CLOPIDOGREL HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H16ClNO2S.ClH
Molecular Weight	358.283
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XIHVAFJSGWDBGA-RSAXXLAASA-N

InChI=1S/C16H16ClNO2S.ClH/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	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	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020839s044lbl.pdf | https://www.drugbank.ca/drugs/DB00758 | https://www.ncbi.nlm.nih.gov/pubmed/15199474

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
Purinergic receptor P2Y12 23 Target ID: CHEMBL2001 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15199474 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020839s044lbl.pdf \| https://www.drugbank.ca/drugs/DB00758	Antagonist 2737		6.9 null [pKi]
Purinergic receptor P2Y12 23 Target ID: CHEMBL2001 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=0078fb3d-3595-4ae1-a059-1d5e81c879cf&type=display\|https://www.ncbi.nlm.nih.gov/pubmed/10446085	Antagonist 2737

Conditions

Condition	Modality	Highest Phase	Product
Atherosclerosis 74 Sources: https://www.drugs.com/pro/clopidogrel.html	Primary	Approved 8307	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
Acute coronary syndrome 32 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020839s044lbl.pdf	Primary	Approved 8307	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
Peripheral arterial disease 22 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020839s044lbl.pdf	Primary	Approved 8307	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
Myocardial infarction 103 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020839s044lbl.pdf	Preventing	Approved 8307	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

C_max

Value	Dose	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	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:

T_1/2

Value	Dose	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020839s044lbl.pdf	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: https://pubmed.ncbi.nlm.nih.gov/26063503	healthy, 20-45 years n = 27 Health Status: healthy Age Group: 20-45 years Sex: M Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/26063503	Other AEs: Uric acid abnormal... Other AEs: Uric acid abnormal (5 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/26063503
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: https://pubmed.ncbi.nlm.nih.gov/17286151	unknown, 49 years n = 1 Health Status: unknown Age Group: 49 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17286151	Sources: https://pubmed.ncbi.nlm.nih.gov/17286151
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: https://pubmed.ncbi.nlm.nih.gov/16878371	unhealthy, 59 years n = 1 Health Status: unhealthy Age Group: 59 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/16878371	Disc. AE: Transaminases increased, Fever... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Fever (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/16878371

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: https://pubmed.ncbi.nlm.nih.gov/26063503	healthy, 20-45 years n = 27 Health Status: healthy Age Group: 20-45 years Sex: M Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/26063503
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: https://pubmed.ncbi.nlm.nih.gov/16878371	unhealthy, 59 years n = 1 Health Status: unhealthy Age Group: 59 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/16878371
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: https://pubmed.ncbi.nlm.nih.gov/16878371	unhealthy, 59 years n = 1 Health Status: unhealthy Age Group: 59 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/16878371

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:37941	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:37941
MolPort	MolPort-002-885-817	https://www.molport.com/shop/molecule-link/MolPort-002-885-817
ZINC	ZINC000034781704	http://zinc15.docking.org/substances/ZINC000034781704
eMolecules	2735330	https://www.emolecules.com/cgi-bin/more?vid=2735330

