150. Adapalene

Nomenclature

CAS number: 106685-40-9
6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid; 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid; CD-271; Differin (Galderma).
C28H28O3; mol wt 412.52.
C 81.52%, H 6.84%, O 11.64%.

Description and references

Retinoid selective for retinoic acid receptor (RAR) subtypes β and γ. Prepn: B. Shroot et al., EP 199636; eidem, US 4717720 (1986, 1988 both to Cent. Int. Recher. Dermatol.); and structure-activity study: B. Charpentier et al., J. Med. Chem. 38, 4993 (1995). Pilot-scale synthesis: Z. Liu, J. Xiang, Org. Process Res. Dev. 10, 285 (2006). HPLC determn in plasma and tissue: R. Ruhl, H. Nau, Chromatographia 45, 269 (1997). Clinical pharmacology: C. E. M. Griffiths et al., J. Invest. Dermatol. 101, 325 (1993). Clinical trial in acne: A. Shalita et al., J. Am. Acad. Dermatol. 34, 482 (1996). Reviews of pharmacology and clinical potential: B. A. Bernard, Skin Pharmacol. 6, Suppl. 1, 61-69 (1993); R. N. Brogden, K. L. Goa, Drugs 53, 511-519 (1997); of clinical use in acne vulgaris: J. Waugh et al., Drugs 64, 1465-1478 (2004).

Chemical structure

Properties

White crystals from THF and ethyl acetate, mp 319-322°. pK 4.2. Stable to light.

Therapeutic Category

Antiacne.

Keywords

Antiacne