Identification

Name
Ticagrelor
Accession Number
DB08816  (DB04902)
Type
Small Molecule
Groups
Approved
Description

Ticagrelor (trade name Brilinta in the US, Brilique and Possia in the EU) is a platelet aggregation inhibitor produced by AstraZeneca. Unlike clopidogrel, ticagrelor is not a prodrug and does not require metabolic activation. The drug was approved for use in the European Union by the European Commission on December 3, 2010. The drug was approved by the US Food and Drug Administration on July 20, 2011.

Structure
Thumb
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
External IDs
AR-C126532XX / AZD 6140 / AZD-6140 / AZD6140
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BrilintaTablet90 mgOralAstra Zeneca2011-06-01Not applicableCanada
BrilintaTablet90 mg/1OralCardinal Health2011-08-05Not applicableUs55154 961820180907 15195 153xv46
BrilintaTablet60 mg/1OralAstra Zeneca Lp2015-09-04Not applicableUs
BrilintaTablet60 mgOralAstra Zeneca2016-06-13Not applicableCanada
BrilintaTablet90 mg/1Oralbryant ranch prepack2011-08-052018-05-29Us63629 529220180907 15195 loebzm
BrilintaTablet90 mg/1OralAstra Zeneca Lp2011-08-05Not applicableUs00186 0777 60 nlmimage10 8639c32e
BriliqueTablet, film coated60 mgOralAstra Zeneca Ab2010-12-03Not applicableEu
BriliqueTablet, film coated90 mgOralAstra Zeneca Ab2010-12-03Not applicableEu
BriliqueTablet, film coated60 mgOralAstra Zeneca Ab2010-12-03Not applicableEu
BriliqueTablet, film coated90 mgOralAstra Zeneca Ab2010-12-03Not applicableEu
International/Other Brands
Brilique (AstraZeneca) / Possia (AstraZeneca)
Categories
UNII
GLH0314RVC
CAS number
274693-27-5
Weight
Average: 522.568
Monoisotopic: 522.186080514
Chemical Formula
C23H28F2N6O4S
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

Pharmacology

Indication

For the prevention of thrombotic events (for example stroke or heart attack) in patients with acute coronary syndrome or myocardial infarction with ST elevation.

Associated Conditions
Pharmacodynamics

Plasma concentrations of ticagrelor are slightly increased (12–23%) in elderly patients, women, patients of Asian ethnicity, and patients with mild hepatic impairment. They are decreased in patients that described themselves as 'coloured' and such with severe renal impairment. These differences are considered clinically irrelevant. In Japanese people, concentrations are 40% higher than in Caucasians, or 20% after body weight correction. The drug has not been tested in patients with severe hepatic impairment.

Mechanism of action

Like the thienopyridines prasugrel, clopidogrel and ticlopidine, ticagrelor blocks adenosine diphosphate (ADP) receptors of subtype P2Y12. In contrast to the other antiplatelet drugs, ticagrelor has a binding site different from ADP, making it an allosteric antagonist, and the blockage is reversible. Moreover, the drug does not need hepatic activation, which might work better for patients with genetic variants regarding the enzyme CYP2C19 (although it is not certain whether clopidogrel is significantly influenced by such variants).

TargetActionsOrganism
AP2Y purinoceptor 12
inhibitor
Human
Absorption

Absorbed quickly from the gut, the bioavailability being 36%.

Volume of distribution

The steady state volume of distribution of ticagrelor is 88 L.

Protein binding

Both ticagrelor and AR-C124910XX are bound to plasma proteins (>99.7%), and both are pharmacologically active.

Metabolism

The main metabolite, AR-C124910XX, is formed quickly via CYP3A4 by de-hydroxyethylation at position 5 of the cyclopentane ring. The metabolite reaches 30–40% of ticagrelor's plasma concentrations.

Route of elimination

The primary route of ticagrelor elimination is hepatic metabolism. When radiolabeled ticagrelor is administered, the mean recovery of radioactivity is approximately 84% (58% in feces, 26% in urine).

Half life

Ticagrelor has a half life of 7 hours, while its active metabolite has a half life of 9 hours.

