Vitamin D5 - Revision history

Fire: Marked this version for translation

2024-04-10T12:36:40Z

Marked this version for translation

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	{{short description\|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D<sub>5</sub>}}		{{short description\|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D<sub>5</sub>}}
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	[[structural analog\|Analogs]] of [[calcitriol]], a form of vitamin D<sub>3</sub>, have been proposed for use as antitumor agents. Studies on vitamin D<sub>3</sub> have shown inhibition of cell proliferation in [[prostate cancer]], but high doses of vitamin D<sub>3</sub> result in [[Hypercalcaemia\|hypercalcemia]]. The effects of vitamin D<sub>5</sub> on prostate cancer have also been studied, and unlike vitamin D<sub>3</sub>, vitamin D<sub>5</sub> does not cause [[Hypercalcaemia\|hypercalcemia]] while inhibiting tumor cell proliferation. The most researched analogue of vitamin D<sub>5</sub> as an antitumor agent is 1α-hydroxyvitamin D<sub>5.</sub>		[[structural analog\|Analogs]] of [[calcitriol]], a form of vitamin D<sub>3</sub>, have been proposed for use as antitumor agents. Studies on vitamin D<sub>3</sub> have shown inhibition of cell proliferation in [[prostate cancer]], but high doses of vitamin D<sub>3</sub> result in [[Hypercalcaemia\|hypercalcemia]]. The effects of vitamin D<sub>5</sub> on prostate cancer have also been studied, and unlike vitamin D<sub>3</sub>, vitamin D<sub>5</sub> does not cause [[Hypercalcaemia\|hypercalcemia]] while inhibiting tumor cell proliferation. The most researched analogue of vitamin D<sub>5</sub> as an antitumor agent is 1α-hydroxyvitamin D<sub>5.</sub>

	=== 1α-Hydroxyvitamin D<sub>5</sub> ===		=== 1α-Hydroxyvitamin D<sub>5</sub> === <!--T:2-->

			<!--T:3-->
	1α-Hydroxyvitamin D<sub>5</sub> is a chemical derivative of vitamin D<sub>5</sub>. The motive to study 1α-hydroxyvitamin D<sub>5</sub> as a potential pharmaceutical drug stemmed from the tendency of calcitriol, a natural metabolite produced in the [[kidney]], to cause toxic hypercalcemia in patients when dosed at concentrations needed to interrupt [[prostate cancer]] cells' cycle and stimulate [[apoptosis]]. And while supplementation with [[dexamethasone]] decreases hypercalcemia, bypassing it with an equally effective tumor suppressant would reduce patient cost and stress. Thus, the therapeutic effects of 1α-Hydroxyvitamin D<sub>5</sub> as a potential antitumor agent without the side effects of calcitriol became a topic of study.		1α-Hydroxyvitamin D<sub>5</sub> is a chemical derivative of vitamin D<sub>5</sub>. The motive to study 1α-hydroxyvitamin D<sub>5</sub> as a potential pharmaceutical drug stemmed from the tendency of calcitriol, a natural metabolite produced in the [[kidney]], to cause toxic hypercalcemia in patients when dosed at concentrations needed to interrupt [[prostate cancer]] cells' cycle and stimulate [[apoptosis]]. And while supplementation with [[dexamethasone]] decreases hypercalcemia, bypassing it with an equally effective tumor suppressant would reduce patient cost and stress. Thus, the therapeutic effects of 1α-Hydroxyvitamin D<sub>5</sub> as a potential antitumor agent without the side effects of calcitriol became a topic of study.

			<!--T:4-->
	1α-Hydroxyvitamin D<sub>5</sub> was first synthesized in 1997 by researchers in the Department of Chemistry at the [[University of Chicago]], under Robert M. Moriarty and Dragos Albinescu. By 2005, the group had revised its synthesis method for a more streamlined, higher yield-producing route. It involved the photochemical conversion of precursor [[7-Dehydrositosterol\|7-dehydrositosteryl]] acetate to contain a conjugated triene system, a hallmark of this analog, followed by [[hydroxylation]], [[photoisomerization]], and [[Protecting group\|deprotection]] steps. Their overall yield was 48%.		1α-Hydroxyvitamin D<sub>5</sub> was first synthesized in 1997 by researchers in the Department of Chemistry at the [[University of Chicago]], under Robert M. Moriarty and Dragos Albinescu. By 2005, the group had revised its synthesis method for a more streamlined, higher yield-producing route. It involved the photochemical conversion of precursor [[7-Dehydrositosterol\|7-dehydrositosteryl]] acetate to contain a conjugated triene system, a hallmark of this analog, followed by [[hydroxylation]], [[photoisomerization]], and [[Protecting group\|deprotection]] steps. Their overall yield was 48%.

			<!--T:5-->
	== See also ==		== See also ==
	* [[7-Dehydrositosterol]]		* [[7-Dehydrositosterol]]
	* [[Calcipotriene]]		* [[Calcipotriene]]

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	{{Vitamin}}		{{Vitamin}}

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	{{二次利用\|date=11 December 2023}}		{{二次利用\|date=11 December 2023}}
	[[Category:Vitamin D]]		[[Category:Vitamin D]]
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Fire at 12:36, 10 April 2024

2024-04-10T12:36:29Z

← Older revision		Revision as of 21:36, 10 April 2024
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			<languages />
			<translate>
	{{short description\|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D<sub>5</sub>}}		{{short description\|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D<sub>5</sub>}}
	{{chembox		{{chembox
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	{{二次利用\|date=11 December 2023}}		{{二次利用\|date=11 December 2023}}
	[[Category:Vitamin D]]		[[Category:Vitamin D]]
			</translate>

