Ergocalciferol

Template:Short description Template:Use dmy dates Template:Cs1 config Template:Main other {{#invoke:Infobox|infobox}}Template:Template other{{#invoke:TemplatePar |check |template=Template:Infobox_drug |all= |opt= pronounce= pronounce_ref= pronounce_comment= ATC_prefix= ATC_suffix= ATC_supplemental= ATCvet= biosimilars= CAS_number_Ref= CAS_number= CAS_supplemental= ChEBI= ChEBI_Ref= ChEMBL_Ref= ChEMBL= ChemSpiderID= ChemSpiderID_Ref= chirality= class= container_only= DailyMedID= data_page= DrugBank_Ref= DrugBank= Drugs.com= duration_of_action= INN= INN_EMA= IUPAC_name= IUPHAR_ligand= KEGG_Ref= KEGG= MedlinePlus= NIAID_ChemDB= PDB_ligand= PubChemSubstance= PubChem= StdInChIKey_Ref= StdInChIKey= StdInChI_Ref= StdInChI_comment= StdInChI= UNII_Ref= UNII= DTXSID= Verifiedfields= Watchedfields= addiction_liability= alt2= altL= altR= alt= bioavailability= boiling_high= boiling_notes= boiling_point= captionLR= caption= caption2= charge= chemical_formula= chemical_formula_ref= chemical_formula_comment= class1= class2= class3= class4= class5= class6= component1= component2= component3= component4= component5= component6= density= density_notes= dependency_liability= drug_name= elimination_half-life= engvar= excretion= image2= imageL= imageR= image= image_class= image_class2= image_classL= image_classR= Jmol= legal_AU= legal_BR= legal_CA= legal_DE= legal_EU= legal_NZ= legal_UK= legal_UN= legal_US= legal_AU_comment= legal_BR_comment= legal_CA_comment= legal_DE_comment= legal_UK_comment= legal_NZ_comment= legal_US_comment= legal_UN_comment= legal_EU_comment= legal_status= licence_CA= licence_EU= licence_US= license_CA= license_EU= license_US= mab_type= melting_high= melting_notes= melting_point= metabolism= metabolites= molecular_weight= molecular_weight_round= molecular_weight_unit= molecular_weight_ref= molecular_weight_comment= onset= pregnancy_AU= pregnancy_AU_comment= pregnancy_category= protein_bound= routes_of_administration= SMILES= smiles= solubility= sol_units= source= specific_rotation= synonyms= target= tradename= type= vaccine_type= verifiedrevid= width2= widthL= widthR= width= AAN= BAN= JAN= USAN= source_tissues= target_tissues= receptors= agonists= antagonists= precursor= biosynthesis= gt_target_gene= gt_vector= gt_nucleic_acid_type= gt_editing_method= gt_delivery_method= sec_combustion= Ac=Ag=Al=Am=Ar=As=At=Au=B=Ba=Be=Bh=Bi=Bk=Br=C=Ca=Cd=Ce=Cf=Cl=Cm=Cn=Co=Cr=Cs=Cu= D=Db=Ds=Dy=Er=Es=Eu=F=Fe=Fl=Fm=Fr=Ga=Gd=Ge=H=He=Hf=Hg=Ho=Hs=I=In=Ir=K=Kr=La=Li=Lr=Lu=Lv= Mc=Md=Mg=Mn=Mo=Mt=N=Na=Nb=Nd=Ne=Nh=Ni=No=Np=O=Og=Os=P=Pa=Pb=Pd=Pm=Po=Pr=Pt=Pu=Ra=Rb=Re=Rf=Rg=Rh=Rn=Ru=S=Sb=Sc=Se=Sg=Si=Sm=Sn=Sr=Ta=Tb=Tc=Te=Th=Ti=Tl=Tm=Ts=U=V=W=Xe=Y=Yb=Zn=Zr= index_label= index2_label= index_comment= index2_comment= CAS_number2= CAS_supplemental2= ATC_prefix2= ATC_suffix2= ATC_supplemental2= PubChem2= PubChemSubstance2= IUPHAR_ligand2= DrugBank2= ChemSpiderID2= UNII2= KEGG2= ChEBI2= ChEMBL2= PDB_ligand2= NIAID_ChemDB2= SMILES2= smiles2= StdInChI2= StdInChIKey2= CAS_number2_Ref= ChEBI2_Ref= ChEMBL2_Ref= ChemSpiderID2_Ref= DrugBank2_Ref= KEGG2_Ref= StdInChI2_Ref= StdInChIKey2_Ref= UNII2_Ref= DTXSID2= QID= QID2=PLLR= pregnancy_US= pregnancy_US_comment= |cat=Pages using infobox drug with unknown parameters |format=0|errNS=0

|preview=

}}{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =

| _has_physiological_data= | _has_gene_therapy=

| vaccine_type= | mab_type= | _number_of_combo_chemicals={{#invoke:ParameterCount |main |component1 |component2 |component3 |component4|component5|component6 }} | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=28441O[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)C1S/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/s1MECHNRXZTMCUDQ-RKHKHRCZSA-NTemplate:Stdinchicite114118 | _combo_data= | _physiological_data= | _clinical_data=Template:Drugs.coma616042Ergocalciferol By mouth, intramuscularDrisdol, Calcidol, othersA11 | _legal_data=<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>Rx-only<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>POM/ Rx-onlyOTC

