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Identification
- Summary
Ticagrelor is a P2Y12 platelet inhibitor used in patients with a history of myocardial infarction or with acute coronary syndrome (ACS) to prevent future myocardial infarction, stroke and cardiovascular death.
- Brand Names
- Brilinta, Brilique
- Generic Name
- Ticagrelor
- DrugBank Accession Number
- DB08816
- Background
Ticagrelor, or AZD6140, was first described in the literature in 2003.4,5 Ticagrelor is an ADP derivative developed for its P2Y12 receptor antagonism.5 Unlike clopidogrel, ticagrelor is not a prodrug.5 It is marketed by Astra Zeneca as Brilinta in the US6 and Brilique or Possia in the EU,7.
Ticagrelor was granted EMA approval on 3 December 2010.7 Ticagrelor was granted FDA approval on 20 July 2011.6
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Ticagrelor (DB08816)
- Weight
- Average: 522.568
Monoisotopic: 522.186080514 - Chemical Formula
- C23H28F2N6O4S
- Synonyms
- (1S,2S,3R,5S)-3-(7-((1R,2S)-2-(3,4-Difluorophenyl)cyclopropylamino)-5-(propylthio)-3H-(1,2,3)triazolo(4,5-d)pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
- Ticagrelor
- External IDs
- AR-C126532XX
- AZD 6140
- AZD-6140
- AZD6140
Pharmacology
- Indication
Ticagrelor is indicated to reduce the risk of cardiovascular death, myocardial infarction, and stroke in patients with acute coronary syndrome or a history of myocardial infarction.6 Ticagrelor is also indicated to reduce the risk of a first myocardial infarction or stroke in high risk patients with coronary artery disease.6
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 Prevention of Cardiovascular mortality •••••••••••• ••••• •••••••• •••••••• ••••• •••••• Prevention of Cardiovascular mortality •••••••••••• ••••••• •• •••••••••• •••••••••• •••••• Prevention of Cerebrovascular accident •••••••••••• •••• •••••••• ••••• ••••••••• •••••••• •••••• •••••• Prevention of Cerebrovascular accident •••••••••••• ••••••• •••••• •••••• •••••••• •••••• Prevention of Cerebrovascular accident •••••••••••• ••••• •••••••• •••••••• ••••• •••••• - 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
Ticagrelor is a P2Y12 receptor antagonist that inhibits the formation of thromboses to reduce the risk of myocardial infarction and ischemic stroke.1,3 It has a moderate duration of action as it is given twice daily, and a wide therapeutic index as high single doses are well tolerated.6,7 Patients should be counselled regarding the risk of bleeding, dyspnea, and bradyarrhythmias.6
- Mechanism of action
Ticagrelor is a P2Y12 receptor antagonist.1
The P2Y12 receptor couples with Gαi2 and other Gi proteins which inhibit adenylyl cyclase.3 Gi mediated signalling also activates PI3K, Akt, Rap1b, and potassium channels.3 The downstream effects of these activities mediate hemostasis and lead to platelet aggregation.3
Antagonism of the P2Y12 receptor reduces development of occlusive thromboses, which can reduce the risk of myocardial infarction and ischemic stroke.3
Target Actions Organism AP2Y purinoceptor 12 inhibitorHumans - Absorption
Ticagrelor is 36% orally bioavailable.6 A single 200mg oral dose of ticagrelor reaches a Cmax of 923ng/mL, with a Tmax of 1.5 hours and an AUC of 6675ng*h/mL.1 The active metabolite of ticagrelor reaches a Cmax of 264ng/mL, with a Tmax of 3.0 hours and an AUC of 2538ng*h/mL.1
- Volume of distribution
The steady state volume of distribution of ticagrelor is 88 L.6
- Protein binding
Ticagrelor and its active metabolite ate >99% protein bound in plasma, particularly albumin.2,6
- Metabolism
The complete structure of all ticagrelor metabolites are not well defined.1 Ticagrelor can be dealkylated at postition 5 of the cyclopentane ring to form the active AR-C124910XX.1 AR-C124910XX's cyclopentane ring can be further glucuronidated or the alkyl chain attached to the sulfur can be hydroxylated.1 Ticagrelor can also be glucuronidated or hydroxylated.1 Ticagrelor can also be N-dealkylated to form AR-C133913XX, which is further glucuronidated or hydroxylated.1
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- Route of elimination
A radiolabelled dose of ticagrelor is 57.8% recovered in feces and 26.5% recovered in urine.1,6 Less than 1% of the dose is recovered as the unmetabolized parent drug.6 The active metabolite AC-C124910XX makes up 21.7% of the recovery in the feces.1 The metabolite AR-C133913XX makes up 9.2% of the recovery in the urine and 2.7% of the recovery in the feces.1 Other minor metabolites are predominantly recovered in the urine.1
- Half-life
Ticagrelor has a plasma half life of approximately 8 hours, while the active metabolite has a plasma half life of approximately 12 hours.1
- Clearance
The renal clearance of ticagrelor is 0.00584L/h.1
- 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
Patients experiencing an overdose may present with bleeding, nausea, vomiting, diarrhea, and ventricular pauses.6 Overdose can be managed through symptomatic and supportive treatment, including ECG monitoring.6,7 Dialysis is not expected to remove ticagrelor from the blood due to it being highly protein bound.6
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
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 Ticagrelor can be increased when it is combined with Abametapir. Abatacept The metabolism of Ticagrelor can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Ticagrelor. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Ticagrelor. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Ticagrelor is combined with Abrocitinib. - Food Interactions
- Avoid grapefruit products. Grapefruit inhibits the CYP3A4 metabolism of ticagrelor, which may increase its serum concentration.
- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Herbs with antiplatelet activity may increase the risk of bleeding. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
- Avoid St. John's Wort. This herb induces the CYP3A4 metabolism of ticagrelor and may reduce its serum concentration.
- 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 Images
- International/Other Brands
- Brilinta / Possia (AstraZeneca)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Brilinta Tablet 90 mg/1 Oral AstraZeneca Pharmaceuticals LP 2011-08-05 Not applicable US 
Brilinta Tablet 90 mg/1 Oral bryant ranch prepack 2011-08-05 2016-04-30 US 
Brilinta Tablet 90 mg/1 Oral Cardinal Health 107, LLC 2011-08-05 Not applicable US 
Brilinta Tablet 60 mg Oral Astrazeneca Ab 2016-06-13 Not applicable Canada 
Brilinta Tablet 90 mg/1 Oral Aphena Pharma Solutions - Tennessee, LLC 2011-08-05 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-ticagrelor Tablet 90 mg Oral Angita Pharma Inc. 2024-03-28 Not applicable Canada Ag-ticagrelor Tablet 60 mg Oral Angita Pharma Inc. 2024-03-28 Not applicable Canada Apo-ticagrelor Tablet 60 mg Oral Apotex Corporation 2022-12-22 Not applicable Canada Apo-ticagrelor Tablet 90 mg Oral Apotex Corporation 2022-12-14 Not applicable Canada Jamp Ticagrelor Tablet 60 mg Oral Jamp Pharma Corporation 2024-03-28 Not applicable Canada
Categories
- ATC Codes
- B01AC24 — Ticagrelor
- Drug Categories
- Anticoagulants
- Antiplatelet agents
- Blood and Blood Forming Organs
- Carbohydrates
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (weak)
- Cytochrome P-450 CYP2C9 Inducers
- Cytochrome P-450 CYP2C9 Inducers (strength unknown)
- Cytochrome P-450 CYP2C9 Inducers (weak)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Decreased Platelet Aggregation
- Glycosides
- Hematologic Agents
- Heterocyclic Compounds, Fused-Ring
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleosides
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- P2Y12 Platelet Inhibitor
- Phenylalanine Hydroxylase Activators
- Platelet Aggregation Inhibitors Excl. Heparin
- Purine Nucleosides
- Purinergic Agents
- Purinergic Antagonists
- Purinergic P2 Receptor Antagonists
- Purinergic P2Y Receptor Antagonists
- Purines
- Ribonucleosides
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as triazolopyrimidines. These are polycyclic aromatic compounds containing triazole ring fused to a pyrimidine ring. Triazole is a five-membered ring consisting of two carbon atoms and three nitrogen atoms. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Triazolopyrimidines
- Sub Class
- Not Available
- Direct Parent
- Triazolopyrimidines
- Alternative Parents
- Alkylarylthioethers / Aminopyrimidines and derivatives / Secondary alkylarylamines / Fluorobenzenes / Aryl fluorides / Cyclitols and derivatives / Cyclopentanols / Imidolactams / Triazoles / Heteroaromatic compounds show 7 more
- Substituents
- 1,2,3-triazole / Alcohol / Alkylarylthioether / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Aryl thioether / Azacycle show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, aryl sulfide, secondary amino compound, triazolopyrimidines, hydroxyether (CHEBI:68558)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- GLH0314RVC
- CAS number
- 274693-27-5
- InChI Key
- OEKWJQXRCDYSHL-FNOIDJSQSA-N
- InChI
- InChI=1S/C23H28F2N6O4S/c1-2-7-36-23-27-21(26-15-9-12(15)11-3-4-13(24)14(25)8-11)18-22(28-23)31(30-29-18)16-10-17(35-6-5-32)20(34)19(16)33/h3-4,8,12,15-17,19-20,32-34H,2,5-7,9-10H2,1H3,(H,26,27,28)/t12-,15+,16+,17-,19-,20+/m0/s1
- IUPAC Name
- (1S,2S,3R,5S)-3-(7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
- SMILES
- CCCSC1=NC2=C(N=NN2[C@@H]2C[C@H](OCCO)[C@@H](O)[C@H]2O)C(N[C@@H]2C[C@H]2C2=CC(F)=C(F)C=C2)=N1
References
- Synthesis Reference
Anil Shahaji Khile, "NOVEL PROCESSES FOR THE PREPARATION OF PHENYLCYCLOPROPYLAMINE DERIVATIVES AND USE THEREOF FOR PREPARING TICAGRELOR." U.S. Patent US20130165696, issued June 27, 2013.
