Ergocalciferol

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Ergocalciferol
Ergocalciferol.svg
Ergocalciferol 3D ball.png
Clinical data
Trade names Drisdol, Calcidol, others
Other namesvitamin D2
AHFS/Drugs.com Monograph
MedlinePlus a616042
License data
Routes of
administration 		By mouth, intramuscular
ATC code
Legal status
Legal status
Identifiers
  • (3S,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.014 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C28H44O
Molar mass 396.659 g·mol−1
3D model (JSmol)
Melting point 114 to 118 °C (237 to 244 °F)
  • 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
  • InChI=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 Yes check.svgY
  • Key:MECHNRXZTMCUDQ-RKHKHRCZSA-N

Ergocalciferol, also known as vitamin D2 and nonspecifically calciferol, is a type of vitamin D found in food. It is used as a dietary supplement [3] to prevent and treat vitamin D deficiency [4] 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 taken by mouth or via injection into a muscle. [4] [5]

Contents

Excessive doses can result in vitamin D toxicity causing increased urine production, high blood pressure, kidney stones, kidney failure, muscle 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 reabsorbed by the 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 2022, it was the 38th most commonly prescribed medication in the United States, with more than 15 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 Vitamin D pills.jpg
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]

Lichen

Plantae

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 sold under various brand names, including Deltalin (Eli Lilly and Company), Drisdol (Sanofi-Synthelabo), and Calcidol (Patrin Pharma).[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Mushroom</span> Spore-bearing fruiting body of a fungus

A mushroom or toadstool is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground, on soil, or on its food source. Toadstool generally denotes one poisonous to humans.

<span class="mw-page-title-main">Rickets</span> Childhood bone disorder

Rickets, scientific nomenclature: rachitis, is a condition that results in weak or soft bones in children and is caused by either dietary deficiency or genetic causes. Symptoms include bowed legs, stunted growth, bone pain, large forehead, and trouble sleeping. Complications may include bone deformities, bone pseudofractures and fractures, muscle spasms, or an abnormally curved spine. The analogous condition in adults is osteomalacia.

<span class="mw-page-title-main">7-Dehydrocholesterol</span> Chemical compound

7-Dehydrocholesterol (7-DHC) is a zoosterol that functions in the serum as a cholesterol precursor, and is photochemically converted to vitamin D3 in the skin, therefore functioning as provitamin-D3. The presence of this compound in human skin enables humans to manufacture vitamin D3 (cholecalciferol). Upon exposure to ultraviolet UV-B rays in the sun light, 7-DHC is converted into vitamin D3 via previtamin D3 as an intermediate isomer. It is also found in the milk of several mammalian species. Lanolin, a waxy substance that is naturally secreted by wool-bearing mammals, contains 7-DHC which is converted into vitamin D by sunlight and then ingested during grooming as a nutrient. In insects 7-dehydrocholesterol is a precursor for the hormone ecdysone, required for reaching adulthood. 7-DHC was discovered by Nobel-laureate organic chemist Adolf Windaus.

<span class="mw-page-title-main">Shiitake</span> Species of edible mushroom

The shiitake is an edible mushroom native to East Asia, which is cultivated and consumed around the globe.

<span class="mw-page-title-main">Edible mushroom</span> Edible fungi fruit bodies

Edible mushrooms are the fleshy fruit bodies of numerous species of macrofungi. Edibility may be defined by criteria including the absence of poisonous effects on humans and desirable taste and aroma. Mushrooms that have a particularly desirable taste are described as "choice". Edible mushrooms are consumed for their nutritional and culinary value. Mushrooms, especially dried shiitake, are sources of umami flavor.

<i>Agaricus bisporus</i> Species of fungus

Agaricus bisporus, commonly known as the cultivated mushroom, is a basidiomycete mushroom native to grasslands in Eurasia and North America. It is cultivated in more than 70 countries and is one of the most commonly and widely consumed mushrooms in the world. It has two color states while immature – white and brown – both of which have various names, with additional names for the mature state, such as chestnut, portobello, portabellini, button and champignon de Paris.

<span class="mw-page-title-main">Cholecalciferol</span> Vitamin D3, a chemical compound

Cholecalciferol, also known as vitamin D3 or colecalciferol, is a type of vitamin D that is produced by the skin when exposed to UVB light; it is found in certain foods and can be taken as a dietary supplement.

