U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16ClNO2S
Molecular Weight 321.8234
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOPIDOGREL

SMILES

COC(=O)[C@]([H])(c1ccccc1Cl)N2CCc3c(ccs3)C2

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
of platelet activation by released ADP. Plavix (clopidogrel bisulfate) is indicated for the reduction of atherothrombotic events.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PLAVIX

Approved Use

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. 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 Date

879724800000
Primary
PLAVIX

Approved Use

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 Date

879638400000
Primary
PLAVIX

Approved Use

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 Date

879724800000
Preventing
PLAVIX

Approved Use

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 Date

879724800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1500 pg/mL
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
15800 pg/mL
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
2520 pg/mL
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
4600 pg/mL
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
0.521 ng/mL
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:
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3130 pg × h/mL
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
50600 pg × h/mL
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
7440 pg × h/mL
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
9890 pg × h/mL
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
0.767 ng*h/mL
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:
1.09 ng*h/mL
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:
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.5 h
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
5.4 h
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
7.4 h
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
7.9 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
unknown, unknown
CLOPIDOGREL BISULFATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Health Status: healthy
Age Group: 20-45 years
Sex: M
Sources:
Other AEs: Uric acid abnormal...
Other AEs:
Uric acid abnormal (5 patients)
Sources:
1650 mg single, oral
Overdose
Dose: 1650 mg
Route: oral
Route: single
Dose: 1650 mg
Sources:
unknown, 49 years
Health Status: unknown
Age Group: 49 years
Sex: M
Sources:
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
Health Status: unhealthy
Age Group: 59 years
Sex: F
Sources:
Disc. AE: Transaminases increased, Fever...
AEs leading to
discontinuation/dose reduction:
Transaminases increased (1 patient)
Fever (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: healthy
Age Group: 20-45 years
Sex: M
Sources:
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
Health Status: unhealthy
Age Group: 59 years
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 59 years
Sex: F
Sources:
PubMed

PubMed

TitleDatePubMed
Drug-induced thrombotic microangiopathy: incidence, prevention and management.
2001
The use of antiplatelet agents in acute cardiac care.
2001 Apr
Clinical application of procedural platelet monitoring during percutaneous coronary intervention among patients at increased bleeding risk.
2001 Apr
Aspirin in patients with coronary artery disease: is it simply irresistible?
2001 Apr
Management of neurological complications of carotid artery stenting.
2001 Aug
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
Antithrombotic drugs for older subjects. Guidelines formulated jointly by the Italian Societies of Haemostasis and Thrombosis (SISET) and of Gerontology and Geriatrics (SIGG).
2001 Feb
[Can we use clopidogrel in patients with coronary stent?].
2001 Jan-Mar
ADP receptors of platelets and their inhibition.
2001 Jul
Current perspectives on British use of adjunctive therapies during coronary interventions.
2001 Jul
The role of adenosine 5'-diphosphate receptor blockade in patients with cardiovascular disease.
2001 Jul
Multiple intracranial aneurysms as delayed complications of an atrial myxoma: case report.
2001 Jul
Extensive thrombus prior to elective percutaneous coronary intervention.
2001 Jul
Diffuse alveolar hemorrhage after clopidogrel use.
2001 Jul
Randomized comparison of ticlopidine and clopidogrel after intracoronary stent implantation in a broad patient population.
2001 Jul 31
Acute coronary syndrome: are intervention and IIb/IIIa platelet inhibitors epiphenomena?
2001 Jul-Aug
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
Incidence of thrombotic occlusion and major adverse cardiac events between two and four weeks after coronary stent placement: analysis of 5,678 patients with a four-week ticlopidine regimen.
2001 Jun 15
Comparison of two platelet glycoprotein IIb/IIIa inhibitors, tirofiban and abciximab, for the prevention of ischemic events with percutaneous coronary revascularization.
2001 Jun 21
[Cost effectiveness of clopidogrel in secondary cardiovascular prevention: a cost-effectiveness analysis based on the Caprie Study].
2001 Mar 29
[Superiority of clopidogrel versus aspirin in patients with prior cardiac surgery].
2001 May
The inhibition of oxygen radical release from human neutrophils by resting platelets is reversed by administration of acetylsalicylic acid or clopidogrel.
2001 May
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
Clopidogrel and aplastic anaemia.
2001 May 5
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
Antiplatelet agents for secondary prevention of ischemic stroke.
2001 Oct
[Clopidogrel in acute coronary syndromes with non-ST elevation. Clinical implications of the CURE trial].
2001 Oct
Prevention of venous graft sclerosis with clopidogrel and aspirin combined with a mesh tubing in a dog model of arteriovenous bypass grafting.
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
Recovery of platelet function after discontinuation of clopidogrel treatment in healthy volunteers.
2001 Sep
Adjunctive therapies in the cath lab. Subacute stent thrombosis developing twelve days after discontinuation of ticlopidine treatment.
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
Patents

Sample Use Guides

Recent MI, Recent Stroke, or Established Peripheral Arterial Disease
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.
Name Type Language
CLOPIDOGREL
EMA EPAR   HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CLOPIDOGREL [INN]
Common Name English
(S)-METHYL .ALPHA.-(4,5,6,7-TETRAHYDROTHIENO(3,2-C)PYRIDIN-5-YL)-.ALPHA.-(O-CHLOROPHENYL)ACETATE
Common Name English
SR-25990
Code English
CLOPIDOGREL [HSDB]
Common Name English
NSC-758613
Code English
THROMBO
Common Name English
(+)-(S)-CLOPIDOGREL
Common Name English
SR 25990
Code English
CLOPIDOGREL [VANDF]
Common Name English
R 130964
Code English
METHYL 2-(2-CHLOROPHENYL)-2-(4,5,6,7-TETRAHYDROTHIENO(3,2-C)PYRIDIN-5-YL)ACETATE
Systematic Name English
ZYLLT
Common Name English
CLOPIDOGREL [EMA EPAR]
Common Name English
CLOPIDOGREL [MI]
Common Name English
CLOPIDOGREL [WHO-DD]
Common Name English
R-130964
Code English
Classification Tree Code System Code
NDF-RT N0000008832
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
WHO-VATC QB01AC04
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
WHO-ATC B01AC04
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
NCI_THESAURUS C80483
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
EMA ASSESSMENT REPORTS CLOPIDOGREL ACINO (AUTHORIZED:ACUTE CORONARY SYNDROME)
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
NDF-RT N0000008832
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
NDF-RT N0000182142
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
NDF-RT N0000175578
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
LIVERTOX 226
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
EMA ASSESSMENT REPORTS CLOPIDOGREL ACINO (AUTHORIZED: MYOCARDIAL INFARCTION)
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1771
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
MESH
C055162
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
DRUG BANK
DB00758
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
HSDB
7430
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
MERCK INDEX
M3655
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY Merck Index
CAS
113665-84-2
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
WIKIPEDIA
CLOPIDOGREL
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
INN
5908
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
NDF-RT
N0000182143
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY P2Y12 Receptor Antagonists [MoA]
IUPHAR
7150
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
EVMPD
SUB13395MIG
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
EPA CompTox
113665-84-2
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
DRUG CENTRAL
708
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
LACTMED
Clopidogrel
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
FDA UNII
A74586SNO7
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
RXCUI
32968
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C61686
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY
PUBCHEM
60606
Created by admin on Fri Jun 25 21:53:34 UTC 2021 , Edited by admin on Fri Jun 25 21:53:34 UTC 2021
PRIMARY