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| Other names | Ro 7-2340; 6α-Bromo-4-oxa-17α-methyl-5α-dihydrotestosterone; 6α-Bromo-4-oxa-17α-methyl-5α-androstan-17β-ol-3-one |
| Routes of administration | By mouth |
| Drug class | Steroidal antiandrogen |
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| Chemical and physical data | |
| Formula | C19H29BrO3 |
| Molar mass | 385.342 g·mol−1 |
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BOMT, also known by its developmental code nameRo 7-2340 and as6α-bromo-4-oxa-17α-methyl-5α-dihydrotestosterone, is asyntheticsteroidal antiandrogen which was first produced in 1970 and was never marketed for medical use.[1][2][3][4] It is the 6α-brominated, 4-oxygenated, and 17α-methylatedderivative of theandrogendihydrotestosterone (DHT). Along withbenorterone,cyproterone (and its C17αacetateester,cyproterone acetate), andflutamide,[5] BOMT was among the earliest antiandrogens to be developed and extensively studied,[2][3][6][7] although it is less well-documented in comparison to the others.[8] BOMT has been investigated clinically in the treatment ofbenign prostatic hyperplasia, though development for this use did not continue.[9] There was also interest in BOMT for the potential applications ofacne,pattern hair loss, and possiblyprostate cancer, but it was not developed for these indications either.[10]
BOMT is aselectivecompetitive antagonist of theandrogen receptor (AR),[3][4][11][12][13] although it is described as an "only relatively weak competitor."[14] Therelative binding affinity of the drug for the androgen receptor is about 2.7% of that ofmetribolone.[15] BOMT shows noandrogenic,estrogenic, orprogestogenic activity even at high doses, nor anyinhibition of5α-reductase,[16] though it has been reported to possess weakantigonadotropic effects.[3][4][11][12] Due to its selectivity for and competitive inhibition of the AR, BOMT has been described as a pure or "true" antiandrogen, similarly to benorterone, cyproterone, and flutamide.[17] Like other steroidal antiandrogens, BOMT may actually be a weakpartial agonist of the AR, as it appears to have the potential for weak androgenic effects in specific situations.[18] On the basis ofanimal research, BOMT does not appear to act as an AR antagonist incentral nervous systemtissues, and in relation to this, does not disinhibit thehypothalamic–pituitary–gonadal axis or increasetestosterone levels.[19]
[It is shown that 6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one, has significant anti-androgenic activity. Isomers of this compound with different configuration at C-5 and C-6 were found to be inactive.]
Several androstane derivatives have also demonstrated an antiandrogenic activity; 17α-methyl-B-nortestosterone 8 was prepared and tested in 1964 for antihormonal activity [43]. Within the next decades, several other androstane analogs were prepared and found to possess antiandrogenic activity [43, 44, 45, 46] including BOMT 9 "figure 2", R2956 10, SC9420 11, and oxendolone 12 "figure 3".
However, a less well documented antiandrogen, BOMT possesses the ideal characteristics of negligible androgenic, estrogenic and progestational activity (55) and would therefore appear to be a valuable compound for use in future investigations.
Another steroidal compound with anti-androgenic activity is BOMT (6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one). This compound has no androgenic, oestrogenic or progestational activity but is a potent anti-androgen and (Boris et al., 1970); it competes effectively for the specific, high-affinity binding sites for DHT in the rat prostate (Mangan and Mainwaring, 1972) and depresses testis weight (Boris et al., 1970).
Finally, the steroidal antiandrogen BOMT and the non-steroidal antiandrogen DIMP are only relatively weak competitors.
Flutamide, cyproterone, benorterone, RU-2956, BOMT and cimetidine are recognized as true antiandrogens because they act as competitive inhibitors of specific ligand binding to androgen receptors.
