEMBL15908919C24H35N5O5BBL101508MFCD05861056A880297
物性
構造計算による物性
- XLogP
- 2.2
- 極性表面積
- 146 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 7
- 回転可能結合数
- 11
- 重原子数
- 34
- 形式電荷
- 0
- 複雑度
- 731
実験および物理化学的性質
Solubility8.45e-02 g/L
Physical DescriptionSolid
物理化学的性質
- 融点
- 65 · 65-68C
- 比重(密度)
- 1.35 · 1.35±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 250 mg/mL · DMSO : 250 mg/mL (527.91 mM; Need ultrasonic)Methanol : 62.5 mg/mL (131.98 mM; Need ultrasonic)
- 外見
- 粉
- 酸解離定数(Pka)
- 6.87 · 6.87±0.69(Predicted)
- 色
- 白からベージュ
- 安定性
- Hygroscopic
- InChIKey
- PMOVWDINZOACJB-RBBKRZOGSA-N
- SMILES
- C(OCC)(=O)CN[C@H](C1CCCCC1)C(N1CC[C@H]1C(NCC1=CC=C(C=NNO)C=C1)=O)=O
化学的性質
化学的特性Off-White Amorphous Solid
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 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Mechanism of ActionXimelagatran was the first member of the drug class of direct thrombin inhibitors that can be taken orally. Its effect is solely related to the inhibition of thrombin.
Biological Half-Life3-5 hours
Metabolism/MetabolitesXimelagatran is a prodrug, and hence, it requires in vivo conversion to the active agent, melagatran. The activation of ximelagatran is produced in the liver and many other tissues mainly by reactions of dealkylation and dehydroxylation.
Absorption, Distribution and ExcretionRapidly absorbed by the small intestine with an oral bioavailability of 20%.
Cellular LocationsExtracellular
Metabolite PathwaysXimelagatran Action Pathway
応用分野
説明Ximelagatran is an ester prodrug of melagatran, a potent, direct, and reversible thrombin inhibitor (Ki = 1.2 nM). While melagatran has poor oral bioavailability, ximelagatran displays good bioavailability resulting, in part, from rapid absorption at the gastrointestinal tract, as well as rapid onset of action. Ximelagatran is converted to melagatran by reduction and hydrolysis at the liver and other tissues. It is used as an anticoagulant in a variety of situations, including thromboembolic disorders, stroke prevention in atrial fibrillation, and therapy in vein thrombosis.
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