3-(3-{2-[(4E)-1-(3,4-dimethylphenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-ylidene]hydrazin-1-yl}-2-hydroxyphenyl)benzoic acid

• ChemBase ID: 72671
• Molecular Formular: C25H22N4O4
• Molecular Mass: 442.46658
• Monoisotopic Mass: 442.1641052
• SMILES: c1c(c(c(cc1)c1cccc(c1)C(=O)O)O)N/N=C\1/C(=O)N(N=C1C)c1ccc(c(c1)C)C
• Canonical 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+
• InChIKey: XDXWLKQMMKQXPV-HPNDGRJYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-{2-[(4E)-1-(3,4-dimethylphenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-ylidene]hydrazin-1-yl}-2-hydroxyphenyl)benzoic acid
• IUPAC Traditional name: eltrombopag
• Synonyms: SB-497115-GR; Revolade; Promacta; Eltrombopag

Database IDs

• CAS Number: 496775-61-2
• PubChem SID: 162037592
• PubChem CID: 9846180

CALCULATED PROPERTIES

• Acid pKa: 3.9870398
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 4.5041704
• LogD (pH = 7.4): 2.8513787
• Log P: 6.0262365
• Molar Refractivity: 126.4827 cm^3
• Polarizability: 47.734787 Å^3
• Polar Surface Area: 114.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: TpoR

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2229

Research Area: Cancer
Biological Activity:
Eltrombopag (SB-497115-GR, Promacta, Revolade) is a small molecule agonist of the c-mpl (TpoR) receptor with an IC50 of 0.69 μM for the inhibition of hERG K+ channel tail current. In preclinical studies, the compound was shown to interact selectively with the thrombopoeitin receptor, leading to activation of the JAK-STAT signaling pathway and increased proliferation and differentiation of megakaryocytes. Animal studies confirmed that administration could increase platelet counts.In addition, eltrombopag (SB-497115-GR, Promacta, Revolade) decreased proliferation of all cancer cell lines. [1][2]

REFERENCES

• Erickson-Miller CL et al. Leuk Res. 2010 Sep;34(9):1224-31.