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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.050.253
KEGG
UNII
Properties
C27H44O2
Molar mass 400.64 g/mol
Pharmacology
A11CC03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

Trade names

Pharmaceutical trade names include AlphaD and One-Alpha.

References

  1. ↑ "Biological effects of various regimes of 25-hydroxyvitamin D3 (calcidiol) administration on bone mineral metabolism in postmenopausal women". Clin Cases Miner Bone Metab. 6 (2): 169–173. 2009. PMC 2781231. PMID 22461169.
  2. ↑ "Oral calcitriol versus oral alfacalcidol for the treatment of secondary hyperparathyroidism in patients receiving hemodialysis: a randomized, crossover trial". Can J Clin Pharmacol. 15 (1): e36–e43. 2008. Archived from the original on 2014-10-06. Retrieved 2013-12-04.
  3. ↑ Alfacalcidol treatment restores derailed immune-regulation in patients with undifferentiated connective tissue disease, Autoimmunity Reviews, August 2010;
  4. ↑ "Superiority of alfacalcidol compared to vitamin D plus calcium in lumbar bone mineral density in postmenopausal osteoporosis". Rheumatol Int. 26 (5): 445–53. Mar 2006. doi:10.1007/s00296-005-0073-4. PMID 16283320.
  5. ↑ "Alfacalcidol in the therapy of renal bone disease". Int J Clin Pharmacol Ther. 39: 546–50. Dec 2001. doi:10.5414/cpp39546. PMID 11770836.
  6. ↑ VDI Product Data


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