3892. Etretinate

Nomenclature

CAS number: 54350-48-0
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid ethyl ester; Ro-10-9359; Tigason (Roche).
C23H30O3; mol wt 354.48.
C 77.93%, H 8.53%, O 13.54%.

Description and references

Aromatic analog of retinoic acid, q.v. Prepn: W. Bollag et al., DE 2414619; eidem, US 4105681 and US 4215215 (1974, 1978, 1980 all to Hoffmann-La Roche). Effects on skin metabolism: W. P. Raab, B. M. Gmeiner, Arch. Dermatol. Res. 256, 247 (1976). Toxicity study in organ culture: D. R. Bard, I. Lasnitzki, Br. J. Cancer 35, 110 (1977). Pharmacokinetics: R. Haenni, Dermatologica 157, Suppl, 5 (1978). Mutation study: H. J. Juhl et al., Mutat. Res. 58, 317 (1978). HPLC determn in plasma: R. Haenni et al., J. Chromatogr. 162, 615 (1979). Toxicology, carcinogenicity and teratogenicity study: J. J. Kamm, J. Am. Acad. Dermatol. 6, 652 (1982). Clinical evaluation in psoriatic arthritis: M. L. Ciompi et al., Int. J. Tissue React. 10, 25 (1988). Review: H. Mayer et al., Experientia 34, 1105-1119 (1978). Review of pharmacology and therapeutic efficacy: A. Ward et al., Drugs 26, 9-43 (1983); of clinical pharmacology: A. Vahlquist, O. Rollman, Dermatologica 175, Suppl. 1, 20-27 (1987).

Chemical structure

Properties

Crystals, mp 104-105°. LD50 in mice (1 day): >4000 mg/kg i.p. (Bollag). LD50 (20 day) in mice, rats (mg/kg): 1176, >2000 i.p.; >2000, >4000 orally (Kamm).

Derivative

Free acid see Acitretin.

Therapeutic Category

Antipsoriatic.

Keywords

Antipsoriatic