eltrombopag   Click here for help

GtoPdb Ligand ID: 6961

Synonyms: AMG531 | Promacta® | Revolade® | SB-497115-GR
Approved drug
eltrombopag is an approved drug (FDA (2008), EMA (2010))
Compound class: Synthetic organic
Comment: Eltrombopag is a thrombopoietin receptor agonist that increases production of platelets. The structure shown here represents the compound with double bond stereochemistry as stipulated in the INN record for this drug. Representations on other chemistry databases may show alternative tautomers. The marketed drug contains eltrombopag olamine (PubChem CID 71719015, again note tautomer difference).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 114.59
Molecular weight 442.16
XLogP 6.36
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)c1cccc(c1)c1cccc(c1O)NN=C1C(=NN(C1=O)c1ccc(c(c1)C)C)C
Isomeric SMILES OC(=O)c1cccc(c1)c1cccc(c1O)N/N=C\1/C(=NN(C1=O)c1ccc(c(c1)C)C)C
InChI InChI=1S/C25H22N4O4/c1-14-10-11-19(12-15(14)2)29-24(31)22(16(3)28-29)27-26-21-9-5-8-20(23(21)30)17-6-4-7-18(13-17)25(32)33/h4-13,26,30H,1-3H3,(H,32,33)/b27-22-
InChI Key XDXWLKQMMKQXPV-QYQHSDTDSA-N
No information available.
Summary of Clinical Use Click here for help
Used to stimulate platelet production in the bone marrow, in patients with chronic immune (idiopathic) thrombocytopenia (ITP, a rare blood disorder) or in patients with chronic hepatitis C who have low blood platelet counts. In August 2014, the US FDA granted approval for the additional indication, severe aplastic anemia (SAA). In June 2015, eltrombopag was granted approval from the US FDA for the treatment of children (≥ 6 yrs) with ITP.
Eltrombopag is being evaluated in clinical trials for additional indications such as myelodysplastic syndromes (Phase 3) and acute myeloid leukaemia (AML, Phase 2).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Eltrombopag activates the JAK-STAT pathway via interaction with the transmembrane domain of the thrombopoeitin receptor, leading to increased platelet production in the bone marrow (by increasing megakaryocytopoiesis).
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