Alfacalcidol

Alfacalcidol
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
CAS Number	41294-56-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL32540 ;
ChemSpider	4445376 ;
DrugBank	DB01436 ;
ECHA InfoCard	100.050.253
KEGG	D01518 ;
PubChem CID	5282181;
UNII	URQ2517572 ;
CompTox Dashboard (EPA)	DTXSID0022569 ;
	InChI 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 Key: OFHCOWSQAMBJIW-AVJTYSNKSA-N ; 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;
	SMILES 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
Chemical formula	C27H44O2
Molar mass	400.64 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 than calcitriol,^[1] and on parathyroid hormone levels^[2], however alfacalcidiol has significant effects on the immune system, including regulatory T cells.^[3] It is considered^{[by whom?]} to be a more useful form of vitamin D supplementation, mostly due to much longer half-life and lower kidney load.^[4]

Used as a poultry feed additive, it prevents tibial dyschondroplasia and increases phytate bioavailability.^[5]^{[original research?]}

References

^ Biological effects of various regimes of 25-hydroxyvitamin D3 (calcidiol) administration on bone mineral metabolism in postmenopausal women, Clin Cases Miner Bone Metab. 2009 May–Aug; 6(2): 169–173; [1]
^ Oral calcitriol versus oral alfacalcidol for the treatment of secondary hyperparathyroidism in patients receiving hemodialysis: a randomized, crossover trial, Can J ,Clin Pharmacol Vol 15 (1) Winter 2008:e36 -e43; January 9, 2008; [2]
^ Alfacalcidol treatment restores derailed immune-regulation in patients with undifferentiated connective tissue disease, Autoimmunity Reviews, August 2010;
^ Superiority of alfacalcidol compared to vitamin D plus calcium in lumbar bone mineral density in postmenopausal osteoporosis, Rheumatol Int. 2006 Mar;26(5):445-53. Epub 2005 Nov 10; [3]
^ VDI Product Data