2-Oxoclopidogrel (BioDeep_00000033153)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S)Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno(3,2-c)pyridin-5(2H,4H,6H)-yl)acetate

化学式: C16H16ClNO3S (337.05393760000004)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 1.89%

分子结构信息

SMILES: COC(=O)C(C1=CC=CC=C1Cl)N2CCC3C(=CC(=O)S3)C2
InChI: InChI=1S/C16H16ClNO3S/c1-21-16(20)15(11-4-2-3-5-12(11)17)18-7-6-13-10(9-18)8-14(19)22-13/h2-5,8,13,15H,6-7,9H2,1H3/t13?,15-/m0/s1

描述信息

2-Oxoclopidogrel is a thiolactone intermediate of clopidogrel, an antithrombotic prodrug (PMID: 23249383).. Hepatic cytochrome P450 (P450) enzymes catalyze the conversion of clopidogrel to 2-oxo-clopidogrel via CYP3A oxidation. After oxidation, 2-oxoclopidogrel is then subsequently hydrolyzed to the clopidogrel active metabolite known as CAM (PMID: 25970225). 2-oxoclopidogrel can form four isomers (H1, H2, H3 and H4) of CAM, in which H4 only found in humans. The H4 isomer exhibits twice the activity of the H2 isomer (PMID: 28602635). The H4 isomer blocks adenosine diphosphate (ADP) binding to the P2Y12 receptor which thereby inhibits ADP induced platelet aggregation. 2-oxoclopidogrel is only found in individuals that have used or taken Clopidogrel.
Clopidogrel thiolactone is an important intermediate in the metabolism of clopidogrel (HY-15283). Clopidogrel thiolactone has antiplatelet aggregatione effects. Clopidogrel is a P2Y12 receptor inhibitor that exerts antiplatelet effects[1][2].

同义名列表

6 个代谢物同义名

(2S)Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno(3,2-c)pyridin-5(2H,4H,6H)-yl)acetate; methyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-2H,4H,5H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate; methyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-4H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate; 2-oxo-Clopidogrel; 2-Oxoclopidogrel; Clopidogrel thiolactone



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • S Casey Laizure, Zhe-Yi Hu, Philip M Potter, Robert B Parker. Inhibition of carboxylesterase-1 alters clopidogrel metabolism and disposition. Xenobiotica; the fate of foreign compounds in biological systems. 2020 Mar; 50(3):245-251. doi: 10.1080/00498254.2019.1612535. [PMID: 31039046]
  • Milan Pavlovic, Svetlana Apostolovic, Dragana Stokanovic, Jelena Lilic, Sandra S Konstantinovic, Jelena B Zvezdanovic, Valentina Marinkovic, Valentina N Nikolic. The association of clopidogrel and 2-oxo-clopidogrel plasma levels and the 40 months clinical outcome after primary PCI. International journal of clinical pharmacy. 2018 Dec; 40(6):1482-1489. doi: 10.1007/s11096-018-0730-9. [PMID: 30367373]
  • Janne G Lyngby, Michael H Court, Pamela M Lee. Validation of a method for quantitation of the clopidogrel active metabolite, clopidogrel, clopidogrel carboxylic acid, and 2-oxo-clopidogrel in feline plasma. Journal of veterinary cardiology : the official journal of the European Society of Veterinary Cardiology. 2017 Aug; 19(4):384-395. doi: 10.1016/j.jvc.2017.03.004. [PMID: 28602635]
  • C F Zhou, Y H Ren, Y Q Song, J Yi, B S Han, Q Xue, Z H Fu, D Y Li. [Relationship between ATP-binding cassette subfamily B member 1 and cytochrome P450 2C19 polymorphisms and the effect of clopidogrel post percutaneous coronary intervention in patients with acute coronary syndrome]. Zhonghua xin xue guan bing za zhi. 2016 Apr; 44(4):309-14. doi: 10.3760/cma.j.issn.0253-3758.2016.04.007. [PMID: 27112608]
  • Dragana Stokanovic, Valentina N Nikolic, Sandra S Konstantinovic, Jelena B Zvezdanovic, Jelena Lilic, Svetlana R Apostolovic, Milan Pavlovic, Vladimir S Zivkovic, Tatjana Jevtovic-Stoimenov, Slobodan M Jankovic. P-Glycoprotein Polymorphism C3435T Is Associated with Dose-Adjusted Clopidogrel and 2-Oxo-Clopidogrel Concentration. Pharmacology. 2016; 97(3-4):101-6. doi: 10.1159/000442712. [PMID: 26695516]
  • Zhixia Qiu, Ning Li, Ling Song, Yang Lu, Jing Jing, Harendra S Parekha, Wenchao Gao, Fengjie Tian, Xin Wang, Shuangxia Ren, Xijing Chen. Contributions of intestine and plasma to the presystemic bioconversion of vicagrel, an acetate of clopidogrel. Pharmaceutical research. 2014 Jan; 31(1):238-51. doi: 10.1007/s11095-013-1158-5. [PMID: 24037619]
  • Hao-Jie Zhu, Xinwen Wang, Brian E Gawronski, Bryan J Brinda, Dominick J Angiolillo, John S Markowitz. Carboxylesterase 1 as a determinant of clopidogrel metabolism and activation. The Journal of pharmacology and experimental therapeutics. 2013 Mar; 344(3):665-72. doi: 10.1124/jpet.112.201640. [PMID: 23275066]
  • Patrick M Dansette, Julien Rosi, Gildas Bertho, Daniel Mansuy. Cytochromes P450 catalyze both steps of the major pathway of clopidogrel bioactivation, whereas paraoxonase catalyzes the formation of a minor thiol metabolite isomer. Chemical research in toxicology. 2012 Feb; 25(2):348-56. doi: 10.1021/tx2004085. [PMID: 22103858]
  • Lynn M Abell, Eddie C-K Liu. Dissecting the activation of thienopyridines by cytochromes P450 using a pharmacodynamic assay in vitro. The Journal of pharmacology and experimental therapeutics. 2011 Nov; 339(2):589-96. doi: 10.1124/jpet.111.184895. [PMID: 21828263]