| Revision as of 16:02, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{chembox}} taken from revid 402878632 of page Vitamin_D5 for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 01:58, 12 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
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{{short description|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D<sub>5</sub>}}{{distinguish|decamethylcyclopentasiloxane}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 402877141 |
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| verifiedrevid = 470631138 |
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|Name=Vitamin D<sub>5</sub> |
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| Name=Vitamin D<sub>5</sub> |
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|ImageFile=VitaminD5_structure.png |
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| ImageFile=Vitamin D5 structure.svg |
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| ImageClass = skin-invert-image |
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|IUPACName=(1''S'',3''Z'')-3--7a-methyl-2,3,3a,5,6,7-hexahydro-1''H''-inden-4-ylidene]ethylidene]-4-methylene-1-cyclohexanol |
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| IUPACName=(1''S'',3''Z'')-3--7a-methyl-2,3,3a,5,6,7-hexahydro-1''H''-inden-4-ylidene]ethylidene]-4-methylene-1-cyclohexanol |
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| OtherNames= Sitocalciferol <br> (5''Z'',7''E'')-(3''S'')-9,10-secoporiferasta-5,7,10(19)-trien-3-ol |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7826639 |
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| ChemSpiderID = 7826639 |
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| ChEBI = 33279 |
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| 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 |
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| 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 |
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| InChIKey = RMDJVOZETBHEAR-GHTRHTQZBN |
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| InChIKey = RMDJVOZETBHEAR-GHTRHTQZBN |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RMDJVOZETBHEAR-GHTRHTQZSA-N |
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| StdInChIKey = RMDJVOZETBHEAR-GHTRHTQZSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 71761-06-3 --> |
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| CASNo=71761-06-3 |
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| PubChem=9547700 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = O1CC(\C(=C)CC1)=C\C=C2/CCC3(2CC3(C)CC(CC)C(C)C)C |
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| UNII = 0W2I161LCL |
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| PubChem=9547700 |
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| SMILES = O1CC(\C(=C)CC1)=C\C=C2/CCC3(2CC3(C)CC(CC)C(C)C)C |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>29</sub>H<sub>48</sub>O |
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| C=29 | H=48 | O=1 |
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| MolarMass=412.69082 |
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|Section3={{Chembox Hazards |
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'''Vitamin D<sub>5</sub>''' ('''sitocalciferol''') is a form of ]. |
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== Research == |
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] of ], a form of vitamin D<sub>3</sub>, have been proposed for use as antitumor agents.<ref name="pmid90170012">{{cite journal|vauthors=Mehta RG, Moriarty RM, Mehta RR, Penmasta R, Lazzaro G, Constantinou A, Guo L|date=February 1997|title=Prevention of preneoplastic mammary lesion development by a novel vitamin D analogue, 1alpha-hydroxyvitamin D5|url=http://jnci.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=9017001|journal=Journal of the National Cancer Institute|volume=89|issue=3|pages=212–8|doi=10.1093/jnci/89.3.212|pmid=9017001|doi-access=free}}</ref><ref name="pmid160514822">{{cite journal|vauthors=Murillo G, Mehta RG|date=October 2005|title=Chemoprevention of chemically-induced mammary and colon carcinogenesis by 1alpha-hydroxyvitamin D5|journal=The Journal of Steroid Biochemistry and Molecular Biology|volume=97|issue=1–2|pages=129–36|doi=10.1016/j.jsbmb.2005.06.008|pmid=16051482|s2cid=24400116}}</ref><ref name="pmid154542602">{{cite journal|vauthors=Mehta RG|date=October 2004|title=Stage-specific inhibition of mammary carcinogenesis by 1alpha-hydroxyvitamin D5|journal=European Journal of Cancer|volume=40|issue=15|pages=2331–7|doi=10.1016/j.ejca.2004.05.025|pmid=15454260}}</ref> Studies on vitamin D<sub>3</sub> have shown inhibition of cell proliferation in ], but high doses of vitamin D<sub>3</sub> result in ]. 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 ] while inhibiting tumor cell proliferation.<ref>{{cite journal|vauthors=Mooso B, Madhav A, Johnson S, Roy M, Moore ME, Moy C, Loredo GA, Mehta RG, Vaughan AT, Ghosh PM|date=November 2010|title=Androgen Receptor regulation of Vitamin D receptor in response of castration-resistant prostate cancer cells to 1α-Hydroxyvitamin D5 - a calcitriol analog|journal=Genes & Cancer|volume=1|issue=9|pages=927–940|doi=10.1177/1947601910385450|pmc=3089062|pmid=21552398}}</ref> The most researched analogue of vitamin D<sub>5</sub> as an antitumor agent is 1α-hydroxyvitamin D<sub>5.</sub> |
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=== 1α-Hydroxyvitamin D<sub>5</sub> === |
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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 ], to cause toxic hypercalcemia in patients when dosed at concentrations needed to interrupt ] cells' cycle and stimulate ].<ref>{{Cite journal|last1=Beer|first1=Tomasz M.|last2=Myrthue|first2=Anne|date=March 2004|title=Calcitriol in cancer treatment: from the lab to the clinic|journal=Molecular Cancer Therapeutics|volume=3|issue=3|pages=373–381|doi=10.1158/1535-7163.373.3.3 |issn=1535-7163|pmid=15026558|s2cid=7540584 |doi-access=free}}</ref><ref>{{Cite journal|last1=Mooso|first1=Benjamin|last2=Madhav|first2=Anisha|last3=Johnson|first3=Sherra|last4=Roy|first4=Mohana|last5=Moore|first5=Mary E.|last6=Moy|first6=Christabel|last7=Loredo|first7=Grace A.|last8=Mehta|first8=Rajendra G.|last9=Vaughan|first9=Andrew T.M.|last10=Ghosh|first10=Paramita M.|date=September 2010|title=Androgen Receptor Regulation of Vitamin D Receptor in Response of Castration-Resistant Prostate Cancer Cells to 1α-Hydroxyvitamin D5|journal=Genes & Cancer|volume=1|issue=9|pages=927–940|doi=10.1177/1947601910385450|issn=1947-6019|pmc=3089062|pmid=21552398}}</ref> And while supplementation with ] decreases hypercalcemia,<ref>{{Cite journal|last1=Johnson|first1=Candace S.|last2=Muindi|first2=Josephia R.|last3=Hershberger|first3=Pamela A.|last4=Trump|first4=Donald L.|date=July 2006|title=The antitumor efficacy of calcitriol: preclinical studies|journal=Anticancer Research|volume=26|issue=4A|pages=2543–2549|issn=0250-7005|pmid=16886662}}</ref> 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. |
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1α-Hydroxyvitamin D<sub>5</sub> was first synthesized in 1997 by researchers in the Department of Chemistry at the ], 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 ] acetate to contain a conjugated triene system, a hallmark of this analog, followed by ], ], and ] steps. Their overall yield was 48%.<ref>{{Cite journal|last1=Moriarty|first1=Robert M.|last2=Albinescu|first2=Dragos|date=September 2005|title=Synthesis of 1α-Hydroxyvitamin D5Using a Modified Two Wavelength Photolysis for Vitamin D Formation|journal=The Journal of Organic Chemistry|volume=70|issue=19|pages=7624–7628|doi=10.1021/jo050853f|pmid=16149791|issn=0022-3263}}</ref> |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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{{Vitamin}} |
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] |