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| IUPAC_name = (1''S'',3a''S'',3b''R'',5''S'',5a''S'',9a''R'',9b''S'',11a''S'')-5-Bromo-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydroindeno[5,4-''f'']chromen-7-one
| IUPAC_name = (1''S'',3a''S'',3b''R'',5''S'',5a''S'',9a''R'',9b''S'',11a''S'')-5-Bromo-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydroindeno[5,4-''f'']chromen-7-one
| image = BOMT.svg
| image = BOMT.svg
| width =200px
| width = 250


<!--Clinical data-->
<!--Clinical data-->

Revision as of 05:42, 1 May 2017

BOMT
Clinical data
Other namesRo 7-2340; 6α-bromo-4-oxa-17α-methyl-5α-dihydrotestosterone
Routes of
administration		Oral
ATC code
  • None
Identifiers
  • (1S,3aS,3bR,5S,5aS,9aR,9bS,11aS)-5-Bromo-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydroindeno[5,4-f]chromen-7-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H29BrO3
Molar mass385.33576 g/mol g·mol−1
3D model (JSmol)
  • CC12CCC(=O)OC1C(CC3C2CCC4(C3CCC4(C)O)C)Br
  • InChI=1S/C19H29BrO3/c1-17-7-6-15(21)23-16(17)14(20)10-11-12(17)4-8-18(2)13(11)5-9-19(18,3)22/h11-14,16,22H,4-10H2,1-3H3/t11-,12+,13+,14+,16-,17-,18+,19+/m1/s1
  • Key:ZUIGZKIOHUNINA-LWPUPYOYSA-N

BOMT (developmental code name Ro 7-2340), also known as 6α-bromo-4-oxa-17α-methyl-5α-androstan-17β-ol-3-one, is a synthetic, steroidal, pure antiandrogen that was first developed in 1970 and was never marketed for clinical use.[1][2][3][4] It is the 6α-brominated, 4-oxygenated, and 17α-methylated derivative of dihydrotestosterone (DHT). Along with benorterone, cyproterone (and its acetate ester, cyproterone acetate), and flutamide,[5] BOMT was among the earliest antiandrogens to be developed and extensively studied,[2][3][6][7][8] although it is less well-documented in comparison to the others.[9] BOMT has been investigated clinically in the treatment of benign prostatic hyperplasia, though development for this use did not continue.[10] There was also interest in BOMT for the potential applications of acne, androgenetic alopecia, and possibly prostate cancer, but it was not developed for these indications either.[11]

BOMT is a selective competitive antagonist of the androgen receptor (AR),[3][4][12][13][14] although it is described as an "only relatively weak competitor."[15] The drug shows no androgenic, estrogenic, or progestogenic activity even at high doses, nor any inhibition of 5α-reductase,[16] though it does show weak antigonadotropic effects.[3][4][12][13] Due to its selectivity for and competitive inhibition of the AR, BOMT has been described as a "true" antiandrogen, similarly to benorterone, cyproterone, and flutamide.[17] Like other steroidal antiandrogens, BOMT may actually be a weak partial agonist of the AR, as it appears to have the potential for weak androgenic effects in specific situations.[18] On the basis of animal research, BOMT does not appear to act as an AR antagonist in central nervous system tissues, and in relation to this, does not disinhibit the hypothalamic-pituitary-gonadal axis or increase testosterone levels.[19]

See also

References

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 178–. ISBN 978-1-4757-2085-3.
  2. ^ a b Boris, A.; Uskokovic, M. (1970). "A new antiandrogen. 6α-Bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one". Experientia. 26 (1): 9–10. doi:10.1007/BF01900355. ISSN 0014-4754. [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.]
  3. ^ a b c d Boris, Alfred; Demartino, Louis; Trmal, Thelma (1971). "Some Endocrine Studies of a New Antiandrogen, 6 α-Bromo-17β-hydroxy-17α-methyl-4-oxa-5α:-androstan-3-one (BOMT)". Endocrinology. 88 (4): 1086–1091. doi:10.1210/endo-88-4-1086. ISSN 0013-7227. PMID 5542403.
  4. ^ a b c Mangan, F.R.; Mainwaring, W.I.P. (1972). "An explanatiom of the antiandrogenic properties of 6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstane-3-one". Steroids. 20 (3): 331–343. doi:10.1016/0039-128X(72)90092-X. ISSN 0039-128X.
  5. ^ T. Mann; C. Lutwak-Mann (6 December 2012). 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.
  6. ^ W.I.P. Mainwaring (6 December 2012). The Mechanism of Action of Androgens. Springer Science & Business Media. pp. 10–. ISBN 978-3-642-88429-0.
  7. ^ Bentham Science Publishers (December 1999). Current Medicinal Chemistry. Bentham Science Publishers. pp. 1110–1111. 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".
  8. ^ Anthony W. Norman; Gerald Litwack (28 June 2014). Hormones. Elsevier Science. pp. 508–. ISBN 978-1-4832-5810-2.
  9. ^ Clark, C.R.; Nowell, N.W. (1979). "Binding properties of testosterone receptors in the hypothalamic-preoptic area of the adult kale mouse brain". Steroids. 33 (4): 407–426. doi:10.1016/0039-128X(79)90015-1. ISSN 0039-128X. 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.
  10. ^ John Kent; Arthur Bischoff; Harry Herr; William O'Connell (1973), Study of antiandrogen (Ro–7–2340) (6α-bromo-17β-methyl-4-oxa-5α-andronstan-3-one) in benign prostatic hypertrophy {{citation}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)
  11. ^ Bert O'Malley (11 November 2013). Receptors for Reproductive Hormones. Springer Science & Business Media. pp. 208–. ISBN 978-1-4684-3237-4.
  12. ^ a b Brian Peter Setchell (1978). The mammalian testis. P. Elek. p. 144. ISBN 978-0-236-31057-9. 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 (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).
  13. ^ a b R. J. B. King; W. I. P. Mainwaring (20 May 2014). Steroid–Cell Interactions. Elsevier. pp. 52, 61, 70–71, 300, 401–403. ISBN 978-1-4831-6510-3.
  14. ^ Singh, Shankar; Gauthier, Sylvain; Labrie, Fernand (2000). "Androgen Receptor Antagonists (Antiandrogens) Structure-Activity Relationships" (PDF). Current Medicinal Chemistry. 7 (2): 211–247. doi:10.2174/0929867003375371. ISSN 0929-8673. PMID 10637363.
  15. ^ Heyns, W.; G., Verhoeven; De Moor, P. (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. ISSN 0022-4731. Finally, the steroidal antiandrogen BOMT and the non-steroidal antiandrogen DIMP are only relatively weak competitors.
  16. ^ Mangan, F.R.; Mainwaring, W.I.P. (1971). "The Biochemical Basis for the Antagonism hy BOMT of the Effects of Dihydrotesterone on the Rat Ventral Prostate Gland". Gynecologic and Obstetric Investigation. 2 (1–6): 300–304. doi:10.1159/000301871. ISSN 1423-002X.
  17. ^ Tremblay, Roland R. (1986). "10 Treatment of hirsutism with spironolactone". Clinics in Endocrinology and Metabolism. 15 (2): 363–371. doi:10.1016/S0300-595X(86)80030-5. ISSN 0300-595X. 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.
  18. ^ 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". Arch Anat Microsc Morphol Exp. 64 (1): 27–44. PMID 1217898.
  19. ^ Clark, C.R.; Nowell, N.W. (1979). "Bomt (6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-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. ISSN 0039-128X.
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