US20130165696- General References
- Teng R, Oliver S, Hayes MA, Butler K: Absorption, distribution, metabolism, and excretion of ticagrelor in healthy subjects. Drug Metab Dispos. 2010 Sep;38(9):1514-21. doi: 10.1124/dmd.110.032250. Epub 2010 Jun 15. [Article]
- Angheloiu GO, Gugiu GB, Ruse C, Pandey R, Dasari RR, Whatling C: Ticagrelor Removal From Human Blood. JACC Basic Transl Sci. 2017 Apr 24;2(2):135-145. doi: 10.1016/j.jacbts.2017.01.007. eCollection 2017 Apr. [Article]
- Dorsam RT, Kunapuli SP: Central role of the P2Y12 receptor in platelet activation. J Clin Invest. 2004 Feb;113(3):340-5. doi: 10.1172/JCI20986. [Article]
- Jacobson KA, Costanzi S, Ohno M, Joshi BV, Besada P, Xu B, Tchilibon S: Molecular recognition at purine and pyrimidine nucleotide (P2) receptors. Curr Top Med Chem. 2004;4(8):805-19. doi: 10.2174/1568026043450961. [Article]
- Springthorpe B, Bailey A, Barton P, Birkinshaw TN, Bonnert RV, Brown RC, Chapman D, Dixon J, Guile SD, Humphries RG, Hunt SF, Ince F, Ingall AH, Kirk IP, Leeson PD, Leff P, Lewis RJ, Martin BP, McGinnity DF, Mortimore MP, Paine SW, Pairaudeau G, Patel A, Rigby AJ, Riley RJ, Teobald BJ, Tomlinson W, Webborn PJ, Willis PA: From ATP to AZD6140: the discovery of an orally active reversible P2Y12 receptor antagonist for the prevention of thrombosis. Bioorg Med Chem Lett. 2007 Nov 1;17(21):6013-8. Epub 2007 Aug 19. [Article]
- FDA Approved Drug Products: BRILINTA (ticagrelor) tablets, for oral use [Link]
- EMA Summary of Product Characteristics: Brilique Ticagrelor Oral Tablet [Link]
- External Links
- Human Metabolome Database
- HMDB0015702
- KEGG Drug
- D09017
- PubChem Compound
- 9871419
- PubChem Substance
- 175427101
- ChemSpider
- 8047109
- BindingDB
- 50397205
- 1116632
- ChEBI
- 68558
- ChEMBL
- CHEMBL398435
- ZINC
- ZINC000028957444
- PharmGKB
- PA165374673
- PDBe Ligand
- TIQ
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ticagrelor
- PDB Entries
- 5alb / 5alc
- FDA label
- Download (1.21 MB)
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 Treatment Acute Coronary Syndrome (ACS) / Angioplasty, Balloon / Antiplatelet Drugs 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Coronary Artery Disease (CAD) 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 Completed Not Available Acute Coronary Syndrome (ACS) 6 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
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 60 mg Tablet Oral 90 mg Tablet, coated Oral 60 mg Tablet, film coated Oral Tablet, orally disintegrating Oral 90 MG Tablet Oral 60 mg/1 Tablet Oral 90.000 mg Tablet Oral 90 mg/1 Tablet, film coated Oral 60 MG Tablet, film coated Oral 90 mg Tablet, coated Oral 90 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2296665 No 2008-06-10 2018-07-15 Canada CA2351709 No 2010-04-06 2019-12-02 Canada CA2408596 No 2010-12-21 2021-05-31 Canada US7265124 No 2007-09-04 2021-07-09 US US6525060 No 2003-02-25 2019-12-02 US US7250419 No 2007-07-31 2019-12-02 US US6251910 No 2001-06-26 2018-07-15 US US8425934 Yes 2013-04-23 2030-10-17 US USRE46276 Yes 2017-01-17 2025-04-30 US US10300065 Yes 2019-05-28 2036-07-27 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 10 μg/mL FDA Label - Predicted Properties
