Clopidogrel

Identification

Summary

Clopidogrel is an antiplatelet agent used to prevent blood clots in peripheral vascular disease, coronary artery disease, and cerebrovascular disease.

Brand Names
Duoplavin, Plavix, Zyllt
Generic Name
Clopidogrel
DrugBank Accession Number
DB00758
Background

Clopidogrel is a prodrug of a platelet inhibitor used to reduce the risk of myocardial infarction and stroke.3,9 Clopidogrel is indicated to reduce the risk of myocardial infarction for patients with non-ST elevated acute coronary syndrome (ACS), patients with ST-elevated myocardial infarction, and in recent MI, stroke, or established peripheral arterial disease,9

It has been shown to be superior to aspirin in reducing cardiovascular outcomes in patients with cardiovascular disease and provides additional benefit to patients with acute coronary syndromes already taking aspirin.8

Clopidogrel was granted FDA approval on 17 November 1997.9

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 321.822
Monoisotopic: 321.059027158
Chemical Formula
C16H16ClNO2S
Synonyms
  • (+)-Clopidogrel
  • Clopidogrel
  • Clopidogrelum
External IDs
  • R 130964
  • R-130964
  • SR 25990
  • SR-25990

Pharmacology

Indication

Clopidogrel is indicated to reduce the risk of myocardial infarction for patients with non-ST elevated acute coronary syndrome (ACS), patients with ST-elevated myocardial infarction, and in recent MI, stroke, or established peripheral arterial disease,9

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageAcute coronary syndrome (acs)Combination Product in combination with: Acetylsalicylic acid (DB00945)•••••••••••••••••
Used in combination to manageAcute myocardial infarctionCombination Product in combination with: Acetylsalicylic acid (DB00945)••••••••••••••••••••••••• ••• •••••••••••• •••••••
Prevention ofCardiovascular event••••••••••••
Prevention ofCardiovascular event••••••••••••
Prevention ofCardiovascular event••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Clopidogrel is a prodrug of a platelet inhibitor used to reduce the risk of myocardial infarction and stroke.3,9 It has a long duration of action as it is taken once daily and a large therapeutic window as it is given in doses of 75-300mg daily.9

Mechanism of action

Clopidogrel is activated via a 2 steps reaction to an active thiol-containing metabolite.3 This active form is a platelet inhibitor that irreversibly binds to P2Y12 ADP receptors on platelets.9 This binding prevents ADP binding to P2Y12 receptors, activation of the glycoprotein GPIIb/IIIa complex, and platelet aggregation.9

TargetActionsOrganism
AP2Y purinoceptor 12
antagonist
Humans
Absorption

A 75mg oral dose of clopidogrel is 50% absorbed from the intestine.9 Clopidogrel can be taken with or without food.9 A meal decreases the AUC of the active metabolite by 57%.9 The active metabolite of clopidogrel reaches a maximum concentration after 30-60 minutes.9 Clopidogrel reached a Cmax of 2.04±2.0ng/mL in 1.40±1.07h.5

The AUC for a 300mg oral dose of clopidogrel was 45.1±16.2ng*h/mL for poor metabolizers, 65.6±19.1ng*h/mL for intermediate metabolizers, and 104.3±57.3ng*h/mL for extensive metabolizers.6 The Cmax was 31.3±13ng/mL for poor metabolizers, 43.9±14ng/mL for intermediate metabolizers, and 60.8±34.3ng/mL for extensive metabolizers.6

Volume of distribution

The apparent volume of distribution of clopidogrel is 39,240±33,520L.5

Protein binding

Both the active and inactive metabolites of clopidogrel are 98% protein bound in plasma.1 Studies in cows show clopidogrel 71-85.5% bound to serum albumin.2

Metabolism

85-90% of an oral dose undergoes first pass metabolism by carboxylesterase 1 in the liver to an inactive carboxylic acid metabolite.4 about 2% of clopidogrel is oxidized to 2-oxoclopidogrel.4 This conversion is 35.8% by CYP1A2, 19.4% by CYP2B6, and 44.9% by CYP2C194 though other studies suggest CYP3A4, CYP3A5, and CYP2C9 also contribute.3 2-oxoclopidogrel is further metabolized to the active metabolite.3,4 This conversion is 32.9% by CYP2B6, 6.79% by CYP2C9, 20.6% by CYP2C19, and 39.8% by CYP3A4.3,4

