Ticagrelor (CHEM022378)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:30:30 UTC
Update Date2016-11-09 01:17:29 UTC
Accession NumberCHEM022378
Identification
Common NameTicagrelor
ClassSmall Molecule
DescriptionA triazolopyrimidine that is an adenosine isostere; the cyclopentane ring is similar to ribose and the nitrogen-rich [1,2,3]triazolo[4,5-d]pyrimidine moiety resembles the nucleobase adenine. A platelet aggregation inhibitor which is used for prevention of thromboembolic events in patients with acute coronary syndrome.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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-diolHMDB
BriliqueHMDB
Chemical FormulaC23H28F2N6O4S
Average Molecular Mass522.568 g/mol
Monoisotopic Mass522.186 g/mol
CAS Registry Number274693-27-5
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
Traditional Nameticagrelor
SMILESCCCSC1=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 IdentifierInChI=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 KeyOEKWJQXRCDYSHL-FNOIDJSQSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazolopyrimidines
Sub ClassNot Available
Direct ParentTriazolopyrimidines
Alternative Parents
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
  • Secondary amine
  • Azacycle
  • Sulfenyl compound
  • Thioether
  • Dialkyl ether
  • Ether
  • Amine
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organic nitrogen compound
  • Alcohol
  • Primary alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity142.13 m³·mol⁻¹ChemAxon
Polarizability51.27 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-090c-3200910000-8b79fcacb4bbd3c8fab8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uei-5810579000-20481db318bcc027bef1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-7102390000-5ddf85cefc95eb7cfd00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000200000-b1a384d3e0d350dd568cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9602000000-b1c6a485f456d4e53cd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-024i-1004970000-5da4a33eeb60b4a3850eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2211900000-13d60262b192397cc4dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-9302000000-8855f16a2d39f5e7b117Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-17c084128bca3f965b75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0004910000-87f14bc691b30704b0ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03y3-0059500000-9cd03ba6ec0a41188c2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ox-0000910000-5bf0d0b014f726f6db67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009510000-c180eccd8007f884d435Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03e9-4019200000-93d3e549ebb942a0dc23Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB08816
HMDB IDHMDB0015702
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDTIQ
Wikipedia LinkTicagrelor
Chemspider ID8047109
ChEBI ID68558
PubChem Compound ID9871419
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22991347
2. FDA label