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
References
1. Marsilje TH, Alper PB, Lu W, Mutnick D, Michellys PY, He Y, Karanewsky DS, Chow D, Gerken A, Lao J et al.. (2008)
Optimization of small molecule agonists of the thrombopoietin (Tpo) receptor derived from a benzo[a]carbazole hit scaffold.
Bioorg Med Chem Lett, 18 (19): 5259-62. [PMID:18783949]