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{{short description|Vitamin D2, a chemical compound}}
{{Short description|Vitamin D2, a chemical compound}}
{{Use dmy dates|date=December 2019}}
{{Use dmy dates|date=October 2022}}
{{Infobox drug
{{Infobox drug
⚫
| drug_name =
| INN =
| type =<!-- empty -->
⚫
| IUPAC_name = (3''S'',5''Z'',7''E'',22''E'')-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
| image = Ergocalciferol.svg
| image = Ergocalciferol.svg
| width =
| width =
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| width2 =
| width2 =
| alt2 = Ball-and-stick model of the ergocalciferol molecule
| alt2 = Ball-and-stick model of the ergocalciferol molecule
| imageL =
| caption =

⚫
| widthL =
⚫
| altL =
| imageR =
| widthR =
| altR =
| caption =
<!-- Clinical data -->
<!-- Clinical data -->
| pronounce =
| pronounce =
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| Drugs.com = {{Drugs.com|monograph|ergocalciferol}}
| Drugs.com = {{Drugs.com|monograph|ergocalciferol}}
| MedlinePlus = a616042
| MedlinePlus = a616042
| licence_EU = <!-- EMA requires brand name -->
| licence_US = <!-- FDA may use generic name -->
| DailyMedID = Ergocalciferol
| DailyMedID = Ergocalciferol
| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X -->
| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X -->
| pregnancy_AU_comment =
| pregnancy_AU_comment =
| pregnancy_US = A
| pregnancy_US_comment = and C
| pregnancy_category=
| pregnancy_category=
| routes_of_administration = [[Oral administration|By mouth]], [[intramuscular]]
| dependency_liability =
| addiction_liability =
| class =
⚫
| ATCvet =
| routes_of_administration =
⚫
| ATC_prefix = A11
⚫
| ATC_suffix = CC01
⚫
| ATC_supplemental =

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU_comment =
| legal_AU_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Summary Basis of Decision (SBD) for Rayaldee | website=[[Health Canada]] | date=23 October 2014 | url=https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00409&lang=en | access-date=29 May 2022 | archive-date=31 May 2022 | archive-url=https://web.archive.org/web/20220531071351/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00409&lang=en | url-status=live }}</ref>
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment =
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_NZ_comment =
| legal_UK = POM
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment = <ref>{{cite web | title=Ergocalciferol Injection BP 300,000IU - Summary of Product Characteristics (SmPC) | website=(emc) | date=8 July 2020 | url=https://www.medicines.org.uk/emc/product/9133/smpc | access-date=10 June 2022 | archive-date=19 January 2021 | archive-url=https://web.archive.org/web/20210119095620/https://www.medicines.org.uk/emc/product/9133/smpc | url-status=live }}</ref>
| legal_UK_comment =
| legal_US =OTC
| legal_US = OTC
| legal_US_comment =
| legal_US_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment =
| legal_UN_comment =
| legal_status = <!--For countries not listed above-->
| legal_status = <!--For countries not listed above-->

<!-- Pharmacokinetic data -->
<!-- Pharmacokinetic data -->
| bioavailability =
| bioavailability =
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| duration_of_action =
| duration_of_action =
| excretion =
| excretion =

<!-- Identifiers -->
<!-- Identifiers -->
| CAS_number = 50-14-6
| CAS_number = 50-14-6
| CAS_supplemental = {{cascite|correct|CAS}}
| CAS_supplemental = {{cascite|correct|CAS}}
| class =
| ATCvet =
| ATC_prefix = A11
| ATC_suffix = CC01
⚫
| ATC_supplemental =
| PubChem = 5280793
| PubChem = 5280793
| PubChemSubstance =
| PubChemSubstance =
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| NIAID_ChemDB =
| NIAID_ChemDB =
| synonyms = viosterol
| synonyms = viosterol

<!-- Chemical and physical data -->
<!-- Chemical and physical data -->
⚫
| IUPAC_name = (3''S'',5''Z'',7''E'',22''E'')-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
| chemical_formula = | C=28 | H=44 | O=1
| C=28 | H=44 | O=1
| charge=
| 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
| 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
| Jmol =
| 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
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| density =
| density =
| density_notes =
| density_notes =
| melting_point = 114 to 118
| melting_point = 114
| melting_high =
| melting_high = 118
| melting_notes =
| melting_notes =
| boiling_point =
| boiling_point =
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| specific_rotation =
| specific_rotation =
}}
}}

<!-- Definition and medical uses -->
<!-- Definition and medical uses -->
'''Ergocalciferol''', also known as '''vitamin D<sub>2</sub>''' and '''calciferol''', is a type of [[vitamin D]] found in food and used as a [[dietary supplement]].<ref>{{cite book|last1=Coulston|first1=Ann M.|last2=Boushey|first2=Carol|last3=Ferruzzi|first3=Mario | name-list-style = vanc |title=Nutrition in the Prevention and Treatment of Disease|date=2013|publisher=Academic Press|isbn=9780123918840|page=818|url=https://books.google.com/books?id=pmapb3rvzpYC&pg=PA818 | url-status=live|archive-url=https://web.archive.org/web/20161230000458/https://books.google.ca/books?id=pmapb3rvzpYC&pg=PA818|archive-date=2016-12-30}}</ref> As a supplement it is used to prevent and treat [[vitamin D deficiency]].<ref name=BNF69/> This includes vitamin D deficiency due to [[malabsorption|poor absorption by the intestines]] or [[liver disease]].<ref name=WHO2008/> It may also be used for [[hypocalcemia|low blood calcium]] due to [[hypoparathyroidism]].<ref name=WHO2008/> It is used by mouth or [[intramuscular|injection into a muscle]].<ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|pages=703–704|edition=69}}</ref><ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free |page=498 }}</ref>
'''Ergocalciferol''', also known as '''vitamin D<sub>2</sub>''' and nonspecifically '''calciferol''', is a type of [[vitamin D]] found in food and used as a [[dietary supplement]].<ref>{{cite book| vauthors = Coulston AM, Boushey C, Ferruzzi M |title=Nutrition in the Prevention and Treatment of Disease|date=2013|publisher=Academic Press|isbn=9780123918840|page=818|url=https://books.google.com/books?id=pmapb3rvzpYC&pg=PA818 | url-status=live|archive-url=https://web.archive.org/web/20161230000458/https://books.google.ca/books?id=pmapb3rvzpYC&pg=PA818|archive-date=30 December 2016}}</ref> As a supplement it is used to prevent and treat [[vitamin D deficiency]].<ref name=BNF69/> This includes vitamin D deficiency due to [[malabsorption|poor absorption by the intestines]] or [[liver disease]].<ref name=WHO2008/> It may also be used for [[hypocalcemia|low blood calcium]] due to [[hypoparathyroidism]].<ref name=WHO2008/> It is used by mouth or [[intramuscular|injection into a muscle]].<ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|pages=703–704|edition=69}}</ref><ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free |page=498 }}</ref>


<!-- Side effects and mechanism -->
<!-- Side effects and mechanism -->
Excessive doses can result in increased urine production, [[high blood pressure]], [[kidney stones]], [[kidney failure]], weakness, and constipation.<ref name=AHFS2016>{{cite web|title=Ergocalciferol|url=https://www.drugs.com/monograph/ergocalciferol.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161230002716/https://www.drugs.com/monograph/ergocalciferol.html|archive-date=30 December 2016}}</ref> If high doses are taken for a long period of time, [[tissue calcification]] may occur.<ref name=WHO2008/> Normal doses are safe in [[pregnancy]].<ref name=Ric2015>{{cite book|last1=Hamilton|first1=Richart| name-list-style = vanc |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=227}}</ref> It works by increasing the amount of [[calcium]] absorbed by the intestines and kidneys.<ref name=AHFS2016/> Food in which it is found include some [[mushrooms]].<ref name=NIH2016>{{cite web|title=Office of Dietary Supplements - Vitamin D|url=https://ods.od.nih.gov/factsheets/VitaminD-HealthProfessional/|website=ods.od.nih.gov|access-date=30 December 2016|date=11 February 2016|url-status=live|archive-url=https://web.archive.org/web/20161231073744/https://ods.od.nih.gov/factsheets/VitaminD-HealthProfessional/|archive-date=31 December 2016}}</ref>
Excessive doses can result in increased urine production, [[high blood pressure]], [[kidney stones]], [[kidney failure]], weakness, and constipation.<ref name=AHFS2016>{{cite web|title=Ergocalciferol|url=https://www.drugs.com/monograph/ergocalciferol.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161230002716/https://www.drugs.com/monograph/ergocalciferol.html|archive-date=30 December 2016}}</ref> If high doses are taken for a long period of time, [[tissue calcification]] may occur.<ref name=WHO2008/> Normal doses are safe in [[pregnancy]].<ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=227}}</ref> It works by increasing the amount of [[calcium]] absorbed by the intestines and kidneys.<ref name=AHFS2016/> Food in which it is found include some [[mushrooms]].<ref name=NIH2016>{{cite web|title=Office of Dietary Supplements - Vitamin D|url=https://ods.od.nih.gov/factsheets/VitaminD-HealthProfessional/|website=ods.od.nih.gov|access-date=30 December 2016|date=11 February 2016|url-status=live|archive-url=https://web.archive.org/web/20161231073744/https://ods.od.nih.gov/factsheets/VitaminD-HealthProfessional/|archive-date=31 December 2016}}</ref>


<!-- History and culture -->
<!-- History and culture -->
Ergocalciferol was first described in 1936.<ref name=Fis2006>{{cite book|last1=Fischer|first1=Janos|last2=Ganellin|first2=C. Robin| name-list-style = vanc |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=451|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA451 | url-status=live|archive-url=https://web.archive.org/web/20161230085612/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA451|archive-date=2016-12-30}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> Ergocalciferol is available as a [[generic medication]] and [[over the counter]].<ref name=AHFS2016/> In 2017, it was the 55th most commonly prescribed medication in the United States, with more than 14 million prescriptions.<ref>{{cite web |title=The Top 300 of 2020 |url=https://clincalc.com/DrugStats/Top300Drugs.aspx |website=ClinCalc |access-date=11 April 2020}}</ref><ref>{{cite web | title=Ergocalciferol - Drug Usage Statistics | website=ClinCalc | url=https://clincalc.com/DrugStats/Drugs/Ergocalciferol | access-date=11 April 2020}}</ref> Certain foods such as [[breakfast cereal]] and [[margarine]] have ergocalciferol added to them in some countries.<ref>{{cite book |last1=Feral |first1=Priscilla |last2=Hall |first2=Lee | name-list-style = vanc |title=Dining with Friends: The Art of North American Vegan Cuisine|date=2005|publisher=Friends of Animals/Nectar Bat Press|isbn=9780976915904|page=[https://archive.org/details/diningwithfriend0000fera/page/160 160]|url=https://archive.org/details/diningwithfriend0000fera |url-access=registration }}</ref><ref>{{cite book |last1=Bennett |first1=Beverly |last2=Sammartano |first2=Ray | name-list-style = vanc |title= The Complete Idiot's Guide to Vegan Living | edition = Second |date=2012|publisher=Penguin|isbn=9781615642793|page=Chapter 15|url=https://books.google.com/books?id=MbzIcj32RzEC&pg=PT215 | url-status=live|archive-url=https://web.archive.org/web/20161230230633/https://books.google.ca/books?id=MbzIcj32RzEC&pg=PT215|archive-date=2016-12-30}}</ref>
Ergocalciferol was first described in 1936.<ref name=Fis2006>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=451|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA451 | url-status=live|archive-url=https://web.archive.org/web/20161230085612/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA451|archive-date=30 December 2016}}</ref> Ergocalciferol is available as a [[generic medication]] and [[over the counter]].<ref name=AHFS2016/> In 2021, it was the 35th most commonly prescribed medication in the United States, with more than 17{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title=Ergocalciferol - Drug Usage Statistics | website=ClinCalc | url=https://clincalc.com/DrugStats/Drugs/Ergocalciferol | access-date=14 January 2024 | archive-date=13 April 2020 | archive-url=https://web.archive.org/web/20200413044817/https://clincalc.com/DrugStats/Drugs/Ergocalciferol | url-status=live }}</ref> Certain foods such as [[breakfast cereal]] and [[margarine]] have ergocalciferol added to them in some countries.<ref>{{cite book | vauthors = Feral P, Hall L |title=Dining with Friends: The Art of North American Vegan Cuisine|date=2005|publisher=Friends of Animals/Nectar Bat Press|isbn=9780976915904|page=[https://archive.org/details/diningwithfriend0000fera/page/160 160]|url=https://archive.org/details/diningwithfriend0000fera |url-access=registration }}</ref><ref>{{cite book | vauthors = Bennett B, Sammartano R |title= The Complete Idiot's Guide to Vegan Living | edition = Second |date=2012|publisher=Penguin|isbn=9781615642793|page=Chapter 15|url=https://books.google.com/books?id=MbzIcj32RzEC&pg=PT215 | url-status=live|archive-url=https://web.archive.org/web/20161230230633/https://books.google.ca/books?id=MbzIcj32RzEC&pg=PT215|archive-date=30 December 2016}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref>


==Use==
==Use==
[[File:Vitamin D pills.jpg|thumb|Vitamin D2 supplements]]
[[File:Vitamin D pills.jpg|thumb|Vitamin D<sub>2</sub> supplements]]
Ergocalciferol may be used as a vitamin D [[dietary supplement|supplement]], whereas [[cholecalciferol]] (vitamin D<sub>3</sub>) is produced naturally by the skin when exposed to ultraviolet light.<ref name="holick guideline">{{cite journal | vauthors = Holick MF, Binkley NC, Bischoff-Ferrari HA, Gordon CM, Hanley DA, Heaney RP, Murad MH, Weaver CM | display-authors = 6 | title = Evaluation, treatment, and prevention of vitamin D deficiency: an Endocrine Society clinical practice guideline | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 96 | issue = 7 | pages = 1911–30 | date = July 2011 | pmid = 21646368 | pmc = | doi = 10.1210/jc.2011-0385 | doi-access = free }}</ref> Ergocalciferol (D<sub>2</sub>) and cholecalciferol (D<sub>3</sub>) are considered to be equivalent for vitamin D production, as both forms appear to have similar efficacy in ameliorating [[rickets]]<ref>{{cite journal | vauthors = Thacher TD, Fischer PR, Obadofin MO, Levine MA, Singh RJ, Pettifor JM | title = Comparison of metabolism of vitamins D2 and D3 in children with nutritional rickets | journal = Journal of Bone and Mineral Research | volume = 25 | issue = 9 | pages = 1988–95 | date = September 2010 | pmid = 20499377 | pmc = 3153403 | doi = 10.1002/jbmr.99 }}</ref> and reducing the incidence of falls in elderly patients.<ref>{{cite journal | vauthors = Fosnight SM, Zafirau WJ, Hazelett SE | title = Vitamin D supplementation to prevent falls in the elderly: evidence and practical considerations | journal = Pharmacotherapy | volume = 28 | issue = 2 | pages = 225–34 | date = February 2008 | pmid = 18225968 | pmc = | doi = 10.1592/phco.28.2.225 | s2cid = 37034292 }}</ref> 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.<ref name="ajcn">{{cite journal | vauthors = Tripkovic L, Lambert H, Hart K, Smith CP, Bucca G, Penson S, Chope G, Hyppönen E, Berry J, Vieth R, Lanham-New S | display-authors = 6 | title = Comparison of vitamin D2 and vitamin D3 supplementation in raising serum 25-hydroxyvitamin D status: a systematic review and meta-analysis | journal = The American Journal of Clinical Nutrition | volume = 95 | issue = 6 | pages = 1357–64 | date = June 2012 | pmid = 22552031 | pmc = 3349454 | doi = 10.3945/ajcn.111.031070 }}</ref> A [[meta-analysis]] concluded that evidence usually favors cholecalciferol in raising vitamin D levels in blood, although it stated more research is needed.<ref name=ajcn/>
Ergocalciferol may be used as a vitamin D [[dietary supplement|supplement]], whereas [[cholecalciferol]] (vitamin D<sub>3</sub>) is produced naturally by the skin when exposed to ultraviolet light.<ref name="holick guideline">{{cite journal | vauthors = Holick MF, Binkley NC, Bischoff-Ferrari HA, Gordon CM, Hanley DA, Heaney RP, Murad MH, Weaver CM | display-authors = 6 | title = Evaluation, treatment, and prevention of vitamin D deficiency: an Endocrine Society clinical practice guideline | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 96 | issue = 7 | pages = 1911–1930 | date = July 2011 | pmid = 21646368 | doi = 10.1210/jc.2011-0385 | doi-access = free }}</ref> Ergocalciferol (D<sub>2</sub>) and cholecalciferol (D<sub>3</sub>) are considered to be equivalent for vitamin D production, as both forms appear to have similar efficacy in ameliorating [[rickets]]<ref>{{cite journal | vauthors = Thacher TD, Fischer PR, Obadofin MO, Levine MA, Singh RJ, Pettifor JM | title = Comparison of metabolism of vitamins D2 and D3 in children with nutritional rickets | journal = Journal of Bone and Mineral Research | volume = 25 | issue = 9 | pages = 1988–1995 | date = September 2010 | pmid = 20499377 | pmc = 3153403 | doi = 10.1002/jbmr.99 }}</ref> and reducing the incidence of falls in elderly patients.<ref>{{cite journal | vauthors = Fosnight SM, Zafirau WJ, Hazelett SE | title = Vitamin D supplementation to prevent falls in the elderly: evidence and practical considerations | journal = Pharmacotherapy | volume = 28 | issue = 2 | pages = 225–234 | date = February 2008 | pmid = 18225968 | doi = 10.1592/phco.28.2.225 | s2cid = 37034292 | doi-access = free }}</ref> 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.<ref name="ajcn">{{cite journal | vauthors = Tripkovic L, Lambert H, Hart K, Smith CP, Bucca G, Penson S, Chope G, Hyppönen E, Berry J, Vieth R, Lanham-New S | display-authors = 6 | title = Comparison of vitamin D2 and vitamin D3 supplementation in raising serum 25-hydroxyvitamin D status: a systematic review and meta-analysis | journal = The American Journal of Clinical Nutrition | volume = 95 | issue = 6 | pages = 1357–1364 | date = June 2012 | pmid = 22552031 | pmc = 3349454 | doi = 10.3945/ajcn.111.031070 }}</ref> A [[meta-analysis]] concluded that evidence usually favors cholecalciferol in raising vitamin D levels in blood, although it stated more research is needed.<ref name=ajcn/>


