Ergocalciferol Explained

Alt2:Ball-and-stick model of the ergocalciferol molecule
Tradename:Drisdol, Calcidol, others
Dailymedid:Ergocalciferol
Routes Of Administration:By mouth, intramuscular
Atc Prefix:A11
Atc Suffix:CC01
Legal Ca:Rx-only
Legal Ca Comment:[1]
Legal Uk:POM
Legal Uk Comment:[2]
Legal Us:OTC
Cas Number:50-14-6
Pubchem:5280793
Drugbank:DB00153
Chemspiderid:4444351
Unii:VS041H42XC
Kegg:C05441
Chebi:28934
Chembl:1536
Synonyms:viosterol
Iupac Name:(3S,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
C:28
H:44
O:1
Smiles:O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@H](C)C(C)C)C)C
Stdinchi:1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
Stdinchikey:MECHNRXZTMCUDQ-RKHKHRCZSA-N
Melting Point:114
Melting High:118

Ergocalciferol, also known as vitamin D2 and nonspecifically calciferol, is a type of vitamin D found in food and used as a dietary supplement.[3] As a supplement it is used to prevent and treat vitamin D deficiency. This includes vitamin D deficiency due to poor absorption by the intestines or liver disease. It may also be used for low blood calcium due to hypoparathyroidism. It is used by mouth or injection into a muscle.[4] [5]

Excessive doses can result in increased urine production, high blood pressure, kidney stones, kidney failure, weakness, and constipation.[6] If high doses are taken for a long period of time, tissue calcification may occur.[5] Normal doses are safe in pregnancy.[7] It works by increasing the amount of calcium absorbed by the intestines and kidneys.[6] Food in which it is found include some mushrooms.[8]

Ergocalciferol was first described in 1936.[9] Ergocalciferol is available as a generic medication and over the counter.[6] In 2021, it was the 35th most commonly prescribed medication in the United States, with more than 17million prescriptions.[10] [11] Certain foods such as breakfast cereal and margarine have ergocalciferol added to them in some countries.[12] [13] It is on the World Health Organization's List of Essential Medicines.[14]

Use

Ergocalciferol may be used as a vitamin D supplement, whereas cholecalciferol (vitamin D3) is produced naturally by the skin when exposed to ultraviolet light.[15] Ergocalciferol (D2) and cholecalciferol (D3) are considered to be equivalent for vitamin D production, as both forms appear to have similar efficacy in ameliorating rickets[16] and reducing the incidence of falls in elderly patients.[17] Conflicting reports exist, however, concerning the relative effectiveness, with some studies suggesting that ergocalciferol has less efficacy based on limitations in absorption, binding, and inactivation.[18] A meta-analysis concluded that evidence usually favors cholecalciferol in raising vitamin D levels in blood, although it stated more research is needed.[18]

Mechanism

Ergocalciferol is a secosteroid formed by a photochemical bond breaking of a steroid, specifically, by the action of ultraviolet light (UV-B or UV-C) on ergosterol, a form of provitamin D2.[19]

Like cholecalciferol, ergocalciferol is inactive by itself. It requires two hydroxylations to become active: the first in the liver by CYP2R1 to form 25-hydroxyergocalciferol (ercalcidiol or 25-OH D2[20]), and the second in the kidney by CYP27B1, to form the active 1,25-dihydroxyergocalciferol (ercalcitriol or 1,25-(OH)2D2), which activates the vitamin D receptor.[21] Unlike cholecalciferol, 25-hydroxylation is not performed by CYP27A1 for ergocalciferol.

