Ergocalciferol

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Ergocalciferol
Skeletal formula of ergocalciferol
Ball-and-stick model of the ergocalciferol molecule
Clinical data
Trade names Drisdol, Calcidol, others
Synonyms viosterol
AHFS/Drugs.com Monograph
Pregnancy
category
  • US: A (No risk in human studies) and C
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.000.014
Chemical and physical data
Formula C28H44O
Molar mass 396.65 g/mol
3D model (JSmol)
Melting point 114 to 118 °C (237 to 244 °F)

Ergocalciferol, also known as vitamin D2 and calciferol, is a type of vitamin D found in food and used as a dietary supplement.[1] As a supplement it is used to prevent and treat vitamin D deficiency.[2] This includes vitamin D deficiency due to poor absorption by the intestines or liver disease.[3] It may also be used for low blood calcium due to hypoparathyroidism.[3] It is used by mouth or injection into a muscle.[2][3]

Excessive doses can result in increased urine production, high blood pressure, kidney stones, kidney failure, weakness, and constipation.[4] If high doses are taken for a long period of time, tissue calcification may occur.[3] It is recommended that people on high doses have their blood calcium levels regularly checked.[2] Normal doses are safe in pregnancy.[5] It works by increasing the amount of calcium absorbed by the intestines and kidneys.[4] Food in which it is found include some mushrooms.[6]

Ergocalciferol was first described in 1936.[7] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[8] Ergocalciferol is available as a generic medication and over the counter.[4] In the United Kingdom a typical dose costs the NHS less than 10 pounds a month.[2] Certain foods such as breakfast cereal and margarine have ergocalciferol added to them in some countries.[9][10]

Medical uses[edit]

Ergocalciferol may be used as a vitamin D supplement, as is cholecalciferol (vitamin D3), which is also produced naturally by the skin when exposed to ultraviolet light.[11]

Ergocalciferol (D2) and cholecalciferol (D3) have been considered as equivalent, as both forms appear to have similar efficacy in ameliorating rickets[12] and reducing the incidence of falls in elderly patients.[13] Conflicting reports exist however concerning the relative effectiveness, with some studies suggesting that ergocalciferol has less efficacy. Ergocalciferol and colecalciferol have some differences in absorption, binding and inactivation. A meta-analysis concluded that evidence usually favors cholecalciferol in raising levels in blood, although it stated more research is needed.[14]

Mechanism[edit]

Ergocalciferol is a secosteroid formed by a photochemical bond breaking of a steroid, specifically, by the action of ultraviolet light on ergosterol.

Sources[edit]

Lichen

  • Cladina arbuscula specimens grown under different natural conditions: The contents of vitamin D3 range from 0.67 to 2.04 μg/g dry matter in the thalli of C. arbuscula specimens grown under different natural conditions, while provitamin D3 could not be detected. The ranges for provitamin D2 and vitamin D2 were 89-146 and 0.22-0.55 μg/g dry matter, respectively, while the contents of provitamin D3 were below the detection limit (0.01 μg/g dry matter).[15]

Fungus, from USDA nutrient database (per 100g) [16]

  • Mushrooms, portobello, exposed to ultraviolet light, raw: Vitamin D (D2 + D3): 11.2 µg (446 IU)
  • Mushrooms, portobello, exposed to ultraviolet light, grilled: Vitamin D (D2 + D3): 13.1 µg (524 IU)
  • Mushrooms, shiitake, dried: Vitamin D (D2 + D3): 3.9 μg (154 IU)
  • Mushrooms, shiitake, raw: Vitamin D (D2 + D3): 0.4 μg (18 IU)
  • Mushrooms, portobello, raw: Vitamin D (D2 + D3): 0.3 μg (10 IU)

Plantae

  • Alfalfa (Medicago sativa subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D2, 0.1 μg (4 IU) vitamin D3[17]

Ergocalciferol is produced in fungi synthetically through irradiation of ergosterol.[18] Human bioavailability of vitamin D2 from vitamin D2-enhanced button mushrooms via UV-B irradiation is effective in improving vitamin D status and not different from a vitamin D2 supplement.[19] Vitamin D2 from UV-irradiated yeast baked into bread is bioavailable.[20] By visual assessment or using a chromometer, no significant discoloration of irradiated mushrooms, as measured by the degree of "whiteness", was observed.[21] Claims that a normal serving of mushrooms treated with ultraviolet light provides the equivalent of 3,500 International Units of vitamin D when exposed to ultraviolet light after harvest have gained popular attention.[22]

Names[edit]

Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol.[23][24]

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

References[edit]

