10320. Eltrombopag

Nomenclature

CAS number: 496775-61-2; 376591-99-0 (unspecified stereo)
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.
C25H22N4O4; mol wt 442.47.
C 67.86%, H 5.01%, N 12.66%, O 14.46%.

Description and references

Thrombopoeitin receptor agonist; stimulates production of platelets from megakaryocytes. Prepn (unspecified stereo): K. J. Duffy et al., WO 01089457; eidem, US 7160870 (2001, 2008 both to SmithKline Beecham; Glaxo). Prepn of Z-form bis-monoethanolamine salt: S. Moore, WO 03098992 (2003 to SmithKline Beecham). Clinical pharmacokinetics and effect on platelet counts: J. M. Jenkins et al., Blood 109, 4739 (2007) DOI PubMed. Clinical evaluation in hepatitis C related thrombocytopenia: J. G. McHutchison et al., N. Engl. J. Med. 357, 2227 (2007) DOI PubMed; in idiopathic thrombocytopenic purpura: J. B. Bussel et al., ibid. 2237 DOI PubMed. Review of discovery and pharmacology: K. J. Duffy, C. L. Erickson-Miller in Target Validaton in Drug Discovery (Academic Press, Burlington, MA, 2007) pp 241-254.

Chemical structure

Properties

Orange solid. Soly at 25° (mg/ml): <0.001 in water; 1.9 in methanol. Sol in THF.

Derivative

Compd with 2-aminoethanol (1:2).

Nomenclature

CAS number: 496775-62-3
Eltrombopag olamine; eltrombopag bis-monoethanolamine; Promacta (GSK); Revolade (GSK).
C25H22N4O4..2(C2H7NO); mol wt 564.63.
C 61.69%, H 6.43%, N 14.88%, O 17.00%.

Properties

Soly at 25° (mg/ml): 14.2 in water; 6.4 in methanol.

Therapeutic Category

Antithrombocytopenic.

Keywords

Antithrombocytopenic