==Mechanism==
==Mechanism==
Ergocalciferol is a [[secosteroid]] formed by a [[photochemistry|photochemical]] bond breaking of a [[steroid]], specifically, by the action of [[ultraviolet light]] (UV-B or UV-C) on [[ergosterol]], a form of provitamin D<sub>2</sub>.<ref name=pmid30322118>{{cite journal |last1=Cardwell |first1=G |last2=Bornman |first2=JF |last3=James |first3=AP |last4=Black |first4=LJ |title=A Review of Mushrooms as a Potential Source of Dietary Vitamin D. |journal=Nutrients |date=13 October 2018 |volume=10 |issue=10 |page=1498 |doi=10.3390/nu10101498 |pmid=30322118 |pmc=6213178}}</ref>
Ergocalciferol is a [[secosteroid]] formed by a [[photochemistry|photochemical]] bond breaking of a [[steroid]], specifically, by the action of [[ultraviolet light]] (UV-B or UV-C) on [[ergosterol]], a form of provitamin D<sub>2</sub>.<ref name=pmid30322118>{{cite journal | vauthors = Cardwell G, Bornman JF, James AP, Black LJ | title = A Review of Mushrooms as a Potential Source of Dietary Vitamin D | journal = Nutrients | volume = 10 | issue = 10 | page = 1498 | date = October 2018 | pmid = 30322118 | pmc = 6213178 | doi = 10.3390/nu10101498 | doi-access = free }}</ref>