Clearance
Not Available
Toxicity

Bleeding is the expected pharmacologic effect of overdosing. If bleeding occurs, appropriate supportive measures should be taken. Other effects of overdose may include gastrointestinal effects (nausea, vomiting, diarrhea) or ventricular pauses.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(1,2,6,7-3H)TestosteroneThe therapeutic efficacy of Ticagrelor can be increased when used in combination with (1,2,6,7-3H)Testosterone.
(R)-warfarinThe metabolism of Ticagrelor can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Ticagrelor can be decreased when combined with (S)-Warfarin.
1-TestosteroneThe therapeutic efficacy of Ticagrelor can be increased when used in combination with 1-Testosterone.
18-methyl-19-nortestosteroneThe therapeutic efficacy of Ticagrelor can be increased when used in combination with 18-methyl-19-nortestosterone.
3,5-diiodothyropropionic acidThe metabolism of Ticagrelor can be decreased when combined with 3,5-diiodothyropropionic acid.
4-hydroxycoumarinThe metabolism of Ticagrelor can be decreased when combined with 4-hydroxycoumarin.
4-HydroxytestosteroneThe therapeutic efficacy of Ticagrelor can be increased when used in combination with 4-Hydroxytestosterone.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ticagrelor.
5-androstenedioneThe metabolism of Ticagrelor can be decreased when combined with 5-androstenedione.
Food Interactions
Not Available

