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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16ClNO2S.BrH
Molecular Weight 402.734
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOPIDOGREL HYDROBROMIDE

SMILES

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

InChI

InChIKey=QKLHYWAZTQRTBR-RSAXXLAASA-N
InChI=1S/C16H16ClNO2S.BrH/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;1H/t15-;/m0./s1

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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.

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

1997
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

1997
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

1997
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

1997
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 (starting)
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 20-45 years
n = 27
Health Status: healthy
Age Group: 20-45 years
Sex: M
Population Size: 27
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
Co-administed with::
phenytoin sodium(1400 mg; single)
simvastatin(120 mg; single)
Sources:
unknown, 49 years
n = 1
Health Status: unknown
Age Group: 49 years
Sex: M
Population Size: 1
Sources:
600 mg 1 times / day multiple, oral (starting)
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
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 (starting)
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 20-45 years
n = 27
Health Status: healthy
Age Group: 20-45 years
Sex: M
Population Size: 27
Sources:
Fever 1 patient
Disc. AE
600 mg 1 times / day multiple, oral (starting)
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
Sources:
Transaminases increased 1 patient
Disc. AE
600 mg 1 times / day multiple, oral (starting)
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Drug-induced thrombotic microangiopathy: incidence, prevention and management.
2001
Current oral antiplatelet agents to prevent atherothrombosis.
2001
Benefit of ADP receptor antagonists in atherothrombotic patients: new evidence.
2001
Atherothrombosis: a major health burden.
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
[Optimal platelet inhibition therapy in unstable angina pectoris and after coronary interventions].
2001 Apr
[Pathophysiology of platelet activation and pharmacology of GPIIb/IIIa inhibitors].
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
Management of neurological complications of carotid artery stenting.
2001 Aug
Deaggregation is an integral component of the response of platelets to ADP in vitro: kinetic studies of literature and original data.
2001 Aug
Effects of clopidogrel in addition to aspirin in patients with acute coronary syndromes without ST-segment elevation.
2001 Aug 16
Clopidogrel in invasive management of non-ST-elevation ACS.
2001 Aug 18
Severe hypersensitivity associated with clopidogrel.
2001 Aug 21
Current perspectives on British use of adjunctive therapies during coronary interventions.
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
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
[Acute coronary syndromes: an update. I. Pathogenesis and drug therapy].
2001 Mar
[Pharmacy clinics. Medication of the month. Clopidogrel (Plavix)].
2001 Mar
[New platelet inhibitors].
2001 Mar
Activation of Gi-coupled receptors releases a tonic state of inhibited platelet aggregation.
2001 Mar
Platelet CD40 ligand (CD40L)--subcellular localization, regulation of expression, and inhibition by clopidogrel.
2001 Mar
[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
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
P2y(12), a new platelet ADP receptor, target of clopidogrel.
2001 May 4
Prospective controlled study of carotid endarterectomy with hemashield patch: is it thrombogenic?
2001 May-Jun
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
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
Thrombotic thrombocytopenic purpura associated with clopidogrel administration: case report and brief review.
2001 Sep
Recovery of platelet function after discontinuation of clopidogrel treatment in healthy volunteers.
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
Patents

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:23:09 GMT 2023
Edited
by admin
on Fri Dec 15 20:23:09 GMT 2023
Record UNII
96AAH2D689
Record Status Validated (UNII)
Record Version
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Name Type Language
CLOPIDOGREL HYDROBROMIDE
WHO-DD  
Common Name English
CLOPIDOGREL TEVA PHARMA B.V.
Brand Name English
Clopidogrel hydrobromide [WHO-DD]
Common Name English
THIENO(3,2-C)PYRIDINE-5(4H)-ACETIC ACID, .ALPHA.-(2-CHLOROPHENYL)-6,7-DIHYDRO-, METHYL ESTER, HYDROBROMIDE (1:1), (.ALPHA.S)-
Common Name English
(S)-(+)-CLOPIDOGREL HYDROBROMIDE
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS CLOPIDOGREL TEVA PHARMA B.V. (WITHDRAWN: MYOCARDIAL INFARCTION)
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
EMA ASSESSMENT REPORTS CLOPIDOGREL TEVA PHARMA B.V. (AUTHORIZED: PERIPHERAL VASCULAR DISEASES)+
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
EMA ASSESSMENT REPORTS CLOPIDOGREL TEVA PHARMA B.V. (WITHDRAWN: ACUTE CORONARY SYNDROME)
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
EMA ASSESSMENT REPORTS CLOPIDOGREL TEVA PHARMA B.V. (WITHDRAWN: STROKE)
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
Code System Code Type Description
FDA UNII
96AAH2D689
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
PRIMARY
PUBCHEM
11304210
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
PRIMARY
CAS
120202-67-7
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
PRIMARY
EVMPD
SUB76368
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
PRIMARY
SMS_ID
100000137773
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID00152735
Created by admin on Fri Dec 15 20:23:09 GMT 2023 , Edited by admin on Fri Dec 15 20:23:09 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY