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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

AZD1283 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key NEMHKCNXXRQYRF-UHFFFAOYSA-N
References
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]