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
  1. Husted S, Emanuelsson H, Heptinstall S, Sandset PM, Wickens M, Peters G: Pharmacodynamics, pharmacokinetics, and safety of the oral reversible P2Y12 antagonist AZD6140 with aspirin in patients with atherosclerosis: a double-blind comparison to clopidogrel with aspirin. Eur Heart J. 2006 May;27(9):1038-47. Epub 2006 Feb 13. [PubMed:16476694]
  2. Storey RF, Husted S, Harrington RA, Heptinstall S, Wilcox RG, Peters G, Wickens M, Emanuelsson H, Gurbel P, Grande P, Cannon CP: Inhibition of platelet aggregation by AZD6140, a reversible oral P2Y12 receptor antagonist, compared with clopidogrel in patients with acute coronary syndromes. J Am Coll Cardiol. 2007 Nov 6;50(19):1852-6. Epub 2007 Oct 23. [PubMed:17980251]
  3. Tantry US, Bliden KP, Gurbel PA: AZD6140. Expert Opin Investig Drugs. 2007 Feb;16(2):225-9. [PubMed:17243942]
  4. Serebruany VL, Stebbing J, Atar D: Dyspnoea after antiplatelet agents: the AZD6140 controversy. Int J Clin Pract. 2007 Mar;61(3):529-33. [PubMed:17313629]
  5. 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. [PubMed:17827008]
  6. Cannon CP, Husted S, Harrington RA, Scirica BM, Emanuelsson H, Peters G, Storey RF: Safety, tolerability, and initial efficacy of AZD6140, the first reversible oral adenosine diphosphate receptor antagonist, compared with clopidogrel, in patients with non-ST-segment elevation acute coronary syndrome: primary results of the DISPERSE-2 trial. J Am Coll Cardiol. 2007 Nov 6;50(19):1844-51. Epub 2007 Oct 23. [PubMed:17980250]
External Links
Human Metabolome Database
HMDB0015702
KEGG Drug
D09017
PubChem Compound
9871419
PubChem Substance
175427101
ChemSpider
8047109
BindingDB
50397205
ChEBI
68558
ChEMBL
CHEMBL398435
PharmGKB
PA165374673
HET
TIQ
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ticagrelor
ATC Codes
B01AC24 — Ticagrelor
AHFS Codes
  • 20:12.18 — Platelet Aggregation Inhibitors
PDB Entries
5alb / 5alc
FDA label
Download (1.21 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingBasic ScienceAortic Valve Stenosis / Inflammatory Reaction / Thrombotic events1
1CompletedBasic ScienceAcute Gouty Arthritis / Coronary Artery Disease1
1CompletedBasic ScienceDrug Drug Interaction (DDI)1
1CompletedBasic ScienceHealthy Volunteers4
1CompletedBasic ScienceImpaired Renal Function1
1CompletedBasic ScienceInhibition on Platelet Aggregation1
1CompletedBasic SciencePharmacokinetics1
1CompletedOtherSickle Cell Disorders1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentAcute Coronary Syndromes (ACS)2
1CompletedTreatmentAcute Coronary Syndromes (ACS) / Nonvalvular Atrial Fibrillation1
1CompletedTreatmentAcute Lung Injury (ALI) / Community Acquired Pneumonia (CAP) / Hospital-acquired bacterial pneumonia / Pneumonia1
1CompletedTreatmentBlood Flow Speed / Coronary Flow Velocity1
1CompletedTreatmentChronic Renal Failure (CRF)1
1CompletedTreatmentHealthy Volunteers3
1RecruitingOtherHealthy Volunteers1
1RecruitingOtherSickle Cell Disorders1
1, 2RecruitingTreatmentEnd Stage Renal Disease (ESRD) / Vascular Access Patency1
1, 2Unknown StatusScreeningCritical Limb Ischemia (CLI)1
2CompletedNot AvailableCoronary Artery Disease1
2CompletedOtherHealthy Volunteers1
2CompletedPreventionSickle Cell Disorders1
2CompletedTreatmentAbdominal Aortic Aneurysms (AAA)1
2CompletedTreatmentAcute Coronary Syndromes (ACS)4
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Coronary Artery Disease1
2CompletedTreatmentCoronary Artery Disease3
2CompletedTreatmentStable Coronary Artery Disease2
2RecruitingTreatmentAcute Coronary Syndromes (ACS) / Stable Angina (SA) / Unstable Angina (UA)1
2RecruitingTreatmentAdenosine / Antiplatelet Therapy / Coronary Artery Disease / Platelet Aggregation / Renal Function Abnormal1
2RecruitingTreatmentCarotid Artery Stenosis1
2RecruitingTreatmentCritical Illness1
2TerminatedTreatmentCommunity Acquired Pneumonia, Severe1
2TerminatedTreatmentPeripheral Artery Disease (PAD)1
