AZD1283   Click here for help

GtoPdb Ligand ID: 7360

Synonyms: AZD 1283 | AZD-1283
PDB Ligand
Compound class: Synthetic organic
Comment: Antagonist of P2Y12 developed as non-nucleoside analogue alternative to marketed inhibitors such as ticagrelor [1,4]. An antiplatelet agent that is orally bioavailable and has improved drug-like properties was discovered through optimization of AZD1283 [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 137.84
Molecular weight 470.16
XLogP 2.97
No. Lipinski's rules broken 0
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Canonical SMILES CCOC(=O)c1cc(C#N)c(nc1C)N1CCC(CC1)C(=O)NS(=O)(=O)Cc1ccccc1
Isomeric SMILES CCOC(=O)c1cc(C#N)c(nc1C)N1CCC(CC1)C(=O)NS(=O)(=O)Cc1ccccc1
InChI InChI=1S/C23H26N4O5S/c1-3-32-23(29)20-13-19(14-24)21(25-16(20)2)27-11-9-18(10-12-27)22(28)26-33(30,31)15-17-7-5-4-6-8-17/h4-8,13,18H,3,9-12,15H2,1-2H3,(H,26,28)
1. Bach P, Antonsson T, Bylund R, Björkman JA, Österlund K, Giordanetto F, van Giezen JJ, Andersen SM, Zachrisson H, Zetterberg F. (2013)
Lead optimization of ethyl 6-aminonicotinate acyl sulfonamides as antagonists of the P2Y12 receptor. separation of the antithrombotic effect and bleeding for candidate drug AZD1283.
J Med Chem, 56 (17): 7015-24. [PMID:23899349]
2. Bach P, Boström J, Brickmann K, Burgess LE, Clarke D, Groneberg RD, Harvey DM, Laird ER, O'Sullivan M, Zetterberg F. (2013)
5-alkyl-1,3-oxazole derivatives of 6-amino-nicotinic acids as alkyl ester bioisosteres are antagonists of the P2Y12 receptor.
Future Med Chem, 5 (17): 2037-56. [PMID:24215345]
3. Kong D, Xue T, Guo B, Cheng J, Liu S, Wei J, Lu Z, Liu H, Gong G, Lan T et al.. (2019)
Optimization of P2Y12 Antagonist Ethyl 6-(4-((Benzylsulfonyl)carbamoyl)piperidin-1-yl)-5-cyano-2-methylnicotinate (AZD1283) Led to the Discovery of an Oral Antiplatelet Agent with Improved Druglike Properties.
J Med Chem, 62 (6): 3088-3106. [PMID:30843696]
4. Zhang K, Zhang J, Gao ZG, Zhang D, Zhu L, Han GW, Moss SM, Paoletta S, Kiselev E, Lu W et al.. (2014)
Structure of the human P2Y12 receptor in complex with an antithrombotic drug.
Nature, 509 (7498): 115-8. [PMID:24670650]