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Alfacalcidol information


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
CAS Number
  • 41294-56-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:31186 ☒N
ChEMBL
  • ChEMBL32540 ☒N
ChemSpider
  • 4445376 checkY
DrugBank
  • DB01436 checkY
ECHA InfoCard 100.050.253 Edit this at Wikidata
KEGG
  • D01518 checkY
PubChem CID
  • 5282181
UNII
  • URQ2517572 checkY
CompTox Dashboard (EPA)
  • DTXSID0022569 Edit this at Wikidata
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 checkY
    Key: OFHCOWSQAMBJIW-AVJTYSNKSA-N checkY
  • 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
Melting point 136 °C (277 °F; 409 K)
Solubility in water
0.016 g/100 mL
Pharmacology
ATC code
A11CC03 (WHO)
License data
  • EU EMA: by INN
Legal status
  • UK: POM (Prescription only)[1]
  • EU: Rx-only[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
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]

  1. ^ "One-Alpha Capsules - Summary of Product Characteristics (SmPC)". (emc). 9 November 2017. Retrieved 17 February 2021.
  2. ^ "List of nationally authorised medicinal products" (PDF). ema.europa.eu. 11 February 2021. Retrieved 14 April 2023.
  3. ^ Cavalli L, Cavalli T, Marcucci G, Falchetti A, Masi L, Brandi ML (May 2009). "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. PMC 2781231. PMID 22461169.
  4. ^ Moe S, Wazny LD, Martin JE (2008). "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. PMID 18192704. Archived from the original on 2014-10-06. Retrieved 2013-12-04.
  5. ^ Zold E, Szodoray P, Nakken B, Barath S, Kappelmayer J, Csathy L, et al. (January 2011). "Alfacalcidol treatment restores derailed immune-regulation in patients with undifferentiated connective tissue disease". Autoimmunity Reviews. 10 (3): 155–62. doi:10.1016/j.autrev.2010.09.018. hdl:2437/180066. PMID 20868777.
  6. ^ Nuti R, Bianchi G, Brandi ML, Caudarella R, D'Erasmo E, Fiore C, et al. (March 2006). "Superiority of alfacalcidol compared to vitamin D plus calcium in lumbar bone mineral density in postmenopausal osteoporosis". Rheumatology International. 26 (5): 445–53. doi:10.1007/s00296-005-0073-4. PMID 16283320. S2CID 9931256.
  7. ^ Ritzerfeld M, Klasser M, Mann H (December 2001). "Alfacalcidol in the therapy of renal bone disease". International Journal of Clinical Pharmacology and Therapeutics. 39 (12): 546–50. doi:10.5414/cpp39546. PMID 11770836.
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. XXX. ISBN 9783527607495.

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Alfacalcidol

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

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Vitamin D

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to make taking supplements recommendable. Other forms (vitamin D2, alfacalcidol, and calcitriol) do not appear to have any beneficial effects with regard...

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Vitamin D analogues

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potentially greater, or selective, therapeutic actions. These include: Alfacalcidol Calcipotriol (calcipotriene) Doxercalciferol Falecalcitriol Paricalcitol...

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Calcitriol

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tissues including placenta and activated macrophages. When the drug alfacalcidol is used, 25-hydroxylation in the liver produces calcitriol as the active...

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ATC code A11

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Betacarotene A11CC01 Ergocalciferol A11CC02 Dihydrotachysterol A11CC03 Alfacalcidol A11CC04 Calcitriol A11CC05 Colecalciferol A11CC06 Calcifediol A11CC20...

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Hypoparathyroidism

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hypoparathyroidism is with vitamin D analogs (such as calcitriol or alfacalcidol), vitamin D supplementation and calcium supplementation. Potential risks...

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Cholecalciferol

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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Eldecalcitol

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than its counterpart alfacalcidol, another vitamin D analog. Studies have shown eldecalcitol is more effective than alfacalcidol in preventing vertebral...

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Ergocalciferol

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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Calcifediol

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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Simcere Pharmaceutical

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diclofenac sodium sustained-release capsules, the Faneng-branded generic alfacalcidol soft capsules and the Yineng-branded generic lentinan injection, all...

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Vitamin D toxicity

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with coronary calcification. Moreover, the active vitamin D analog, alfacalcidol, seems to protect patients from developing vascular calcification. Serum...

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Renal osteodystrophy

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ferric citrate among others active forms of vitamin D (calcitriol, alfacalcidol, paricalcitol, maxacalcitol, doxercalciferol, among others) cinacalcet...

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Calcipotriol

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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C27H44O2

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The molecular formula C27H44O2 may refer to: Alfacalcidol Calcifediol, or calcidiol Colestolone, or 5α-cholest-8(14)-en-3β-ol-15-one Gefarnate...

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Lithocholic acid

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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Hydroxycholecalciferol

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Hydroxycholecalciferol may refer to: 1-Hydroxycholecalciferol (Alfacalcidol) 25-Hydroxycholecalciferol (Calcifediol or calcidiol) 1,25-Dihydroxycholecalciferol...

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ATC code M05

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calcium and colecalciferol, sequential M05BB06 Alendronic acid and alfacalcidol, sequential M05BB07 Risedronic acid and colecalciferol M05BB08 Zoledronic...

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Doxercalciferol

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synthesis and secretion. Docercalciferol is the vitamin D2 analogue of alfacalcidol. It undergoes 25-hydroxylation in the liver to become the active ercalcitriol...

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Paricalcitol

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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Osteitis fibrosa cystica

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Medical management of OFC consists of vitamin D treatment, generally alfacalcidol or calcitriol, delivered intravenously. Studies have shown that in cases...

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Dihydrotachysterol

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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Vitamin D receptor

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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Tacalcitol

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Agonists: 7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin...

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