2Unknown StatusTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
2WithdrawnDiagnosticCardiovascular Disease (CVD)1
2, 3Active Not RecruitingTreatmentCoronary Artery Disease1
2, 3Active Not RecruitingTreatmentStrokes / Transient Ischaemic Attack (TIA)1
2, 3CompletedTreatmentAcute Coronary Syndromes (ACS) / Percutaneous Coronary Intervention1
2, 3CompletedTreatmentCoronary Artery Disease1
2, 3RecruitingPreventionCoronary Artery Disease1
2, 3RecruitingTreatmentAcute Coronary Syndromes (ACS)1
2, 3RecruitingTreatmentClopidogrel, Poor Metabolism of / Coronary Artery Disease1
2, 3RecruitingTreatmentPeripheral Arterial Disease (PAD)1
2, 3Unknown StatusTreatmentCLOPIDOGREL, POOR METABOLISM of (Disorder)1
3Active Not RecruitingPreventionType 2 Diabetes Mellitus1
3Active Not RecruitingTreatmentMyocardial Infarction / ST Segment Elevation Myocardial Infarction (STEMI)1
3Active Not RecruitingTreatmentST Segment Elevation Acute Myocardial Infarction / Thrombolysis in Myocardial Infarction Flow1
3CompletedDiagnosticCoronary Artery Disease / Endothelial Function1
3CompletedHealth Services ResearchPharmacodynamics / Pharmacodynamics of Antiplatelet Agent1
3CompletedPreventionAcute Ischaemic Stroke / Transient Ischaemic Attack (TIA)1
3CompletedPreventionAtherothrombosis / Cardiovascular Mortality / Myocardial Infarction / Strokes1
3CompletedPreventionPeripheral Artery Disease (PAD)1
3CompletedTreatmentAcute Coronary Syndromes (ACS)1
3CompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease1
3CompletedTreatmentAcute Coronary Syndromes (ACS) / Percutaneous Coronary Intervention1
3CompletedTreatmentAcute Coronary Syndromes (ACS) / ST Elevation Myocardial Infarction (STEMI)1
3CompletedTreatmentAcute Myocardial Infarction (AMI)1
3CompletedTreatmentChronic Kidney Disease (CKD)1
3CompletedTreatmentCoronary Artery Disease2
3CompletedTreatmentCoronary Stent Implantation / Platelet Inhibition1
3CompletedTreatmentMyocardial Infarction1
3CompletedTreatmentNonvalvular Atrial Fibrillation / Percutaneous Coronary Intervention1
3CompletedTreatmentPlatelet Reactivity2
3Not Yet RecruitingTreatmentAcute Coronary Syndromes (ACS)1
3RecruitingPreventionAcute Coronary Syndromes (ACS) / Nonvalvular Atrial Fibrillation1
3RecruitingPreventionCoronary Artery Disease1
3RecruitingTreatmentAcute Coronary Syndromes (ACS)2
3RecruitingTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease / Stable Angina (SA)1
3RecruitingTreatmentAcute Ischaemic Stroke / Transient Ischaemic Attack (TIA)1
3RecruitingTreatmentCardiovascular Disease (CVD) / Coronary Artery Disease / Myocardial Infarction / Myocardial Ischemia / Stent Thrombosis1
3RecruitingTreatmentCerebral Aneurysms1
3RecruitingTreatmentChronic Kidney Disease (CKD)2
3RecruitingTreatmentChronic Kidney Disease (CKD) / Heart Attacks / Stroke, Ischemic1
3RecruitingTreatmentNonvalvular Atrial Fibrillation1
3RecruitingTreatmentPeripheral Artery Disease (PAD) / Type 2 Diabetes Mellitus1
3RecruitingTreatmentSickle Cell Disorders1
3TerminatedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease / Stable Angina (SA)1
3TerminatedTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
3Unknown StatusTreatmentNon-ST Segment Elevation Acute Coronary Syndrome1
3WithdrawnBasic ScienceCoronary Heart Disease (CHD)1
4Active Not RecruitingNot AvailableAcute Coronary Syndromes (ACS)1
4Active Not RecruitingSupportive CareCardiovascular Disease (CVD) / Interventional Cardiology1
4Active Not RecruitingTreatmentAntiplatelet Agents / Coronary Artery Bypass Graft Surgery Patients1
4Active Not RecruitingTreatmentHeadaches / Migraines / Migrainous Headache1
4Active Not RecruitingTreatmentLOVASTATIN/TICAGRELOR [VA Drug Interaction]1
4Active Not RecruitingTreatmentMyocardial Infarction1
4Active Not RecruitingTreatmentPatients Who Are Scheduled to Undergo a PCI (Percutaneous Coronary Intervention) for CTO (Chronic Total Occlusion)1
4CompletedNot AvailableHealthy Volunteers1
4CompletedBasic ScienceAcute Coronary Syndromes (ACS) / Nonvalvular Atrial Fibrillation1
