Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H16ClNO2S.C10H16O4S |
Molecular Weight | 554.118 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)[C@@H]2CC[C@@]1(CS(O)(=O)=O)C(=O)C2.COC(=O)[C@@H](N3CCC4=C(C3)C=CS4)C5=CC=CC=C5Cl
InChI
InChIKey=XEENARPWPCQXST-DDJQTTAYSA-N
InChI=1S/C16H16ClNO2S.C10H16O4S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14;1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h2-5,7,9,15H,6,8,10H2,1H3;7H,3-6H2,1-2H3,(H,12,13,14)/t15-;7-,10-/m01/s1
Molecular Formula | C16H16ClNO2S |
Molecular Weight | 321.822 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C10H16O4S |
Molecular Weight | 232.297 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
6.9 null [pKi] | |||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PLAVIX Approved UsePlavix (clopidogrel bisulfate) is indicated for the reduction of atherothrombotic events as
follows:
• Recent MI, Recent Stroke or Established Peripheral Arterial Disease
For patients with a history of recent myocardial infarction (MI), recent stroke, or established
peripheral arterial disease, Plavix has been shown to reduce the rate of a combined endpoint
of new ischemic stroke (fatal or not), new MI (fatal or not), and other vascular death.
• Acute Coronary Syndrome
-For patients with non-ST-segment elevation acute coronary syndrome (unstable angina/nonQ-wave
MI) including patients who are to be managed medically and those who are to be
managed with percutaneous coronary intervention (with or without stent) or CABG, Plavix
has been shown to decrease the rate of a combined endpoint of cardiovascular death, MI, or
stroke as well as the rate of a combined endpoint of cardiovascular death, MI, stroke, or
refractory ischemia.
Plavix (clopidogrel bisulfate) is indicated for the reduction of atherothrombotic events as
follows:
• Recent MI, Recent Stroke or Established Peripheral Arterial Disease
For patients with a history of recent myocardial infarction (MI), recent stroke, or established
peripheral arterial disease, Plavix has been shown to reduce the rate of a combined endpoint
of new ischemic stroke (fatal or not), new MI (fatal or not), and other vascular death.
• Acute Coronary Syndrome
-For patients with non-ST-segment elevation acute coronary syndrome (unstable angina/nonQ-wave
MI) including patients who are to be managed medically and those who are to be
managed with percutaneous coronary intervention (with or without stent) or CABG, Plavix
has been shown to decrease the rate of a combined endpoint of cardiovascular death, MI, or
stroke as well as the rate of a combined endpoint of cardiovascular death, MI, stroke, or
refractory ischemia. Launch Date1997 |
|||
Primary | PLAVIX Approved UsePlavix (clopidogrel bisulfate) is indicated for the reduction of atherothrombotic events as
follows:
• Recent MI, Recent Stroke or Established Peripheral Arterial Disease
For patients with a history of recent myocardial infarction (MI), recent stroke, or established
peripheral arterial disease, Plavix has been shown to reduce the rate of a combined endpoint
of new ischemic stroke (fatal or not), new MI (fatal or not), and other vascular death.
• Acute Coronary Syndrome
-For patients with non-ST-segment elevation acute coronary syndrome (unstable angina/nonQ-wave
MI) including patients who are to be managed medically and those who are to be
managed with percutaneous coronary intervention (with or without stent) or CABG, Plavix
has been shown to decrease the rate of a combined endpoint of cardiovascular death, MI, or
stroke as well as the rate of a combined endpoint of cardiovascular death, MI, stroke, or
refractory ischemia. Launch Date1997 |
|||
Primary | PLAVIX Approved UsePlavix (clopidogrel bisulfate) is indicated for the reduction of atherothrombotic events as
follows:
• Recent MI, Recent Stroke or Established Peripheral Arterial Disease
For patients with a history of recent myocardial infarction (MI), recent stroke, or established
peripheral arterial disease, Plavix has been shown to reduce the rate of a combined endpoint
of new ischemic stroke (fatal or not), new MI (fatal or not), and other vascular death.
• Acute Coronary Syndrome
-For patients with non-ST-segment elevation acute coronary syndrome (unstable angina/nonQ-wave
MI) including patients who are to be managed medically and those who are to be
managed with percutaneous coronary intervention (with or without stent) or CABG, Plavix
has been shown to decrease the rate of a combined endpoint of cardiovascular death, MI, or
stroke as well as the rate of a combined endpoint of cardiovascular death, MI, stroke, or
refractory ischemia. Launch Date1997 |
|||
Preventing | PLAVIX Approved UsePlavix (clopidogrel bisulfate) is indicated for the reduction of atherothrombotic events as
follows:
• Recent MI, Recent Stroke or Established Peripheral Arterial Disease
For patients with a history of recent myocardial infarction (MI), recent stroke, or established
peripheral arterial disease, Plavix has been shown to reduce the rate of a combined endpoint
of new ischemic stroke (fatal or not), new MI (fatal or not), and other vascular death.
