Chemistry:Alfacalcidol
| |
| |
| Names | |
|---|---|
| Preferred IUPAC name
(1R,3S,5Z)-4-Methylidene-5-[(2E)-2-{(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]octahydro-4H-inden-4-ylidene}ethylidene]cyclohexane-1,3-diol | |
| Other names
Alphacalcidol; 1-Hydroxycholecalciferol
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| KEGG | |
PubChem CID
|
|
| UNII | |
| |
| |
| Properties | |
| C27H44O2 | |
| Molar mass | 400.64 g/mol |
| Melting point | 136 °C (277 °F; 409 K) |
| 0.016 g/100 mL | |
| Pharmacology | |
| 1=ATC code }} | A11CC03 (WHO) |
| License data | |
| Legal status | |
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[3] and parathyroid hormone levels[4] than calcitriol; but significant effects on the immune system, including regulatory T cells.[5] It is considered to be a more useful form of vitamin D supplementation, mostly due to much longer half-life and lower kidney load.[6] 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.[7]
It was patented in 1971 and approved for medical use in 1978.[8]
Trade names
Pharmaceutical trade names include AlphaD and One-Alpha.
Other animals
Used as a poultry feed additive, it prevents tibial dyschondroplasia and increases phytate bioavailability.[9][original research?]
References
- ↑ "One-Alpha Capsules - Summary of Product Characteristics (SmPC)". 9 November 2017. https://www.medicines.org.uk/emc/product/5516/smpc.
- ↑ "List of nationally authorised medicinal products". 11 February 2021. https://www.ema.europa.eu/documents/psusa/alfacalcidol-list-nationally-authorised-medicinal-products-psusa/00000080/202006_en.pdf.
- ↑ "Biological effects of various regimes of 25-hydroxyvitamin D3 (calcidiol) administration on bone mineral metabolism in postmenopausal women". Clinical Cases in Mineral and Bone Metabolism 6 (2): 169–73. May 2009. PMID 22461169.
- ↑ "Oral calcitriol versus oral alfacalcidol for the treatment of secondary hyperparathyroidism in patients receiving hemodialysis: a randomized, crossover trial". The Canadian Journal of Clinical Pharmacology 15 (1): e36-43. 2008. PMID 18192704. http://www.jptcp.com/cjcp07017_wazny_e36-e43v2-r101690. Retrieved 2013-12-04.
- ↑ "Alfacalcidol treatment restores derailed immune-regulation in patients with undifferentiated connective tissue disease". Autoimmunity Reviews 10 (3): 155–62. January 2011. doi:10.1016/j.autrev.2010.09.018. PMID 20868777.
- ↑ "Superiority of alfacalcidol compared to vitamin D plus calcium in lumbar bone mineral density in postmenopausal osteoporosis". Rheumatology International 26 (5): 445–53. March 2006. doi:10.1007/s00296-005-0073-4. PMID 16283320.
- ↑ "Alfacalcidol in the therapy of renal bone disease". International Journal of Clinical Pharmacology and Therapeutics 39 (12): 546–50. December 2001. doi:10.5414/cpp39546. PMID 11770836.
- ↑ Fischer, Jnos; Ganellin, C. Robin (2006) (in en). Analogue-based Drug Discovery. John Wiley & Sons. p. XXX. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PAXXX.
- ↑ "Vitamin Derivatives". http://www.vitaminderivatives.com/.
 |  |
