기본 정보
- CAS
113665-84-2- 표준 SMILES
COC(=O)[C@H](c1ccccc1Cl)N1CCc2sccc2C1.O=S(=O)(O)O- InChIKey
FDEODCTUSIWGLK-RSAXXLAASA-N- 분자식
- C16H18ClNO6S2
- 평균 분자량
- 419.9 g/mol
- 단동위원소 질량
- 419.0264073
개요
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)
이름 및 식별자
- 우선 이름
- Clopidogrel Bisulfate
- IUPAC
- methyl (2S)-2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate;sulfuric acid
- 현지명
- 클로피도그렐
- 영어명
- Clopidogrel
- 분자식
- C16H16ClNO2S
- 분자량
- 321.82
이름 및 동의어
Clopidogrel bisulfate120202-66-6CLOPIDOGREL SULFATEClopidogrel bisulphateClopidogrel hemisulfateclopidogrel hydrogen sulphateIsocoverClopidogrel BMSPidogrelClopidogrel-bgrClopidogrel-bmsClopidogrel teva
이름 더 보기
클로피도그렐(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–d4Clopidogrel APIClopidogrel-13C3Clopidogrel Pellets
SR 25990CClopidogrel zentivaClopidogrel (as bisulfate)Clopidogrel ratiopharm08I79HTP27SR-25990CCLOPIDOGREL (AS HYDROGEN SULFATE)DTXSID601016080
데이터베이스 식별자
- CAS
물성
구조 계산 물성
- 극성 표면적
- 141 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 8
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 26
- 형식 전하
- 0
- 복잡도
- 463
실험 및 물리화학적 성질
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]
물리화학적 성질
- 끓는 점
- 423.7 · 423.7±45.0 °C(Predicted)
- 밀도
- 1.317 · 1.317±0.06 g/cm3(Predicted)
- 저장 조건
- 2 · 2-8°C
- 용해도
- 50 mg/ml · DMSO: 50mg/ml in DMSO
- 물리적 상태
- Oil
- 산도 계수 (pKa)
- 4.56 · 4.56±0.20(Predicted)
- 색상
- 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
- InChIKey
- GKTWGGQPFAXNFI-UJHUVDBMNA-N
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
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]
유해성 정보
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%)
독성 정보
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
안전 데이터
- risk_code
- 22-36/37/38
- hazard_code
- Xn
- safety_code
- 26-36
화학 및 산업
약리 정보
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.
응용 분야
개요Clopidogrel 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.
역사Clopidogrel, 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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