| Revision as of 18:16, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443352466 of page 4-Hydroxytestosterone for the Chem/Drugbox validation project (updated: 'CASNo'). |
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{{Short description|Chemical compound}} |
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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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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 399321383 |
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| Watchedfields = |
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| ImageFile = 4-hydroxytestosterone.png |
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| verifiedrevid = 477222394 |
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| ImageSize = 200px |
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| IUPACName = <small>4,17-Dihydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopentaphenanthren-3-one</small> |
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| IUPAC_name = 4,17-Dihydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopentaphenanthren-3-one |
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| image = 4-Hydroxytestosterone.svg |
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| OtherNames = 4,17β-Dihydroxy-4-androstene-3-one; (17β)-4,17-dihydroxyandrost-4-en-3-one |
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| alt = Skeletal formula of 4-hydroxytestosterone |
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| Section1 = {{Chembox Identifiers |
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| width = 225px |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| image2 = 4-Hydroxytestosterone-3D-balls.png |
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| alt2 = Ball-and-stick model of the 4-hydroxytestosterone molecule |
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| width2 = 225px |
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<!--Clinical data--> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| metabolism = |
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| excretion = |
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<!-- Identifiers --> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = 2141-17-5 |
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| CAS_supplemental = |
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| ATC_supplemental = |
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| PubChem = 160615 |
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| IUPHAR_ligand = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01485 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 141138 |
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| ChemSpiderID = 141138 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| InChI = 1/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1 |
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| UNII = 912GOZ167T |
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| InChIKey = BQOIJSIMMIDHMO-FBPKJDBXBD |
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| KEGG = |
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| synonyms = 4,17β-Dihydroxyandrost-4-en-3-one; Androst-4-ene-4,17β-diol-3-one; Desmethylenestebol |
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<!--Chemical data--> |
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| C=19 | H=28 | O=3 |
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| SMILES = O=C4C(\O)=C2/(1CC3((O)CC31CC2)C)(C)CC4 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1 |
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| StdInChI = 1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BQOIJSIMMIDHMO-FBPKJDBXSA-N |
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| StdInChIKey = BQOIJSIMMIDHMO-FBPKJDBXSA-N |
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| CASNo = <!-- blanked - oldvalue: 2141-17-5 --> |
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| PubChem = 160615 |
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| DrugBank = DB01485 |
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| SMILES = O=C4C(\O)=C2/(1CC3((O)CC31CC2)C)(C)CC4 |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>19</sub>H<sub>28</sub>O<sub>3</sub> |
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| MolarMass = 304.42 g/mol |
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| Section3 = {{Chembox Hazards |
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}} |
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}} |
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'''4-Hydroxytestosterone''' ('''4-OHT'''), also known as '''4,17β-dihydroxyandrost-4-en-3-one''', is a ] ] (AAS) and a ] of ] that was never marketed. It was first patented by ] in 1955<ref>{{cite patent | country = US | number = 2762818 | inventor = Levy H, Mednick ML | assign1 = GD Searle | title = 4-Hydroxytestosterone and esters | postscript = . | pridate = 26 May 1955 | gdate = 11 September 1956 }}</ref> and is ] with a hydroxy group at the four position. 4-OHT has moderate ], mild ], and ] properties and is similar to the steroid ] (4-chlorotestosterone).<ref name="Kohler_2007">{{cite journal | vauthors = Kohler M, Parr MK, Opfermann G, Thevis M, Schlörer N, Marner FJ, Schänzer W | title = Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites | journal = Steroids | volume = 72 | issue = 3 | pages = 278–86 | date = March 2007 | pmid = 17207827 | doi = 10.1016/j.steroids.2006.11.018 | s2cid = 34982808 }}</ref> |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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{{Androgen receptor modulators}} |
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{{DEFAULTSORT:Hydroxytestosterone, 4-}} |
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] |
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] |
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] |
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] |
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] |
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{{Steroid-stub}} |
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{{Genito-urinary-drug-stub}} |