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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16ClNO2S
Molecular Weight 321.822
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOPIDOGREL

SMILES

COC(=O)[C@@H](N1CCC2=C(C1)C=CS2)C3=CC=CC=C3Cl

InChI

InChIKey=GKTWGGQPFAXNFI-HNNXBMFYSA-N
InChI=1S/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-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H16ClNO2S
Molecular Weight 321.822
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Clopidogrel, an antiplatelet agent structurally and pharmacologically similar to ticlopidine, is used to inhibit blood clots in a variety of conditions such as peripheral vascular disease, coronary artery disease, and cerebrovascular disease. Clopidogrel is sold under the name Plavix by Sanofi and Bristol-Myers Squibb. Plavix (clopidogrel bisulfate) is an inhibitor of ADP-induced platelet aggregation acting by direct inhibition of adenosine diphosphate (ADP) binding to its receptor and of the subsequent ADPmediated activation of the glycoprotein GPIIb/IIIa complex. Clopidogrel must be metabolized by CYP450 enzymes to produce the active metabolite that inhibits platelet aggregation. The active metabolite of clopidogrel selectively inhibits the binding of adenosine diphosphate (ADP) to its platelet P2Y12 receptor and the subsequent ADPmediated activation of the glycoprotein GPIIb/IIIa complex, thereby inhibiting platelet aggregation. This action is irreversible. Consequently, platelets exposed to clopidogrel’s active metabolite are affected for the remainder of their lifespan (about 7 to 10 days). Platelet aggregation induced by agonists other than ADP is also inhibited by blocking the amplification of platelet activation by released ADP. Plavix (clopidogrel bisulfate) is indicated for the reduction of atherothrombotic events.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
6.9 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PLAVIX
Primary
PLAVIX
Primary
PLAVIX
Preventing
PLAVIX

Cmax

ValueDoseCo-administeredAnalytePopulation
0.521 ng/mL
75 mg single, oral
CLOPIDOGREL plasma
Homo sapiens
15800 pg/mL
300 mg single, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
4600 pg/mL
300 mg single, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
2520 pg/mL
75 mg 1 times / day multiple, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
1500 pg/mL
75 mg 1 times / day multiple, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.09 ng*h/mL
75 mg single, oral
CLOPIDOGREL plasma
Homo sapiens
0.767 ng*h/mL
75 mg single, oral
CLOPIDOGREL plasma
Homo sapiens
50600 pg × h/mL
300 mg single, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
9890 pg × h/mL
300 mg single, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
7440 pg × h/mL
75 mg 1 times / day multiple, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
3130 pg × h/mL
75 mg 1 times / day multiple, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.4 h
300 mg single, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
7.9 h
300 mg single, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
7.4 h
75 mg 1 times / day multiple, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens
8.5 h
75 mg 1 times / day multiple, oral
CLOPIDOGREL BISULFATE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
unknown, unknown
CLOPIDOGREL BISULFATE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Recent MI, Recent Stroke, or Established Peripheral Arterial Disease The recommended daily dose of is 75 mg once daily.
Route of Administration: Oral
In Vitro Use Guide
Incubation of human washed platelets with clopidogrel resulted in a time- (maximum effects after 30 min) and concentration-dependent (IC50 1.9+/-0.3 uM) inhibition of ADP (6 uM)-induced platelet aggregation. Clopidogrel (30 uM) did not inhibit collagen (2.5 ug ml(-1))-, U46619 (1 uM)- or thrombin (0.1 u ml(-1))-induced platelet aggregation.
Substance Class Chemical
Record UNII
A74586SNO7
Record Status Validated (UNII)
Record Version