Like [[cholecalciferol]], Ergocalciferol is inactive by itself. It requires two [[hydroxylation]]s to become active: the first in the liver by [[CYP2R1]] to form 25-hydroxyergocalciferol (ercalcidiol or 25-OH D<sub>2</sub><ref>{{cite journal | vauthors = Suda T, DeLuca HF, Schnoes H, Blunt JW | title = 25-hydroxyergocalciferol: a biologically active metabolite of vitamin D2 | journal = Biochemical and Biophysical Research Communications | volume = 35 | issue = 2 | pages = 182–5 | date = April 1969 | pmid = 5305760 | doi = 10.1016/0006-291X(69)90264-2 }}</ref>), and the second in the kidney by [[CYP27B1]], to form the active 1,25-dihydroxyergocalciferol (ercalcitriol or 1,25-(OH)<sub>2</sub>D<sub>2</sub>), which activates the [[vitamin D receptor]].<ref>{{cite journal | vauthors = | title = IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Nomenclature of vitamin D. Recommendations 1981 | journal = European Journal of Biochemistry | volume = 124 | issue = 2 | pages = 223–7 | date = May 1982 | pmid = 7094913 | doi = 10.1111/j.1432-1033.1982.tb06581.x }}</ref> Unlike [[cholecalciferol]], 25-hydroxylation is not performed by [[CYP27A1]] for ergocalciferol.<ref name=Bikle/>
Like [[cholecalciferol]], ergocalciferol is inactive by itself. It requires two [[hydroxylation]]s to become active: the first in the liver by [[CYP2R1]] to form 25-hydroxyergocalciferol (ercalcidiol or 25-OH D<sub>2</sub><ref>{{cite journal | vauthors = Suda T, DeLuca HF, Schnoes H, Blunt JW | title = 25-hydroxyergocalciferol: a biologically active metabolite of vitamin D2 | journal = Biochemical and Biophysical Research Communications | volume = 35 | issue = 2 | pages = 182–185 | date = April 1969 | pmid = 5305760 | doi = 10.1016/0006-291X(69)90264-2 }}</ref>), and the second in the kidney by [[CYP27B1]], to form the active 1,25-dihydroxyergocalciferol (ercalcitriol or 1,25-(OH)<sub>2</sub>D<sub>2</sub>), which activates the [[vitamin D receptor]].<ref>{{cite journal | vauthors = | title = IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Nomenclature of vitamin D. Recommendations 1981 | journal = European Journal of Biochemistry | volume = 124 | issue = 2 | pages = 223–227 | date = May 1982 | pmid = 7094913 | doi = 10.1111/j.1432-1033.1982.tb06581.x | doi-access = free }}</ref> Unlike [[cholecalciferol]], 25-hydroxylation is not performed by [[CYP27A1]] for ergocalciferol.<ref name=Bikle/>


Ergocalciferol and metabolites have lower affinity to the [[vitamin D-binding protein]] compared to the D<sub>3</sub> counterparts. The binding affinity of ercalcitriol to the vitamin D receptor is similar to that of [[calcitriol]].<ref name=Bikle>{{cite journal | vauthors = Bikle DD | title = Vitamin D metabolism, mechanism of action, and clinical applications | journal = Chemistry & Biology | volume = 21 | issue = 3 | pages = 319–29 | date = March 2014 | pmid = 24529992 | pmc = 3968073 | doi = 10.1016/j.chembiol.2013.12.016 }}</ref> Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation.<ref>{{cite journal | vauthors = Houghton LA, Vieth R | title = The case against ergocalciferol (vitamin D2) as a vitamin supplement | journal = The American Journal of Clinical Nutrition | volume = 84 | issue = 4 | pages = 694–7 | date = October 2006 | pmid = 17023693 | doi = 10.1093/ajcn/84.4.694 | doi-access = free }}</ref>
Ergocalciferol and metabolites have lower affinity to the [[vitamin D-binding protein]] compared to the D<sub>3</sub> counterparts. The binding affinity of ercalcitriol to the vitamin D receptor is similar to that of [[calcitriol]].<ref name=Bikle>{{cite journal | vauthors = Bikle DD | title = Vitamin D metabolism, mechanism of action, and clinical applications | journal = Chemistry & Biology | volume = 21 | issue = 3 | pages = 319–329 | date = March 2014 | pmid = 24529992 | pmc = 3968073 | doi = 10.1016/j.chembiol.2013.12.016 }}</ref> Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation.<ref>{{cite journal | vauthors = Houghton LA, Vieth R | title = The case against ergocalciferol (vitamin D2) as a vitamin supplement | journal = The American Journal of Clinical Nutrition | volume = 84 | issue = 4 | pages = 694–697 | date = October 2006 | pmid = 17023693 | doi = 10.1093/ajcn/84.4.694 | doi-access = free }}</ref>


==Sources==
==Sources==
'''Fungus''', from USDA nutrient database (per 100g), D<sub>2</sub> + D<sub>3</sub>:<ref>{{cite web |url=http://www.nal.usda.gov/fnic/foodcomp/search/index.html |title=USDA nutrient database – ''use the keyword 'portabello' and then click submit'' |url-status=live |archive-url=https://web.archive.org/web/20150222164135/http://www.nal.usda.gov/fnic/foodcomp/search/index.html |archive-date=2015-02-22 }}</ref><ref name=Haytowitz-USDA>{{cite web|author=Haytowitz DB|title=Vitamin D in mushrooms|url=https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|publisher=Nutrient Data Laboratory, US Department of Agriculture|access-date=16 April 2018|date=2009}}</ref>
'''Fungus''', from USDA nutrient database (per 100g), D<sub>2</sub> + D<sub>3</sub>:<ref>{{cite web |url=http://www.nal.usda.gov/fnic/foodcomp/search/index.html |title=USDA nutrient database – ''use the keyword 'portabello' and then click submit'' |url-status=live |archive-url=https://web.archive.org/web/20150222164135/http://www.nal.usda.gov/fnic/foodcomp/search/index.html |archive-date=22 February 2015 }}</ref><ref name=Haytowitz-USDA>{{cite web|author=Haytowitz DB|title=Vitamin D in mushrooms|url=https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|publisher=Nutrient Data Laboratory, US Department of Agriculture|access-date=16 April 2018|date=2009|archive-date=1 February 2021|archive-url=https://web.archive.org/web/20210201181749/https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|url-status=live}}</ref>
* [[Agaricus bisporus]]:
* [[Agaricus bisporus|Mushrooms, ''Agaricus bisporus'']]:
** raw portobello: 0.3&nbsp;μg (10 IU); exposed to ultraviolet light: 11.2&nbsp;µg (446 IU)
** raw portobello: 0.3&nbsp;μg (10 IU); exposed to ultraviolet light: 11.2&nbsp;μg (446 IU)
** raw crimini: 0.1&nbsp;μg (3 IU); exposed to ultraviolet light: 31.9&nbsp;µg (1276 IU)
** raw crimini: 0.1&nbsp;μg (3 IU); exposed to ultraviolet light: 31.9&nbsp;μg (1276 IU)
* [[Shiitake|Mushrooms, shiitake]]:
* [[Shiitake|Mushrooms, shiitake]]:
** raw: Vitamin D (D<sub>2</sub> + D<sub>3</sub>): 0.4 μg (18 IU)
** raw: Vitamin D (D<sub>2</sub> + D<sub>3</sub>): 0.4 μg (18 IU)
Line 126: Line 115:


