Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | 2C16H16ClNO2S.C10H8O6S2 |
| Molecular Weight | 931.94 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(=O)(=O)C1=CC=CC2=C1C=CC=C2S(O)(=O)=O.COC(=O)[C@@H](N3CCC4=C(C3)C=CS4)C5=CC=CC=C5Cl.COC(=O)[C@@H](N6CCC7=C(C6)C=CS7)C8=CC=CC=C8Cl
InChI
InChIKey=UNGVWAKVHQSXGE-ZFQYHYQMSA-N
InChI=1S/2C16H16ClNO2S.C10H8O6S2/c2*1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14;11-17(12,13)9-5-1-3-7-8(9)4-2-6-10(7)18(14,15)16/h2*2-5,7,9,15H,6,8,10H2,1H3;1-6H,(H,11,12,13)(H,14,15,16)/t2*15-;/m00./s1
| Molecular Formula | C10H8O6S2 |
| Molecular Weight | 288.297 |
| 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.
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 Date8.7972479E11 |
|||
| 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 Date8.7963841E11 |
|||
| 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 Date8.7972479E11 |
|||
| 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 Date8.7972479E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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: |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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: |
|
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: |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
|
7.4 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 |
|
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 |
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 (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... |
1650 mg single, oral Overdose Dose: 1650 mg Route: oral Route: single Dose: 1650 mg Co-administed with:: phenytoin sodium(1400 mg; single) Sources: simvastatin(120 mg; single) |
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) Sources: Fever (1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| CURE--clopidogrel's major advance. | 2001 Apr |
|
| 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 |
|
| 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 |
|
| [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 |
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
Edited
Sat Dec 16 18:11:07 UTC 2023
by
admin
on
Sat Dec 16 18:11:07 UTC 2023
|
| Record UNII |
MP4UYS4N4U
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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164888948
Created by
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945775-34-8
Created by
admin on Sat Dec 16 18:11:07 UTC 2023 , Edited by admin on Sat Dec 16 18:11:07 UTC 2023
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MP4UYS4N4U
Created by
admin on Sat Dec 16 18:11:07 UTC 2023 , Edited by admin on Sat Dec 16 18:11:07 UTC 2023
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PARENT -> SALT/SOLVATE |
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SOLVATE->ANHYDROUS |
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