Title: Maxacalcitol
CAS Registry Number: 103909-75-7
CAS Name: (1R,3S,5Z)-4-Methylene-5-[(2E)-[(1S,3aS,7aS)-octahydro-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol
Additional Names: (+)-(5Z,7E,20S)-20a-(3-hydroxy-3-methylbutoxy)-9,10-secopregna-5,7,10(19)-trien-1a,3b-diol; 1a,25-dihydroxy-22-oxavitamin D3; 22-oxa-1a,25-dihydroxyvitamin D3; 22-oxacalcitriol; 22-oxa-1,25(OH)2D3
Manufacturers' Codes: MC-1275; Sch-209579
Trademarks: Oxarol (Chugai); Prezios (Chugai)
Molecular Formula: C26H42O4
Molecular Weight: 418.61
Percent Composition: C 74.60%, H 10.11%, O 15.29%
Literature References: Noncalcemic analog of vitamin D. Prepn: N. Kubodera et al., EP 184112; eidem, US 4891364 (1986, 1990 both to Chugai); E. Murayama et al., Chem. Pharm. Bull. 34, 4410 (1986). Industrial synthesis: H. Shimizu et al., Org. Process Res. Dev. 9, 278 (2005). Pharmacology: A. J. Brown et al., J. Clin. Invest. 84, 728 (1989). Immunomodulatory effects: M. Komine et al., Arch. Dermatol. Res. 291, 500 (1999). Metabolism study: M. Ishigai et al., J. Steroid Biochem. Mol. Biol. 66, 281 (1998). LC-MS determn in serum: idem et al., J. Chromatogr. B 706, 261 (1998). Clinical evaluation in psoriasis: J. Barker et al., Br. J. Dermatol. 141, 274 (1999); in secondary hyperparathyroidism: Y. Tsukamoto et al., Am. J. Kidney Dis. 35, 458 (2000).
Properties: Colorless crystals from hexane + ethyl acetate, mp 122°. [a]D20 +49.4° (c = l.00 in ethanol). uv max (ethanol): 263 nm.
Melting point: mp 122°
Optical Rotation: [a]D20 +49.4° (c = l.00 in ethanol)
Absorption maximum: uv max (ethanol): 263 nm
Therap-Cat: Antihyperparathyroid; antipsoriatic.
Keywords: Antipsoriatic; Antihyperparathyroid. |