Formebolone
Clinical data | |
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Trade names | Esiclene, Hubernol, Metanor |
Other names | Formyldienolone; 2-Formyl-11α-hydroxy-17α-methyl-δ1-testosterone |
Routes of administration | Oral |
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CompTox Dashboard(EPA) | |
ECHA InfoCard | 100.017.749 |
Chemical and physical data | |
Formula | C21H28O4 |
Molar mass | 344.451g·mol−1 |
3D model (JSmol) | |
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Formebolone(INN,BAN) (brand namesEsiclene,Hubernol,Metanor), also known asformyldienolone,as well as2-formyl-11α-hydroxy-17α-methyl-δ1-testosterone,is anorally activeanabolic-androgenic steroid(AAS) described as ananticatabolicandanabolicdrugthat is or has been marketed inSpainandItaly.[2][3][4]As an AAS, it shows some anabolic activity, though it is inferior totestosteronein terms ofpotency,but is said to have virtually noandrogenicactivity.[5]Formebolone counteracts thecataboliceffects (control ofnitrogen balance) of potentglucocorticoidslikedexamethasone phosphate.[5][6]A closeanalogue,roxibolone(and its long-actingestervariantdecylroxibolone), shows similar antiglucocorticoid activity to formebolone but, in contrast, is devoid of activity as an AAS.[7]
Roxibolone has been found not to bind to theglucocorticoid receptor,and it has been suggested that the antiglucocorticoid activity of roxibolone and formebolone may instead be mediated bymodulationofenzymaticprocesses.[8]Indeed,11α-and11β-hydroxyprogesterone(formebolone and roxibolone being 11α- and 11β-hydroxylated (respectively) similarly) are known to be potentinhibitorsof11β-hydroxysteroid dehydrogenase(11β-HSD), which is responsible for thebiosynthesisof the potentendogenousglucocorticoidscortisolandcorticosterone(from theprecursorsdeoxycortisolanddeoxycorticosterone,respectively).[9][10]However, formebolone was found to be a very weak inhibitor of11β-HSD type 2(IC50> 10 μM), although this specificisoenzymeof 11β-HSD is responsible for the inactivation of glucocorticoids rather than their production.[11]
References
[edit]- ^Anvisa(2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 2023-04-04).Archivedfrom the original on 2023-08-03.Retrieved2023-08-15.
- ^Index Nominum 2000: International Drug Directory.Taylor & Francis. January 2000. pp. 471–.ISBN978-3-88763-075-1.
- ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies.Springer. pp. 577–.ISBN978-1-4757-2085-3.
- ^Morton IK, Hall JM (31 October 1999).Concise Dictionary of Pharmacological Agents: Properties and Synonyms.Springer Science & Business Media. pp. 125–.ISBN978-0-7514-0499-9.
- ^abGelli D, Vignati E (1976). "Metabolic studies with formebolone (2-formyl-17 ( Alpha )-methyl-androsta-1,4-diene-11 ( Alpha ), 17 (beta)-diol-3-one) in humans".The Journal of International Medical Research.4(2): 96–105.doi:10.1177/030006057600400203.PMID799985.S2CID86157607.
- ^Cerutti S, Forlani A, Galimberti E (1976). "Anticatabolic action of formebolone in the castrated rat treated with dexamethasone".Arzneimittel-Forschung.26(9): 1673–1677.PMID1036699.
- ^Felippone F, Resnati G, Scolastico C, Tronconi G (March 1984). "Synthesis of 2-carboxy-11 beta, 17 beta-dihydroxy-17-methyl-1, 4-androstadien-3-one and related compounds".Steroids.43(3): 271–282.doi:10.1016/0039-128x(84)90045-x.PMID6523544.S2CID54289377.
- ^Dahlberg E, Snochowski M, Gustafsson JA (April 1981). "Regulation of the androgen and glucocorticoid receptors in rat and mouse skeletal muscle cytosol".Endocrinology.108(4): 1431–1440.doi:10.1210/endo-108-4-1431.PMID6970661.
- ^Souness GW, Latif SA, Laurenzo JL, Morris DJ (April 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): 1809–1812.doi:10.1210/endo.136.4.7895695.PMID7895695.
- ^Souness GW, Morris DJ (March 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): 421–425.doi:10.1161/01.hyp.27.3.421.PMID8698448.
- ^Fürstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A (April 2012)."The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation".Toxicological Sciences.126(2): 353–361.doi:10.1093/toxsci/kfs022.PMID22273746.