Title: Calcitriol
CAS Registry Number: 32222-06-3
CAS Name: (1a,3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol
Additional Names: 1a,25-dihydroxycholecalciferol; 1a,25-dihydroxyvitamin D3; 1,25-DHCC
Manufacturers' Codes: Ro-21-5535
Trademarks: Calcijex (Abbott); Rocaltrol (Roche); Silkis (Galderma)
Molecular Formula: C27H44O3
Molecular Weight: 416.64
Percent Composition: C 77.83%, H 10.64%, O 11.52%
Literature References: The biologically active form of vitamin D3, q.v., in intestinal calcium transport and bone calcium resorption. First obtained from chick intestine and designated as metabolite 4B: J. F. Myrtle et al., J. Biol. Chem. 245, 1190 (1970); M. R. Haussler et al., Proc. Natl. Acad. Sci. USA 68, 177 (1971). Isoln and identification: M. F. Holick et al., ibid. 803; D. E. M. Lawson et al., Nature 230, 228 (1971); A. W. Norman et al., Science 173, 51 (1971). Synthesis: D. H. R. Barton et al., J. Chem. Soc. Chem. Commun. 1974, 203; T. Sato et al., Chem. Pharm. Bull. 26, 2933 (1978). Effect of calcium on in vivo synthesis: I. T. Boyle et al., Proc. Natl. Acad. Sci. USA 68, 2131 (1971). Stimulation of bone resorption in tissue culture: L. G. Raisz et al., Science 175, 768 (1972). Classification as a steroid hormone: J. S. Emtage et al., Nature 246, 100 (1973). Pharmacokinetics: J. R. Muindi et al., Clin. Pharmacol. Ther. 72, 648 (2002). Clinical evaluation in prostate cancer: C. Gross et al., J. Urol. 159, 2035 (1998); in secondary hyperparathyroidism: S. Koshikawa et al., Nephron 90, 413 (2002). Comprehensive description: T. Suda, Vitamins 45, 175-188 (1972); E. Debesis, Anal. Profiles Drug Subs. 8, 83-100 (1979). Review of clinical efficacy in osteoporosis: K. L. Dechant, K. L. Goa, Drugs Aging 5, 300-317 (1994); of mechanism of action in renal failure: C. H. Hsu et al., Kidney Int. 46, 605-612 (1994); of clinical experience in treatment of psoriasis: L. Kowalzick, Br. J. Dermatol. 144, Suppl. 58, 21-25 (2001).
Properties: White crystalline powder, mp 111-115°. uv max (abs ethanol): 264 nm (e 19000). [a]D25 +48° (methanol). Slightly sol in methanol, ethanol, ethyl acetate, THF. Air and light sensitive.
Melting point: mp 111-115°
Optical Rotation: [a]D25 +48° (methanol)
Absorption maximum: uv max (abs ethanol): 264 nm (e 19000)
Therap-Cat: Calcium regulator; vitamin (antirachitic); antihyperparathyroid; antineoplastic; antipsoriatic.
Keywords: Calcium Regulator; Vitamin/Vitamin Source; Vitamin D; Antihyperparathyroid; Antineoplastic; Antipsoriatic. |