• Acute Coronary Syndrome
-For patients with non-ST-segment elevation acute coronary syndrome (unstable angina/nonQ-wave
MI) including patients who are to be managed medically and those who are to be
managed with percutaneous coronary intervention (with or without stent) or CABG, Plavix
has been shown to decrease the rate of a combined endpoint of cardiovascular death, MI, or
stroke as well as the rate of a combined endpoint of cardiovascular death, MI, stroke, or
refractory ischemia. Launch Date1997 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.521 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02185534 |
75 mg single, oral dose: 75 mg route of administration: oral experiment type: single co-administered: |
CLOPIDOGREL plasma | Homo sapiens population: healthy age: sex: food status: |
|
15800 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4600 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2520 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
75 mg 1 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
1500 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
75 mg 1 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.09 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02185534 |
75 mg single, oral dose: 75 mg route of administration: oral experiment type: single co-administered: |
CLOPIDOGREL plasma | Homo sapiens population: healthy age: sex: food status: |
|
0.767 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02185534 |
75 mg single, oral dose: 75 mg route of administration: oral experiment type: single co-administered: |
CLOPIDOGREL plasma | Homo sapiens population: healthy age: sex: food status: |
|
50600 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
9890 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7440 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
75 mg 1 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3130 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
75 mg 1 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
7.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
75 mg 1 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
8.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22128201 |
75 mg 1 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% |
unknown, unknown |
CLOPIDOGREL BISULFATE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
healthy, 20-45 years |
Other AEs: Uric acid abnormal... |
1650 mg single, oral Overdose |
unknown, 49 years |
|
600 mg 1 times / day multiple, oral Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 59 years |
Disc. AE: Transaminases increased, Fever... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Sources: Fever (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Uric acid abnormal | 5 patients | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
healthy, 20-45 years |
Fever | 1 patient Disc. AE |
600 mg 1 times / day multiple, oral Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 59 years |
Transaminases increased | 1 patient Disc. AE |
600 mg 1 times / day multiple, oral Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 59 years |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 169.0 |
no | |||
Page: 91, 169 |
no | |||
no | ||||
Page: 91, 169 |
no | |||
Page: 169.0 |
no | |||
Page: 91, 169 |
no | |||
Page: 169.0 |
no | |||
Page: 91, 169 |
no | |||
Page: 169.0 |
no | |||
Page: 91, 169 |
no | |||
Page: 169.0 |
no | |||
Page: 91, 169 |
no | |||
Page: 74.0 |
no | |||
weak | ||||
weak | ||||
yes [IC50 0.307 uM] | ||||
yes [IC50 6.25 uM] | ||||
Page: 91, 170 |
yes [Ki 28 uM] | |||
yes | ||||
Page: 22.0 |
yes | |||
yes | ||||
Page: 74.0 |
yes | |||
Page: 74.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 168.0 |
likely | |||
Page: 168.0 |
likely | |||
Page: 168.0 |
likely | |||
Page: 168.0 |
no | |||
Page: 168.0 |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
yes [Km 181 uM] | ||||
yes [Km 19 uM] | ||||
yes [Km 20.9 uM] | ||||
yes [Km 5.61 uM] | ||||
yes | ||||
Page: 168.0 |
yes | |||
Page: 168.0 |
yes | |||
Page: 168.0 |
yes | |||
yes | ||||
Page: 74.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Atherothrombosis: a major health burden. | 2001 |
|
Novel platelet inhibitors. | 2001 |
|
Clinical application of procedural platelet monitoring during percutaneous coronary intervention among patients at increased bleeding risk. | 2001 Apr |
|
CURE--clopidogrel's major advance. | 2001 Apr |
|
Antithrombotic drugs for secondary stroke prophylaxis. | 2001 Apr |
|
Results of CURE trial for acute coronary syndrome. | 2001 Apr 11 |
|
[Acute heart attacks. Prognosis can be further improved]. | 2001 Apr 5 |
|
Radiation-induced glomerular thrombus formation and nephropathy are not prevented by the ADP receptor antagonist clopidogrel. | 2001 Aug 1 |
|
Effects of clopidogrel in addition to aspirin in patients with acute coronary syndromes without ST-segment elevation. | 2001 Aug 16 |
|
Effects of pretreatment with clopidogrel and aspirin followed by long-term therapy in patients undergoing percutaneous coronary intervention: the PCI-CURE study. | 2001 Aug 18 |
