apixaban   

GtoPdb Ligand ID: 6390

Synonyms: BMS-562247 | Eliquis®
apixaban is an approved drug (EMA (2011), FDA (2012))
Compound class: Synthetic organic
Comment: Apixaban belongs to the direct factor Xa inhibitor family of drugs, which also includes rivaroxaban and edoxaban.

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

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View more information in the IUPHAR Pharmacology Education Project: apixaban

2D Structure

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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Click here for structure editor
Physico-chemical Properties

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 7
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 110.24
Molecular weight 459.19
XLogP 1.81
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey

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 COc1ccc(cc1)n1nc(c2c1C(=O)N(CC2)c1ccc(cc1)N1CCCCC1=O)C(=O)N
Isomeric SMILES COc1ccc(cc1)n1nc(c2c1C(=O)N(CC2)c1ccc(cc1)N1CCCCC1=O)C(=O)N
InChI InChI=1S/C25H25N5O4/c1-34-19-11-9-18(10-12-19)30-23-20(22(27-30)24(26)32)13-15-29(25(23)33)17-7-5-16(6-8-17)28-14-3-2-4-21(28)31/h5-12H,2-4,13-15H2,1H3,(H2,26,32)
InChI Key QNZCBYKSOIHPEH-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (EMA (2011), FDA (2012))
IUPAC Name
1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxamide
International Nonproprietary Names
INN number INN
8626 apixaban
Synonyms
BMS-562247 | Eliquis®
Database Links
CAS Registry No. 503612-47-3 (source: PubChem)
ChEBI CHEBI:72296
ChEMBL Ligand CHEMBL231779
DrugBank Ligand DB06605
DrugCentral Ligand 4298
GtoPdb PubChem SID 178103006
PubChem CID 10182969
RCSB PDB Ligand GG2
Search Google for chemical match using the InChIKey QNZCBYKSOIHPEH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone QNZCBYKSOIHPEH
Search PubMed clinical trials apixaban
Search PubMed titles apixaban
Search PubMed titles/abstracts apixaban
Search UniChem for chemical match using the InChIKey QNZCBYKSOIHPEH-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone QNZCBYKSOIHPEH
SynPHARM 78505 (in complex with coagulation factor X)
Wikipedia Apixaban