Ergocalciferol: Difference between revisions
No edit summary |
Marked this version for translation |
||
| Line 1: | Line 1: | ||
<languages /> | <languages /> | ||
<translate> | <translate> | ||
<!--T:1--> | |||
{{Short description|Vitamin D2, a chemical compound}} | {{Short description|Vitamin D2, a chemical compound}} | ||
{{Infobox drug | {{Infobox drug | ||
| Line 11: | Line 12: | ||
| caption = | | caption = | ||
<!--T:2--> | |||
<!-- Clinical data --> | <!-- Clinical data --> | ||
| pronounce = | | pronounce = | ||
| Line 27: | Line 29: | ||
| ATC_supplemental = | | ATC_supplemental = | ||
<!--T:3--> | |||
| 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 = | ||
| Line 43: | Line 46: | ||
| legal_status = <!--For countries not listed above--> | | legal_status = <!--For countries not listed above--> | ||
<!--T:4--> | |||
<!-- Pharmacokinetic data --> | <!-- Pharmacokinetic data --> | ||
| bioavailability = | | bioavailability = | ||
| Line 53: | Line 57: | ||
| excretion = | | excretion = | ||
<!--T:5--> | |||
<!-- Identifiers --> | <!-- Identifiers --> | ||
| CAS_number = 50-14-6 | | CAS_number = 50-14-6 | ||
| Line 68: | Line 73: | ||
| synonyms = viosterol | | synonyms = viosterol | ||
<!--T:6--> | |||
<!-- 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 | | IUPAC_name = (3''S'',5''Z'',7''E'',22''E'')-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol | ||
| Line 86: | Line 92: | ||
}} | }} | ||
<!--T:7--> | |||
<!-- Definition and medical uses --> | <!-- Definition and medical uses --> | ||
'''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]]. As a supplement it is used to prevent and treat [[vitamin D deficiency]]. This includes vitamin D deficiency due to [[malabsorption|poor absorption by the intestines]] or [[liver disease]]. It may also be used for [[hypocalcemia|low blood calcium]] due to [[hypoparathyroidism]]. It is used by mouth or [[intramuscular|injection into a muscle]]. | '''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]]. As a supplement it is used to prevent and treat [[vitamin D deficiency]]. This includes vitamin D deficiency due to [[malabsorption|poor absorption by the intestines]] or [[liver disease]]. It may also be used for [[hypocalcemia|low blood calcium]] due to [[hypoparathyroidism]]. It is used by mouth or [[intramuscular|injection into a muscle]]. | ||
<!--T:8--> | |||
<!-- 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. If high doses are taken for a long period of time, [[tissue calcification]] may occur. Normal doses are safe in [[pregnancy]]. It works by increasing the amount of [[calcium]] absorbed by the intestines and kidneys. Food in which it is found include some [[mushrooms]]. | Excessive doses can result in increased urine production, [[high blood pressure]], [[kidney stones]], [[kidney failure]], weakness, and constipation. If high doses are taken for a long period of time, [[tissue calcification]] may occur. Normal doses are safe in [[pregnancy]]. It works by increasing the amount of [[calcium]] absorbed by the intestines and kidneys. Food in which it is found include some [[mushrooms]]. | ||
<!--T:9--> | |||
<!-- History and culture --> | <!-- History and culture --> | ||
Ergocalciferol was first described in 1936. Ergocalciferol is available as a [[generic medication]] and [[over the counter]]. Certain foods such as [[breakfast cereal]] and [[margarine]] have ergocalciferol added to them in some countries. | Ergocalciferol was first described in 1936. Ergocalciferol is available as a [[generic medication]] and [[over the counter]]. Certain foods such as [[breakfast cereal]] and [[margarine]] have ergocalciferol added to them in some countries. | ||
<!--T:10--> | |||
==Use== | ==Use== | ||
[[File:Vitamin D pills.jpg|thumb|Vitamin D<sub>2</sub> 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. 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]] 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. A [[meta-analysis]] concluded that evidence usually favors cholecalciferol in raising vitamin D levels in blood, although it stated more research is needed. | 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. 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]] 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. A [[meta-analysis]] concluded that evidence usually favors cholecalciferol in raising vitamin D levels in blood, although it stated more research is needed. | ||
<!--T:11--> | |||
==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>. | 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>. | ||
<!--T:12--> | |||
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>), 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]]. Unlike [[cholecalciferol]], 25-hydroxylation is not performed by [[CYP27A1]] for ergocalciferol. | 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>), 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]]. Unlike [[cholecalciferol]], 25-hydroxylation is not performed by [[CYP27A1]] for ergocalciferol. | ||
<!--T:13--> | |||
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]]. Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation. | 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]]. Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation. | ||
<!--T:14--> | |||
==Sources== | ==Sources== | ||
'''Fungus''', from USDA nutrient database (per 100g), D<sub>2</sub> + D<sub>3</sub>: | '''Fungus''', from USDA nutrient database (per 100g), D<sub>2</sub> + D<sub>3</sub>: | ||
| Line 115: | Line 129: | ||
** dried: Vitamin D (D<sub>2</sub> + D<sub>3</sub>): 3.9 μg (154 IU) | ** dried: Vitamin D (D<sub>2</sub> + D<sub>3</sub>): 3.9 μg (154 IU) | ||
<!--T:15--> | |||
'''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 μg/g dry matter respectively. They also contain vitamin D<sub>3</sub> (range 0.67 to 2.04 μg/g) although provitamin D<sub>3</sub> could not be detected. Vitamin D levels correlate positively with UV irradiation. | * ''[[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 μg/g dry matter respectively. They also contain vitamin D<sub>3</sub> (range 0.67 to 2.04 μg/g) although provitamin D<sub>3</sub> could not be detected. Vitamin D levels correlate positively with UV irradiation. | ||
