83805-11-2

Usage

Uses

Used in Pharmaceutical Industry:
Falecalcitriol is used as a therapeutic agent for the treatment of secondary hyperparathyroidism (SHPT). It is more potent than alfacalcidol in suppressing parathyroid hormone without triggering hypercalcemia, making it a preferred choice for patients with moderate to severe SHPT, particularly those undergoing hemodialysis.

Originator

University of Wisconsin (US)

Hazard

A poison by ingestion.

InChI:InChI=1/C27H38F6O3/c1-16(6-4-13-25(36,26(28,29)30)27(31,32)33)21-10-11-22-18(7-5-12-24(21,22)3)8-9-19-14-20(34)15-23(35)17(19)2/h8-9,16,20-23,34-36H,2,4-7,10-15H2,1,3H3/b18-8+,19-9-/t16-,20-,21-,22+,23+,24-/m1/s1

Upstream product

• 85382-46-3 25,26,27-trisnorcholest-5-ene-1α,3β,24-triol 1,3-diacetate 
• 117467-20-6 (R)-4-((8S,9S,10R,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 85382-50-9 1α,3β,25-thihydroxy-26,26,26,27,27,27-hexafluorocholest-5-ene-24-yl phenyl sulfone 1,3-bis(triethylsilyl) ether 
• 85382-52-1 26,26,26,27,27,27-hexafluoro-1α,3β,25-triacetoxycholest-5,7-diene 
• 85382-51-0 1α,25-dihydroxy-26,26,26,27,27,27-hexafluorocholesterol triacetate 
• 89084-29-7 (1S,3R,8S,9S,10R,13R,14S,17R)-17-((R)-4-Benzenesulfonyl-6,6,6-trifluoro-5-hydroxy-1-methyl-5-trifluoromethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol 
• 89084-28-6 Acetic acid (1S,3R,8S,9S,10R,13R,14S,17R)-3-acetoxy-10,13-dimethyl-17-[(R)-1-methyl-4-(toluene-4-sulfonyloxy)-butyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 
• 85382-49-6 25,26,27-trisnor-1α,3β-bistriethylsiloxycholest-5-ene-24-yl phenyl sulfone 
• 85382-48-5 25,26,27-trisnor-1α,3β-diacetoxycholest-5-ene-24-yl phenyl sulfone 
• 75303-38-7 (R)-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-2-trifluoromethyl-heptan-2-ol 
• 84983-20-0 26,26,26,27,27,27-hexafluoro-25-hydroxy-1α,2α-epoxycholest-4,6-dien-3-one 
• 84983-21-1 1α,25-dihydroxy-26,26,26,27,27,27-hexafluorocholesterol 
• 84983-19-7 26,26,26,27,27,27-hexafluoro-25-hydroxycholest-1,4,6-trien-3-one 
• 85382-47-4 25,26,27-trisnorcholest-24-bromo-5-ene-1α,3β-diol diacetate 

Downstream Products

• 210907-40-7 (6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol 
• 210907-37-2 (6Z)-(3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5⁽¹⁰⁾,6,8-cholestatriene-3,25-diol-1-one 

Relevant academic research and scientific papers

Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3

The activated vitamin D3 derivative 26,27-F6-1α,25(OH)2D3 (2a), its three A-ring diastereomers (2b, 2c, 2d), and 5,6-trans isomer (2e) were prepared. Two analogues (2b, 2c) of these isomers were synthesized by a palladium catalyzed coupling reaction using vinyl bromide 5 and enynes (6a, 6b), which were derived from readily commercially available 2S-(+)-glycidyl p-toluenesulfonate 7, as a common starting material. Competitive vitamin D receptor (VDR) binding affinities of these diastereomers of 2a were evaluated. Interestingly, the stereochemical effects at C-1,3 of 2a were considerably more moderate than those of 1α,25(OH)2D3 (1). In particular, isomerization at the 5,6-double bond of 2a only slightly reduced VDR affinity, whereas 5,6-trans-1α,25(OH)2D3 had a significantly lower binding affinity than 1. Copyright (C) 2000 Elsevier Science Ltd.

Kinetics of thermal [1,7A]-sigmatropic shift of hexafluoro vitamin D3 and vitamin D3 derivatives. Evaluation of conformations of the A ring affected by 1-OH and 3-OH groups

The quantitative evaluation of the [1,7a]-sigmatropic rearrangement of vitamin D3 and its analogs affected by the conformations of the A ring using the 1H-NMR method was described. Although the side chain of the D ring had no effect on the hydrogen migration, the rearrangement was influenced by the hydroxy groups of the A ring.

Immunosuppressive agents

The invention relates to pharmaceutical compositions comprising at least one Vitamin D derivative and a method of using the pharmaceutical compositions in suppressing immune responses.