9081. Tazarotene
Nomenclature
CAS number: 118292-40-3
6-[(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic
acid ethyl ester; ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinate; AGN-190168; Avage (Allergan); Tazorac (Allergan); Zorac (Allergan). C21H21NO2S; mol wt 351.46.
C 71.76%, H 6.02%, N 3.99%, O 9.10%, S 9.12%.
Description and references
Acetylenic retinoid prodrug converted to the active metabolite, tazarotenic acid, with selective affinity for retinoic acid receptors RARĪ² and RARĪ³. Prepn: R. A. S. Chandraratna, EP 284288; idem, US 5089509 (1988, 1992 both to Allergan). Clinical evaluation in psoriasis: T. Esgleyes-Ribot et al., J. Am. Acad. Dermatol. 30, 581 (1994). Clinical trial in treatment of photodamage: S. Kang et al., ibid. 52, 268 (2005). Review of pharmacokinetics and metabolism: D. D.-S. Tang-Liu et al., Clin. Pharmacokinet. 37, 273-287 (1999); of mechanism of action and treatment strategies: A. Roeder et al., Skin Pharmacol. Physiol. 17, 111-118 (2004).
Properties
White solid.Therapeutic Category
Antiacne; antipsoriatic. In treatment of photodamaged skin.
Keywords
Antiacne; Antipsoriatic