77372-59-9

Usage

Naturally occurring vitamin D metabolite

1,25,26-trihydroxyvitamin D3 is a naturally occurring form of vitamin D that is produced in the body.

Regulates calcium and phosphate levels

This metabolite plays a crucial role in regulating the levels of calcium and phosphate in the body, which are essential for maintaining healthy bones and teeth.

Formed from 25-hydroxyvitamin D3 in the kidneys

1,25,26-trihydroxyvitamin D3 is formed from 25-hydroxyvitamin D3, another form of vitamin D, in the kidneys.

Potent regulator of calcium absorption in the intestines

This metabolite acts as a potent regulator of calcium absorption in the intestines, which is important for maintaining healthy levels of calcium in the body.

Immunomodulatory effects

This metabolite has been found to have immunomodulatory effects, which means that it can influence the immune system and help regulate the body's response to infections and other immune challenges.

InChI:InChI=1/C27H44O4/c1-18(7-5-13-26(3,31)17-28)23-11-12-24-20(8-6-14-27(23,24)4)9-10-21-15-22(29)16-25(30)19(21)2/h9-10,18,22-25,28-31H,2,5-8,11-17H2,1,3-4H3/b20-9+,21-10-/t18-,22+,23-,24+,25-,26+,27-/m1/s1

Upstream product

• 93511-78-5 (S)-4-((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-2,2,4-trimethyl-[1,3]dioxolane 
• 81131-50-2 Acetic acid (1S,3R,8S,9S,10R,13R,14S,17R)-3-acetoxy-10,13-dimethyl-17-[(R)-1-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 
• 88128-74-9 Acetic acid (1S,3R,8S,9S,10R,13R,14S,17R)-3-acetoxy-7-bromo-10,13-dimethyl-17-[(R)-1-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 
• 88128-76-1 Acetic acid (1S,3R,9S,10R,13R,14R,17R)-3-acetoxy-10,13-dimethyl-17-[(R)-1-methyl-4-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-butyl]-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 
• 93489-53-3 <1S-(1β,3aα,4β,7aβ)>-1-ethanone 
• 93489-58-8 (3aR,4S,7aS)-(Z)-1-ethylidene-7a-methyloctahydro-1H-4-indenol 
• 93489-62-4 (3S,5S)-3-[(R)-2-((1R,3aR,4S,7aR)-4-Hydroxy-7a-methyl-octahydro-inden-1-yl)-propyl]-5-methoxycarbonyl-2,2,5-trimethyl-isoxazolidin-2-ium; iodide 

Relevant academic research and scientific papers

Chemical Synthesis of Side-Chain-Hydroxylated Vitamin D3 Derivatives and Their Metabolism by CYP27B1

1α,25-Dihydroxyvitamin D3 (abbreviated here as 1,25D3) is a hormonally active form of vitamin D3 (D3), and is produced from D3 by CYP27 A1-mediated hydroxylation at C25, followed by CYP27B1-mediated hydroxylation at C1. Further hydroxylation of 25D3 and 1,25D3 occurs at C23, C24 and C26 to generate corresponding metabolites, except for 1,25R,26D3. Since the capability of CYP27B1 to hydroxylate C1 of side-chain-hydroxylated metabolites other than 23S,25D3 and 24R,25D3 has not been examined, we have here explored the role of CYP27B1 in the C1 hydroxylation of a series of side-chain-hydroxylated D3 derivatives. We found that CYP27B1 hydroxylates the R diastereomers of 24,25D3 and 25,26D3 more effectively than the S diastereomers, but shows almost no activity towards either diastereomer of 23,25D3. This is the first report to show that CYP27B1 metabolizes 25,26D3 to the corresponding 1α-hydroxylated derivative, 1,25,26D3. It will be interesting to examine the physiological relevance of this finding.

Method of treating disease states by the administration of 1α,25,26-trihydroxycholecalciferol

The present invention relates to the method of treating disease states characterized by higher than normal levels of endogenously produced 1α,25 dihydroxy-cholecalciferol or conditions where there is an increased sensitivity to 1α, 25 dihydroxy-cholecalciferol by administering to an organism suffering from such a disease state a pharmaceutically effective amount of the R or S epimer of 1α,25,26 trihydroxy-cholecalciferol.