<span class="mw-page-title-main">Adolf Windaus</span> German chemist (1876–1959)

Adolf Otto Reinhold Windaus was a German chemist who won a Nobel Prize in Chemistry in 1928 for his work on sterols and their relation to vitamins. He was the doctoral advisor of Adolf Butenandt who also won a Nobel Prize in Chemistry in 1939.

<span class="mw-page-title-main">Ergosterol</span> Chemical compound

Ergosterol (ergosta-5,7,22-trien-3β-ol) is a mycosterol found in cell membranes of fungi and protozoa, serving many of the same functions that cholesterol serves in animal cells. Because many fungi and protozoa cannot survive without ergosterol, the enzymes that synthesize it have become important targets for drug discovery. In human nutrition, ergosterol is a provitamin form of vitamin D2; exposure to ultraviolet (UV) light causes a chemical reaction that produces vitamin D2.

<span class="mw-page-title-main">International unit</span> Pharmacological measurement unit for the amount of a biologically active substance

In pharmacology, the international unit (IU) is a unit of measurement for the effect or biological activity of a substance, for the purpose of easier comparison across similar forms of substances. International units are used to quantify vitamins and biologics.

<span class="mw-page-title-main">Rodenticide</span> Chemical used to kill rodents

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A provitamin is a substance that may be converted within the body to a vitamin. The term previtamin is a synonym.

<span class="mw-page-title-main">Dihydrotachysterol</span> Chemical compound

Dihydrotachysterol (DHT) is a synthetic vitamin D analog activated in the liver that does not require renal hydroxylation like vitamin D2 (ergocalciferol) and vitamin D3 (cholecalciferol). DHT has a rapid onset of action (2 hours), a shorter half-life, and a greater effect on mineralization of bone salts than does vitamin D.

<span class="mw-page-title-main">Vitamin D toxicity</span> Human disease

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<span class="mw-page-title-main">Calcifediol</span> Chemical compound

Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D3 (abbreviated 25(OH)D3), is a form of vitamin D produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme vitamin D 25-hydroxylase. Calcifediol can be further hydroxylated by the enzyme 25(OH)D-1α-hydroxylase, primarily in the kidney, to form calcitriol (1,25-(OH)2D3), which is the active hormonal form of vitamin D.

<span class="mw-page-title-main">Vitamin D deficiency</span> Human disorder

Vitamin D deficiency or hypovitaminosis D is a vitamin D level that is below normal. It most commonly occurs in people when they have inadequate exposure to sunlight, particularly sunlight with adequate ultraviolet B rays (UVB). Vitamin D deficiency can also be caused by inadequate nutritional intake of vitamin D; disorders that limit vitamin D absorption; and disorders that impair the conversion of vitamin D to active metabolites, including certain liver, kidney, and hereditary disorders. Deficiency impairs bone mineralization, leading to bone-softening diseases, such as rickets in children. It can also worsen osteomalacia and osteoporosis in adults, increasing the risk of bone fractures. Muscle weakness is also a common symptom of vitamin D deficiency, further increasing the risk of fall and bone fractures in adults. Vitamin D deficiency is associated with the development of schizophrenia.

