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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
Structure of CLOPIDOGREL CAMSYLATE

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

HIDE SMILES / InChI

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.

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
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:
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
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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:
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:
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
7.9 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
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
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
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:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
weak
weak
yes [IC50 0.307 uM]
yes [IC50 6.25 uM]
yes [Ki 28 uM]
yes
yes
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
likely
no
no
no
no
no
no
yes [Km 181 uM]
yes [Km 19 uM]
yes [Km 20.9 uM]
yes [Km 5.61 uM]
yes
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
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
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 Mon Mar 31 18:41:24 GMT 2025
Edited
by admin
on Mon Mar 31 18:41:24 GMT 2025
Record UNII
57X57906KK
Record Status Validated (UNII)
Record Version
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Name Type Language
CLOPIDOGREL CAMSILATE
Preferred Name English
CLOPIDOGREL CAMSYLATE
Common Name English
CLOPIDOGREL CAMPHOR SULFONATE
Common Name English
THIENO(3,2-C)PYRIDINE-5(4H)-ACETIC ACID, .ALPHA.-(2-CHLOROPHENYL)-6,7-DIHYDRO-, METHYL ESTER, (.ALPHA.S)-, (1R,4S)-7,7-DIMETHYL-2-OXOBICYCLO(2.2.1)HEPTANE-1-METHANESULFONATE (1:1)
Systematic Name English
CLOPIDOGREL CAMPHOR SULPHONATE SALT
Common Name English
Clopidogrel camsilate [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
57X57906KK
Created by admin on Mon Mar 31 18:41:24 GMT 2025 , Edited by admin on Mon Mar 31 18:41:24 GMT 2025
PRIMARY
SMS_ID
100000164669
Created by admin on Mon Mar 31 18:41:24 GMT 2025 , Edited by admin on Mon Mar 31 18:41:24 GMT 2025
PRIMARY
CAS
120202-68-8
Created by admin on Mon Mar 31 18:41:24 GMT 2025 , Edited by admin on Mon Mar 31 18:41:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID30621848
Created by admin on Mon Mar 31 18:41:24 GMT 2025 , Edited by admin on Mon Mar 31 18:41:24 GMT 2025
PRIMARY
PUBCHEM
10460309
Created by admin on Mon Mar 31 18:41:24 GMT 2025 , Edited by admin on Mon Mar 31 18:41:24 GMT 2025
PRIMARY
EVMPD
SUB179173
Created by admin on Mon Mar 31 18:41:24 GMT 2025 , Edited by admin on Mon Mar 31 18:41:24 GMT 2025
PRIMARY
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PARENT -> SALT/SOLVATE
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