3998. Fenretinide
Nomenclature
CAS number: 65646-68-6
N-(4-Hydroxyphenyl)retinamide; 4-HPR; all-trans-N-4′-hydroxyretinanilide; 4-(all-trans-retinoyl)aminophenol; McN-R-1967. C26H33NO2; mol wt 391.55.
C 79.75%, H 8.49%, N 3.58%, O 8.17%.
Description and references
Synthetic analog of vitamin A, q.v. Prepn: R. J. Gander, J. A. Gurney, BE 847942; eidem, US 4190594 (1977, 1980 both to J & J); and pharmacology: R. C. Moon et al., Cancer Res. 39, 1339 (1979). Large scale prepn and physical properties: Y. F. Shealy et al., J. Pharm. Sci. 73, 745 (1984). Clinical efficacy and safety in bladder cancer: A. Decensi et al., Eur. J. Cancer Prev. 3, 377 (1994). Review of pharmacology and clinical evaluation in breast cancer prevention: idem et al., Oncol. Rep. 1, 817-824 (1994); M. A. Cobleigh, Leukemia 8, Suppl. 3, s59-s63 (1994); and oral leukoplakia: A. Costa et al., Cancer Res. 54, Suppl., 2032s-2037s (1994).
Properties
Crystallizes in several polymorphic or solvated forms. Crystals from ethanol/water, mp 173-175° (Shealy). Crystals from chloroform/hexanes, mp 162-163°; solvated form obtained by slow crystallization from methanol, mp 178-181° (Moon). uv max (chloroform): 370 nm (ε 44500). uv max (methanol): 362 nm (47900).Therapeutic Category
Antineoplastic.
Keywords
Antineoplastic; Retinoids and Analogs