CAS No 106685-40-9 , 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid

Title: Adapalene
CAS Registry Number: 106685-40-9
CAS Name: 6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid
Synonyms: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid
Manufacturers' Codes: CD-271
Trademarks: Differin (Galderma)
Molecular Formula: C28H28O3
Molecular Weight: 412.52
Percent Composition: C 81.52%, H 6.84%, O 11.64%
Literature References: Retinoid selective for retinoic acid receptor (RAR) subtypes b and g. 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).
Properties: White crystals from THF and ethyl acetate, mp 319-322°. pK 4.2. Stable to light.
Melting point: mp 319-322°
pKa: pK 4.2
Therap-Cat: Antiacne.
Keywords: Antiacne.