  1. ^ Coulston, Ann M.; Boushey, Carol; Ferruzzi, Mario (2013). Nutrition in the Prevention and Treatment of Disease. Academic Press. p. 818. ISBN 9780123918840. Archived from the original on 2016-12-30. 
  2. ^ a b c d British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 703–704. ISBN 9780857111562. 
  3. ^ a b c d WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. 498. ISBN 9789241547659. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016. 
  4. ^ a b c "Ergocalciferol". The American Society of Health-System Pharmacists. Archived from the original on 30 December 2016. Retrieved 8 December 2016. 
  5. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 227. ISBN 9781284057560. 
  6. ^ "Office of Dietary Supplements - Vitamin D". ods.od.nih.gov. 11 February 2016. Archived from the original on 31 December 2016. Retrieved 30 December 2016. 
  7. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 451. ISBN 9783527607495. Archived from the original on 2016-12-30. 
  8. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016. 
  9. ^ Feral, Priscilla; Hall, Lee; Animals, Friends of (2005). Dining with Friends: The Art of North American Vegan Cuisine. Friends of Animals/Nectar Bat Press. p. 160. ISBN 9780976915904. Archived from the original on 2016-12-31. 
  10. ^ Bennett, Beverly; Sammartano, Ray (2012). The Complete Idiot's Guide to Vegan Living, Second Edition. Penguin. p. Chapter 15. ISBN 9781615642793. Archived from the original on 2016-12-30. 
  11. ^ Holick, M. F.; Binkley, N. C.; Bischoff-Ferrari, H. A.; Gordon, C. M.; Hanley, D. A.; Heaney, R. P.; Murad, M. H.; Weaver, C. M. (2011). "Evaluation, Treatment, and Prevention of Vitamin D Deficiency: An Endocrine Society Clinical Practice Guideline". Journal of Clinical Endocrinology & Metabolism. 96 (7): 1911–1930. doi:10.1210/jc.2011-0385. PMID 21646368. 
  12. ^ Thacher, TD; Fischer, PR; Obadofin, MO; Levine, MA; Singh, RJ; Pettifor, JM (2010). "Comparison of Metabolism of Vitamins D2 and D3 in Children with Nutritional Rickets". Journal of Bone and Mineral Research. 25 (9): 1988–1995. doi:10.1002/jbmr.99. PMC 3153403Freely accessible. PMID 20499377. 
  13. ^ Fosnight, S. M.; Zafirau, W. J.; Hazelett, S. E. (2008). "Vitamin D Supplementation to Prevent Falls in the Elderly: Evidence and Practical Considerations". Pharmacotherapy. 28 (2): 225–234. doi:10.1592/phco.28.2.225. PMID 18225968. 
  14. ^ Tripkovic, L; Lambert, H; Hart, K; Smith, CP; Bucca, G; Penson, S; Chope, G; Hyppönen, E; Berry, J; Vieth, R; Lanham-New, S (June 2012). "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): 1357–64. doi:10.3945/ajcn.111.031070. PMID 22552031. 
  15. ^ Wang, T; Bengtsson, G; Kärnefelt, I; Björn, LO (2001). "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): 118–22. doi:10.1016/S1011-1344(01)00160-9. PMID 11693362. 
  16. ^ "USDA nutrient database – use the keyword 'portabella' and then click submit". Archived from the original on 2015-02-22. 
  17. ^ "Dr. Duke's Phytochemical and Ethnobotanical Databases". Archived from the original on 2015-10-16. 
  18. ^ Simon, R. R.; Borzelleca, J. F.; Deluca, H. F.; Weaver, C. M. (2013). "Safety assessment of the post-harvest treatment of button mushrooms (Agaricus bisporus) using ultraviolet light". Food and Chemical Toxicology. 56: 278–89. doi:10.1016/j.fct.2013.02.009. PMID 23485617. 
  19. ^ P Urbain; F Singler; G Ihorst; H-K Biesalski; H Bertz (August 2011). "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. doi:10.1038/ejcn.2011.53. PMID 21540874. Archived from the original on 2016-02-03. 
  20. ^ Hohman, E. E.; Martin, B. R.; Lachcik, P. J.; Gordon, D. T.; Fleet, J. C.; Weaver, C. M. (2011). "Bioavailability and Efficacy of Vitamin D2from UV-Irradiated Yeast in Growing, Vitamin D-Deficient Rats". Journal of Agricultural and Food Chemistry. 59 (6): 2341–2346. doi:10.1021/jf104679c. PMC 3235799Freely accessible. PMID 21332187. 
  21. ^ Koyyalamudi, SR; Jeong, SC; Song, CH; Cho, KY; Pang, G (2009). "Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation". J Agric Food Chem. 57 (8): 3351–5. doi:10.1021/jf803908q. PMID 19281276. 
  22. ^ "Bringing Mushrooms Out of the Dark". MSNBC. April 18, 2006. Archived from the original on November 1, 2007. Retrieved 2007-08-06. 
  23. ^ Science Service (1930) Viosterol official name for irradiated ergosterol, J. Chem. Educ. 7(1) 166, DOI: 10.1021/ed007p166, see [pubs.acs.org/doi/abs/10.1021/ed007p166, accessed 10 July 2014.
  24. ^ See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., "Archived copy". Archived from the original on 2014-07-14. Retrieved 2014-07-10.  and "Archived copy". Archived from the original on 2014-07-14. Retrieved 2014-07-10. , accessed 10 July 2014.

External links[edit]