'''Lichen'''
'''Lichen'''
* ''[[Cladina]] arbuscula'' specimens grown under different natural conditions contain provitamin D<sub>2</sub> and vitamin D<sub>2</sub>, ranges 89-146 and 0.22-0.55&nbsp;μg/g dry matter respectively. They also contain vitamin D<sub>3</sub> (range 0.67 to 2.04&nbsp;μg/g) although provitamin D<sub>3</sub> could not be detected. Vitamin D levels correlate positively with UV irradiation.<ref>{{cite journal | vauthors = Wang T, Bengtsson G, Kärnefelt I, Björn LO | title = Provitamins and vitamins D₂and D₃in Cladina spp. over a latitudinal gradient: possible correlation with UV levels | journal = Journal of Photochemistry and Photobiology. B, Biology | volume = 62 | issue = 1–2 | pages = 118–22 | date = September 2001 | pmid = 11693362 | doi = 10.1016/S1011-1344(01)00160-9 | url = http://lup.lub.lu.se/record/133512 }}</ref>
* ''[[Cladina]] arbuscula'' specimens grown under different natural conditions contain provitamin D<sub>2</sub> and vitamin D<sub>2</sub>, ranges 89-146 and 0.22-0.55&nbsp;μg/g dry matter respectively. They also contain vitamin D<sub>3</sub> (range 0.67 to 2.04&nbsp;μg/g) although provitamin D<sub>3</sub> could not be detected. Vitamin D levels correlate positively with UV irradiation.<ref name="pmid11693362"/>


'''Plantae'''
'''Plantae'''
* [[Alfalfa]] (''Medicago sativa'' subsp. sativa), shoot: 4.8&nbsp;μg (192 IU) vitamin D<sub>2</sub>, 0.1&nbsp;μg (4 IU) vitamin D<sub>3</sub><ref>{{cite web |url=http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=606 |title=Dr. Duke's Phytochemical and Ethnobotanical Databases |url-status=dead |archive-url=https://web.archive.org/web/20151016051622/http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=606 |archive-date=2015-10-16 }}</ref>
* [[Alfalfa]] (''Medicago sativa'' subsp. sativa), shoot: 4.8&nbsp;μg (192 IU) vitamin D<sub>2</sub>, 0.1&nbsp;μg (4 IU) vitamin D<sub>3</sub><ref>{{cite web |url=http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=606 |title=Dr. Duke's Phytochemical and Ethnobotanical Databases |url-status=dead |archive-url=https://web.archive.org/web/20151016051622/http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=606 |archive-date=16 October 2015 }}</ref>


=== Biosynthesis ===
=== Biosynthesis ===
<!-- Principle -->
<!-- Principle -->
The vitamin D<sub>2</sub> content in mushrooms and ''C. arbuscula'' increase with exposure to ultraviolet light.<ref name="pmid11693362">{{cite journal | vauthors = Wang T, Bengtsson G, Kärnefelt I, Björn LO | title = Provitamins and vitamins D₂ and D₃ in Cladina spp. over a latitudinal gradient: possible correlation with UV levels | journal = Journal of Photochemistry and Photobiology. B, Biology | volume = 62 | issue = 1–2 | pages = 118–22 | date = September 2001 | pmid = 11693362 | doi = 10.1016/S1011-1344(01)00160-9 | url = http://lup.lub.lu.se/record/133512 }}</ref><ref name=usda-mush-light>{{cite web|author=Haytowitz DB|title=Vitamin D in mushrooms|url=https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|publisher=Nutrient Data Laboratory, US Department of Agriculture|access-date=16 April 2018|date=2009}}</ref> [[Ergosterol]] (provitamin D<sub>2</sub>) found in these fungi is converted to previtamin D<sub>2</sub> on UV exposure, which then turns into vitamin D<sub>2</sub>. As cultured mushrooms are generally grown in darkness, less vitamin D<sub>2</sub> is found compared to those grown in the wild or dried in the sun.<ref name=pmid30322118/>
The vitamin D<sub>2</sub> content in mushrooms and ''C. arbuscula'' increase with exposure to ultraviolet light.<ref name="pmid11693362">{{cite journal | vauthors = Wang T, Bengtsson G, Kärnefelt I, Björn LO | title = Provitamins and vitamins D₂and D₃in Cladina spp. over a latitudinal gradient: possible correlation with UV levels | journal = Journal of Photochemistry and Photobiology. B, Biology | volume = 62 | issue = 1–2 | pages = 118–122 | date = September 2001 | pmid = 11693362 | doi = 10.1016/S1011-1344(01)00160-9 | url = http://lup.lub.lu.se/record/133512 | access-date = 27 January 2019 | url-status = live | archive-url = https://web.archive.org/web/20200528231009/https://lup.lub.lu.se/search/publication/133512 | archive-date = 28 May 2020 }}</ref><ref name=usda-mush-light>{{cite web|author=Haytowitz DB|title=Vitamin D in mushrooms|url=https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|publisher=Nutrient Data Laboratory, US Department of Agriculture|access-date=16 April 2018|date=2009|archive-date=1 February 2021|archive-url=https://web.archive.org/web/20210201181749/https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/AICR09_Mushroom_VitD.pdf|url-status=live}}</ref> [[Ergosterol]] (provitamin D<sub>2</sub>) found in these fungi is converted to previtamin D<sub>2</sub> on UV exposure, which then turns into vitamin D<sub>2</sub>. As cultured mushrooms are generally grown in darkness, less vitamin D<sub>2</sub> is found compared to those grown in the wild or dried in the sun.<ref name=pmid30322118/>


