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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Physico-chemical Properties
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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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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
References
1. Fukushima-Shintani M, Suzuki K, Iwatsuki Y, Abe M, Sugasawa K, Hirayama F, Kawasaki T, Nakahata T. (2009)
AKR-501 (YM477) a novel orally-active thrombopoietin receptor agonist.
Eur J Haematol, 82 (4): 247-54. [PMID:19183407]
2. Nomoto M, Pastino G, Rege B, Aluri J, Ferry J, Han D. (2018)
Pharmacokinetics, Pharmacodynamics, Pharmacogenomics, Safety, and Tolerability of Avatrombopag in Healthy Japanese and White Subjects.
Clin Pharmacol Drug Dev, 7 (2): 188-195. [PMID:28339166]
3. Terrault N, Chen YC, Izumi N, Kayali Z, Mitrut P, Tak WY, Allen LF, Hassanein T. (2018)
Avatrombopag Before Procedures Reduces Need for Platelet Transfusion in Patients With Chronic Liver Disease and Thrombocytopenia.
Gastroenterology, 155 (3): 705-718. [PMID:29778606]
4. Terrault NA, Hassanein T, Howell CD, Joshi S, Lake J, Sher L, Vargas H, McIntosh J, Tang S, Jenkins TM. (2014)
Phase II study of avatrombopag in thrombocytopenic patients with cirrhosis undergoing an elective procedure.
J Hepatol, 61 (6): 1253-9. [PMID:25048952]