Chemistry:Ergocalciferol

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Short description: Vitamin D2, a chemical compound
Ergocalciferol
Skeletal formula of ergocalciferol
Ball-and-stick model of the ergocalciferol molecule
Clinical data
Trade namesDrisdol, Calcidol, others
Other namesviosterol
AHFS/Drugs.comMonograph
MedlinePlusa616042
License data
Routes of
administration		By mouth, intramuscular
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC28H44O
Molar mass396.659 g·mol−1
3D model (JSmol)
Melting point114 to 118 °C (237 to 244 °F)

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.[4] This includes vitamin D deficiency due to poor absorption by the intestines or liver disease.[5] It may also be used for low blood calcium due to hypoparathyroidism.[5] 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 17 million 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

Vitamin D2 supplements

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.[22]

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]

  • Mushrooms, Agaricus bisporus:
    • raw portobello: 0.3 μg (10 IU); exposed to ultraviolet light: 11.2 µg (446 IU)
    • raw crimini: 0.1 μg (3 IU); exposed to ultraviolet light: 31.9 µg (1276 IU)
  • Mushrooms, shiitake:
    • raw: Vitamin D (D2 + D3): 0.4 μg (18 IU)
    • dried: Vitamin D (D2 + D3): 3.9 μg (154 IU)

Lichen

  • Cladina arbuscula specimens grown under different natural conditions contain provitamin D2 and vitamin D2, ranges 89-146 and 0.22-0.55 μg/g dry matter respectively. They also contain vitamin D3 (range 0.67 to 2.04 μg/g) although provitamin D3 could not be detected. Vitamin D levels correlate positively with UV irradiation.[26]

Plantae

  • Alfalfa (Medicago sativa subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D2, 0.1 μg (4 IU) vitamin D3[27]

Biosynthesis

The vitamin D2 content in mushrooms and C. arbuscula increase with exposure to ultraviolet light.[26][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][31] The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms.[32] 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.[30]

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).

