112. Acitretin

Nomenclature

CAS number: 55079-83-9
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid; etretin; Ro-10-1670; Neotigason (Roche); Soriatane (Roche).
C21H26O3; mol wt 326.43.
C 77.27%, H 8.03%, O 14.70%.

Description and references

Synthetic retinoid; free acid form and major metabolite of etretinate, q.v. Prepn: W. Bollag et al., DE 2414619; eidem, US 4105681 (1974, 1978 both to Hoffmann-La Roche). Teratogenicity study: A. Kistler, H. Hummler, Arch. Toxicol. 58, 50 (1985) DOI PubMed. HPLC determn in plasma: N. R. Al-Mallah et al., Anal. Lett. 21, 1603 (1988). Pharmacokinetics in humans: F. G. Larsen et al., Pharmacol. Toxicol. 62, 159 (1988) PubMed. Clinical evaluation in cutaneous lupus erythematosus: T. Ruzicka et al., Arch. Dermatol. 124, 897 (1988) DOI PubMed. Review of clinical pharmacology: A. Vahlquist, O. Rollman, Dermatologica 175, Suppl. 1, 20-27 (1987) PubMed. Review of clinical studies in psoriatic and nonpsoriatic dermatoses: J.-M. Geiger, B. M. Czarnetzki, ibid. 176, 182-190 (1988) PubMed; of clinical efficacy in psoriasis: C. S. Lee, J. Koo, Expert Opin. Pharmacother. 6, 1725-1734 (2005) DOI PubMed.

Chemical structure

Properties

Green-yellow crystalline powder. Crystals from hexane, mp 228-230°. Sparingly sol in tetrahydrofuran. Slightly sol in acetone, alcohol. Very slightly sol in cyclohexane. Practically insol in water (<0.1 mg/100 mg). pKa ≈5. LD50 i.p. in mice (mg/kg): >4000 (1 day), 700 (10 days), 700 (20 days) (Bollag, 1978).

Therapeutic Category

Antipsoriatic.

Therapeutic Category (Veterinary)

In treatment of dermatologic conditions in small animals.

Keywords

Antipsoriatic