Stereochemistry | ABSOLUTE |
Molecular Formula | C16H16ClNO2S |
Molecular Weight | 321.822 |
Optical Activity | ( + ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
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 |
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
Cmax
AUC
T1/2
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Sourcing
Sample Use Guides
Recent MI, Recent Stroke, or Established Peripheral Arterial Disease
The recommended daily dose of is 75 mg once daily.
Route of Administration:
Oral
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.