Ergocalciferol and metabolites have lower affinity to the vitamin D-binding protein compared to the D3 counterparts. The binding affinity of ercalcitriol to the vitamin D receptor is similar to that of calcitriol.[22] Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation.[23]

Sources

Fungus, from USDA nutrient database (per 100g), D2 + D3:[24] [25]

Lichen

Plantae

Biosynthesis

The vitamin D2 content in mushrooms and C. arbuscula increase with exposure to ultraviolet light.[27] [28] Ergosterol (provitamin D2) found in these fungi is converted to previtamin D2 on UV exposure, which then turns into vitamin D2. As cultured mushrooms are generally grown in darkness, less vitamin D2 is found compared to those grown in the wild or dried in the sun.[19]

When fresh mushrooms or dried powders are purposely exposed to ultraviolet light, vitamin D2 levels can be concentrated to much higher levels.[29] [30] The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms.[31] Claims have been made that a normal serving (approx. 2 oz or 60 grams) of fresh mushrooms treated with ultraviolet light have increased vitamin D content to levels up to 80 micrograms or 3200 IU if exposed to just five minutes of UV light after being harvested.[32]

Button mushrooms with enhanced vitamin D2 content produced this way functions similarly to a vitamin D2 supplement; both effectively improves vitamin D status.[29] [33] Vitamin D2 from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D.[29]

Names

Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol.[34] [35] However, currently, Viosterol is also the brand name for cholecalciferol (vitamin D3) in some countries.[36] [37]

Ergocalciferol is manufactured and marketed under various names, including Deltalin (Eli Lilly and Company), Drisdol (Sanofi-Synthelabo), and Calcidol (Patrin Pharma).

