avatrombopag   

GtoPdb Ligand ID: 9953

Synonyms: AKR-501 [1] | Doptelet® | E5501 [4] | YM477
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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Physico-chemical Properties
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
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
Compound class Synthetic organic
Approved drug? Yes (FDA (2018), EMA (2019))
IUPAC Name
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
INN number INN
9571 avatrombopag
Synonyms
AKR-501 [1] | Doptelet® | E5501 [4] | YM477
Database Links
ChEMBL Ligand CHEMBL2103883
DrugBank Ligand DB11995
DrugCentral Ligand 5285
GtoPdb PubChem SID 374883840
PubChem CID 9852519
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