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

• ChemBase ID: 167971
• Molecular Formular: C25H22N4O4
• Molecular Mass: 442.46658
• Monoisotopic Mass: 442.1641052
• SMILES: c1(cc(ccc1C)N1N=C(/C(=N/Nc2cccc(c2O)c2cc(ccc2)C(=O)O)/C1=O)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-QYQHSDTDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-{2-[(4Z)-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: 3-(3-{2-[(4Z)-1-(3,4-dimethylphenyl)-3-methyl-5-oxopyrazol-4-ylidene]hydrazin-1-yl}-2-hydroxyphenyl)benzoic acid
• Synonyms: 3'-[2-[(2Z)-1-(3,4-Dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid; SB 497115; Eltrombopag

Database IDs

• CAS Number: 496775-61-2
• PubChem SID: 162262104
• PubChem CID: 9846180

CALCULATED PROPERTIES

• Acid pKa: 3.987072
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 4.5041695
• 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

Physical Property

• Solubility: DMSO
• Apperance: Orange to Red Solid
• Melting Point: 236-238°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E508000

An agonist of the Thrombopoietin (Tpo) receptor, used as treatment for thrombocytopenia

REFERENCES

• Bussel, J., et al.: New Eng. J. Med., 357, 2237 (2007)
• Marsilje, T., et al.: Bioorg. Med. Chem. Lett., 18, 5259 (2007)
• Alper, P., et al.: Bioorg. Med. Chem. Lett., 18, 5255 (2007)