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Alfacalcidol

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

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
  • 41294-56-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:31186 N
ChEMBL
  • ChEMBL32540 N
ChemSpider
  • 4445376 Y
DrugBank
  • DB01436 Y
ECHA InfoCard 100.050.253
KEGG
  • D01518 Y
  • 5282181
UNII
  • URQ2517572 Y
  • DTXSID0022569
  • 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 Y
    Key: OFHCOWSQAMBJIW-AVJTYSNKSA-N Y
  • 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
  • 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
C27H44O2
Molar mass 400.64 g/mol
Melting point 136 °C (277 °F; 409 K)
0.016 g/100 mL
Pharmacology
A11CC03 (WHO)
License data
  • EU EMAby 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 YN ?)

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 edit

Pharmaceutical trade names include AlphaD and One-Alpha.

Other animals edit

Used as a poultry feed additive, it prevents tibial dyschondroplasia and increases phytate bioavailability.[9][original research?]

References edit

  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). . 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.
  9. ^ "Vitamin Derivatives". vitaminderivatives.com. Retrieved 14 April 2023.

alfacalcidol, hydroxycholecalciferol, analogue, vitamin, used, supplementation, humans, poultry, feed, additive, namespreferred, iupac, name, methylidene, methyl, methylheptan, octahydro, inden, ylidene, ethylidene, cyclohexane, diolother, names, alphacalcidol. Alfacalcidol or 1 hydroxycholecalciferol is an analogue of vitamin D used for supplementation in humans and as a poultry feed additive Alfacalcidol NamesPreferred 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 diolOther names Alphacalcidol 1 HydroxycholecalciferolIdentifiersCAS Number 41294 56 8 Y3D model JSmol Interactive imageChEBI CHEBI 31186 NChEMBL ChEMBL32540 NChemSpider 4445376 YDrugBank DB01436 YECHA InfoCard 100 050 253KEGG D01518 YPubChem CID 5282181UNII URQ2517572 YCompTox Dashboard EPA DTXSID0022569InChI 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 YKey OFHCOWSQAMBJIW AVJTYSNKSA N YInChI 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 s1Key OFHCOWSQAMBJIW AVJTYSNKBMSMILES 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 CPropertiesChemical formula C27H44O2Molar mass 400 64 g molMelting point 136 C 277 F 409 K Solubility in water 0 016 g 100 mLPharmacologyATC code A11CC03 WHO License data EU EMA by INNLegal 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 Y N Infobox references 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 editPharmaceutical trade names include AlphaD and One Alpha Other animals editUsed as a poultry feed additive it prevents tibial dyschondroplasia and increases phytate bioavailability 9 original research References edit One Alpha Capsules Summary of Product Characteristics SmPC emc 9 November 2017 Retrieved 17 February 2021 List of nationally authorised medicinal products PDF ema europa eu 11 February 2021 Retrieved 14 April 2023 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 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 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 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 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 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p XXX ISBN 9783527607495 Vitamin Derivatives vitaminderivatives com Retrieved 14 April 2023 Retrieved from https en wikipedia org w index php title Alfacalcidol amp oldid 1189653213, wikipedia, wiki, book, books, library,

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