Hover over products below to view reaction partners

Route of elimination

An oral dose of radiolabelled clopidogrel is excreted 50% in the urine and 46% in the feces over 5 days.9 The remainder of clopidogrel is irreversibly bound to platelets for their lifetime, or approximately 8-11 days.7

Half-life

That half life of clopidogrel is approximately 6 hours following a 75mg oral dose while the half life of the active metabolite is approximately 30 minutes.9

Clearance

The clearance of a 75mg oral dose was 18,960±15,890L/h and for a 300mg oral dose was 16,980±10,410L/h.5

Adverse Effects
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Toxicity

A single dose of clopidogrel at 1500-2000mg/kg was lethal to mice and rats while 3000mg/kg was lethal to baboons.9 Symptoms of overdose include vomiting, breathing difficulty, gastrointestinal hemorrhage, and prostration.9 Clopidogrel is irreversibly bound to platelets for their lifetime, which is approximately 11 days.9 Overdoses of clopidogrel can be treated with platelet transfusions to restore clotting ability.9

Pathways
PathwayCategory
Clopidogrel Action PathwayDrug action
Clopidogrel Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*3(C;C) / (A;C)C AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of clopidogrel resulting in reduced plasma concentrations of its active metabolite.Details
Cytochrome P450 2C19CYP2C19*2(A;A) / (A;G)G > AEffect Directly StudiedPatients with this genotype have reduced metabolism of clopidogrel resulting in reduced plasma concentrations of its active metabolite.Details
Cytochrome P450 2C19CYP2C19*2Not Available681G>AADR Directly StudiedPatients with this polymorphism in CYP2C19 are poor metabolizers of clopidogrel and are associated with diminished platelet response and increased risk of adverse cardiovascular events in response to clopidogrel therapy.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>ADirectly Studied EffectThe presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of clopidogrel.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all ADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GADR InferredPoor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer, lower dose requirements, higher risk for drug-drug interactionsDetails

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Clopidogrel can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Clopidogrel can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Clopidogrel is combined with Abciximab.
AbirateroneThe serum concentration of Clopidogrel can be increased when it is combined with Abiraterone.
AbrocitinibThe risk or severity of bleeding and thrombocytopenia can be increased when Clopidogrel is combined with Abrocitinib.
Food Interactions
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Clopidogrel besilateBL9VGG8BHW744256-69-7CUZIJKLLBDXNFV-RSAXXLAASA-N
Clopidogrel bisulfate08I79HTP27120202-66-6FDEODCTUSIWGLK-RSAXXLAASA-N
Clopidogrel hydrochloride426O7XWS6Y120202-65-5XIHVAFJSGWDBGA-RSAXXLAASA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act ClopidogrelTablet75 mgOralTEVA Canada Limited2011-12-07Not applicableCanada flag
Clopido Grel 1a PharmaTablet, film coated75 mgOralAcino Pharma Gmb H2016-09-082011-02-28EU flag
Clopidogre RatiopharmTablet, film coated75 mgOralTeva B.V.2016-09-08Not applicableEU flag
ClopidogrelTablet75 mgOralSanis Health Inc2013-02-13Not applicableCanada flag
ClopidogrelTablet75 mgOralPro Doc Limitee2012-11-22Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Abbott-clopidogrelTablet75 mgOralAbbott2014-03-172015-12-31Canada flag
Accel-clopidogrelTablet300 mgOralAccel Pharma IncNot applicableNot applicableCanada flag
Accel-clopidogrelTablet75 mgOralAccel Pharma Inc2014-09-042015-11-09Canada flag
Ag-clopidogrelTablet75 mgOralAngita Pharma Inc.2022-02-10Not applicableCanada flag
Apo-clopidogrelTablet300 mgOralApotex Corporation2013-01-21Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CLOPIDOGREL E ACIDO ACETILSALICILICO MYLANClopidogrel (75 mg) + Acetylsalicylic acid (100 mg)Tablet, film coatedOralMylan Pharmaceuticals Limited2020-05-08Not applicableItaly flag
CLOPIDOGREL E ACIDO ACETILSALICILICO MYLANClopidogrel (75 mg) + Acetylsalicylic acid (75 mg)Tablet, film coatedOralMylan Pharmaceuticals Limited2020-05-08Not applicableItaly flag
CLOPIDOGREL E ACIDO ACETILSALICILICO MYLANClopidogrel (75 mg) + Acetylsalicylic acid (100 mg)Tablet, film coatedOralMylan Pharmaceuticals Limited2020-05-08Not applicableItaly flag
CLOPIDOGREL E ACIDO ACETILSALICILICO MYLANClopidogrel (75 mg) + Acetylsalicylic acid (100 mg)Tablet, film coatedOralMylan Pharmaceuticals Limited2020-05-08Not applicableItaly flag
CLOPIDOGREL E ACIDO ACETILSALICILICO MYLANClopidogrel (75 mg) + Acetylsalicylic acid (75 mg)Tablet, film coatedOralMylan Pharmaceuticals Limited2020-05-08Not applicableItaly flag

Categories

ATC Codes
B01AC04 — Clopidogrel
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid esters
Alternative Parents
Thienopyridines / Aralkylamines / Chlorobenzenes / Aryl chlorides / Pyridines and derivatives / Methyl esters / Heteroaromatic compounds / Thiophenes / Trialkylamines / Monocarboxylic acids and derivatives
show 6 more
Substituents
Alpha-amino acid ester / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid ester
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
methyl ester, monochlorobenzenes, thienopyridine (CHEBI:37941)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
A74586SNO7
CAS number
113665-84-2
InChI Key
GKTWGGQPFAXNFI-HNNXBMFYSA-N
InChI
InChI=1S/C16H16ClNO2S/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/t15-/m0/s1
IUPAC Name
methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
SMILES
[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl

References

Synthesis Reference

Revital Lifshitz-Liron, "Novel crystal forms III, IV, V, and novel amorphous form of clopidogrel hydrogensulfate, processes for their preparation, processes for the preparation of form I, compositions containing the new forms and methods of administering the new forms." U.S. Patent US20030114479, issued June 19, 2003.

US20030114479
General References
  1. Ganesan S, Williams C, Maslen CL, Cherala G: Clopidogrel variability: role of plasma protein binding alterations. Br J Clin Pharmacol. 2013 Jun;75(6):1468-77. doi: 10.1111/bcp.12017. [Article]
  2. Mostafizar M, Haque P, Mazid A, Shohel M, Shazly G, Kazi M, Reza HM: CHARACTERIZATION OF BINDING SITES OF CLOPIDOGREL AND INTERFERENCE OF LINOLEIC ACID AT THE BINDING SITE ON BOVINE SERUM ALBUMIN. Acta Pol Pharm. 2017 Jan;74(1):119-125. [Article]
  3. Zhang YJ, Li MP, Tang J, Chen XP: Pharmacokinetic and Pharmacodynamic Responses to Clopidogrel: Evidences and Perspectives. Int J Environ Res Public Health. 2017 Mar 14;14(3). pii: ijerph14030301. doi: 10.3390/ijerph14030301. [Article]
  4. Jiang XL, Samant S, Lesko LJ, Schmidt S: Clinical pharmacokinetics and pharmacodynamics of clopidogrel. Clin Pharmacokinet. 2015 Feb;54(2):147-66. doi: 10.1007/s40262-014-0230-6. [Article]
  5. Karazniewicz-Lada M, Danielak D, Burchardt P, Kruszyna L, Komosa A, Lesiak M, Glowka F: Clinical pharmacokinetics of clopidogrel and its metabolites in patients with cardiovascular diseases. Clin Pharmacokinet. 2014 Feb;53(2):155-64. doi: 10.1007/s40262-013-0105-2. [Article]
  6. Umemura K, Iwaki T: The Pharmacokinetics and Pharmacodynamics of Prasugrel and Clopidogrel in Healthy Japanese Volunteers. Clin Pharmacol Drug Dev. 2016 Nov;5(6):480-487. doi: 10.1002/cpdd.259. Epub 2016 Apr 25. [Article]
  7. Frelinger AL 3rd, Barnard MR, Fox ML, Michelson AD: The Platelet Activity After Clopidogrel Termination (PACT) study. Circ Cardiovasc Interv. 2010 Oct;3(5):442-9. doi: 10.1161/CIRCINTERVENTIONS.110.937961. Epub 2010 Aug 24. [Article]
  8. Plosker GL, Lyseng-Williamson KA: Clopidogrel: a review of its use in the prevention of thrombosis. Drugs. 2007;67(4):613-46. doi: 10.2165/00003495-200767040-00013. [Article]
  9. FDA Approved Drug Products: Clopidogrel Oral Tablets [Link]
Human Metabolome Database
HMDB0005011
KEGG Drug
D00769
PubChem Compound
60606
PubChem Substance
46507295
ChemSpider
54632
BindingDB
50318910
RxNav
32968
ChEBI
37941
ChEMBL
CHEMBL1771
ZINC
ZINC000034781704
Therapeutic Targets Database
DAP000178
PharmGKB
PA449053
PDBe Ligand
CGE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Clopidogrel
PDB Entries
4h1n
FDA label
Download (402 KB)
MSDS
Download (57.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAngioplasty, Transluminal, Percutaneous Coronary / Coronary Heart Disease (CHD)1
4Active Not RecruitingTreatmentCoronary Artery Disease (CAD) / DES1
4Active Not RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19)1
4Active Not RecruitingTreatmentMyocardial Infarction1
4CompletedNot AvailableCoronary Heart Disease (CHD)1

Pharmacoeconomics

Manufacturers
  • Dr reddys laboratories inc
  • Sanofi aventis us llc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Bristol-Myers Squibb Co.
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Dept Health Central Pharmacy
  • Doctor Reddys Laboratories Ltd.
  • PD-Rx Pharmaceuticals Inc.
  • Physician Partners Ltd.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Promex Medical Inc.
  • Remedy Repack
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • Squibb Manufacturing Co.
  • Stat Rx Usa
  • Vangard Labs Inc.
Dosage Forms
FormRouteStrength
TabletOral97.857 mg
Tablet, coatedOral
Tablet, coatedOral75 mg
TabletOral97.900 mg
Tablet, film coatedOral98 MG
TabletOral300 mg/1
Tablet, film coatedOral300 mg/1
Tablet, coatedOral7500000 mg
TabletOral7500000 mg
Tablet, film coatedOral75 MG/75MG
Tablet, film coatedOral75 MG/100MG
TabletOral75 mg/1
Tablet, film coatedOral97.875 mg
Tablet, film coatedOral97875 MG
KitOral
Tablet, film coatedOral75 mg
TabletOral
Tablet, film coatedOral
Tablet, film coatedOral100 mg
TabletOral97.875 mg
TabletOral75 mg
TabletOral75.00 mg
TabletOral97.86 mg
TabletOral97.854 mg
CapsuleOral
TabletOral75.000 MG
TabletOral98.000 mg
TabletOral75. mg
Tablet, film coatedOral75.00 mg
Tablet, film coatedOral
TabletOral300 mg
Tablet, film coatedOral75 mg/1
Tablet, film coatedOral300 mg
TabletOral97.830 mg
TabletOral
Prices
Unit descriptionCostUnit
Plavix 300 mg tablet24.86USD tablet
Plavix 75 mg tablet9.23USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US4847265No1989-07-112011-11-17US flag
CA2334870No2005-03-152019-06-10Canada flag
CA1336777No1995-08-222012-08-22Canada flag
US6429210Yes2002-08-062019-12-10US flag
US6504030Yes2003-01-072019-12-10US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)158 °Chttp://www.chemspider.com/Chemical-Structure.54632.html?rid=9b9b483b-9db2-454c-a1be-2494307b6b23&page_num=0
Predicted Properties
PropertyValueSource
Water Solubility0.0118 mg/mLALOGPS
logP3.84ALOGPS
logP4.03Chemaxon
logS-4.4ALOGPS
pKa (Strongest Basic)4.77Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area29.54 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity84.93 m3·mol-1Chemaxon
Polarizability33.19 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9847
Caco-2 permeable+0.5777
P-glycoprotein substrateSubstrate0.6664
P-glycoprotein inhibitor IInhibitor0.6556
P-glycoprotein inhibitor IIInhibitor0.5558
Renal organic cation transporterInhibitor0.6368
CYP450 2C9 substrateNon-substrate0.7407
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6339
CYP450 1A2 substrateInhibitor0.724
CYP450 2C9 inhibitorNon-inhibitor0.5223
CYP450 2D6 inhibitorInhibitor0.5712
CYP450 2C19 inhibitorInhibitor0.8071
CYP450 3A4 inhibitorNon-inhibitor0.7389
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9188
Ames testNon AMES toxic0.7112
CarcinogenicityNon-carcinogens0.9597
BiodegradationNot ready biodegradable0.9911
Rat acute toxicity2.4887 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7548
hERG inhibition (predictor II)Non-inhibitor0.6329
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (71.9 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03di-3980000000-d577843e19cf599f8a0b
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0229-0967000000-6c51c479e90818ec703b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0229-0967000000-6c51c479e90818ec703b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2900000000-be6dbedd4a0c4f60d0dd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0059000000-bfd69ae718755c36c017
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0089000000-05d22eeaa0e9f436aaa7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-022c-0398000000-c49336f7a25961f037a7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-9271000000-d2d6301de1e4d8e69274
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0960000000-c208a61443ad2b5f73aa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-6690000000-e45518a10087289cedf9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-174.5010461
predicted
DarkChem Lite v0.1.0
[M-H]-160.82198
predicted
DeepCCS 1.0 (2019)
[M+H]+175.5254461
predicted
DarkChem Lite v0.1.0
[M+H]+163.17998
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.8746461
predicted
DarkChem Lite v0.1.0
[M+Na]+170.03798
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Required for normal platelet aggregation and blood coagulation.
Gene Name
P2RY12
Uniprot ID
Q9H244
Uniprot Name
P2Y purinoceptor 12
Molecular Weight
39438.355 Da
References
  1. Dorsam RT, Murugappan S, Ding Z, Kunapuli SP: Clopidogrel: interactions with the P2Y12 receptor and clinical relevance. Hematology. 2003 Dec;8(6):359-65. [Article]
  2. Herbert JM, Savi P: P2Y12, a new platelet ADP receptor, target of clopidogrel. Semin Vasc Med. 2003 May;3(2):113-22. [Article]
  3. Taubert D, Kastrati A, Harlfinger S, Gorchakova O, Lazar A, von Beckerath N, Schomig A, Schomig E: Pharmacokinetics of clopidogrel after administration of a high loading dose. Thromb Haemost. 2004 Aug;92(2):311-6. [Article]
  4. Wang L, Jacobsen SE, Bengtsson A, Erlinge D: P2 receptor mRNA expression profiles in human lymphocytes, monocytes and CD34+ stem and progenitor cells. BMC Immunol. 2004 Aug 3;5:16. [Article]
  5. Wihlborg AK, Wang L, Braun OO, Eyjolfsson A, Gustafsson R, Gudbjartsson T, Erlinge D: ADP receptor P2Y12 is expressed in vascular smooth muscle cells and stimulates contraction in human blood vessels. Arterioscler Thromb Vasc Biol. 2004 Oct;24(10):1810-5. Epub 2004 Aug 12. [Article]
  6. Gladding P, Webster M, Zeng I, Farrell H, Stewart J, Ruygrok P, Ormiston J, El-Jack S, Armstrong G, Kay P, Scott D, Gunes A, Dahl ML: The pharmacogenetics and pharmacodynamics of clopidogrel response: an analysis from the PRINC (Plavix Response in Coronary Intervention) trial. JACC Cardiovasc Interv. 2008 Dec;1(6):620-7. doi: 10.1016/j.jcin.2008.09.008. [Article]
  7. Savi P, Zachayus JL, Delesque-Touchard N, Labouret C, Herve C, Uzabiaga MF, Pereillo JM, Culouscou JM, Bono F, Ferrara P, Herbert JM: The active metabolite of Clopidogrel disrupts P2Y12 receptor oligomers and partitions them out of lipid rafts. Proc Natl Acad Sci U S A. 2006 Jul 18;103(29):11069-74. Epub 2006 Jul 11. [Article]
  8. van Gestel MA, Heemskerk JW, Slaaf DW, Heijnen VV, Reneman RS, oude Egbrink MG: In vivo blockade of platelet ADP receptor P2Y12 reduces embolus and thrombus formation but not thrombus stability. Arterioscler Thromb Vasc Biol. 2003 Mar 1;23(3):518-23. Epub 2003 Jan 23. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
Curator comments
Clopidogrel inhibited CYP2C9 at high concentrations in vitro, but showed no effects on the pharmacokinetics of warfarin (CYP2C9 substrate) when clopidogrel was administered at 75 mg a day [F1912].
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Richter T, Murdter TE, Heinkele G, Pleiss J, Tatzel S, Schwab M, Eichelbaum M, Zanger UM: Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J Pharmacol Exp Ther. 2004 Jan;308(1):189-97. doi: 10.1124/jpet.103.056127. Epub 2003 Oct 16. [Article]
  2. Farid NA, Payne CD, Small DS, Winters KJ, Ernest CS 2nd, Brandt JT, Darstein C, Jakubowski JA, Salazar DE: Cytochrome P450 3A inhibition by ketoconazole affects prasugrel and clopidogrel pharmacokinetics and pharmacodynamics differently. Clin Pharmacol Ther. 2007 May;81(5):735-41. doi: 10.1038/sj.clpt.6100139. Epub 2007 Mar 14. [Article]
  3. Clopidogrel FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Sangkuhl K, Klein TE, Altman RB: Clopidogrel pathway. Pharmacogenet Genomics. 2010 Jul;20(7):463-5. doi: 10.1097/FPC.0b013e3283385420. [Article]
  2. Jiang XL, Samant S, Lesko LJ, Schmidt S: Clinical pharmacokinetics and pharmacodynamics of clopidogrel. Clin Pharmacokinet. 2015 Feb;54(2):147-66. doi: 10.1007/s40262-014-0230-6. [Article]
  3. Polasek TM, Doogue MP, Miners JO: Metabolic activation of clopidogrel: in vitro data provide conflicting evidence for the contributions of CYP2C19 and PON1. Ther Adv Drug Saf. 2011 Dec;2(6):253-61. doi: 10.1177/2042098611422559. [Article]
  4. Clopidogrel FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Itkonen MK, Tornio A, Filppula AM, Neuvonen M, Neuvonen PJ, Niemi M, Backman JT: Clopidogrel but Not Prasugrel Significantly Inhibits the CYP2C8-Mediated Metabolism of Montelukast in Humans. Clin Pharmacol Ther. 2018 Sep;104(3):495-504. doi: 10.1002/cpt.947. Epub 2017 Dec 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Zhu HJ, Wang X, Gawronski BE, Brinda BJ, Angiolillo DJ, Markowitz JS: Carboxylesterase 1 as a determinant of clopidogrel metabolism and activation. J Pharmacol Exp Ther. 2013 Mar;344(3):665-72. doi: 10.1124/jpet.112.201640. Epub 2012 Dec 28. [Article]
  2. Qiu Z, Li N, Song L, Lu Y, Jing J, Parekha HS, Gao W, Tian F, Wang X, Ren S, Chen X: Contributions of intestine and plasma to the presystemic bioconversion of vicagrel, an acetate of clopidogrel. Pharm Res. 2014 Jan;31(1):238-51. doi: 10.1007/s11095-013-1158-5. Epub 2013 Sep 14. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Saw J, Steinhubl SR, Berger PB, Kereiakes DJ, Serebruany VL, Brennan D, Topol EJ: Lack of adverse clopidogrel-atorvastatin clinical interaction from secondary analysis of a randomized, placebo-controlled clopidogrel trial. Circulation. 2003 Aug 26;108(8):921-4. Epub 2003 Aug 18. [Article]
  3. Neubauer H, Gunesdogan B, Hanefeld C, Spiecker M, Mugge A: Lipophilic statins interfere with the inhibitory effects of clopidogrel on platelet function--a flow cytometry study. Eur Heart J. 2003 Oct;24(19):1744-9. [Article]
  4. Lau WC, Gurbel PA, Watkins PB, Neer CJ, Hopp AS, Carville DG, Guyer KE, Tait AR, Bates ER: Contribution of hepatic cytochrome P450 3A4 metabolic activity to the phenomenon of clopidogrel resistance. Circulation. 2004 Jan 20;109(2):166-71. Epub 2004 Jan 5. [Article]
  5. Mukherjee D, Kline-Rogers E, Fang J, Munir K, Eagle KA: Lack of clopidogrel-CYP3A4 statin interaction in patients with acute coronary syndrome. Heart. 2005 Jan;91(1):23-6. [Article]
  6. Poulsen TS, Vinholt P, Mickley H, Korsholm L, Kristensen SR, Damkier P: Existence of a clinically relevant interaction between clopidogrel and HMG-CoA reductase inhibitors? Re-evaluating the evidence. Basic Clin Pharmacol Toxicol. 2005 Feb;96(2):103-10. [Article]
  7. Clarke TA, Waskell LA: The metabolism of clopidogrel is catalyzed by human cytochrome P450 3A and is inhibited by atorvastatin. Drug Metab Dispos. 2003 Jan;31(1):53-9. [Article]