<!--T:16--> | |||
'''Plantae''' | '''Plantae''' | ||
* [[Alfalfa]] (''Medicago sativa'' subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D<sub>2</sub>, 0.1 μg (4 IU) vitamin D<sub>3</sub> | * [[Alfalfa]] (''Medicago sativa'' subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D<sub>2</sub>, 0.1 μg (4 IU) vitamin D<sub>3</sub> | ||
<!--T:17--> | |||
=== Biosynthesis === | === Biosynthesis === | ||
<!-- Principle --> | <!-- Principle --> | ||
The vitamin D<sub>2</sub> content in mushrooms and ''C. arbuscula'' increase with exposure to ultraviolet light. [[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. | The vitamin D<sub>2</sub> content in mushrooms and ''C. arbuscula'' increase with exposure to ultraviolet light. [[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. | ||
<!--T:18--> | |||
<!-- 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. The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms. 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. | 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. The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms. 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. | ||
<!--T:19--> | |||
<!-- 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. Vitamin D<sub>2</sub> from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D. | 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. Vitamin D<sub>2</sub> from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D. | ||
<!--T:20--> | |||
==Names== | ==Names== | ||
Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol. However, currently, Viosterol is also the brand name for [[cholecalciferol]] (vitamin D<sub>3</sub>) in some countries. | Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol. However, currently, Viosterol is also the brand name for [[cholecalciferol]] (vitamin D<sub>3</sub>) in some countries. | ||
<!--T:21--> | |||
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). | ||
<!--T:22--> | |||
== External links == | == External links == | ||
* [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] | ||
<!--T:23--> | |||
{{Vitamins}} | {{Vitamins}} | ||
{{Sterols}} | {{Sterols}} | ||
| Line 146: | Line 169: | ||
{{Portal bar|Medicine}} | {{Portal bar|Medicine}} | ||
<!--T:24--> | |||
{{二次利用|date=22 March 2024}} | {{二次利用|date=22 March 2024}} | ||
[[Category:Cyclohexanols]] | [[Category:Cyclohexanols]] | ||
Latest revision as of 22:35, 10 April 2024
 | |
 | |
| Clinical data | |
|---|---|
| Trade names | Drisdol, Calcidol, others |
| Other names | viosterol |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a616042 |
| License data | |
| Routes of administration | By mouth, intramuscular |
| ATC code | |
| Legal status | |
| Legal status | |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| 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) |
| |
| |
Ergocalciferol, also known as vitamin D2 and nonspecifically calciferol, is a type of vitamin D found in food and used as a dietary supplement. As a supplement it is used to prevent and treat vitamin D deficiency. This includes vitamin D deficiency due to poor absorption by the intestines or liver disease. It may also be used for low blood calcium due to hypoparathyroidism. It is used by mouth or injection into a muscle.
Excessive doses can result in increased urine production, high blood pressure, kidney stones, kidney failure, weakness, and constipation. If high doses are taken for a long period of time, tissue calcification may occur. Normal doses are safe in pregnancy. It works by increasing the amount of calcium absorbed by the intestines and kidneys. Food in which it is found include some mushrooms.
Ergocalciferol was first described in 1936. Ergocalciferol is available as a generic medication and over the counter. Certain foods such as breakfast cereal and margarine have ergocalciferol added to them in some countries.
Use
Ergocalciferol may be used as a vitamin D supplement, whereas cholecalciferol (vitamin D3) is produced naturally by the skin when exposed to ultraviolet light. 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 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. A meta-analysis concluded that evidence usually favors cholecalciferol in raising vitamin D levels in blood, although it stated more research is needed.
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.
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), 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. Unlike cholecalciferol, 25-hydroxylation is not performed by CYP27A1 for ergocalciferol.
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. Ergocalciferol itself and metabolites can be deactivated by 24-hydroxylation.
Sources
Fungus, from USDA nutrient database (per 100g), D2 + D3:
- 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.
Plantae
- Alfalfa (Medicago sativa subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D2, 0.1 μg (4 IU) vitamin D3
Biosynthesis
The vitamin D2 content in mushrooms and C. arbuscula increase with exposure to ultraviolet light. 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.
When fresh mushrooms or dried powders are purposely exposed to ultraviolet light, vitamin D2 levels can be concentrated to much higher levels. The irradiation procedure does not cause significant discoloration, or whitening, of mushrooms. 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.
Button mushrooms with enhanced vitamin D2 content produced this way functions similarly to a vitamin D2 supplement; both effectively improves vitamin D status. Vitamin D2 from UV-irradiated yeast baked into bread or mushrooms is bioavailable and increases blood levels of 25(OH)D.
Names
Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol. However, currently, Viosterol is also the brand name for cholecalciferol (vitamin D3) in some countries.
Ergocalciferol is manufactured and marketed under various names, including Deltalin (Eli Lilly and Company), Drisdol (Sanofi-Synthelabo), and Calcidol (Patrin Pharma).
External links
 | この記事は、クリエイティブ・コモンズ・表示・継承ライセンス3.0のもとで公表されたウィキペディアの項目Ergocalciferol(22 March 2024編集記事参照)を素材として二次利用しています。 Item:Q21903  |