4CompletedBasic ScienceCoronary Artery Disease1
4CompletedBasic ScienceCoronary Artery Disease / Endothelial Dysfunction / Myocardial Ischemia1
4CompletedPreventionCoronary Artery Disease2
4CompletedSupportive CareAcute Coronary Syndromes (ACS) / Platelet Function1
4CompletedTreatmentAcute Coronary Syndromes (ACS)5
4CompletedTreatmentAcute Coronary Syndromes (ACS) / Angina Pectoris / Cardiovascular Disease (CVD) / Heart Diseases / Myocardial Ischemia1
4CompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease1
4CompletedTreatmentAcute Coronary Syndromes (ACS) / High On-treatment Platelet Reactivity (HTPR) / Microvascular Obstruction (MVO) / ST Segment Elevation Myocardial Infarction (STEMI) / Thrombolysis in Myocardial Infarction (TIMI) / Unstable Angina (UA)1
4CompletedTreatmentAcute Coronary Syndromes (ACS) / ST Elevation Myocardial Infarction1
4CompletedTreatmentAngioplasty, Balloon, Coronary / Myocardial Infarction / Platelet Aggregation Inhibitors1
4CompletedTreatmentAntiplatelet Therapy of Coronary Artery Bypass1
4CompletedTreatmentCardiac Arrest / Postresuscitation Syndrome / ST Elevation (STEMI) and Non-ST Elevation (NSTEMI) Myocardial Infarction1
4CompletedTreatmentCardiovascular Disease (CVD)1
4CompletedTreatmentCoronary Artery Disease7
4CompletedTreatmentCoronary Artery Disease / Diabetes Mellitus (DM)1
4CompletedTreatmentCoronary Artery Disease / Endothelial Function1
4CompletedTreatmentCoronary Artery Disease / Type 2 Diabetes Mellitus1
4CompletedTreatmentCoronary Heart Disease (CHD)1
4CompletedTreatmentFibrinolysis / P2Y12 Inhibitor / ST Elevation Myocardial Infarction1
4CompletedTreatmentFractional Flow Reserve1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentMyocardial Infarction1
4CompletedTreatmentMyocardial Infarction / Segment Elevation Myocardial Infarction (STEMI)1
4CompletedTreatmentNon ST Segment Elevation Acute Coronary Syndrome1
4CompletedTreatmentNon ST Segment Elevation Myocardial Infarction (NSTEMI) / ST Segment Elevation Myocardial Infarction (STEMI)1
4CompletedTreatmentNon ST Segment Elevation Myocardial Infarction (NSTEMI) / ST Segment Elevation Myocardial Infarction (STEMI) / VA Drug Interactions / VA Drug Interactions [VA Drug Interaction]1
4CompletedTreatmentNon-ST or ST Elevation Acute Coronary Syndromes1
4CompletedTreatmentPlaque, Atherosclerotic1
4CompletedTreatmentPlatelet Reactivity1
4CompletedTreatmentST Elevation Myocardial Infarction (STEMI)2
4CompletedTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
4CompletedTreatmentStable Coronary Artery Disease2
4CompletedTreatmentStable Coronary Heart Disease (CHD)1
4CompletedTreatmentUnstable Angina Pectoris1
4CompletedTreatmentThrombotic events1
4CompletedTreatmentTransient ischemia attacks2
4Enrolling by InvitationTreatmentChronic Total Occlusion of Coronary Artery / Coronary Artery Disease / Percutaneous Coronary Intervention / Viable Myocardium1
4Enrolling by InvitationTreatmentComplete Occlusion of Coronary Artery / Hibernation, Myocardial1
4Not Yet RecruitingBasic ScienceDiabetes Mellitus (DM)2
4Not Yet RecruitingTreatmentAcute Coronary Syndromes (ACS) / Myocardial Infarction / ST Elevation Myocardial Infarction (STEMI)1
4Not Yet RecruitingTreatmentCoronary Artery Disease / Myocardial Infarction1
4Not Yet RecruitingTreatmentInflammatory Reaction / Thrombotic events1
4Not Yet RecruitingTreatmentMicrovascular Angina1
4RecruitingNot AvailableAcute Coronary Syndromes (ACS)1
4RecruitingBasic ScienceMyocardial Infarction1
4RecruitingBasic ScienceMyocardial Infarction / Platelets Dysfunction / Thrombotic events1
4RecruitingPreventionAcute Coronary Syndromes (ACS) / Chronic Kidney Disease (CKD)1
4RecruitingPreventionAtherosclerosis1
4RecruitingPreventionSaphenous Vein Graft Disease1
4RecruitingTreatmentACS - Acute Coronary Syndrome / Cardiopulmonary Arrest With Successful Resuscitation / Hypothermia, Induced1
4RecruitingTreatmentAcute Coronary Syndromes (ACS)2
4RecruitingTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease / Stenosis1
4RecruitingTreatmentAcute Myocardial Infarction (AMI)2
4RecruitingTreatmentAcute Myocardial Infarction (AMI) / Shock, Cardiogenic1
4RecruitingTreatmentAngina Pectoris / Cardiovascular Disease (CVD) / Coronary Artery Disease / Heart Diseases / Infarction / Myocardial Infarction / Systemic Embolism / Thoracic Pain / Thrombotic events / Transient ischemia attacks / Vascular Diseases1
4RecruitingTreatmentAtherosclerosis1
4RecruitingTreatmentAtherosclerosis / Coronary Artery Disease / Stents1
4RecruitingTreatmentChronic Kidney Disease (CKD) / Non ST Segment Elevation Acute Coronary Syndrome1
4RecruitingTreatmentCoronary Artery Disease4
4RecruitingTreatmentCoronary Artery Disease / Diabetes Mellitus (DM)1
4RecruitingTreatmentCoronary Artery Disease / Diabetes Mellitus (DM) / Kidney Diseases / Myocardial Infarction2
4RecruitingTreatmentCoronary Artery Disease / Nonvalvular Atrial Fibrillation1
4RecruitingTreatmentCoronary Artery Disease / Type 2 Diabetes Mellitus3
4RecruitingTreatmentCoronary Heart Disease (CHD)1
4RecruitingTreatmentCoronary Stent Implantation / Unstable Angina Pectoris1
4RecruitingTreatmentEndothelial Dysfunction / Vascular Inflammation1
4RecruitingTreatmentHeart Attacks1
4RecruitingTreatmentMyocardial Fibrosis1
4RecruitingTreatmentMyocardial Infarction1
4RecruitingTreatmentPercutaneous Coronary Intervention2
4RecruitingTreatmentPlatelet Reactivity1
4RecruitingTreatmentRheumatoid Arthritis1
4RecruitingTreatmentST Elevation Myocardial Infarction / ST Segment Elevation Myocardial Infarction (STEMI)1
4RecruitingTreatmentUnstable Angina Pectoris2
4TerminatedPreventionMyocardial Injury1
4TerminatedTreatmentAntiplatelet Therapy / Percutaneous Coronary Intervention / Stable Coronary Syndrome / Ticagrelor1
4TerminatedTreatmentNon ST Segment Elevation Acute Coronary Syndrome1
4TerminatedTreatmentNon-ST Elevation Acute Coronary Syndrome1
4TerminatedTreatmentPeripheral Arterial Disease (PAD)1
4Unknown StatusHealth Services ResearchAcute Coronary Syndromes (ACS) / ST Segment Elevation Acute Myocardial Infarction1
4Unknown StatusTreatmentAcute Coronary Syndromes (ACS)3
4Unknown StatusTreatmentAntiplatelet Agents; Endothelial Function; Pleotropic Effects1
4Unknown StatusTreatmentCardiovascular Disease (CVD) / Coronary Artery Disease / Myocardial Infarction / Stable Angina (SA)1
4Unknown StatusTreatmentCoronary Artery Disease1
4Unknown StatusTreatmentCoronary Heart Disease (CHD)1
4Unknown StatusTreatmentCoronary Heart Disease (CHD) / Diabetes Mellitus (DM)1
4Unknown StatusTreatmentMyocardial Infarction / No-Reflow Phenomenon1
4Unknown StatusTreatmentPatients Who Are Hospitalized and Expected to Undergo PCI for Acute Coronary Syndrome, Including Acute Myocardial Infarction and Unstable Angina1
4Unknown StatusTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
4WithdrawnNot AvailableAcute Coronary Syndromes (ACS) / Coronary Artery Disease1
4WithdrawnTreatmentAnkle Brachial Index (0.9 or Less) / Arterial Occlusion Disease / Intermittent Claudication / Peripheral Artery Disease (PAD) / Vascular Diseases1
Not AvailableActive Not RecruitingNot AvailableACS (Acute Coronary Syndrome) / Patients Alredy on Ticagrelor 2-3 Months Prior to Study Start1
Not AvailableActive Not RecruitingDiagnosticPlatelet Dysfunction Due to Drugs / Risk Factor, Cardiovascular1
Not AvailableActive Not RecruitingTreatmentAcute Coronary Syndromes (ACS)1
Not AvailableCompletedNot AvailableAPT(Antiplatelet Therapy) / HOTPR(High on Treat Platelet Reactivity) / PRU(Platelet Reactivity Unit)1
Not AvailableCompletedNot AvailableAcute Coronary Syndromes (ACS)2
Not AvailableCompletedNot AvailableAcute Coronary Syndromes (ACS) / Clopidogrel / Haemorrhage / Novel Anti-platelets / Ticagrelor1
Not AvailableCompletedNot AvailableAcute Coronary Syndromes (ACS) / Drug-eluting Stent (DES) / Percutaneous Coronary Intervention1
Not AvailableCompletedNot AvailableCoronary Artery Disease1
Not AvailableCompletedNot AvailableMyocardial Infarction3
