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Ticagrelor

July 24, 2017
Common Name

Ticagrelor Description

Ticagrelor (trade name Brilinta in the US, Brilique and Possia in the EU) is a platelet aggregation inhibitor produced by AstraZeneca. 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 Jliy 20, 2011. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (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-diolChEBI AZD 6140ChEBI AZD-6140ChEBI AZD6140ChEBI BrilintaChEBI 3-(7-((2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-(1-3)-triazolo(4,5-D)pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diolMeSH BriliqueMeSH

Chemical Formlia

C23H28F2N6O4S Average Molecliar Weight

522.568 Monoisotopic Molecliar Weight

522.186080514 IUPAC Name

(1S,2S,3R,5S)-3-(7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylslifanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol Traditional Name

ticagrelor CAS Registry Number

274693-27-5 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

InChI Identifier

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

InChI Key

OEKWJQXRCDYSHL-FNOIDJSQSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Triazolopyrimidines Direct Parent

Triazolopyrimidines Alternative Parents

  • Alkylarylthioethers
  • Aminopyrimidines and derivatives
  • Secondary alkylarylamines
  • Fluorobenzenes
  • Aryl fluorides
  • Cyclitols and derivatives
  • Cyclopentanols
  • Imidolactams
  • Triazoles
  • Heteroaromatic compounds
  • Dialkyl ethers
  • Azacyclic compounds
  • Slifenyl compounds
  • Organofluorides
  • Organopnictogen compounds
  • Primary alcohols
  • Hydrocarbon derivatives

    • Substituents

  • Triazolopyrimidine
  • Aryl thioether
  • Aminopyrimidine
  • Fluorobenzene
  • Halobenzene
  • Secondary aliphatic/aromatic amine
  • Alkylarylthioether
  • Cyclitol or derivatives
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Cyclopentanol
  • Pyrimidine
  • Benzenoid
  • Imidolactam
  • Azole
  • Heteroaromatic compound
  • 1,2,3-triazole
  • Triazole
  • Cyclic alcohol
  • Secondary alcohol
  • Azacycle
  • Slifenyl compound
  • Thioether
  • Dialkyl ether
  • Ether
  • Organic nitrogen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organoslifur compound
  • Primary alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • organofluorine compound (CHEBI:68558 )
  • aryl slifide (CHEBI:68558 )
  • secondary amino compound (CHEBI:68558 )
  • triazolopyrimidines (CHEBI:68558 )
  • hydroxyether (CHEBI:68558 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

    Not Available Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility6.30e-02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08816

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08816

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB08816 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    8047109 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Ticagrelor NuGOwiki Link

    HMDB15702 Metagene Link

    HMDB15702 METLIN ID

    Not Available PubChem Compound

    9871419 PDB ID

    Not Available ChEBI ID

    516772

    Product: Nabumetone

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. (). FDA label . .

    Enzymes

    General function:
    Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    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 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    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. Involved in platelets aggregation
    Gene Name:
    P2RY12
    Uniprot ID:
    Q9H244
    Molecular weight:
    39438.4

    PMID: 8393786

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