| Record Information |
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| Version | 2.0 |
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| Created at | 2024-09-10 19:03:39 UTC |
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| Updated at | 2024-09-10 19:03:39 UTC |
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| NP-MRD ID | NP0334593 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Formebolone |
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| Description | Formebolone, also known as esiclene or formyldienolone, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Formebolone is an extremely weak basic (essentially neutral) compound (based on its pKa). Indeed, 11α- and 11β-hydroxyprogesterone (formebolone and roxibolone being 11α- and 11β-hydroxylated (respectively) similarly) 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). Formebolone counteracts the catabolic effects (control of nitrogen balance) of potent glucocorticoids like dexamethasone phosphate. As an AAS, it shows some anabolic activity, though it is inferior to testosterone in terms of potency, but is said to have virtually no androgenic activity. However, formebolone was found to be a very weak inhibitor of 11β-HSD type 2 (IC50 > 10 μM), although this specific isoenzyme of 11β-HSD is responsible for the inactivation of glucocorticoids rather than their production. A close analogue, roxibolone (and its long-acting ester variant decylroxibolone), shows similar antiglucocorticoid activity to formebolone but, in contrast, is devoid of activity as an AAS.Roxibolone has been found not to bind to the glucocorticoid receptor, and it has been suggested that the antiglucocorticoid activity of roxibolone and formebolone may instead be mediated by modulation of enzymatic processes. Formebolone (INN, BAN) (brand names Esiclene, Hubernol, Metanor), also known (confusingly) as formyldienolone, as well as 2-formyl-11α-hydroxy-17α-methyl-δ1-testosterone, is an orally active anabolic-androgenic steroid (AAS) described as an anticatabolic and anabolic drug that is or has been marketed in Spain and Italy. |
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| Structure | [H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C 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 |
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| Synonyms | | Value | Source |
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| (11a,17b)-11,17-Dihydroxy-17-methyl-3-oxo-androsta-1,4-diene-2-carboxaldehyde | HMDB | | 11a,17b-Dihydroxy-17-methyl-3-oxo-androsta-1,4-diene-2-carboxaldehyde | HMDB | | 11a,17b-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehyde | HMDB | | 2-Formyl-11a-hydroxy-D1-methyltestosterone | HMDB | | 2-Formyl-17a-methylandrosta-1,4-dien-11a,17b-diol-3-one | HMDB | | 2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-dihydroxy-3-one | HMDB | | 2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-diol-3-one | HMDB | | Esiclene | HMDB | | Formyldienolone | HMDB | | 2-Formyl-17 alpha-methylandrosta-1,4-diene-11 alpha,17 beta-diol-3-one | HMDB | | Formyldienolone, (11 beta,17beta)-isomer | HMDB | | Formildienolone | HMDB | | Formebolone | MeSH |
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| Chemical Formula | C21H28O4 |
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| Average Mass | 344.4446 Da |
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| Monoisotopic Mass | 344.19876 Da |
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| IUPAC Name | (1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-4-carbaldehyde |
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| Traditional Name | formebolone |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C |
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| InChI Identifier | 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 |
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| InChI Key | AMVODTGMYSRMNP-GNIMZFFESA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | Not Available |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Androstane steroids |
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| Direct Parent | Androgens and derivatives |
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| Alternative Parents | |
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| Substituents | - Androgen-skeleton
- 3-oxo-delta-1,4-steroid
- 3-oxosteroid
- Hydroxysteroid
- Oxosteroid
- 11-alpha-hydroxysteroid
- 11-hydroxysteroid
- 17-hydroxysteroid
- Delta-1,4-steroid
- Cyclic alcohol
- Tertiary alcohol
- Secondary alcohol
- Ketone
- Cyclic ketone
- Aldehyde
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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