BOMT
Clinical data | |
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Other names | Ro 7-2340; 6 |
Routes of administration | By mouth |
Drug class | Steroidal antiandrogen |
ATC code |
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CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C19H29BrO3 |
Molar mass | 385.342 g·mol−1 |
3D model (JSmol) | |
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BOMT, also known by its developmental code name Ro 7-2340 and as 6
BOMT is a selective competitive antagonist of the androgen receptor (AR),[3][4][11][12][13] although it is described as an "only relatively weak competitor."[14] The relative binding affinity of the drug for the androgen receptor is about 2.7% of that of metribolone.[15] BOMT shows no androgenic, estrogenic, or progestogenic activity even at high doses, nor any inhibition of 5
See also
[edit]References
[edit]- ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 178–. ISBN 978-1-4757-2085-3.
- ^ a b Boris A, Uskoković M (January 1970). "A new antiandrogen, 6alpha-bromo-17 beta-hydroxy-17 alpha-methyl-4-oxa-5 alpha-androstan-3-one". Experientia. 26 (1): 9–10. doi:10.1007/BF01900355. PMID 5412314. S2CID 39460337.
[It is shown that 6
α -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.] - ^ a b c d Boris A, DeMartino L, Trmal T (April 1971). "Some endocrine studies of a new antiandrogen, 6-alpha-bromo-17-beta-hydroxy-17-alpha-methyl-4-oxa-5-alpha-androstan-3-one (BOMT)". Endocrinology. 88 (4): 1086–1091. doi:10.1210/endo-88-4-1086. PMID 5542403.
- ^ a b c Mangan FR, Mainwaring WI (September 1972). "An explanation of the antiandrogenic properties of 6 -bromo-17 -hydroxy-17 -methyl-4-oxa-5 -androstane-3-one". Steroids. 20 (3): 331–343. doi:10.1016/0039-128X(72)90092-X. PMID 5073580.
- ^ Mann T, Lutwak-Mann C (6 December 2012). "Antiandrogens". Male Reproductive Function and Semen: Themes and Trends in Physiology, Biochemistry and Investigative Andrology. Springer Science & Business Media. pp. 352–. ISBN 978-1-4471-1300-3.
- ^ Mainwaring WI (6 December 2012). The Mechanism of Action of Androgens. Springer Science & Business Media. pp. 10–. ISBN 978-3-642-88429-0.
- ^ Bratoeff E, Ramírez E, Murillo E, Flores G, Cabeza M (December 1999). "Steroidal antiandrogens and 5alpha-reductase inhibitors". Current Medicinal Chemistry. 6 (12): 1107–23. doi:10.2174/0929867306666220401180500. PMID 10519917. S2CID 248057720.
Several androstane derivatives have also demonstrated an antiandrogenic activity; 17
α -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". - ^ Clark CR, Nowell NW (April 1979). "Binding properties of testosterone receptors in the hypothalamic-preoptic area of the adult male mouse brain". Steroids. 33 (4): 407–426. doi:10.1016/0039-128X(79)90015-1. PMID 442132. S2CID 42014129.
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.
- ^ Kent J, Bischoff A, Herr H, O'Connell W (1973), Study of antiandrogen (Ro–7–2340) (6
α -bromo-17β -methyl-4-oxa-5α -andronstan-3-one) in benign prostatic hypertrophy - ^ Mainwaring WI, Mangan FR, Wilce PA, Milroy EG (1973). "Androgens I. — A Review of Current Research on the Binding and Mechanism of Action of Androgenic Steroids, Notably 5
α -Dihydrotestosterone". Receptors for Reproductive Hormones. Advances in Experimental Medicine and Biology. Vol. 36. pp. 197–231 (208). doi:10.1007/978-1-4684-3237-4_10. ISBN 978-1-4684-3239-8. PMID 4368414. - ^ a b Setchell BP (1978). The mammalian testis. P. Elek. p. 144. ISBN 978-0-236-31057-9.
Another steroidal compound with anti-androgenic activity is BOMT (6
α -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). - ^ a b King RJ, Mainwaring WI (20 May 2014). Steroid–Cell Interactions. Elsevier. pp. 52, 61, 70–71, 300, 401–403. ISBN 978-1-4831-6510-3.
- ^ Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Current Medicinal Chemistry. 7 (2): 211–247. doi:10.2174/0929867003375371. PMID 10637363.
- ^ Heyns W, Verhoeven G, De Moor P (May 1976). "Androgen binding in rat uterus cytosol. Study of the specificity". Journal of Steroid Biochemistry. 7 (5): 335–343. doi:10.1016/0022-4731(76)90092-3. PMID 180344.
Finally, the steroidal antiandrogen BOMT and the non-steroidal antiandrogen DIMP are only relatively weak competitors.
- ^ Wakeling AE, Furr BJ, Glen AT, Hughes LR (December 1981). "Receptor binding and biological activity of steroidal and nonsteroidal antiandrogens". Journal of Steroid Biochemistry. 15: 355–359. doi:10.1016/0022-4731(81)90297-1. PMID 7339263.
- ^ Mangan FR, Mainwaring WI (1971). "The biochemical basis for the antagonism by BOMT of the effects of dihydrotesterone on the rat ventral prostate gland". Gynecologic Investigation. 2 (1): 300–304. doi:10.1159/000301871. PMID 5161490.
- ^ Tremblay RR (May 1986). "Treatment of hirsutism with spironolactone". Clinics in Endocrinology and Metabolism. 15 (2): 363–371. doi:10.1016/S0300-595X(86)80030-5. PMID 2941190.
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.
- ^ Ahlin K, Forsberg JG, Jacobsohn D, Thore-Berger B (1975). "The male genital tract and the nipples of male and female offspring of rats given the non-steroidal antiandrogens DIMP and Sch 13521, during pregnancy". Archives d'Anatomie Microscopique et de Morphologie Expérimentale. 64 (1): 27–44. PMID 1217898.
- ^ Clark CR, Nowell NW (August 1979). "BOMT (6 alpha-bromo-17 beta-hydroxy-17 alpha-methyl-4-oxa-5 alpha-androstan-3-one) is not an androgen antagonist within the central nervous system". Steroids. 34 (2): 139–149. doi:10.1016/0039-128X(79)90043-6. PMID 494357. S2CID 54290381.