| _other_data=(3S,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol

| _image_0_or_2 = Ergocalciferol.svgErgocalciferol 3D ball.png | _image_LR =

| _datapage = Ergocalciferol (data page) | _vaccine_target={{#ifeq: | vaccine | | _type_not_vaccine }} | _legal_all=Rx-onlyPOMOTC | _ATC_prefix_supplemental=A11 | _has_EMA_link = | CAS_number=50-14-6 | PubChem=5280793 | ChemSpiderID=4444351 | ChEBI=28934 | ChEMBL=1536 | DrugBank=DB00153 | KEGG=C05441 | _hasInChI_or_Key={{#if: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/s1MECHNRXZTMCUDQ-RKHKHRCZSA-N |yes}} | UNII=VS041H42XC | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs={{#invoke:ParameterCount |main |CAS_number2 |ATC_prefix2 |PubChem2 |PubChemStructure2 |IUPHAR_ligand2 |DrugBank2 |ChemSpiderID2 |UNII2 |KEGG2 |ChEBI2 |ChEMBL2 |PDB_ligand2 |NIAID_ChemDB2 |SMILES2 |smiles2 |StdInChI2 |StdInChIKey2 |DTXCID2}} | _countIndexlabels={{#invoke:ParameterCount |main |index_label |index2_label}} | _trackListSortletter= |QID = |QID2 = |Verifiedfields= |Watchedfields= |verifiedrevid=}}

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<ref>Template:Cite book</ref> to prevent and treat vitamin D deficiency<ref name=BNF69/> due to poor absorption by the intestines or liver disease.<ref name=WHO2008/> It may also be used for low blood calcium due to hypoparathyroidism.<ref name=WHO2008/> It is taken by mouth or via injection into a muscle.<ref name=BNF69>Template:Cite book</ref><ref name=WHO2008>Template:Cite book</ref>

Excessive doses can result in vitamin D toxicity causing increased urine production, high blood pressure, kidney stones, kidney failure, muscle weakness, and constipation.<ref name=AHFS2016>{{#invoke:citation/CS1|citation |CitationClass=web }}</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>Template:Cite book</ref> It works by increasing the amount of calcium absorbed by the intestines and reabsorbed by the kidneys.<ref name=AHFS2016/> Food in which it is found include some mushrooms.<ref name=NIH2016>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Ergocalciferol was first described in 1936.<ref name=Fis2006>Template:Cite book</ref> Ergocalciferol is available as a generic medication and over the counter.<ref name=AHFS2016/> In 2022, it was the 38th most commonly prescribed medication in the United States, with more than 15Template:Nbspmillion prescriptions.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Certain foods such as breakfast cereal and margarine have ergocalciferol added to them in some countries.<ref>Template:Cite book</ref><ref>Template:Cite book</ref> It is on the World Health Organization's List of Essential Medicines.<ref name="WHO23rd">Template:Cite book</ref>

Use

File: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.<ref name="holick guideline">Template:Cite journal</ref> 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<ref>Template:Cite journal</ref> and reducing the incidence of falls in elderly patients.<ref>Template:Cite journal</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">Template:Cite journal</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

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.<ref name=pmid30322118>Template:Cite journal</ref>

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<ref>Template:Cite journal</ref>), 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.<ref>Template:Cite journal</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 D₃ counterparts. The binding affinity of ercalcitriol to the vitamin D receptor is similar to that of calcitriol.<ref name=Bikle>Template:Cite journal</ref> Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation.<ref>Template:Cite journal</ref>

Sources

Fungus, from USDA nutrient database (per 100g), D₂ + D₃:<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=Haytowitz-USDA>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

• 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.<ref name="pmid11693362"/>

Plantae

• Alfalfa (Medicago sativa subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D₂, 0.1 μg (4 IU) vitamin D₃<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

Biosynthesis

The vitamin D₂ content in mushrooms and C. arbuscula increase with exposure to ultraviolet light.<ref name="pmid11693362">Template:Cite journal</ref><ref name=usda-mush-light>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> 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.<ref name=pmid30322118/>

When fresh mushrooms or dried powders are purposely exposed to ultraviolet light, vitamin D₂ levels can be concentrated to much higher levels.<ref name="keegan">Template:Cite journal</ref><ref name=msnbc/><ref name="simon">Template:Cite journal</ref> The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms.<ref>Template:Cite journal</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">Template:Cite news</ref>

Button mushrooms with enhanced vitamin D₂ content produced this way functions similarly to a vitamin D₂ supplement; both effectively improves vitamin D status.<ref name=keegan/><ref name="pmid21540874">Template:Cite journal</ref> Vitamin D₂ from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D.<ref name=keegan/>

Names

Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol.<ref>Template:Cite journal</ref><ref>See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., {{#invoke:citation/CS1|citation |CitationClass=web }} and {{#invoke:citation/CS1|citation |CitationClass=web }}, accessed 10 July 2014.</ref> However, currently, Viosterol is also the brand name for cholecalciferol (vitamin D₃) in some countries.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Ergocalciferol is manufactured and sold under various brand names, including Deltalin (Eli Lilly and Company), Drisdol (Sanofi-Synthelabo), and Calcidol (Patrin Pharma).Template:Cn

External links

• NIST Chemistry WebBook page for ergocalciferol