Alfacalcidol
Alfacalcidol is an active metabolite of Vitamin D, which performs important functions in regulation of the calcium balance and the bone metabolism. Alfacalcidol is Vitamin D-hormone analog which is activated by the enzyme 25-hydroxylase in the liver for systemic and in osteoblasts for local D-hormone actions. It possesses a unique pattern of pleiotropic effects on, e.g. gut, bone, pararthyroids, muscle and brain. Alfacalcidol is superior to plain vitamin D (cholecalciferol) because the final kidney activation of the latter is regulated by a negative feedback mechanism.
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Chemical Information
| Name | Alfacalcidol |
|---|---|
| Iupac Chemical 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 |
| Synonyms | Alfacalcidol; Alfarol; Alpha D 3; alpha-Calcidol; Alpha-D3; Bondiol; EB 644; |
| Molecular Formula | C27H44O2 |
| Molecular Weight | 400.64 |
| Smile | CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C |
| InChiKey | OFHCOWSQAMBJIW-UHFFFAOYSA-N |
| 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 |
| CAS Number | 41294-56-8 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
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| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Solubility | Soluble in DMSO |
| Handling | |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| HS Code |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Sambrook P. Alfacalcidol and calcitriol in the prevention of bone loss after organ transplantation. Calcif Tissue Int. 1999 Oct;65(4):341-3. doi: 10.1007/s002239900709. PMID: 10485989.
2: Scharla SH, Schacht E, Lempert UG. Alfacalcidol versus plain vitamin D in inflammation induced bone loss. J Rheumatol Suppl. 2005 Sep;76:26-32. PMID: 16142848.
3: Ardron M. Alfacalcidol and hypercalcaemia. Br Med J (Clin Res Ed). 1987 Jan 10;294(6564):125. doi: 10.1136/bmj.294.6564.125-c. PMID: 3105654; PMCID: PMC1245144.
4: Richy F, Deroisy R, Lecart MP, Hanssens L, Mawet A, Reginster JY. D-hormone analog alfacalcidol: an update on its role in post-menopausal osteoporosis and rheumatoid arthritis management. Aging Clin Exp Res. 2005 Apr;17(2):133-42. doi: 10.1007/BF03324586. PMID: 15977462.
5: Oka T, Sakaguchi Y, Isaka Y, Ishii H, Kabata D, Shintani A, Nakatani S, Morioka T, Mori K, Inaba M, Emoto M, Shoji T. Effects of alfacalcidol on cardiovascular outcomes according to alkaline phosphatase levels in the J-DAVID trial. Sci Rep. 2022 Sep 14;12(1):15463. doi: 10.1038/s41598-022-19820-2. PMID: 36104443; PMCID: PMC9475027.
6: Saha S, Sreenivas V, Goswami R. Alfacalcidol vs Calcitriol in the Management of Patient With Hypoparathyroidism: A Randomized Controlled Trial. J Clin Endocrinol Metab. 2021 Jun 16;106(7):2092-2102. doi: 10.1210/clinem/dgab114. PMID: 33616655.
7: Ureña-Torres PA, Cozzolino M, Bover J. Utilisation de l’alfacalcidol et des analogues actifs de la vitamine D dans la maladie rénale chronique [Utilization of alfacalcidol and active vitamin D analogs in chronic kidney disease]. Nephrol Ther. 2018 Jun;14(4):189-200. French. doi: 10.1016/j.nephro.2017.03.003. Epub 2018 Mar 12. PMID: 29545131.
8: Francis RM. Is there a differential response to alfacalcidol and vitamin D in the treatment of osteoporosis? Calcif Tissue Int. 1997 Jan;60(1):111-4. doi: 10.1007/s002239900197. PMID: 9030491.
9: Schacht E. Osteoporose bei rheumatoider Arthritis--Bedeutung von Alfacalcidol in Prävention und Therapie [Osteoporosis in rheumatoid arthritis--significance of alfacalcidol in prevention and therapy]. Z Rheumatol. 2000;59 Suppl 1:10-20. German. doi: 10.1007/s003930070032. PMID: 10769429.
