Alfacalcidol

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Alfacalcidol
Alfacalcidol.png
Alfacalcidol ball-and-stick.png
Names
IUPAC name
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-Methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
Other names
Alphacalcidol; 1-Hydroxycholecalciferol
Identifiers
41294-56-8 YesY
ChEBI CHEBI:31186 N
ChEMBL ChEMBL32540 N
ChemSpider 4445376 YesY
DrugBank DB01436 YesY
Jmol 3D model Interactive image
KEGG D01518 YesY
PubChem 5282181
UNII URQ2517572 YesY
  • InChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1 YesY
    Key: OFHCOWSQAMBJIW-AVJTYSNKSA-N YesY
  • InChI=1/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1
    Key: OFHCOWSQAMBJIW-AVJTYSNKBM
  • O[C@@H]1CC(\C(=C)[C@@H](O)C1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C
Properties
C27H44O2
Molar mass 400.64 g/mol
Pharmacology
ATC code A11CC03
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Alfacalcidol (or 1-hydroxycholecalciferol) is an analogue of vitamin D used for supplementation in humans and as a poultry feed additive.

Alfacalcidol has a weaker impact on calcium metabolism[1] and parathyroid hormone levels[2] than calcitriol, however alfacalcidol has significant effects on the immune system, including regulatory T cells.[3] It is considered to be a more useful form of vitamin D supplementation, mostly due to much longer half-life and lower kidney load.[4] It is the most commonly prescribed vitamin D metabolite for patients with end stage renal disease, given that impaired renal function alters the ability to carry out the second hydroxylation step required for the formation of the physiologically active form of vitamin D, 1,25-dihydroxyvitamin D3. Alfacalcidol is an active vitamin D3 metabolite, and therefore does not require the second hydroxylation step in the kidney.[5]

Used as a poultry feed additive, it prevents tibial dyschondroplasia and increases phytate bioavailability.[6][original research?]

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Alfacalcidol treatment restores derailed immune-regulation in patients with undifferentiated connective tissue disease, Autoimmunity Reviews, August 2010;
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ VDI Product Data
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