External links

Notes and References

  1. Web site: Summary Basis of Decision (SBD) for Rayaldee . . 23 October 2014 . 29 May 2022 . 31 May 2022 . https://web.archive.org/web/20220531071351/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00409&lang=en . live .
  2. Web site: Ergocalciferol Injection BP 300,000IU - Summary of Product Characteristics (SmPC) . (emc) . 8 July 2020 . 10 June 2022 . 19 January 2021 . https://web.archive.org/web/20210119095620/https://www.medicines.org.uk/emc/product/9133/smpc . live .
  3. Book: Coulston AM, Boushey C, Ferruzzi M . Nutrition in the Prevention and Treatment of Disease. 2013. Academic Press. 9780123918840. 818. live. https://web.archive.org/web/20161230000458/https://books.google.ca/books?id=pmapb3rvzpYC&pg=PA818. 30 December 2016.
  4. Book: British national formulary : BNF 69. 2015. British Medical Association. 9780857111562. 703–704. 69.
  5. Book: WHO Model Formulary 2008 . 2009 . 9789241547659 . ((World Health Organization)) . Stuart MC, Kouimtzi M, Hill SR . 10665/44053 . World Health Organization . World Health Organization . free . 498 .
  6. Web site: Ergocalciferol. The American Society of Health-System Pharmacists. 8 December 2016. live. https://web.archive.org/web/20161230002716/https://www.drugs.com/monograph/ergocalciferol.html. 30 December 2016.
  7. Book: Hamilton R . Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. 2015. Jones & Bartlett Learning. 9781284057560. 227.
  8. Web site: Office of Dietary Supplements - Vitamin D. ods.od.nih.gov. 30 December 2016. 11 February 2016. live. https://web.archive.org/web/20161231073744/https://ods.od.nih.gov/factsheets/VitaminD-HealthProfessional/. 31 December 2016.
  9. Book: Fischer J, Ganellin CR . Analogue-based Drug Discovery. 2006. John Wiley & Sons. 9783527607495. 451. live. https://web.archive.org/web/20161230085612/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA451. 30 December 2016.
  10. Web site: The Top 300 of 2021 . ClinCalc . 14 January 2024 . 15 January 2024 . https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx . live .
  11. Web site: Ergocalciferol - Drug Usage Statistics . ClinCalc . 14 January 2024 . 13 April 2020 . https://web.archive.org/web/20200413044817/https://clincalc.com/DrugStats/Drugs/Ergocalciferol . live .
  12. Book: Feral P, Hall L . Dining with Friends: The Art of North American Vegan Cuisine. 2005. Friends of Animals/Nectar Bat Press. 9780976915904. 160. registration .
  13. Book: Bennett B, Sammartano R . The Complete Idiot's Guide to Vegan Living . Second . 2012. Penguin. 9781615642793. Chapter 15. live. https://web.archive.org/web/20161230230633/https://books.google.ca/books?id=MbzIcj32RzEC&pg=PT215. 30 December 2016.
  14. Book: ((World Health Organization)) . World Health Organization model list of essential medicines: 22nd list (2021) . 2021 . 10665/345533 . World Health Organization . World Health Organization . Geneva . WHO/MHP/HPS/EML/2021.02 . free .
  15. Holick MF, Binkley NC, Bischoff-Ferrari HA, Gordon CM, Hanley DA, Heaney RP, Murad MH, Weaver CM . 6 . Evaluation, treatment, and prevention of vitamin D deficiency: an Endocrine Society clinical practice guideline . The Journal of Clinical Endocrinology and Metabolism . 96 . 7 . 1911–1930 . July 2011 . 21646368 . 10.1210/jc.2011-0385 . free .
  16. Thacher TD, Fischer PR, Obadofin MO, Levine MA, Singh RJ, Pettifor JM . Comparison of metabolism of vitamins D2 and D3 in children with nutritional rickets . Journal of Bone and Mineral Research . 25 . 9 . 1988–1995 . September 2010 . 20499377 . 3153403 . 10.1002/jbmr.99 .
  17. Fosnight SM, Zafirau WJ, Hazelett SE . Vitamin D supplementation to prevent falls in the elderly: evidence and practical considerations . Pharmacotherapy . 28 . 2 . 225–234 . February 2008 . 18225968 . 10.1592/phco.28.2.225 . 37034292 . free .
  18. Tripkovic L, Lambert H, Hart K, Smith CP, Bucca G, Penson S, Chope G, Hyppönen E, Berry J, Vieth R, Lanham-New S . 6 . Comparison of vitamin D2 and vitamin D3 supplementation in raising serum 25-hydroxyvitamin D status: a systematic review and meta-analysis . The American Journal of Clinical Nutrition . 95 . 6 . 1357–1364 . June 2012 . 22552031 . 3349454 . 10.3945/ajcn.111.031070 .
  19. Cardwell G, Bornman JF, James AP, Black LJ . A Review of Mushrooms as a Potential Source of Dietary Vitamin D . Nutrients . 10 . 10 . 1498 . October 2018 . 30322118 . 6213178 . 10.3390/nu10101498 . free .