Property Value Source Water Solubility 0.063 mg/mL ALOGPS logP 2.31 ALOGPS logP 2.28 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 12.94 Chemaxon pKa (Strongest Basic) 1.11 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 138.44 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 142.13 m3·mol-1 Chemaxon Polarizability 51.31 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.994 Blood Brain Barrier - 0.6719 Caco-2 permeable - 0.5989 P-glycoprotein substrate Substrate 0.7626 P-glycoprotein inhibitor I Non-inhibitor 0.5907 P-glycoprotein inhibitor II Non-inhibitor 0.9617 Renal organic cation transporter Non-inhibitor 0.8606 CYP450 2C9 substrate Non-substrate 0.7734 CYP450 2D6 substrate Non-substrate 0.8048 CYP450 3A4 substrate Substrate 0.5057 CYP450 1A2 substrate Non-inhibitor 0.5372 CYP450 2C9 inhibitor Non-inhibitor 0.5767 CYP450 2D6 inhibitor Non-inhibitor 0.8016 CYP450 2C19 inhibitor Non-inhibitor 0.6016 CYP450 3A4 inhibitor Inhibitor 0.8744 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6243 Ames test Non AMES toxic 0.5075 Carcinogenicity Non-carcinogens 0.7777 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6308 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7742 hERG inhibition (predictor II) Non-inhibitor 0.5914
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 230.1127479 predictedDarkChem Lite v0.1.0 [M-H]- 212.76933 predictedDeepCCS 1.0 (2019) [M+H]+ 230.4299479 predictedDarkChem Lite v0.1.0 [M+H]+ 214.59422 predictedDeepCCS 1.0 (2019) [M+Na]+ 230.0503479 predictedDarkChem Lite v0.1.0 [M+Na]+ 220.20004 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Teng R: Ticagrelor: Pharmacokinetic, Pharmacodynamic and Pharmacogenetic Profile: An Update. Clin Pharmacokinet. 2015 Nov;54(11):1125-38. doi: 10.1007/s40262-015-0290-2. [Article]
- Bhatt DL, Pollack CV, Weitz JI, Jennings LK, Xu S, Arnold SE, Umstead BR, Mays MC, Lee JS: Antibody-Based Ticagrelor Reversal Agent in Healthy Volunteers. N Engl J Med. 2019 May 9;380(19):1825-1833. doi: 10.1056/NEJMoa1901778. Epub 2019 Mar 17. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Teng R, Oliver S, Hayes MA, Butler K: Absorption, distribution, metabolism, and excretion of ticagrelor in healthy subjects. Drug Metab Dispos. 2010 Sep;38(9):1514-21. doi: 10.1124/dmd.110.032250. Epub 2010 Jun 15. [Article]
- FDA Approved Drug Products: BRILINTA (ticagrelor) tablets, for oral use [Link]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateActivator
- 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
- Adamski P, Buszko K, Sikora J, Niezgoda P, Baranska M, Ostrowska M, Paciorek P, Navarese EP, Gorog DA, Kubica J: Metabolism of ticagrelor in patients with acute coronary syndromes. Sci Rep. 2018 Aug 6;8(1):11746. doi: 10.1038/s41598-018-29619-9. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA Approved Drug Products: BRILINTA (ticagrelor) tablets, for oral use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- 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
- Zhou D, Andersson TB, Grimm SW: In vitro evaluation of potential drug-drug interactions with ticagrelor: cytochrome P450 reaction phenotyping, inhibition, induction, and differential kinetics. Drug Metab Dispos. 2011 Apr;39(4):703-10. doi: 10.1124/dmd.110.037143. Epub 2010 Dec 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- 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
- Zhou D, Andersson TB, Grimm SW: In vitro evaluation of potential drug-drug interactions with ticagrelor: cytochrome P450 reaction phenotyping, inhibition, induction, and differential kinetics. Drug Metab Dispos. 2011 Apr;39(4):703-10. doi: 10.1124/dmd.110.037143. Epub 2010 Dec 22. [Article]
- Teng R: Ticagrelor: Pharmacokinetic, Pharmacodynamic and Pharmacogenetic Profile: An Update. Clin Pharmacokinet. 2015 Nov;54(11):1125-38. doi: 10.1007/s40262-015-0290-2. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Angheloiu GO, Gugiu GB, Ruse C, Pandey R, Dasari RR, Whatling C: Ticagrelor Removal From Human Blood. JACC Basic Transl Sci. 2017 Apr 24;2(2):135-145. doi: 10.1016/j.jacbts.2017.01.007. eCollection 2017 Apr. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
Drug created at August 01, 2011 21:32 / Updated at October 21, 2024 08:50