Not AvailableCompletedBasic ScienceEndotoxaemia1
Not AvailableCompletedTreatmentAcute Coronary Syndromes (ACS)2
Not AvailableCompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease1
Not AvailableCompletedTreatmentAcute Myocardial Infarction (AMI)1
Not AvailableCompletedTreatmentCoronary Artery Disease2
Not AvailableCompletedTreatmentCoronary Artery Disease / Diabetes Mellitus (DM)1
Not AvailableCompletedTreatmentCoronary Artery Disease / Ticagrelor1
Not AvailableEnrolling by InvitationPreventionCardiovascular Disease (CVD)1
Not AvailableEnrolling by InvitationTreatmentPeripheral Artery Disease (PAD)1
Not AvailableRecruitingNot AvailableAcute Coronary Syndromes (ACS)1
Not AvailableRecruitingNot AvailableAcute Myocardial Infarction (AMI)1
Not AvailableRecruitingNot AvailableCoronary Artery Disease1
Not AvailableRecruitingNot AvailablePlatelet Aggregation Onhibitors1
Not AvailableRecruitingTreatmentAspirin / Platelet Dysfunction Due to Drugs / Ticagrelor / Transfusions1
Not AvailableRecruitingTreatmentST Elevation Myocardial Infarction1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral60 mg/1
TabletOral60 mg
TabletOral90 mg
TabletOral90 mg/1
Tablet, film coatedOral60 mg
Tablet, film coatedOral90 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2296665No2008-06-102018-07-15Canada
CA2351709No2010-04-062019-12-02Canada
CA2408596No2010-12-212021-05-31Canada
US7265124No2007-09-042021-07-09Us
US6525060No2003-02-252019-12-02Us
US7250419No2007-07-312019-12-02Us
US6251910No2001-06-262018-07-15Us
US8425934No2013-04-232030-04-17Us
USRE46276No2017-01-172019-12-02Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility10 μg/mLFDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.063 mg/mLALOGPS
logP2.31ALOGPS
logP2.28ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.94ChemAxon
pKa (Strongest Basic)2.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area138.44 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity142.13 m3·mol-1ChemAxon
Polarizability51.27 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.994
Blood Brain Barrier-0.6719
Caco-2 permeable-0.5989
P-glycoprotein substrateSubstrate0.7626
P-glycoprotein inhibitor INon-inhibitor0.5907
P-glycoprotein inhibitor IINon-inhibitor0.9617
Renal organic cation transporterNon-inhibitor0.8606
CYP450 2C9 substrateNon-substrate0.7734
CYP450 2D6 substrateNon-substrate0.8048
CYP450 3A4 substrateSubstrate0.5057
CYP450 1A2 substrateNon-inhibitor0.5372
CYP450 2C9 inhibitorNon-inhibitor0.5767
CYP450 2D6 inhibitorNon-inhibitor0.8016
CYP450 2C19 inhibitorNon-inhibitor0.6016
CYP450 3A4 inhibitorInhibitor0.8744
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6243
Ames testNon AMES toxic0.5075
CarcinogenicityNon-carcinogens0.7777
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6308 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7742
hERG inhibition (predictor II)Non-inhibitor0.5914
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Triazolopyrimidine / Aryl thioether / Aminopyrimidine / Fluorobenzene / Halobenzene / Secondary aliphatic/aromatic amine / Alkylarylthioether / Cyclitol or derivatives / Aryl fluoride / Aryl halide
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, aryl sulfide, secondary amino compound, triazolopyrimidines, hydroxyether (CHEBI:68558)

Targets

Details
1. P2Y purinoceptor 12
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
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

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. 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. [PubMed:20551239]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. 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. [PubMed:21177984]
  2. 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. [PubMed:26063049]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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

Drug created on August 01, 2011 15:32 / Updated on December 10, 2018 13:38