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{{Short description|Chemical compound}}
{{chembox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
⚫ | verifiedrevid = 444480217
⚫ | 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
⚫ | image = Roxibolone.png
| width = 250

<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| legal_US =
| legal_status =
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
⚫ | CAS_number = 60023-92-9
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
⚫ | PubChem = 68795
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 62035
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3R7NLP419C | UNII = 3R7NLP419C
| KEGG =
⚫ | verifiedrevid = 437139933
| ChEBI =
⚫ |ImageFile=Roxibolone.png
| ChEMBL =
|ImageSize=200px

⚫ |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
<!--Chemical data-->
⚫ |OtherNames=11β,17β-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid
| C=21 | H=28 | O=5
|Section1={{Chembox Identifiers
⚫ | SMILES = C1(CC21(C(32CCC4=CC(=O)C(=C34C)C(=O)O)O)C)O
⚫ | CASNo=60023-92-9
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | PubChem=68795
| 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
⚫ | SMILES=C1(CC21(C(32CCC4=CC(=O)C(=C34C)C(=O)O)O)C)O
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
}}
| StdInChIKey = JOFBZBDWOWPUMO-QARKFJNLSA-N
|Section2={{Chembox Properties
⚫ | synonyms = BR-906; 11β,17β-Dihydroxy-17α-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid
| Formula=C<sub>21</sub>H<sub>28</sub>O<sub>5</sub>
| MolarMass=360.44 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
}}
}} }}


'''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" />
'''Roxibolone''' is an ].

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>


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" />


==References==
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{{Reflist|2}}


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{{Anabolic steroids}}
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Latest revision as of 23:48, 22 January 2023

Chemical compound Pharmaceutical compound
Roxibolone
Clinical data
Other namesBR-906; 11β,17β-Dihydroxy-17α-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H28O5
Molar mass360.450 g·mol
3D model (JSmol)
SMILES
  • C1(CC21(C(32CCC4=CC(=O)C(=C34C)C(=O)O)O)C)O
InChI
  • InChI=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
  • Key:JOFBZBDWOWPUMO-QARKFJNLSA-N
  (what is this?)  (verify)

Roxibolone (INN) (developmental code name BR-906), also known as 11β,17β-dihydroxy-17α-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid, is a steroidal antiglucocorticoid described as an anticholesterolemic (cholesterol-lowering) and anabolic drug which was never marketed. Roxibolone is closely related to formebolone, which shows antiglucocorticoid activity similarly and, with the exception of having a carboxaldehyde group at the C2 position instead of a carboxylic acid group, roxibolone is structurally almost identical to. The 2-decyl ester of roxibolone, decylroxibolone (developmental code name BR-917), is a long-acting prodrug of roxibolone with similar activity.

In rats, roxibolone counteracts the catabolic effects (control of nitrogen balance) and increased alkaline phosphatase levels induced by the potent glucocorticoid dexamethasone phosphate. It does not bind to the glucocorticoid receptor however, and its antiglucocorticoid activity may instead be mediated by enzyme inhibition. In accordance, 11α- and 11β-hydroxyprogesterone are known to be potent inhibitors of 11β-hydroxysteroid dehydrogenase (11β-HSD), which is responsible for the biosynthesis of the potent endogenous glucocorticoids cortisol and corticosterone (from the precursors deoxycortisol and deoxycorticosterone, respectively). As roxibolone is 11β-hydroxylated similarly, it may act in a likewise fashion. However, formebolone was found to be a very weak inhibitor of 11β-HSD type 2, although this specific isoenzyme is responsible for the inactivation of glucocorticoids rather than their production.

Unlike formebolone, which is additionally an anabolic-androgenic steroid (AAS), roxibolone is devoid of affinity for the androgen receptor and possesses no androgenic or myotrophic activity in animal assays. For this reason, it has been said that roxibolone may be much better tolerated in comparison.

References

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 1082. ISBN 978-1-4757-2085-3.
  2. ^ Felippone F, Resnati G, Scolastico C, Tronconi G (1984). "Synthesis of 2-carboxy-11 beta, 17 beta-dihydroxy-17-methyl-1, 4-androstadien-3-one and related compounds". Steroids. 43 (3): 271–82. doi:10.1016/0039-128x(84)90045-x. PMID 6523544. S2CID 54289377.
  3. Dahlberg E, Snochowski M, Gustafsson JA (1981). "Regulation of the androgen and glucocorticoid receptors in rat and mouse skeletal muscle cytosol". Endocrinology. 108 (4): 1431–40. doi:10.1210/endo-108-4-1431. PMID 6970661.
  4. Souness GW, Latif SA, Laurenzo JL, Morris DJ (1995). "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". Endocrinology. 136 (4): 1809–12. doi:10.1210/endo.136.4.7895695. PMID 7895695.
  5. Souness GW, Morris DJ (1996). "11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase, possess hypertensinogenic activity in the rat". Hypertension. 27 (3 Pt 1): 421–5. doi:10.1161/01.hyp.27.3.421. PMID 8698448.
  6. Fürstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A (2012). "The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation". Toxicol. Sci. 126 (2): 353–61. doi:10.1093/toxsci/kfs022. PMID 22273746.


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