基本情報
- CAS
113665-84-2- 標準SMILES
COC(=O)[C@H](c1ccccc1Cl)N1CCc2sccc2C1.O=S(=O)(O)O- InChIKey
FDEODCTUSIWGLK-RSAXXLAASA-N- 分子式
- C16H18ClNO6S2
- 平均分子量
- 419.9 g/mol
- 単同位体質量
- 419.0264073
概要
Clopidogrel Bisulfate is a thienopyridine with antiplatelet activity. Clopidogrel bisulfate irreversibly alters the platelet receptor for adenosine diphosphate (ADP), thereby blocking the binding of ADP to its receptor, inhibiting ADP-mediated activation of the glycoprotein complex GPIIb/IIIa, and inhibiting fibrinogen binding to platelets and platelet adhesion and aggregation. (NCI04)
名称と識別子
- 優先名称
- Clopidogrel Bisulfate
- IUPAC
- methyl (2S)-2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate;sulfuric acid
- 現地名
- クロピドグレル
- 英語名
- Clopidogrel
- 分子式
- C16H16ClNO2S
- 分子量
- 321.82
名称と別名
Clopidogrel bisulfate120202-66-6CLOPIDOGREL SULFATEClopidogrel bisulphateClopidogrel hemisulfateclopidogrel hydrogen sulphateIsocoverClopidogrel BMSPidogrelClopidogrel-bgrClopidogrel-bmsClopidogrel teva
名称をさらに表示
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)-Clopidogrelmethyl (2s)-2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetateThieno[3,2-c]pyridine-5(4H)-acetic acid, α-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (αS)-CLOPIDOGRELChlopidogrelClopidogrelHclClopidogrel–d4
物性
構造計算による物性
- 極性表面積
- 141 Ų
- 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
実験および物理化学的性質
Human Drugs
Lactation; Breast Feeding; Milk, Human; Platelet Aggregation Inhibitors; Purinergic P2Y Receptor Antagonists
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
Collision Cross Section167.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 比旋光度
- 20 · D20 +51.52° (c = 1.61 in methanol)
- 沸点
- 423.7 · 423.7±45.0 °C(Predicted)
- 比重(密度)
- 1.317 · 1.317±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 50 mg/ml · DMSO: 50mg/ml in DMSO
- 外見
- Oil
- 酸解離定数(Pka)
- 4.56 · 4.56±0.20(Predicted)
- 色
- Colorless to light yellow
- Henry's Law Constant
- 4.5 · 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
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。
GHS分類
GHS Classification
Danger
H290 (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.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
危険有害性情報
Regulatory InformationREACH 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%)
毒性情報
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Clopidogrel bisulfate
vLess-DILI-concern
7
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- risk_code
- 22-36/37/38
- hazard_code
- Xn
- safety_code
- 26-36
化学と産業
薬理情報
FDA Pharmacological Classification
CLOPIDOGREL BISULFATE
P2Y12 Platelet Inhibitor [EPC]; Cytochrome P450 2C8 Inhibitors [MoA]; P2Y12 Receptor Antagonists [MoA]; Decreased Platelet Aggregation [PE]
MeSH Pharmacological Classification
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Compounds that bind to and block the stimulation of PURINERGIC P2Y RECEPTORS. Included under this heading are antagonists for specific P2Y receptor subtypes.
応用分野
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.
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