  20. Suda T, DeLuca HF, Schnoes H, Blunt JW . 25-hydroxyergocalciferol: a biologically active metabolite of vitamin D2 . Biochemical and Biophysical Research Communications . 35 . 2 . 182–185 . April 1969 . 5305760 . 10.1016/0006-291X(69)90264-2 .
  21. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Nomenclature of vitamin D. Recommendations 1981 . European Journal of Biochemistry . 124 . 2 . 223–227 . May 1982 . 7094913 . 10.1111/j.1432-1033.1982.tb06581.x . free .
  22. Bikle DD . Vitamin D metabolism, mechanism of action, and clinical applications . Chemistry & Biology . 21 . 3 . 319–329 . March 2014 . 24529992 . 3968073 . 10.1016/j.chembiol.2013.12.016 .
  23. Houghton LA, Vieth R . The case against ergocalciferol (vitamin D2) as a vitamin supplement . The American Journal of Clinical Nutrition . 84 . 4 . 694–697 . October 2006 . 17023693 . 10.1093/ajcn/84.4.694 . free .
  24. Web site: USDA nutrient database – use the keyword 'portabello' and then click submit . live . https://web.archive.org/web/20150222164135/http://www.nal.usda.gov/fnic/foodcomp/search/index.html . 22 February 2015 .
  25. Web site: Haytowitz DB. Vitamin D in mushrooms. Nutrient Data Laboratory, US Department of Agriculture. 16 April 2018. 2009. 1 February 2021. https://web.archive.org/web/20210201181749/https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf. live.
  26. Web site: Dr. Duke's Phytochemical and Ethnobotanical Databases . dead . https://web.archive.org/web/20151016051622/http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=606 . 16 October 2015 .
  27. Wang T, Bengtsson G, Kärnefelt I, Björn LO . Provitamins and vitamins D₂and D₃in Cladina spp. over a latitudinal gradient: possible correlation with UV levels . Journal of Photochemistry and Photobiology. B, Biology . 62 . 1–2 . 118–122 . September 2001 . 11693362 . 10.1016/S1011-1344(01)00160-9 . 27 January 2019 . live . https://web.archive.org/web/20200528231009/https://lup.lub.lu.se/search/publication/133512 . 28 May 2020 .
  28. Web site: Haytowitz DB. Vitamin D in mushrooms. Nutrient Data Laboratory, US Department of Agriculture. 16 April 2018. 2009. 1 February 2021. https://web.archive.org/web/20210201181749/https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf. live.
  29. Keegan RJ, Lu Z, Bogusz JM, Williams JE, Holick MF . Photobiology of vitamin D in mushrooms and its bioavailability in humans . Dermato-Endocrinology . 5 . 1 . 165–176 . January 2013 . 24494050 . 3897585 . 10.4161/derm.23321 .
  30. Simon RR, Borzelleca JF, DeLuca HF, Weaver CM . Safety assessment of the post-harvest treatment of button mushrooms (Agaricus bisporus) using ultraviolet light . Food and Chemical Toxicology . 56 . 278–289 . June 2013 . 23485617 . 10.1016/j.fct.2013.02.009 .
  31. Koyyalamudi SR, Jeong SC, Song CH, Cho KY, Pang G . Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation . Journal of Agricultural and Food Chemistry . 57 . 8 . 3351–3355 . April 2009 . 19281276 . 10.1021/jf803908q .
  32. News: Bringing Mushrooms Out of the Dark . 18 April 2006 . NBC News . 6 August 2007 . 7 November 2017 . https://web.archive.org/web/20171107112253/http://www.nbcnews.com/id/12370708 . dead .
  33. Urbain P, Singler F, Ihorst G, Biesalski HK, Bertz H . Bioavailability of vitamin D₂ from UV-B-irradiated button mushrooms in healthy adults deficient in serum 25-hydroxyvitamin D: a randomized controlled trial . European Journal of Clinical Nutrition . 65 . 8 . 965–971 . August 2011 . 21540874 . 10.1038/ejcn.2011.53 . free .
  34. 1930 . Viosterol official name for irradiated ergosterol . Journal of Chemical Education . 7 . 1 . 166 . 10.1021/ed007p166 . Science Service . 1930JChEd...7..166S .
  35. See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., Web site: Medical Definition of VIOSTEROL . 10 July 2014 . live . https://web.archive.org/web/20140714154919/http://www.merriam-webster.com/medical/viosterol . 14 July 2014 . and Web site: Definition of CALCIFEROL . 10 July 2014 . live . https://web.archive.org/web/20140714212827/http://www.merriam-webster.com/medical/calciferol . 14 July 2014 ., accessed 10 July 2014.
  36. Web site: Viosterol comprimido 5000 UI . 5 September 2022 . 5 September 2022 . https://web.archive.org/web/20220905231617/https://www.vademecum.es/equivalencia-lista-viosterol+comprimido+5000+ui-uruguay-a11cc05--uy_1 . dead .
  37. Web site: Viosterol 1000 . 6 September 2022 . 6 September 2022 . https://web.archive.org/web/20220906000655/https://www-eticos-com-py.translate.goog//producto/247/viosterol-1000?_x_tr_sch=http&_x_tr_sl=es&_x_tr_tl=en&_x_tr_hl=en&_x_tr_pto=wapp . dead .

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