Fire at 12:19, 10 April 2024

2024-04-10T12:19:33Z

← Older revision		Revision as of 21:19, 10 April 2024
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	{{short description\|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D<sub>5</sub>~~}}{{distinguish\|decamethylcyclopentasiloxane~~}}		{{short description\|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D<sub>5</sub>}}
	{{chembox		{{chembox
	\| Verifiedfields = changed		\| Verifiedfields = changed

Fire: Created page with "{{short description|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D₅}}{{distinguish|decamethylcyclopentasiloxane}} {{chembox | Verifiedfields = changed | verifiedrevid = 470631138 | Name=Vitamin D₅ | ImageFile=Vitamin D5 structure.svg | ImageSize= | IUPACName=(1''S'',3''Z'')-3-[(2''E'')-2-[(1''R'',3a''S'',7a''R'')-1-[(1''R'',4''S'')-4-ethyl-1,5-dimethylhexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1''H''-inden-4-ylidene]ethylidene]-4-methylene-1-cyclohexano..."

2024-04-10T12:19:11Z

Created page with "{{short description|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D5}}{{distinguish|decamethylcyclopentasiloxane}} {{chembox | Verifiedfields = changed | verifiedrevid = 470631138 | Name=Vitamin D5 | ImageFile=Vitamin D5 structure.svg | ImageSize= | IUPACName=(1''S'',3''Z'')-3-[(2''E'')-2-[(1''R'',3a''S'',7a''R'')-1-[(1''R'',4''S'')-4-ethyl-1,5-dimethylhexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1''H''-inden-4-ylidene]ethylidene]-4-methylene-1-cyclohexano..."

New page

{{short description|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D5}}{{distinguish|decamethylcyclopentasiloxane}}
{{chembox
| Verifiedfields = changed
| verifiedrevid = 470631138
| Name=Vitamin D5
| ImageFile=Vitamin D5 structure.svg
| ImageSize=
| IUPACName=(1''S'',3''Z'')-3-[(2''E'')-2-[(1''R'',3a''S'',7a''R'')-1-[(1''R'',4''S'')-4-ethyl-1,5-dimethylhexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1''H''-inden-4-ylidene]ethylidene]-4-methylene-1-cyclohexanol
| OtherNames= Sitocalciferol (5''Z'',7''E'')-(3''S'')-9,10-secoporiferasta-5,7,10(19)-trien-3-ol
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7826639
| ChEBI = 33279
| InChI = 1/C29H48O/c1-7-23(20(2)3)12-10-22(5)27-16-17-28-24(9-8-18-29(27,28)6)13-14-25-19-26(30)15-11-21(25)4/h13-14,20,22-23,26-28,30H,4,7-12,15-19H2,1-3,5-6H3/b24-13+,25-14-/t22-,23+,26+,27-,28+,29-/m1/s1
| InChIKey = RMDJVOZETBHEAR-GHTRHTQZBN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C29H48O/c1-7-23(20(2)3)12-10-22(5)27-16-17-28-24(9-8-18-29(27,28)6)13-14-25-19-26(30)15-11-21(25)4/h13-14,20,22-23,26-28,30H,4,7-12,15-19H2,1-3,5-6H3/b24-13+,25-14-/t22-,23+,26+,27-,28+,29-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RMDJVOZETBHEAR-GHTRHTQZSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=71761-06-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0W2I161LCL
| PubChem=9547700
| SMILES = O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CC[C@H](CC)C(C)C)C
}}
|Section2={{Chembox Properties
| C=29 | H=48 | O=1
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
'''Vitamin D5''' ('''sitocalciferol''') is a form of [[vitamin D]].
== Research ==
[[structural analog|Analogs]] of [[calcitriol]], a form of vitamin D3, have been proposed for use as antitumor agents. Studies on vitamin D3 have shown inhibition of cell proliferation in [[prostate cancer]], but high doses of vitamin D3 result in [[Hypercalcaemia|hypercalcemia]]. The effects of vitamin D5 on prostate cancer have also been studied, and unlike vitamin D3, vitamin D5 does not cause [[Hypercalcaemia|hypercalcemia]] while inhibiting tumor cell proliferation. The most researched analogue of vitamin D5 as an antitumor agent is 1α-hydroxyvitamin D5.

=== 1α-Hydroxyvitamin D5 ===

1α-Hydroxyvitamin D5 is a chemical derivative of vitamin D5. The motive to study 1α-hydroxyvitamin D5 as a potential pharmaceutical drug stemmed from the tendency of calcitriol, a natural metabolite produced in the [[kidney]], to cause toxic hypercalcemia in patients when dosed at concentrations needed to interrupt [[prostate cancer]] cells' cycle and stimulate [[apoptosis]]. And while supplementation with [[dexamethasone]] decreases hypercalcemia, bypassing it with an equally effective tumor suppressant would reduce patient cost and stress. Thus, the therapeutic effects of 1α-Hydroxyvitamin D5 as a potential antitumor agent without the side effects of calcitriol became a topic of study.

1α-Hydroxyvitamin D5 was first synthesized in 1997 by researchers in the Department of Chemistry at the [[University of Chicago]], under Robert M. Moriarty and Dragos Albinescu. By 2005, the group had revised its synthesis method for a more streamlined, higher yield-producing route. It involved the photochemical conversion of precursor [[7-Dehydrositosterol|7-dehydrositosteryl]] acetate to contain a conjugated triene system, a hallmark of this analog, followed by [[hydroxylation]], [[photoisomerization]], and [[Protecting group|deprotection]] steps. Their overall yield was 48%.

== See also ==
* [[7-Dehydrositosterol]]
* [[Calcipotriene]]

{{Vitamin}}

{{二次利用|date=11 December 2023}}
[[Category:Vitamin D]]