|
Clopidogrel in invasive management of non-ST-elevation ACS. | 2001 Aug 18 |
|
Bench to bedside: the development of rapamycin and its application to stent restenosis. | 2001 Aug 21 |
|
Severe hypersensitivity associated with clopidogrel. | 2001 Aug 21 |
|
Acute myocardial infarction 2000 treatment. | 2001 Fall |
|
Thrombolysis and antithrombotic therapy for coronary artery disease. | 2001 Feb |
|
Comparison of effects of clopidogrel versus ticlopidine on platelet function in patients undergoing coronary stent placement. | 2001 Feb 1 |
|
Combination therapy with aspirin plus clopidogrel versus aspirin plus ticlopidine for prevention of subacute thrombosis after successful native coronary stenting. | 2001 Feb 15 |
|
Key role of the P2Y(1) receptor in tissue factor-induced thrombin-dependent acute thromboembolism: studies in P2Y(1)-knockout mice and mice treated with a P2Y(1) antagonist. | 2001 Feb 6 |
|
[Clopidogrel? Known or known?]. | 2001 Jan |
|
Stasis ulcers refractory to therapy--accelerated healing by treatment with clopidogrel +/- dalteparin: a preliminary report. | 2001 Jan |
|
[2 platelet inhibitors administered at the same time. Improved prognosis in myocardial infarct?]]. | 2001 Jan 11 |
|
Superiority of clopidogrel versus aspirin in patients with prior cardiac surgery. | 2001 Jan 23 |
|
Localized intracoronary gamma-radiation therapy to inhibit the recurrence of restenosis after stenting. | 2001 Jan 25 |
|
Febrile pancytopenia associated with clopidogrel. | 2001 Jan 8 |
|
The P2Y12 receptor as a therapeutic target in cardiovascular disease. | 2001 Jun |
|
[Toxic skin reaction to clopidogrel]. | 2001 Jun |
|
Molecular identification and characterization of the platelet ADP receptor targeted by thienopyridine antithrombotic drugs. | 2001 Jun |
|
Comparison of two platelet glycoprotein IIb/IIIa inhibitors, tirofiban and abciximab, for the prevention of ischemic events with percutaneous coronary revascularization. | 2001 Jun 21 |
|
[Acute coronary syndromes: an update. I. Pathogenesis and drug therapy]. | 2001 Mar |
|
[Pharmacy clinics. Medication of the month. Clopidogrel (Plavix)]. | 2001 Mar |
|
Platelet CD40 ligand (CD40L)--subcellular localization, regulation of expression, and inhibition by clopidogrel. | 2001 Mar |
|
Initial experience with a newer generation coronary stent. | 2001 Mar |
|
New recommendations from the 1999 American College of Cardiology/American Heart Association acute myocardial infarction guidelines. | 2001 May |
|
Orbofiban: an orally active GPIIb/IIIa platelet receptor antagonist. | 2001 May |
|
Edge stenosis after intracoronary radiotherapy: angiographic, intravascular, and histological findings. | 2001 May 1 |
|
Prolonged antiplatelet therapy to prevent late thrombosis after intracoronary gamma-radiation in patients with in-stent restenosis: Washington Radiation for In-Stent Restenosis Trial plus 6 months of clopidogrel (WRIST PLUS). | 2001 May 15 |
|
Prospective controlled study of carotid endarterectomy with hemashield patch: is it thrombogenic? | 2001 May-Jun |
|
Coronary stent deployment in situs inversus. | 2001 Nov |
|
Methods and models to evaluate shear-dependent and surface reactivity-dependent antithrombotic efficacy. | 2001 Nov 1 |
|
[Clopidogrel in acute coronary syndromes with non-ST elevation. Clinical implications of the CURE trial]. | 2001 Oct |
|
Effects of clopidogrel pretreatment before percutaneous coronary intervention in patients treated with glycoprotein IIb/IIIa inhibitors (abciximab or tirofiban). | 2001 Oct 15 |
|
Drug-associated thrombotic thrombocytopenic purpura-hemolytic uremic syndrome. | 2001 Sep |
|
Coronary stent thrombosis: insights from the porcine coronary stent model. | 2001 Sep |
|
Cilostazol for prevention of thrombosis and restenosis after intracoronary stenting. | 2001 Sep |
|
Thrombotic thrombocytopenic purpura associated with clopidogrel administration: case report and brief review. | 2001 Sep |
|
Effects of combining three different antiplatelet agents on platelets and leukocytes in whole blood in vitro. | 2001 Sep |
|
Endovascular brachytherapy for prophylaxis against restenosis after long-segment femoropopliteal placement of stents: initial results. | 2001 Sep |
|
Complications of oral antiplatelet medications. | 2001 Sep |
|
Effect of clopidogrel added to aspirin before percutaneous coronary intervention on the risk associated with C-reactive protein. | 2001 Sep 15 |
|
Clopidogrel versus aspirin after cardiac surgery. | 2001 Sep 25 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10077233
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
Created
by
admin
on
Edited
Mon Mar 31 18:41:24 GMT 2025
by
admin
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Record UNII |
57X57906KK
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Record Status |
Validated (UNII)
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Record Version |
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