| Revision as of 18:33, 12 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validati← Previous edit |
Latest revision as of 23:48, 22 January 2023 edit undoEntranced98 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers173,140 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper |
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{{Short description|Chemical compound}} |
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{{chembox |
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{{Drugbox |
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| verifiedrevid = 444480217 |
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| IUPAC_name = (8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopentaphenanthrene-2-carboxylic acid |
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| image = Roxibolone.png |
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| width = 250 |
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<!--Clinical data--> |
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| tradename = |
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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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<!-- Identifiers --> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 60023-92-9 |
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| PubChem = 68795 |
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| DrugBank_Ref = |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 62035 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 3R7NLP419C |
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| UNII = 3R7NLP419C |
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| KEGG = |
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| verifiedrevid = 437139933 |
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| ChEBI = |
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|ImageFile=Roxibolone.png |
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| ChEMBL = |
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|ImageSize=200px |
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|IUPACName=(8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopentaphenanthrene-2-carboxylic acid |
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<!--Chemical data--> |
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|OtherNames=11β,17β-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid |
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| C=21 | H=28 | O=5 |
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|Section1={{Chembox Identifiers |
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| SMILES = C1(CC21(C(32CCC4=CC(=O)C(=C34C)C(=O)O)O)C)O |
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| CASNo=60023-92-9 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| PubChem=68795 |
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| StdInChI = 1S/C21H28O5/c1-19-9-13(18(24)25)15(22)8-11(19)4-5-12-14-6-7-21(3,26)20(14,2)10-16(23)17(12)19/h8-9,12,14,16-17,23,26H,4-7,10H2,1-3H3,(H,24,25)/t12-,14-,16-,17+,19-,20-,21-/m0/s1 |
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| SMILES=C1(CC21(C(32CCC4=CC(=O)C(=C34C)C(=O)O)O)C)O |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JOFBZBDWOWPUMO-QARKFJNLSA-N |
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|Section2={{Chembox Properties |
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| synonyms = BR-906; 11β,17β-Dihydroxy-17α-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid |
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| Formula=C<sub>21</sub>H<sub>28</sub>O<sub>5</sub> |
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| MolarMass=360.44 g/mol |
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|Section3={{Chembox Hazards |
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'''Roxibolone''' (]) (developmental code name '''BR-906'''), also known as '''11β,17β-dihydroxy-17α-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid''', is a ]al ] described as an ] (]-lowering) and ] ] which was never marketed.<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA586|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=1082}}</ref><ref name="pmid6523544">{{cite journal |vauthors=Felippone F, Resnati G, Scolastico C, Tronconi G |title=Synthesis of 2-carboxy-11 beta, 17 beta-dihydroxy-17-methyl-1, 4-androstadien-3-one and related compounds |journal=Steroids |volume=43 |issue=3 |pages=271–82 |year=1984 |pmid=6523544 |doi= 10.1016/0039-128x(84)90045-x|s2cid=54289377 }}</ref> Roxibolone is closely related to ], which shows antiglucocorticoid activity similarly and, with the exception of having a ] ] at the C2 position instead of a ] group, roxibolone is structurally almost identical to.<ref name="pmid6523544" /> The 2-] ] of roxibolone, ] (developmental code name BR-917), is a long-acting ] of roxibolone with similar activity.<ref name="Elks2014" /><ref name="pmid6523544" /> |
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'''Roxibolone''' is an ]. |
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In rats, roxibolone counteracts the ] effects (control of ]) and increased ] levels induced by the potent ] ].<ref name="pmid6523544" /> It does not bind to the ] however, and its antiglucocorticoid activity may instead be mediated by ] ].<ref name="pmid6970661">{{cite journal |vauthors=Dahlberg E, Snochowski M, Gustafsson JA |title=Regulation of the androgen and glucocorticoid receptors in rat and mouse skeletal muscle cytosol |journal=Endocrinology |volume=108 |issue=4 |pages=1431–40 |year=1981 |pmid=6970661 |doi=10.1210/endo-108-4-1431 }}</ref> In accordance, ] and ] are known to be potent ]s of ] (11β-HSD), which is responsible for the ] of the potent ] glucocorticoids ] and ] (from the ]s ] and ], respectively).<ref name="pmid7895695">{{cite journal | vauthors = Souness GW, Latif SA, Laurenzo JL, Morris DJ | title = 11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase (isoforms 1 and 2), confer marked mineralocorticoid activity on corticosterone in the ADX rat | journal = Endocrinology | volume = 136 | issue = 4 | pages = 1809–12 | year = 1995 | pmid = 7895695 | doi = 10.1210/endo.136.4.7895695 }}</ref><ref name="pmid8698448">{{cite journal | vauthors = Souness GW, Morris DJ | title = 11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase, possess hypertensinogenic activity in the rat | journal = Hypertension | volume = 27 | issue = 3 Pt 1 | pages = 421–5 | year = 1996 | pmid = 8698448 | doi = 10.1161/01.hyp.27.3.421}}</ref> As roxibolone is 11β-hydroxylated similarly, it may act in a likewise fashion. However, formebolone was found to be a very weak inhibitor of ], although this specific ] is responsible for the inactivation of glucocorticoids rather than their production.<ref name="pmid22273746">{{cite journal |vauthors=Fürstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A |title=The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation |journal=Toxicol. Sci. |volume=126 |issue=2 |pages=353–61 |year=2012 |pmid=22273746 |doi=10.1093/toxsci/kfs022 |doi-access=free }}</ref> |
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Unlike formebolone, which is additionally an ] (AAS), roxibolone is devoid of ] for the ] and possesses no ]ic or ] activity in ] ]s.<ref name="pmid6523544" /> For this reason, it has been said that roxibolone may be much better tolerated in comparison.<ref name="pmid6523544" /> |
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==References== |
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{{Reflist|2}} |
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