avatrombopag   Click here for help

GtoPdb Ligand ID: 9953

Synonyms: AKR-501 [1] | Doptelet® | E5501 [4] | YM477
Approved drug
avatrombopag is an approved drug (FDA (2018), EMA (2019))
Compound class: Synthetic organic
Comment: Avatrombopag is a second generation, small molecule, orally administered thrombopoietin receptor agonist [1]. It was discovered through its ability to mimic the action of endogenous thrombopoietin which is the primary physiological regulator of normal platelet production. The pharmacokinetics, pharmacodynamics, pharmacogenomics, safety, and tolerability of avatrombopag were reported by Nomoto et al. in 2017 [2].
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 2
Rotatable bonds 8
Topological polar surface area 158.38
Molecular weight 648.15
XLogP 5.6
No. Lipinski's rules broken 1
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 OC(=O)C1CCN(CC1)c1ncc(cc1Cl)C(=O)Nc1sc(c(n1)c1scc(c1)Cl)N1CCN(CC1)C1CCCCC1
Isomeric SMILES OC(=O)C1CCN(CC1)c1ncc(cc1Cl)C(=O)Nc1sc(c(n1)c1scc(c1)Cl)N1CCN(CC1)C1CCCCC1
InChI InChI=1S/C29H34Cl2N6O3S2/c30-20-15-23(41-17-20)24-27(37-12-10-35(11-13-37)21-4-2-1-3-5-21)42-29(33-24)34-26(38)19-14-22(31)25(32-16-19)36-8-6-18(7-9-36)28(39)40/h14-18,21H,1-13H2,(H,39,40)(H,33,34,38)
InChI Key OFZJKCQENFPZBH-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2018), EMA (2019))
IUPAC Name Click here for help
1-[3-chloro-5-[[4-(4-chlorothiophen-2-yl)-5-(4-cyclohexylpiperazin-1-yl)-1,3-thiazol-2-yl]carbamoyl]pyridin-2-yl]piperidine-4-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
9571 avatrombopag
Synonyms Click here for help
AKR-501 [1] | Doptelet® | E5501 [4] | YM477
Database Links Click here for help
ChEMBL Ligand CHEMBL2103883
DrugBank Ligand DB11995
DrugCentral Ligand 5285
GtoPdb PubChem SID 374883840
PubChem CID 9852519
Search Google for chemical match using the InChIKey OFZJKCQENFPZBH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OFZJKCQENFPZBH
Search PubMed clinical trials avatrombopag
Search PubMed titles avatrombopag
Search PubMed titles/abstracts avatrombopag
UniChem Compound Search for chemical match using the InChIKey OFZJKCQENFPZBH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OFZJKCQENFPZBH-UHFFFAOYSA-N