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Calcitriol

Calcitriol is the active form of vitamin D that binds to the vitamin D receptors (VDR), increasing absorption of dietary Ca2+. Calcitriol is produced in the kidney from prodrug forms of vitamin D such as cholecalciferol. Calcitriol is commercially used in dietary supplements to prevent osteoporosis; it exhibits anti-osteoporotic, immunomodulatory, anti-inflammatory, anti-diabetic, anticancer, and chemopreventive activities. In basal cell carcinoma cells, calcitriol decreases hedgehog (Hh) signaling, suppressing cancer progression. In other models, calcitriol stimulates differentiation of skin cells and inhibits skin cancer cell proliferation and tumor formation. Additionally, this compound decreases activation of toll-like receptors (TLRs), protecting against the development of type I diabetes.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18847330

Cas No.

32222-06-3

Purity

≥97%

Formula

C27H44O3

Formula Wt.

416.64

Chemical Name

(1α,3β,5Z,7E)-9,10-Secocholesta-5,710(19)-triene-1,3,25-triol

IUPAC Name

5-[2-[1-(6-hydroxy-6-methylheptan-2-yl)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Synonym

1α,25-Dihydroxyvitamin D3

Melting Point

111-115°C

Solubility

Slightly soluble in ethanol, ethyl acetate. Soluble in DMSO

Appearance

White Solid

Albert B, Hahn H. Interaction of hedgehog and vitamin D signaling pathways in basal cell carcinomas. Adv Exp Med Biol. 2014;810:329-41. PMID: 25207374.

Bikle DD. The vitamin D receptor: a tumor suppressor in skin. Adv Exp Med Biol. 2014;810:282-302. PMID: 25207372.

Adamczak DM, Nowak JK, Frydrychowicz M, et al. The role of Toll-like receptors and vitamin D in diabetes mellitus type 1–a review. Scand J Immunol. 2014 Aug;80(2):75-84. PMID: 24845558.

Vojinovic J. Vitamin D receptor agonists anti-inflammatory properties. Ann N Y Acad Sci. 2014 May;1317:47-56. PMID: 24754474.

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