References

  1. ↑ "Summary Basis of Decision (SBD) for Rayaldee". 23 October 2014. https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00409&lang=en. 
  2. ↑ "Ergocalciferol Injection BP 300,000IU - Summary of Product Characteristics (SmPC)". 8 July 2020. https://www.medicines.org.uk/emc/product/9133/smpc. 
  3. ↑ Nutrition in the Prevention and Treatment of Disease. Academic Press. 2013. p. 818. ISBN 9780123918840. https://books.google.com/books?id=pmapb3rvzpYC&pg=PA818. 
  4. ↑ 4.0 4.1 British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 703–704. ISBN 9780857111562. 
  5. ↑ 5.0 5.1 5.2 5.3 WHO Model Formulary 2008. World Health Organization. 2009. p. 498. ISBN 9789241547659. 
  6. ↑ 6.0 6.1 6.2 "Ergocalciferol". The American Society of Health-System Pharmacists. https://www.drugs.com/monograph/ergocalciferol.html. 
  7. ↑ Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. 2015. p. 227. ISBN 9781284057560. 
  8. ↑ "Office of Dietary Supplements - Vitamin D". 11 February 2016. https://ods.od.nih.gov/factsheets/VitaminD-HealthProfessional/. 
  9. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 451. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA451. 
  10. ↑ "The Top 300 of 2021". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  11. ↑ "Ergocalciferol - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Ergocalciferol. 
  12. ↑ Dining with Friends: The Art of North American Vegan Cuisine. Friends of Animals/Nectar Bat Press. 2005. p. 160. ISBN 9780976915904. https://archive.org/details/diningwithfriend0000fera. 
  13. ↑ The Complete Idiot's Guide to Vegan Living (Second ed.). Penguin. 2012. p. Chapter 15. ISBN 9781615642793. https://books.google.com/books?id=MbzIcj32RzEC&pg=PT215. 
  14. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  15. ↑ "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. doi:10.1210/jc.2011-0385. PMID 21646368. 
  16. ↑ "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. doi:10.1002/jbmr.99. PMID 20499377. 
  17. ↑ "Vitamin D supplementation to prevent falls in the elderly: evidence and practical considerations". Pharmacotherapy 28 (2): 225–234. February 2008. doi:10.1592/phco.28.2.225. PMID 18225968. 
  18. ↑ 18.0 18.1 "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. doi:10.3945/ajcn.111.031070. PMID 22552031. 
  19. ↑ 19.0 19.1 "A Review of Mushrooms as a Potential Source of Dietary Vitamin D". Nutrients 10 (10): 1498. October 2018. doi:10.3390/nu10101498. PMID 30322118. 
  20. ↑ "25-hydroxyergocalciferol: a biologically active metabolite of vitamin D2". Biochemical and Biophysical Research Communications 35 (2): 182–185. April 1969. doi:10.1016/0006-291X(69)90264-2. PMID 5305760. 
  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. doi:10.1111/j.1432-1033.1982.tb06581.x. PMID 7094913. 
  22. ↑ 22.0 22.1 "Vitamin D metabolism, mechanism of action, and clinical applications". Chemistry & Biology 21 (3): 319–329. March 2014. doi:10.1016/j.chembiol.2013.12.016. PMID 24529992. 
  23. ↑ "The case against ergocalciferol (vitamin D2) as a vitamin supplement". The American Journal of Clinical Nutrition 84 (4): 694–697. October 2006. doi:10.1093/ajcn/84.4.694. PMID 17023693. 
  24. ↑ "USDA nutrient database – use the keyword 'portabello' and then click submit". http://www.nal.usda.gov/fnic/foodcomp/search/index.html. 
  25. ↑ Haytowitz DB (2009). "Vitamin D in mushrooms". Nutrient Data Laboratory, US Department of Agriculture. https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf. 
  26. ↑ 26.0 26.1 "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. doi:10.1016/S1011-1344(01)00160-9. PMID 11693362. http://lup.lub.lu.se/record/133512. Retrieved 27 January 2019. 
  27. ↑ "Dr. Duke's Phytochemical and Ethnobotanical Databases". http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=606. 
  28. ↑ Haytowitz DB (2009). "Vitamin D in mushrooms". Nutrient Data Laboratory, US Department of Agriculture. https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf. 
  29. ↑ 29.0 29.1 29.2 "Photobiology of vitamin D in mushrooms and its bioavailability in humans". Dermato-Endocrinology 5 (1): 165–176. January 2013. doi:10.4161/derm.23321. PMID 24494050. 
  30. ↑ 30.0 30.1 "Bringing Mushrooms Out of the Dark". NBC News. 18 April 2006. http://www.nbcnews.com/id/12370708. 
  31. ↑ "Safety assessment of the post-harvest treatment of button mushrooms (Agaricus bisporus) using ultraviolet light". Food and Chemical Toxicology 56: 278–289. June 2013. doi:10.1016/j.fct.2013.02.009. PMID 23485617. 
  32. ↑ "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. doi:10.1021/jf803908q. PMID 19281276. 
  33. ↑ "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. doi:10.1038/ejcn.2011.53. PMID 21540874. 
  34. ↑ Science Service (1930). "Viosterol official name for irradiated ergosterol". Journal of Chemical Education 7 (1): 166. doi:10.1021/ed007p166. Bibcode: 1930JChEd...7..166S. 
  35. ↑ See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., "Medical Definition of VIOSTEROL". http://www.merriam-webster.com/medical/viosterol.  and "Definition of CALCIFEROL". http://www.merriam-webster.com/medical/calciferol. , accessed 10 July 2014.
  36. ↑ "Viosterol comprimido 5000 UI". https://www.vademecum.es/equivalencia-lista-viosterol+comprimido+5000+ui-uruguay-a11cc05--uy_1. 
  37. ↑ "Viosterol 1000". 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. 

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