PubMed

Title	Date	PubMed
Drug-induced thrombotic microangiopathy: incidence, prevention and management.	2001	11444722
Benefit of ADP receptor antagonists in atherothrombotic patients: new evidence.	2001	11316916
Atherothrombosis: a major health burden.	2001	11316915
Clinical application of procedural platelet monitoring during percutaneous coronary intervention among patients at increased bleeding risk.	2001 Apr	11406730
Aspirin in patients with coronary artery disease: is it simply irresistible?	2001 Apr	11406726
CURE--clopidogrel's major advance.	2001 Apr	11351766
[Optimal platelet inhibition therapy in unstable angina pectoris and after coronary interventions].	2001 Apr	11349625
Regular or "super-aspirins"? A review of thienopyridines or aspirin to prevent stroke.	2001 Apr	11347797
Management of neurological complications of carotid artery stenting.	2001 Aug	11552726
Acute myocardial infarction 2000 treatment.	2001 Fall	11569324
Antithrombotic therapy in cardiac stent patients.	2001 Jan	11139803
Active-control trials: how would a new agent compare with placebo? A method illustrated with clopidogrel, aspirin, and placebo.	2001 Jan	11136483
[2 platelet inhibitors administered at the same time. Improved prognosis in myocardial infarct?]].	2001 Jan 11	11219401
Identification of the platelet ADP receptor targeted by antithrombotic drugs.	2001 Jan 11	11196645
The role of adenosine 5'-diphosphate receptor blockade in patients with cardiovascular disease.	2001 Jul	11448660
Diffuse alveolar hemorrhage after clopidogrel use.	2001 Jul	11435642
Acute coronary syndrome: are intervention and IIb/IIIa platelet inhibitors epiphenomena?	2001 Jul-Aug	11501219
Molecular identification and characterization of the platelet ADP receptor targeted by thienopyridine antithrombotic drugs.	2001 Jun	11413167
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	11419889
Comparison of two platelet glycoprotein IIb/IIIa inhibitors, tirofiban and abciximab, for the prevention of ischemic events with percutaneous coronary revascularization.	2001 Jun 21	11419425
[New platelet inhibitors].	2001 Mar	11315485
Activation of Gi-coupled receptors releases a tonic state of inhibited platelet aggregation.	2001 Mar	11297037
Initial experience with a newer generation coronary stent.	2001 Mar	11231647
[Cost effectiveness of clopidogrel in secondary cardiovascular prevention: a cost-effectiveness analysis based on the Caprie Study].	2001 Mar 29	11550619
Orbofiban: an orally active GPIIb/IIIa platelet receptor antagonist.	2001 May	11301411
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	11352879
Coronary stent deployment in situs inversus.	2001 Nov	11602566
Antiplatelet agents for secondary prevention of ischemic stroke.	2001 Oct	11675854
[Clopidogrel in acute coronary syndromes with non-ST elevation. Clinical implications of the CURE trial].	2001 Oct	11591313
Prevention of venous graft sclerosis with clopidogrel and aspirin combined with a mesh tubing in a dog model of arteriovenous bypass grafting.	2001 Oct	11563893
Effects of clopidogrel pretreatment before percutaneous coronary intervention in patients treated with glycoprotein IIb/IIIa inhibitors (abciximab or tirofiban).	2001 Oct 15	11676953
Drug-associated thrombotic thrombocytopenic purpura-hemolytic uremic syndrome.	2001 Sep	11604563
Recovery of platelet function after discontinuation of clopidogrel treatment in healthy volunteers.	2001 Sep	11560568
Effect of clopidogrel added to aspirin before percutaneous coronary intervention on the risk associated with C-reactive protein.	2001 Sep 15	11564394
Clopidogrel versus aspirin after cardiac surgery.	2001 Sep 25	11571262

Patents

Sample Use Guides

In Vivo Use Guide

Recent MI, Recent Stroke, or Established Peripheral Arterial Disease The recommended daily dose of is 75 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

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 16 23:22:11 UTC 2022` Edited by `admin` on `Fri Dec 16 23:22:11 UTC 2022`
Record UNII	426O7XWS6Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLOPIDOGREL HYDROCHLORIDE

Common Name

English

CLOPIDOGREL TEVA GENERICS B.V.

Brand Name

English

CLOPIDOGREL HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

CLOPIDOGREL-TAD

Brand Name

English

CLOPIDOGREL QUALIMED

Brand Name

English

CLOPIDOGREL HYDROCHLORIDE [EMA EPAR]

Common Name

English

CLOPIDOGREL-DURA

Brand Name

English

Clopidogrel hydrochloride [WHO-DD]

Common Name

English

CLOPIDOGREL TEVA PHARMA

Brand Name

English

CLOPIDOGREL-HCS

Brand Name

English

CLOPIDOGREL-KRKA

Brand Name

English

THIENO(3,2-C)PYRIDINE-5(4H)-ACETIC ACID, .ALPHA.-(2-CHLOROPHENYL)-6,7-DIHYDRO-, METHYL ESTER, HYDROCHLORIDE, (S)-

Common Name

English

CLOPIDOGREL MYLAN

Brand Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

CLOPIDOGREL KRKA (AUTHORIZED: MYOCARDIAL INFARCTION)