<!-- Application -->
<!-- Application -->
When fresh mushrooms or dried powders are purposely exposed to ultraviolet light, vitamin D<sub>2</sub> levels can be concentrated to much higher levels.<ref name="keegan">{{cite journal | vauthors = Keegan RJ, Lu Z, Bogusz JM, Williams JE, Holick MF | title = Photobiology of vitamin D in mushrooms and its bioavailability in humans | journal = Dermato-Endocrinology | volume = 5 | issue = 1 | pages = 165–76 | date = January 2013 | pmid = 24494050 | pmc = 3897585 | doi = 10.4161/derm.23321 }}</ref><ref name=msnbc/><ref name="simon">{{cite journal | vauthors = Simon RR, Borzelleca JF, DeLuca HF, Weaver CM | title = Safety assessment of the post-harvest treatment of button mushrooms (Agaricus bisporus) using ultraviolet light | journal = Food and Chemical Toxicology | volume = 56 | pages = 278–89 | date = June 2013 | pmid = 23485617 | doi = 10.1016/j.fct.2013.02.009 }}</ref> The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms.<ref>{{cite journal | vauthors = Koyyalamudi SR, Jeong SC, Song CH, Cho KY, Pang G | title = Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation | journal = Journal of Agricultural and Food Chemistry | volume = 57 | issue = 8 | pages = 3351–5 | date = April 2009 | pmid = 19281276 | doi = 10.1021/jf803908q }}</ref> 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.<ref name="msnbc">{{Cite news|title=Bringing Mushrooms Out of the Dark |date=April 18, 2006 |url =http://www.nbcnews.com/id/12370708|work =NBC News|access-date = August 6, 2007}}</ref>
When fresh mushrooms or dried powders are purposely exposed to ultraviolet light, vitamin D<sub>2</sub> levels can be concentrated to much higher levels.<ref name="keegan">{{cite journal | vauthors = Keegan RJ, Lu Z, Bogusz JM, Williams JE, Holick MF | title = Photobiology of vitamin D in mushrooms and its bioavailability in humans | journal = Dermato-Endocrinology | volume = 5 | issue = 1 | pages = 165–176 | date = January 2013 | pmid = 24494050 | pmc = 3897585 | doi = 10.4161/derm.23321 }}</ref><ref name=msnbc/><ref name="simon">{{cite journal | vauthors = Simon RR, Borzelleca JF, DeLuca HF, Weaver CM | title = Safety assessment of the post-harvest treatment of button mushrooms (Agaricus bisporus) using ultraviolet light | journal = Food and Chemical Toxicology | volume = 56 | pages = 278–289 | date = June 2013 | pmid = 23485617 | doi = 10.1016/j.fct.2013.02.009 }}</ref> The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms.<ref>{{cite journal | vauthors = Koyyalamudi SR, Jeong SC, Song CH, Cho KY, Pang G | title = Vitamin D2 formation and bioavailability from Agaricus bisporus button mushrooms treated with ultraviolet irradiation | journal = Journal of Agricultural and Food Chemistry | volume = 57 | issue = 8 | pages = 3351–3355 | date = April 2009 | pmid = 19281276 | doi = 10.1021/jf803908q }}</ref> 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.<ref name="msnbc">{{Cite news |title=Bringing Mushrooms Out of the Dark |date=18 April 2006 |url=http://www.nbcnews.com/id/12370708 |work=NBC News |access-date=6 August 2007 |archive-date=7 November 2017 |archive-url=https://web.archive.org/web/20171107112253/http://www.nbcnews.com/id/12370708 |url-status=live }}</ref>


<!-- Effect on humans -->
<!-- Effect on humans -->
Button mushrooms with enhanced vitamin D<sub>2</sub> content produced this way functions similarly to a vitamin D<sub>2</sub> supplement; both effectively improves vitamin D status.<ref name=keegan/><ref name="pmid21540874">{{cite journal | vauthors = Urbain P, Singler F, Ihorst G, Biesalski HK, Bertz H | title = Bioavailability of vitamin D₂ from UV-B-irradiated button mushrooms in healthy adults deficient in serum 25-hydroxyvitamin D: a randomized controlled trial | journal = European Journal of Clinical Nutrition | volume = 65 | issue = 8 | pages = 965–71 | date = August 2011 | pmid = 21540874 | doi = 10.1038/ejcn.2011.53 | doi-access = free }}</ref> Vitamin D<sub>2</sub> from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D.<ref name=keegan/>
Button mushrooms with enhanced vitamin D<sub>2</sub> content produced this way functions similarly to a vitamin D<sub>2</sub> supplement; both effectively improves vitamin D status.<ref name=keegan/><ref name="pmid21540874">{{cite journal | vauthors = Urbain P, Singler F, Ihorst G, Biesalski HK, Bertz H | title = Bioavailability of vitamin D₂ from UV-B-irradiated button mushrooms in healthy adults deficient in serum 25-hydroxyvitamin D: a randomized controlled trial | journal = European Journal of Clinical Nutrition | volume = 65 | issue = 8 | pages = 965–971 | date = August 2011 | pmid = 21540874 | doi = 10.1038/ejcn.2011.53 | doi-access = free }}</ref> Vitamin D<sub>2</sub> from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D.<ref name=keegan/>


