クロピドグレル
クロピドグレル · (S)-2-(2-クロロフェニル)-2-(4,5,6,7-テトラヒドロチエノ[3,2-c]ピリジン-5-イル)酢酸メチル · (S)-クロピドグレル · メチル (2S)-2-(2-クロロフェニル)-2-{4H,5H,6H,7H-チエノ[3,2-c]ピリジン-5-イル}アセタート · (αS)-α-(2-クロロフェニル)-4,5,6,7-テトラヒドロチエノ[3,2-c]ピリジン-5-酢酸メチル · (S)-(2-クロロフェニル)[(4,5,6,7-テトラヒドロチエノ[3,2-c]ピリジン)-5-イル]酢酸メチル · (αS)-α-(4,5,6,7-テトラヒドロチエノ[3,2-c]ピリジン-5-イル)-2-クロロベンゼン酢酸メチル · (S)-Clopidogrel
識別子と物理属性
| CAS No. | 113665-84-2 |
|---|---|
| 分子式 | C16H18ClNO6S2 |
| 平均分子量 | 419.9 g/mol |
| 単同位体質量 | 419.0264073 g/mol |
| SMILES | COC(=O)[C@H](c1ccccc1Cl)N1CCc2sccc2C1.O=S(=O)(O)O |
| InChIKey | FDEODCTUSIWGLK-RSAXXLAASA-N |
| PubChem CID | 115366 |
| ChEMBL | CHEMBL1083385 |
| EC No. | 601-679-1 |
| DTXSID | DTXSID601016080 |
| 現地名 | クロピドグレル |
化学・物理的性質
| 極性表面積 | 141 |
|---|---|
| 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 | 26 |
| 形式電荷 | 0 |
| 複雑度 | 463 |
| Human Drugs | LactationBreast FeedingMilk, HumanPlatelet Aggregation InhibitorsPurinergic P2Y Receptor AntagonistsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Collision Cross Section | 167.7 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 比旋光度 | D20 +51.52° (c = 1.61 in methanol) |
| 沸点 | 423.7±45.0 °C(Predicted) |
| 密度 | 1.317±0.06 g/cm3(Predicted) |
| 貯蔵条件 | 2-8°C |
| 溶解度 | DMSO: 50mg/ml in DMSO |
| 外観・状態 | Oil |
| pKa（酸解離定数） | 4.56±0.20(Predicted) |
| 色 | Colorless to light yellow |
| ヘンリー定数 | 4.5×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | InChI=1/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/s3 |
| InChIKey | GKTWGGQPFAXNFI-UJHUVDBMNA-N |
| SMILES | [C@@H](C1C=CC=CC=1Cl)(N1CCC2SC=CC=2C1)C(=O)OC |&1:0,r| |
| CAS データベース | 113665-84-2(CAS DataBase Reference) |
安全性と法規制
| GHS 分類 | DangerH290 (17.4%): May be corrosive to metals [Warning Corrosive to Metals]P203, P234, P260, P261, P263, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P363, P390, P391, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 86 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | REACH registered substance: (S)-( )-Methyl (2-chlorophenyl)(6,7-dihydro-4H-thieno(3,2-c)pyrid-5-yl)acetate bisulfate (EC: 601-679-1) |
| Hazard Classes and Categories | Acute Tox. 4 (25.6%)Acute Tox. 4 (100%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Clopidogrel bisulfatevLess-DILI-concern7Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| 危険文句（R） | 22-36/37/38 |
| 危険表示 | Xn |
| 安全措置（S） | 26-36 |
| 有害物質データ | 113665-84-2(Hazardous Substances Data) |
用途
説明
Clopidogrel was launched in the US as a potent inhibitor of platelet aggregation for the preventive management of secondary ischemic events, including MI, stroke and vascular deaths. Clopidogrel can be synthesized in 4 steps (including an optical resolution to the S active enantiomer) from 2-(2- ch1orophenyl)-glycine, the key step being the cyclization to thienopyridine with formaldehyde and acetic acid. Clopidogrel belongs to the original chemical class of Ticlopidine, but shows fewer side effects (in particular, bone-marrowsuppressing effects) at the dosage generally used. Like Ticlopidine, it is an Adenosine diphosphate (ADP) antagonist acting at the purinergic P2y receptor. In in vivo experiments with rabbits, Clopidogrel shows a maximal antiaggregant effect at 20mg/kg po, reducing adhesion of platelets to the vascular subendothelium ; moreover, it reduces myointimal thickening occuring after endothelial injury of rat carotid artery. Clopigrel does not affect platelet aggregation in vitro ; actually, its in vivo activity is highly dependent on hepatic metabolism. The results of a CAPRIE trial (Clopidogrel versus Aspirin in patients at risk of ischemic events) demonstrated that Clopidogrel was well tolerated and more effective than aspirin.
来歴
Clopidogrel, sold under the brand name Plavix among others, is an antiplatelet medication used to reduce the risk of heart disease and stroke in those at high risk. Clopidogrel was discovered by Dr Fernand Eloy, it was patented in 1982, and approved for medical use in 1997. It is on the World Health Organization's List of Essential Medicines.
使用
anthelmintic, antiparasitic, antimite
一般的な説明
Clopidogrel, methyl (+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetate sulfate (Plavix), is useful for the preventativemanagement of secondary ischemic events, including myocardialinfarction, stroke, and vascular deaths. It may beclassified as a thienopyridine because of its heterocyclicsystem. Several agents possessing this system have beenevaluated as potential antithrombotic agents. These agentshave a unique mechanism, in that they inhibit the purinergicreceptor located on platelets. Normally, nucleotides act asagonists on these receptors, which include the P2Y type.Two P2Y receptor subtypes (P2Y1 and P2Y2) found onplatelets, when stimulated by adenosine diphosphate (ADP),cause platelet aggregation.