ticagrelor   Click here for help

GtoPdb Ligand ID: 1765

Synonyms: AR-C126532XX | AZD6140 | Brilinta® | Brilique® | compound 17 [PMID: 17827008]
Approved drug PDB Ligand
ticagrelor is an approved drug (EMA (2010), FDA (2011))
Compound class: Synthetic organic
Comment: Ticagrelor is a selective P2Y12 receptor antagonist [3].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: ticagrelor

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 10
Topological polar surface area 163.74
Molecular weight 522.19
XLogP 2.01
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CCCSc1nc(NC2CC2c2ccc(c(c2)F)F)c2c(n1)n(nn2)C1CC(C(C1O)O)OCCO
Isomeric SMILES CCCSc1nc(N[C@@H]2C[C@H]2c2ccc(c(c2)F)F)c2c(n1)n(nn2)[C@@H]1C[C@@H]([C@H]([C@H]1O)O)OCCO
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
1. Armstrong D, Summers C, Ewart L, Nylander S, Sidaway JE, van Giezen JJ. (2014)
Characterization of the adenosine pharmacology of ticagrelor reveals therapeutically relevant inhibition of equilibrative nucleoside transporter 1.
J Cardiovasc Pharmacol Ther, 19 (2): 209-19. [PMID:24414167]
2. Hoffmann K, Lutz DA, Straßburger J, Baqi Y, Müller CE, von Kügelgen I. (2014)
Competitive mode and site of interaction of ticagrelor at the human platelet P2Y12 -receptor.
J Thromb Haemost, 12 (11): 1898-905. [PMID:25186974]
3. Springthorpe B, Bailey A, Barton P, Birkinshaw TN, Bonnert RV, Brown RC, Chapman D, Dixon J, Guile SD, Humphries RG et al.. (2007)
From ATP to AZD6140: the discovery of an orally active reversible P2Y12 receptor antagonist for the prevention of thrombosis.
Bioorg Med Chem Lett, 17 (21): 6013-8. [PMID:17827008]
4. Zech G, Hessler G, Evers A, Weiss T, Florian P, Just M, Czech J, Czechtizky W, Görlitzer J, Ruf S et al.. (2012)
Identification of high-affinity P2Y₁₂ antagonists based on a phenylpyrazole glutamic acid piperazine backbone.
J Med Chem, 55 (20): 8615-29. [PMID:22984835]