==Names==
==Names==
Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol.<ref>{{cite journal | date = 1930 | title = Viosterol official name for irradiated ergosterol | journal = Journal of Chemical Education | volume = 7 | issue = 1 | pages = 166 | doi = 10.1021/ed007p166 | last1 = Science Service | bibcode = 1930JChEd...7..166S }}</ref><ref>See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., {{cite web |url=http://www.merriam-webster.com/medical/viosterol |title=Medical Definition of VIOSTEROL |access-date=2014-07-10 |url-status=live |archive-url=https://web.archive.org/web/20140714154919/http://www.merriam-webster.com/medical/viosterol |archive-date=2014-07-14 }} and {{cite web |url=http://www.merriam-webster.com/medical/calciferol |title=Definition of CALCIFEROL |access-date=2014-07-10 |url-status=live |archive-url=https://web.archive.org/web/20140714212827/http://www.merriam-webster.com/medical/calciferol |archive-date=2014-07-14 }}, accessed 10 July 2014.</ref>
Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol.<ref>{{cite journal | date = 1930 | title = Viosterol official name for irradiated ergosterol | journal = Journal of Chemical Education | volume = 7 | issue = 1 | pages = 166 | doi = 10.1021/ed007p166 | last1 = Science Service | bibcode = 1930JChEd...7..166S }}</ref><ref>See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., {{cite web |url=http://www.merriam-webster.com/medical/viosterol |title=Medical Definition of VIOSTEROL |access-date=10 July 2014 |url-status=live |archive-url=https://web.archive.org/web/20140714154919/http://www.merriam-webster.com/medical/viosterol |archive-date=14 July 2014 }} and {{cite web |url=http://www.merriam-webster.com/medical/calciferol |title=Definition of CALCIFEROL |access-date=10 July 2014 |url-status=live |archive-url=https://web.archive.org/web/20140714212827/http://www.merriam-webster.com/medical/calciferol |archive-date=14 July 2014 }}, accessed 10 July 2014.</ref> However, currently, Viosterol is also the brand name for [[cholecalciferol]] (vitamin D<sub>3</sub>) in some countries.<ref>{{cite web |url=https://www.vademecum.es/equivalencia-lista-viosterol+comprimido+5000+ui-uruguay-a11cc05--uy_1 |title=Viosterol comprimido 5000 UI |access-date=5 September 2022 |archive-date=5 September 2022 |archive-url=https://web.archive.org/web/20220905231617/https://www.vademecum.es/equivalencia-lista-viosterol+comprimido+5000+ui-uruguay-a11cc05--uy_1 |url-status=dead }}</ref><ref>{{cite web |url=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 |title=Viosterol 1000 |access-date=6 September 2022 |archive-date=6 September 2022 |archive-url=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 |url-status=dead }}</ref>


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


== References ==
== References ==
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== External links ==
== External links ==
* {{cite web| url = https://druginfo.nlm.nih.gov/drugportal/name/ergocalciferol | publisher = U.S. National Library of Medicine| work = Drug Information Portal| title = Ergocalciferol }}
* [https://webbook.nist.gov/cgi/cbook.cgi?ID=C50146 NIST Chemistry WebBook page for ergocalciferol]
* [https://webbook.nist.gov/cgi/cbook.cgi?ID=C50146 NIST Chemistry WebBook page for ergocalciferol]


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[[Category:Cyclohexanols]]
[[Category:Cyclohexanols]]
[[Category:Eli Lilly and Company brands]]
[[Category:Drugs developed by Eli Lilly and Company]]
[[Category:Polyenes]]
[[Category:Polyenes]]
[[Category:Secosteroids]]
[[Category:Secosteroids]]
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[[Category:World Health Organization essential medicines]]
[[Category:World Health Organization essential medicines]]
[[Category:Wikipedia medicine articles ready to translate]]
[[Category:Wikipedia medicine articles ready to translate]]
[[Category:Vinylidene compounds]]

Revision as of 16:30, 11 May 2024

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
  • (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 InfoCard100.000.014 Edit this at Wikidata
Chemical and physical data
FormulaC28H44O
Molar mass396.659 g·mol−1
3D model (JSmol)
Melting point114 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 checkY
  • Key:MECHNRXZTMCUDQ-RKHKHRCZSA-N

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". 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. ^ a b British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 703–704. ISBN 9780857111562.
  5. ^ a b c d 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. ^ a b c "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.
  8. ^ "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.
  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 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  11. ^ "Ergocalciferol - Drug Usage Statistics". ClinCalc. Archived from the original on 13 April 2020. Retrieved 14 January 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.
  13. ^ Bennett B, Sammartano R (2012). The Complete Idiot's Guide to Vegan Living (Second ed.). Penguin. p. Chapter 15. ISBN 9781615642793. Archived from the original on 30 December 2016.
  14. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  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.
  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. ^ a b 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.
  19. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b c 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. ^ a b "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. 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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