Formebolone

Formebolone
Clinical data
Trade names	Esiclene, Hubernol, Metanor
Other names	Formyldienolone; 2-Formyl-11α-hydroxy-17α-methyl-δ1-testosterone
Routes of; administration	Oral
Legal status
Legal status	BR:Class C5(Anabolic steroids);
Identifiers
	IUPAC name 8S,9S,10R,11R,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde;
CAS Number	2454-11-7;
PubChemCID	17150;
ChemSpider	16234;
UNII	Z2MMV08KUQ;
ChEMBL	ChEMBL2107419;
CompTox Dashboard(EPA)	DTXSID60179286;
ECHA InfoCard	100.017.749
Chemical and physical data
Formula	C21H28O4
Molar mass	344.451g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@]1(CC[C@@H]2[C@@]1(C[C@H]([C@H]3[C@H]2CCC4=CC(=O)C(=C[C@]34C)C=O)O)C)O;
	InChI InChI=1S/C21H28O4/c1-19-9-12(11-22)16(23)8-13(19)4-5-14-15-6-7-21(3,25)20(15,2)10-17(24)18(14)19/h8-9,11,14-15,17-18,24-25H,4-7,10H2,1-3H3/t14-,15-,17+,18+,19-,20-,21-/m0/s1; Key:AMVODTGMYSRMNP-GNIMZFFESA-N;
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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 active anabolic-androgenic steroid(AAS) described as ananticatabolicandanabolic drugthat 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 theprecursors deoxycortisolanddeoxycorticosterone,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

^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–.ISBN 978-3-88763-075-1.
^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies.Springer. pp. 577–.ISBN 978-1-4757-2085-3.
^Morton IK, Hall JM (31 October 1999).Concise Dictionary of Pharmacological Agents: Properties and Synonyms.Springer Science & Business Media. pp. 125–.ISBN 978-0-7514-0499-9.
^^a ^bGelli 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.PMID 799985.S2CID 86157607.
^Cerutti S, Forlani A, Galimberti E (1976). "Anticatabolic action of formebolone in the castrated rat treated with dexamethasone".Arzneimittel-Forschung.26(9): 1673–1677.PMID 1036699.
^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.PMID 6523544.S2CID 54289377.
^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.PMID 6970661.
^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.PMID 7895695.
^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.PMID 8698448.
^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.PMID 22273746.

[1] 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.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory.Taylor & Francis. January 2000. pp. 471–.ISBN 978-3-88763-075-1.

[Elks2014-3] Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies.Springer. pp. 577–.ISBN 978-1-4757-2085-3.

[MortonHall1999-4] Morton IK, Hall JM (31 October 1999).Concise Dictionary of Pharmacological Agents: Properties and Synonyms.Springer Science & Business Media. pp. 125–.ISBN 978-0-7514-0499-9.

[pmid799985-5] Gelli 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.PMID 799985.S2CID 86157607.

[pmid1036699-6] Cerutti S, Forlani A, Galimberti E (1976). "Anticatabolic action of formebolone in the castrated rat treated with dexamethasone".Arzneimittel-Forschung.26(9): 1673–1677.PMID 1036699.

[pmid6523544-7] 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.PMID 6523544.S2CID 54289377.

[pmid6970661-8] 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.PMID 6970661.

[pmid7895695-9] 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.PMID 7895695.

[pmid8698448-10] 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.PMID 8698448.

[pmid22273746-11] 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.PMID 22273746.

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