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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16ClNO2S.BrH.H2O
Molecular Weight 420.749
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOPIDOGREL HYDROBROMIDE MONOHYDRATE

SMILES

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

InChI

InChIKey=HTEWJQMRGUTISZ-CKUXDGONSA-N
InChI=1S/C16H16ClNO2S.BrH.H2O/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;1H2/t15-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

8.7972479E11
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

8.7963841E11
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

8.7972479E11
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

8.7972479E11
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
Effect of clopidogrel on naproxen-induced gastrointestinal blood loss in healthy volunteers.
1998
Specific impairment of human platelet P2Y(AC) ADP receptor-mediated signaling by the antiplatelet drug clopidogrel.
1999 Aug
Benefit of ADP receptor antagonists in atherothrombotic patients: new evidence.
2001
Atherothrombosis: a major health burden.
2001
Novel platelet inhibitors.
2001
Aspirin in patients with coronary artery disease: is it simply irresistible?
2001 Apr
CURE--clopidogrel's major advance.
2001 Apr
[Optimal platelet inhibition therapy in unstable angina pectoris and after coronary interventions].
2001 Apr
[Acute heart attacks. Prognosis can be further improved].
2001 Apr 5
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
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
Antithrombotic therapy in cardiac stent patients.
2001 Jan
Active-control trials: how would a new agent compare with placebo? A method illustrated with clopidogrel, aspirin, and placebo.
2001 Jan
Effect of a high loading dose of clopidogrel on platelet function in patients undergoing coronary stent placement.
2001 Jan
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 role of adenosine 5'-diphosphate receptor blockade in patients with cardiovascular disease.
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
[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
[Pharmacy clinics. Medication of the month. Clopidogrel (Plavix)].
2001 Mar
Initial experience with a newer generation coronary stent.
2001 Mar
[Cost effectiveness of clopidogrel in secondary cardiovascular prevention: a cost-effectiveness analysis based on the Caprie Study].
2001 Mar 29
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
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
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
Effects of combining three different antiplatelet agents on platelets and leukocytes in whole blood in vitro.
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
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 21:17:09 UTC 2023
Edited
by admin
on Fri Dec 15 21:17:09 UTC 2023
Record UNII
T9U0M28798
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOPIDOGREL HYDROBROMIDE MONOHYDRATE
Common Name English
Clopidogrel hydrobromide monohydrate [WHO-DD]
Common Name English
THIENO(3,2-C)PYRIDINE-5(4H)-ACETIC ACID, .ALPHA.-(2-CHLOROPHENYL)-6,7-DIHYDRO-, METHYL ESTER, HYDROBROMIDE, HYDRATE (1:1:1), (.ALPHA.S)-
Common Name English
Code System Code Type Description
FDA UNII
T9U0M28798
Created by admin on Fri Dec 15 21:17:09 UTC 2023 , Edited by admin on Fri Dec 15 21:17:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID50237708
Created by admin on Fri Dec 15 21:17:09 UTC 2023 , Edited by admin on Fri Dec 15 21:17:09 UTC 2023
PRIMARY
PUBCHEM
67019436
Created by admin on Fri Dec 15 21:17:09 UTC 2023 , Edited by admin on Fri Dec 15 21:17:09 UTC 2023
PRIMARY
SMS_ID
100000145056
Created by admin on Fri Dec 15 21:17:09 UTC 2023 , Edited by admin on Fri Dec 15 21:17:09 UTC 2023
PRIMARY
EVMPD
SUB122697
Created by admin on Fri Dec 15 21:17:09 UTC 2023 , Edited by admin on Fri Dec 15 21:17:09 UTC 2023
PRIMARY
CAS
894353-16-3
Created by admin on Fri Dec 15 21:17:09 UTC 2023 , Edited by admin on Fri Dec 15 21:17:09 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE