Explore a selection of our essential drug information below, or:
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
Structure for Clopidogrel (DB00758)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to manage Acute coronary syndrome (acs) Combination Product in combination with: Acetylsalicylic acid (DB00945) •••••••••••• ••••• Used in combination to manage Acute myocardial infarction Combination Product in combination with: Acetylsalicylic acid (DB00945) •••••••••••• ••••• •••••••• ••• •••••••••••• ••••••• Prevention of Cardiovascular event •••••••••••• Prevention of Cardiovascular event •••••••••••• Prevention of Cardiovascular event •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Target Actions Organism AP2Y purinoceptor 12 antagonistHumans - 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
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- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
Pathway Category Clopidogrel Action Pathway Drug action Clopidogrel Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C9 CYP2C9*3 (C;C) / (A;C) C Allele Effect Directly Studied Patients with this genotype have reduced metabolism of clopidogrel resulting in reduced plasma concentrations of its active metabolite. Details Cytochrome P450 2C19 CYP2C19*2 (A;A) / (A;G) G > A Effect Directly Studied Patients with this genotype have reduced metabolism of clopidogrel resulting in reduced plasma concentrations of its active metabolite. Details Cytochrome P450 2C19 CYP2C19*2 Not Available 681G>A ADR Directly Studied Patients 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 2C19 CYP2C19*3 Not Available 636G>A Directly Studied Effect The presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of clopidogrel. Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G ADR Inferred Poor drug metabolizer, increased risk for adverse cardiovascular events and lower efficacy. Alternative recommended. Details Cytochrome P450 2C9 CYP2C9*6 Not Available 818delA Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*15 Not Available 485C>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*25 Not Available 353_362delAGAAATGGAA Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*35 Not Available 374G>T / 430C>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*2 Not Available 430C>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*4 Not Available 1076T>C Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*5 Not Available 1080C>G Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*8 Not Available 449G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*11 Not Available 1003C>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*12 Not Available 1465C>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*13 Not Available 269T>C Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*14 Not Available 374G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*16 Not Available 895A>G Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*18 Not Available 1075A>C / 1190A>C … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*26 Not Available 389C>G Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*28 Not Available 641A>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*30 Not Available 1429G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C9 CYP2C9*33 Not Available 395G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*3 Not Available 636G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G Effect Inferred Poor drug metabolizer, lower dose requirements, higher risk for drug-drug interactions Details
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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Clopidogrel can be increased when it is combined with Abametapir. Abatacept The metabolism of Clopidogrel can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Clopidogrel is combined with Abciximab. Abiraterone The serum concentration of Clopidogrel can be increased when it is combined with Abiraterone. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Clopidogrel is combined with Abrocitinib. - Food Interactions
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Clopidogrel besilate BL9VGG8BHW 744256-69-7 CUZIJKLLBDXNFV-RSAXXLAASA-N Clopidogrel bisulfate 08I79HTP27 120202-66-6 FDEODCTUSIWGLK-RSAXXLAASA-N Clopidogrel hydrochloride 426O7XWS6Y 120202-65-5 XIHVAFJSGWDBGA-RSAXXLAASA-N Clopidogrel resinate F5Q3N98VAM 1023927-71-0 Not applicable - Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Clopidogrel Tablet 75 mg Oral TEVA Canada Limited 2011-12-07 Not applicable Canada 
Clopido Grel 1a Pharma Tablet, film coated 75 mg Oral Acino Pharma Gmb H 2016-09-08 2011-02-01 EU 
Clopidogre Ratiopharm Tablet, film coated 75 mg Oral Teva B.V. 2016-09-08 Not applicable EU Clopidogrel Tablet 75 mg Oral Sivem Pharmaceuticals Ulc 2012-06-11 Not applicable Canada Clopidogrel Tablet 75 mg Oral Sanis Health Inc 2013-02-13 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abbott-clopidogrel Tablet 75 mg Oral Abbott 2014-03-17 2015-12-31 Canada Accel-clopidogrel Tablet 300 mg Oral Accel Pharma Inc Not applicable Not applicable Canada Accel-clopidogrel Tablet 75 mg Oral Accel Pharma Inc 2014-09-04 2015-11-09 Canada Ag-clopidogrel Tablet 75 mg Oral Angita Pharma Inc. 2022-02-10 Not applicable Canada Apo-clopidogrel Tablet 300 mg Oral Apotex Corporation 2013-01-21 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CLOPIDOGREL E ACIDO ACETILSALICILICO VIATRIS Clopidogrel (75 mg) + Acetylsalicylic acid (100 mg) Tablet, film coated Oral Viatris Limited 2020-05-08 Not applicable Italy 
CLOPIDOGREL E ACIDO ACETILSALICILICO VIATRIS Clopidogrel (75 mg) + Acetylsalicylic acid (75 mg) Tablet, film coated Oral Viatris Limited 2020-05-08 Not applicable Italy CLOPIDOGREL E ACIDO ACETILSALICILICO VIATRIS Clopidogrel (75 mg) + Acetylsalicylic acid (100 mg) Tablet, film coated Oral Viatris Limited 2020-05-08 Not applicable Italy CLOPIDOGREL E ACIDO ACETILSALICILICO VIATRIS Clopidogrel (75 mg) + Acetylsalicylic acid (100 mg) Tablet, film coated Oral Viatris Limited 2020-05-08 Not applicable Italy CLOPIDOGREL E ACIDO ACETILSALICILICO VIATRIS Clopidogrel (75 mg) + Acetylsalicylic acid (75 mg) Tablet, film coated Oral Viatris Limited 2020-05-08 Not applicable Italy
Categories
- ATC Codes
- B01AC04 — Clopidogrel
- Drug Categories
- Antiplatelet agents
- Blood and Blood Forming Organs
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (moderate)
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strong)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Decreased Platelet Aggregation
- Hematologic Agents
- Heterocyclic Compounds, Fused-Ring
- Neurotransmitter Agents
- OCT1 inhibitors
- OCT2 Inhibitors
- P-glycoprotein substrates
- P2Y12 Platelet Inhibitor
- Platelet Aggregation Inhibitors Excl. Heparin
- Purinergic Agents
- Purinergic Antagonists
- Purinergic P2 Receptor Antagonists
- Purinergic P2Y Receptor Antagonists
- Pyridines
- Sulfur Compounds
- Thienopyridines
- Thiophenes
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: Clopidogrel Oral Tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0005011
- KEGG Drug
- D00769
- PubChem Compound
- 60606
- PubChem Substance
- 46507295
- ChemSpider
- 54632
- BindingDB
- 50318910
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Coronary Artery Disease (CAD) / Coronary Artery Stenosis 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Coronary Artery Disease (CAD) / Peripheral Arterial Disease (PAD) 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Coronary Artery Disease (CAD) / De Novo Stenosis / Percutaneous Coronary Intervention (PCI) 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Migraine / Patent Foramen Ovale (PFO) 1 somestatus stop reason just information to hide Not Available Completed Not Available Acute Coronary Syndrome (ACS) / Bleeding / Clopidogrel / Novel Anti-platelets / Ticagrelor 1 somestatus stop reason just information to hide
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
Form Route Strength Tablet, film coated Oral Tablet Oral 97.857 mg Tablet, coated Oral Tablet, coated Oral 75 mg Tablet, film coated Oral 112.1 mg Tablet Oral 97.900 mg Tablet Oral 300 mg/1 Tablet, film coated Oral 300 mg/1 Tablet, coated Oral 7500000 mg Tablet Oral 7500000 mg Tablet, film coated Oral 75 MG/75MG Tablet, film coated Oral 75 MG/100MG Tablet Oral 75 mg/1 Tablet, film coated Oral 75 mg/mL Tablet, film coated Oral 97.87 Mg Tablet, film coated Oral 97.88 MG Tablet, film coated Oral 97.9 Mg Tablet, film coated Oral 97875 MG Tablet, film coated Oral 98 MG Kit Oral Tablet, film coated Oral 75 mg Tablet, film coated Oral 100 mg Tablet Oral 97.875 mg Tablet Oral 75 mg Tablet Oral 75.00 mg Tablet Oral Tablet, film coated Oral Tablet Oral 97.86 mg Tablet Oral 97.854 mg Capsule Oral Tablet Oral 75.000 MG Tablet Oral 98.000 mg Tablet Oral 75. mg Tablet, film coated Oral 75.00 mg Tablet, film coated Oral 97.875 MG Tablet Oral 300 mg Tablet, film coated Oral 75 mg/1 Tablet, film coated Oral 300 mg Tablet Oral 97.830 mg Tablet Oral Tablet, film coated Oral 97858 MG - Prices
Unit description Cost Unit Plavix 300 mg tablet 24.86USD tablet Plavix 75 mg tablet 9.23USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US4847265 No 1989-07-11 2011-11-17 US 
CA2334870 No 2005-03-15 2019-06-10 Canada CA1336777 No 1995-08-22 2012-08-22 Canada US6429210 Yes 2002-08-06 2019-12-10 US US6504030 Yes 2003-01-07 2019-12-10 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 158 °C http://www.chemspider.com/Chemical-Structure.54632.html?rid=9b9b483b-9db2-454c-a1be-2494307b6b23&page_num=0 - Predicted Properties
Property Value Source Water Solubility 0.0118 mg/mL ALOGPS logP 3.84 ALOGPS logP 4.03 Chemaxon logS -4.4 ALOGPS pKa (Strongest Basic) 4.77 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 29.54 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 84.93 m3·mol-1 Chemaxon Polarizability 33.19 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9847 Caco-2 permeable + 0.5777 P-glycoprotein substrate Substrate 0.6664 P-glycoprotein inhibitor I Inhibitor 0.6556 P-glycoprotein inhibitor II Inhibitor 0.5558 Renal organic cation transporter Inhibitor 0.6368 CYP450 2C9 substrate Non-substrate 0.7407 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6339 CYP450 1A2 substrate Inhibitor 0.724 CYP450 2C9 inhibitor Non-inhibitor 0.5223 CYP450 2D6 inhibitor Inhibitor 0.5712 CYP450 2C19 inhibitor Inhibitor 0.8071 CYP450 3A4 inhibitor Non-inhibitor 0.7389 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9188 Ames test Non AMES toxic 0.7112 Carcinogenicity Non-carcinogens 0.9597 Biodegradation Not ready biodegradable 0.9911 Rat acute toxicity 2.4887 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7548 hERG inhibition (predictor II) Non-inhibitor 0.6329
Spectra
- Mass Spec (NIST)
- Download (71.9 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.5010461 predictedDarkChem Lite v0.1.0 [M-H]- 160.82198 predictedDeepCCS 1.0 (2019) [M+H]+ 175.5254461 predictedDarkChem Lite v0.1.0 [M+H]+ 163.17998 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.8746461 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.03798 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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
- Specific Function
- G protein-coupled adenosine receptor activity
- Gene Name
- P2RY12
- Uniprot ID
- Q9H244
- Uniprot Name
- P2Y purinoceptor 12
- Molecular Weight
- 39438.355 Da
References
- 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]
- Herbert JM, Savi P: P2Y12, a new platelet ADP receptor, target of clopidogrel. Semin Vasc Med. 2003 May;3(2):113-22. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- 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]
- 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]
- Clopidogrel FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
References
- Sangkuhl K, Klein TE, Altman RB: Clopidogrel pathway. Pharmacogenet Genomics. 2010 Jul;20(7):463-5. doi: 10.1097/FPC.0b013e3283385420. [Article]
- 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]
- 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]
- Clopidogrel FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- 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
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester (PubMed:18762277, PubMed:7980644, PubMed:9169443, PubMed:9490062). Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine (PubMed:7980644). Catalyzes the transesterification of cocaine to form cocaethylene (PubMed:7980644). Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate (PubMed:7980644). Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes of 2-arachidonoylglycerol and prostaglandins (PubMed:21049984). Hydrolyzes cellular cholesteryl esters to free cholesterols and promotes reverse cholesterol transport (RCT) by facilitating both the initial and final steps in the process (PubMed:11015575, PubMed:16024911, PubMed:16971496, PubMed:18762277). First of all, allows free cholesterol efflux from macrophages to extracellular cholesterol acceptors and secondly, releases free cholesterol from lipoprotein-delivered cholesteryl esters in the liver for bile acid synthesis or direct secretion into the bile (PubMed:16971496, PubMed:18599737, PubMed:18762277)
- Specific Function
- carboxylesterase activity
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- 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]
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- 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]
- 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]
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
- Clopidogrel Therapy and CYP2C19 Genotype [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- 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
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:11388889, PubMed:11408531, PubMed:12439218, PubMed:12719534, PubMed:15389554, PubMed:16263091, PubMed:16272756, PubMed:16581093, PubMed:19536068, PubMed:21128598, PubMed:23680637, PubMed:24961373, PubMed:34040533, PubMed:9187257, PubMed:9260930, PubMed:9655880). Functions as a pH- and Na(+)-independent, bidirectional transporter (By similarity). Cation cellular uptake or release is driven by the electrochemical potential (i.e. membrane potential and concentration gradient) and substrate selectivity (By similarity). Hydrophobicity is a major requirement for recognition in polyvalent substrates and inhibitors (By similarity). Primarily expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (By similarity). Most likely functions as an uptake carrier in enterocytes contributing to the intestinal elimination of organic cations from the systemic circulation (PubMed:16263091). Transports endogenous monoamines such as N-1-methylnicotinamide (NMN), guanidine, histamine, neurotransmitters dopamine, serotonin and adrenaline (PubMed:12439218, PubMed:24961373, PubMed:35469921, PubMed:9260930). Also transports natural polyamines such as spermidine, agmatine and putrescine at low affinity, but relatively high turnover (PubMed:21128598). Involved in the hepatic uptake of vitamin B1/thiamine, hence regulating hepatic lipid and energy metabolism (PubMed:24961373). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with lower efficency (PubMed:17460754). Also capable of transporting non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). May contribute to the transport of cationic compounds in testes across the blood-testis-barrier (Probable). Also involved in the uptake of xenobiotics tributylmethylammonium (TBuMA), quinidine, N-methyl-quinine (NMQ), N-methyl-quinidine (NMQD) N-(4,4-azo-n-pentyl)-quinuclidine (APQ), azidoprocainamide methoiodide (AMP), N-(4,4-azo-n-pentyl)-21-deoxyajmalinium (APDA) and 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:11408531, PubMed:15389554, PubMed:35469921, PubMed:9260930)
- Specific Function
- (R)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- 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]
- 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]
- 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
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:9260930, PubMed:9687576). Functions as a Na(+)-independent, bidirectional uniporter (PubMed:21128598, PubMed:9687576). Cation cellular uptake or release is driven by the electrochemical potential, i.e. membrane potential and concentration gradient (PubMed:15212162, PubMed:9260930, PubMed:9687576). However, may also engage electroneutral cation exchange when saturating concentrations of cation substrates are reached (By similarity). Predominantly expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (PubMed:15783073). Implicated in monoamine neurotransmitters uptake such as histamine, dopamine, adrenaline/epinephrine, noradrenaline/norepinephrine, serotonin and tyramine, thereby supporting a physiological role in the central nervous system by regulating interstitial concentrations of neurotransmitters (PubMed:16581093, PubMed:17460754, PubMed:9687576). Also capable of transporting dopaminergic neuromodulators cyclo(his-pro), salsolinol and N-methyl-salsolinol, thereby involved in the maintenance of dopaminergic cell integrity in the central nervous system (PubMed:17460754). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Also transports guanidine and endogenous monoamines such as vitamin B1/thiamine, creatinine and N-1-methylnicotinamide (NMN) (PubMed:12089365, PubMed:15212162, PubMed:17072098, PubMed:24961373, PubMed:9260930). Mediates the uptake and efflux of quaternary ammonium compound choline (PubMed:9260930). Mediates the bidirectional transport of polyamine agmatine and the uptake of polyamines putrescine and spermidine (PubMed:12538837, PubMed:21128598). Able to transport non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). Also involved in the uptake of xenobiotic 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:12395288, PubMed:16394027). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- acetylcholine transmembrane transporter activity
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- 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 October 03, 2024 22:14