Ergocalciferol

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]

Ergocalciferol
Clinical data
Trade namesDrisdol, Calcidol, others
Other namesviosterol
AHFS/Drugs.comMonograph
MedlinePlusa616042
License data
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
    CompTox Dashboard (EPA)
    ECHA InfoCard100.000.014
    Chemical and physical data
    FormulaC28H44O
    Molar mass396.659 g·mol−1
    3D model (JSmol)
    Melting point114 to 118 °C (237 to 244 °F)

    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 safest and most effective 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 GB£10 a month.[2] In 2017, it was the 55th most commonly prescribed medication in the United States, with more than 14 million prescriptions.[9][10] Certain foods such as breakfast cereal and margarine have ergocalciferol added to them in some countries.[11][12]

    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.[13] 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[14] and reducing the incidence of falls in elderly patients.[15] 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.[16] A meta-analysis concluded that evidence usually favors cholecalciferol in raising vitamin D levels in blood, although it stated more research is needed.[16]

    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.[17]

    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[18]), 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.[19] Unlike cholecalciferol, 25-hydroxylation is not performed by CYP27A1 for ergocalciferol.[20]

    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.[20] Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation.[21]

    Sources

    Fungus, from USDA nutrient database (per 100g), D2 + D3:[22][23]

    • 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.[24]

    Plantae

    • Alfalfa (Medicago sativa subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D2, 0.1 μg (4 IU) vitamin D3[25]

    Biosynthesis

    The vitamin D2 content in mushrooms and C. arbuscula increase with exposure to ultraviolet light.[26][27] 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.[17]

    When fresh mushrooms or dried powders are purposely exposed to ultraviolet light, vitamin D2 levels can be concentrated to much higher levels.[28][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 5 minutes of UV light after being harvested.[29]

    Button mushrooms with enhanced vitamin D2 content produced this way functions similarly to a vitamin D2 supplement; both effectively improves vitamin D status.[28][32] Vitamin D2 from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D.[28]

    Names

    Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol.[33][34]

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

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    References
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    21. Houghton LA, Vieth R (October 2006). "The case against ergocalciferol (vitamin D2) as a vitamin supplement". The American Journal of Clinical Nutrition. 84 (4): 694–7. doi:10.1093/ajcn/84.4.694. PMID 17023693.
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    25. "Dr. Duke's Phytochemical and Ethnobotanical Databases". Archived from the original on 16 October 2015.
    26. Wang T, Bengtsson G, Kärnefelt I, Björn LO (September 2001). "Provitamins and vitamins D₂ and D₃ in 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.
    27. Haytowitz DB (2009). "Vitamin D in mushrooms" (PDF). Nutrient Data Laboratory, US Department of Agriculture. Retrieved 16 April 2018.
    28. Keegan RJ, Lu Z, Bogusz JM, Williams JE, Holick MF (January 2013). "Photobiology of vitamin D in mushrooms and its bioavailability in humans". Dermato-Endocrinology. 5 (1): 165–76. doi:10.4161/derm.23321. PMC 3897585. PMID 24494050.
    29. "Bringing Mushrooms Out of the Dark". NBC News. 18 April 2006. Retrieved 6 August 2007.
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    31. Koyyalamudi SR, Jeong SC, Song CH, Cho KY, Pang G (April 2009). "Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation". Journal of Agricultural and Food Chemistry. 57 (8): 3351–5. doi:10.1021/jf803908q. PMID 19281276.
    32. Urbain P, Singler F, Ihorst G, Biesalski HK, Bertz H (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): 965–71. doi:10.1038/ejcn.2011.53. PMID 21540874.
    33. "Viosterol official name for irradiated ergosterol". Journal of Chemical Education. 7 (1): 166. 1930. doi:10.1021/ed007p166.
    34. See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., "Medical Definition of VIOSTEROL". Archived from the original on 14 July 2014. Retrieved 10 July 2014. and "Definition of CALCIFEROL". Archived from the original on 14 July 2014. Retrieved 10 July 2014., accessed 10 July 2014.
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