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References

  1. ↑ "Summary Basis of Decision (SBD) for Rayaldee". Health Canada . 23 October 2014. Archived from the original on 31 May 2022. Retrieved 29 May 2022.
  2. ↑ "Ergocalciferol Injection BP 300,000IU - Summary of Product Characteristics (SmPC)". (emc). 8 July 2020. Archived from the original on 19 January 2021. Retrieved 10 June 2022.
  3. ↑ Coulston AM, Boushey C, Ferruzzi M (2013). Nutrition in the Prevention and Treatment of Disease. Academic Press. p. 818. ISBN   9780123918840. Archived from the original on 30 December 2016.
  4. 1 2 British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 703–704. ISBN   9780857111562.
  5. 1 2 3 4 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 498. hdl: 10665/44053 . ISBN   9789241547659.
  6. 1 2 3 "Ergocalciferol". The American Society of Health-System Pharmacists. Archived from the original on 30 December 2016. Retrieved 8 December 2016.
  7. ↑ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 227. ISBN   9781284057560.
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  9. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 451. ISBN   9783527607495. Archived from the original on 30 December 2016.
  10. ↑ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  11. ↑ "Ergocalciferol Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  12. ↑ Feral P, Hall L (2005). Dining with Friends: The Art of North American Vegan Cuisine . Friends of Animals/Nectar Bat Press. p.  160. ISBN   9780976915904.
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  14. ↑ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl: 10665/371090 . WHO/MHP/HPS/EML/2023.02.
  15. ↑ Holick MF, Binkley NC, Bischoff-Ferrari HA, Gordon CM, Hanley DA, Heaney RP, et al. (July 2011). "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. doi: 10.1210/jc.2011-0385 . PMID   21646368.{{cite journal}}: CS1 maint: overridden setting (link)
  16. ↑ Thacher TD, Fischer PR, Obadofin MO, Levine MA, Singh RJ, Pettifor JM (September 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   3153403 . PMID   20499377.
  17. ↑ Fosnight SM, Zafirau WJ, Hazelett SE (February 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. S2CID   37034292.
  18. 1 2 Tripkovic L, Lambert H, Hart K, Smith CP, Bucca G, Penson S, et al. (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): 1357–1364. doi:10.3945/ajcn.111.031070. PMC   3349454 . PMID   22552031.{{cite journal}}: CS1 maint: overridden setting (link)
  19. 1 2 Cardwell G, Bornman JF, James AP, Black LJ (October 2018). "A Review of Mushrooms as a Potential Source of Dietary Vitamin D". Nutrients. 10 (10): 1498. doi: 10.3390/nu10101498 . PMC   6213178 . PMID   30322118.
  20. ↑ Suda T, DeLuca HF, Schnoes H, Blunt JW (April 1969). "25-hydroxyergocalciferol: a biologically active metabolite of vitamin D2". Biochemical and Biophysical Research Communications. 35 (2): 182–185. 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. 1 2 Bikle DD (March 2014). "Vitamin D metabolism, mechanism of action, and clinical applications". Chemistry & Biology. 21 (3): 319–329. doi:10.1016/j.chembiol.2013.12.016. PMC   3968073 . PMID   24529992.
  23. ↑ Houghton LA, Vieth R (October 2006). "The case against ergocalciferol (vitamin D2) as a vitamin supplement". The American Journal of Clinical Nutrition. 84 (4): 694–697. doi: 10.1093/ajcn/84.4.694 . PMID   17023693.
  24. ↑ "USDA nutrient database – use the keyword 'portabello' and then click submit". Archived from the original on 22 February 2015.
  25. ↑ Haytowitz DB (2009). "Vitamin D in mushrooms" (PDF). Nutrient Data Laboratory, US Department of Agriculture. Archived (PDF) from the original on 1 February 2021. Retrieved 16 April 2018.
  26. 1 2 Wang T, Bengtsson G, Kärnefelt I, Björn LO (September 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): 118–122. doi:10.1016/S1011-1344(01)00160-9. PMID   11693362. Archived from the original on 28 May 2020. Retrieved 27 January 2019.
  27. ↑ "Dr. Duke's Phytochemical and Ethnobotanical Databases". Archived from the original on 16 October 2015.
  28. ↑ Haytowitz DB (2009). "Vitamin D in mushrooms" (PDF). Nutrient Data Laboratory, US Department of Agriculture. Archived (PDF) from the original on 1 February 2021. Retrieved 16 April 2018.
  29. 1 2 3 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): 165–176. doi:10.4161/derm.23321. PMC   3897585 . PMID   24494050.
  30. 1 2 "Bringing Mushrooms Out of the Dark". NBC News. 18 April 2006. Archived from the original on 7 November 2017. Retrieved 6 August 2007.
  31. ↑ Simon RR, Borzelleca JF, DeLuca HF, Weaver CM (June 2013). "Safety assessment of the post-harvest treatment of button mushrooms (Agaricus bisporus) using ultraviolet light". Food and Chemical Toxicology. 56: 278–289. doi:10.1016/j.fct.2013.02.009. PMID   23485617.
  32. ↑ 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): 3351–3355. Bibcode:2009JAFC...57.3351K. doi:10.1021/jf803908q. PMID   19281276.
  33. ↑ 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): 965–971. 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. Bibcode:1930JChEd...7..166S. doi:10.1021/ed007p166.
  35. ↑ 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.
  36. ↑ "Viosterol comprimido 5000 UI". Archived from the original on 5 September 2022. Retrieved 5 September 2022.
  37. ↑ "Viosterol 1000". Archived from the original on 6 September 2022. Retrieved 6 September 2022.
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