3520. Efaproxiral

Nomenclature

CAS number: 131179-95-8
2-[4-[2-[(3,5-Dimethylphenyl)amino]-2-oxoethyl]phenoxy]-2-methylpropanoic acid; 2-4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy-2-methylpropionic acid; RSR-13; Efaproxyn (Allos).
C20H23NO4; mol wt 341.40.
C 70.36%, H 6.79%, N 4.10%, O 18.75%.

Description and references

Allosteric modifier of hemoglobin (Hb). Binds in the central water cavity of the Hb molecule causing a conformational change such that bound oxygen is released more readily. Prepd not claimed: D. J. Abraham et al., US 5049695 (1991 to Center Innovative Technol.); eidem, J. Med. Chem. 34, 752 (1991). LC/MS/MS determn in urine: M. Thevis et al., J. Mass Spectrom. 41, 332 (2006). Oxygen binding affinities and mechanism of action: D. J. Abraham et al., Biochemistry 31, 9141 (1992). Effect on myocardial oxygen concentration: P. S. Pagel et al., J. Pharmacol. Exp. Ther. 285, 1 (1998). Antimetastatic effects: B. A. Teicher et al., Cancer Chemother. Pharmacol. 42, 24 (1998). Clinical pharmacokinetics and pharmacodynamics: L. Kleinberg et al., J. Clin. Oncol. 17, 2593 (1999). Clinical trial in brain metastases from breast cancer: J. H. Suh et al., ibid. 24, 106 (2006).

Chemical structure

Properties

Pale yellow, crystalline solid. mp 85°.

Therapeutic Category

Antineoplastic adjunct (radiosensitizer).

Keywords

Antineoplastic Adjunct; Radiosensitizer