Details
6. Cytochrome P450 2B6
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Richter T, Murdter TE, Heinkele G, Pleiss J, Tatzel S, Schwab M, Eichelbaum M, Zanger UM: Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J Pharmacol Exp Ther. 2004 Jan;308(1):189-97. doi: 10.1124/jpet.103.056127. Epub 2003 Oct 16. [Article]
  2. Turpeinen M, Tolonen A, Uusitalo J, Jalonen J, Pelkonen O, Laine K: Effect of clopidogrel and ticlopidine on cytochrome P450 2B6 activity as measured by bupropion hydroxylation. Clin Pharmacol Ther. 2005 Jun;77(6):553-9. doi: 10.1016/j.clpt.2005.02.010. [Article]
  3. Sangkuhl K, Klein TE, Altman RB: Clopidogrel pathway. Pharmacogenet Genomics. 2010 Jul;20(7):463-5. doi: 10.1097/FPC.0b013e3283385420. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Turgeon J, Pharand C, Michaud V: Understanding clopidogrel efficacy in the presence of cytochrome P450 polymorphism. CMAJ. 2006 Jun 6;174(12):1729. doi: 10.1503/cmaj.060502. [Article]
  2. Clarke TA, Waskell LA: The metabolism of clopidogrel is catalyzed by human cytochrome P450 3A and is inhibited by atorvastatin. Drug Metab Dispos. 2003 Jan;31(1):53-9. [Article]
Details
8. Cytochrome P450 2C19
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Ford NF: The Metabolism of Clopidogrel: CYP2C19 Is a Minor Pathway. J Clin Pharmacol. 2016 Dec;56(12):1474-1483. doi: 10.1002/jcph.769. Epub 2016 Jun 22. [Article]
  2. Chen K, Zhang R, Liu H, Guo X, Li P, Liu X: Impact of the CYP2C19 Gene Polymorphism on Clopidogrel Personalized Drug Regimen and the Clinical Outcomes. Clin Lab. 2016 Sep 1;62(9):1773-1780. doi: 10.7754/Clin.Lab.2016.160216. [Article]
  3. Flockhart Table of Drug Interactions [Link]
  4. Clopidogrel Therapy and CYP2C19 Genotype [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Mostafizar M, Haque P, Mazid A, Shohel M, Shazly G, Kazi M, Reza HM: CHARACTERIZATION OF BINDING SITES OF CLOPIDOGREL AND INTERFERENCE OF LINOLEIC ACID AT THE BINDING SITE ON BOVINE SERUM ALBUMIN. Acta Pol Pharm. 2017 Jan;74(1):119-125. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Taubert D, von Beckerath N, Grimberg G, Lazar A, Jung N, Goeser T, Kastrati A, Schomig A, Schomig E: Impact of P-glycoprotein on clopidogrel absorption. Clin Pharmacol Ther. 2006 Nov;80(5):486-501. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Li L, Song F, Tu M, Wang K, Zhao L, Wu X, Zhou H, Xia Z, Jiang H: In vitro interaction of clopidogrel and its hydrolysate with OCT1, OCT2 and OAT1. Int J Pharm. 2014 Apr 25;465(1-2):5-10. doi: 10.1016/j.ijpharm.2014.02.003. Epub 2014 Feb 11. [Article]
  2. Dujic T, Zhou K, Donnelly LA, Tavendale R, Palmer CN, Pearson ER: Association of Organic Cation Transporter 1 With Intolerance to Metformin in Type 2 Diabetes: A GoDARTS Study. Diabetes. 2015 May;64(5):1786-93. doi: 10.2337/db14-1388. Epub 2014 Dec 15. [Article]
  3. Stage TB, Brosen K, Christensen MM: A Comprehensive Review of Drug-Drug Interactions with Metformin. Clin Pharmacokinet. 2015 Aug;54(8):811-24. doi: 10.1007/s40262-015-0270-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Li L, Song F, Tu M, Wang K, Zhao L, Wu X, Zhou H, Xia Z, Jiang H: In vitro interaction of clopidogrel and its hydrolysate with OCT1, OCT2 and OAT1. Int J Pharm. 2014 Apr 25;465(1-2):5-10. doi: 10.1016/j.ijpharm.2014.02.003. Epub 2014 Feb 11. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48