10: Schacht E. Rationale for treatment of involutional osteoporosis in women and for prevention and treatment of corticosteroid-induced osteoporosis with alfacalcidol. Calcif Tissue Int. 1999 Oct;65(4):317-27. doi: 10.1007/s002239900705. PMID: 10485985.
11: Ringe JD, Schacht E. Improving the outcome of established therapies for osteoporosis by adding the active D-hormone analog alfacalcidol. Rheumatol Int. 2007 Dec;28(2):103-11. doi: 10.1007/s00296-007-0422-6. Epub 2007 Aug 1. PMID: 17668216.
12: Tanemoto M, Kimura T, Yamada S. Daily dose of alfacalcidol at conversion from intravenous maxacalcitol in secondary hyperparathyroidism management. Ther Apher Dial. 2022 Apr;26(2):471-472. doi: 10.1111/1744-9987.13751. Epub 2021 Nov 11. PMID: 34738309.
13: Iseki K, Kabata D, Shoji T, Inaba M, Emoto M, Mori K, Morioka T, Nakatani S, Shintani A. Dialysate calcium, alfacalcidol, and clinical outcomes: A post-hoc analysis of the J-DAVID trial. PLoS One. 2022 Sep 7;17(9):e0273195. doi: 10.1371/journal.pone.0273195. PMID: 36070301; PMCID: PMC9451061.
14: Kanis JA. The use of alfacalcidol in the prevention of bone disease in early renal failure. Nephrol Dial Transplant. 1995;10 Suppl 4:23-8; discussion 37-43. doi: 10.1093/ndt/10.supp4.23. PMID: 7478146.
15: Schacht E, Richy F, Reginster JY. The therapeutic effects of alfacalcidol on bone strength, muscle metabolism and prevention of falls and fractures. J Musculoskelet Neuronal Interact. 2005 Jul-Sep;5(3):273-84. PMID: 16172518.
16: Kubodera N. D-hormone derivatives for the treatment of osteoporosis: from alfacalcidol to eldecalcitol. Mini Rev Med Chem. 2009 Oct;9(12):1416-22. doi: 10.2174/138955709789957486. PMID: 19929815.
17: Soen S, Yamamoto K, Takeuchi T, Tanaka Y, Tanaka S, Ito M, Nakano T, Hagino H, Hirakawa A, Matsumoto T. Minodronate combined with alfacalcidol versus alfacalcidol alone for glucocorticoid-induced osteoporosis: a multicenter, randomized, comparative study. J Bone Miner Metab. 2020 Jul;38(4):511-521. doi: 10.1007/s00774-019-01077-x. Epub 2020 Jan 22. PMID: 31970477.
18: Zhou J, Liu B, Qin MZ, Liu JP. Fall Prevention and Anti-Osteoporosis in Osteopenia Patients of 80 Years of Age and Older: A Randomized Controlled Study. Orthop Surg. 2020 Jun;12(3):890-899. doi: 10.1111/os.12701. Epub 2020 Jun 3. PMID: 32495521; PMCID: PMC7307256.
19: Rosery H, Bergemann R, Marx SE, Boehnke A, Melnick J, Sterz R, Williams L. Health-economic comparison of paricalcitol, calcitriol and alfacalcidol for the treatment of secondary hyperparathyroidism during haemodialysis. Clin Drug Investig. 2006;26(11):629-38. doi: 10.2165/00044011-200626110-00002. PMID: 17163297.
20: O'Donnell S, Moher D, Thomas K, Hanley DA, Cranney A. Systematic review of the benefits and harms of calcitriol and alfacalcidol for fractures and falls. J Bone Miner Metab. 2008;26(6):531-42. doi: 10.1007/s00774-008-0868-y. Epub 2008 Nov 1. PMID: 18979152.
Chemical Structure
