Bromethenmadinone acetate

Bromethenmadinone acetate (BMMA, also known as bromsuperlutin) is a progestin medication which was developed in Czechoslovakia and was described in 1970 but was never marketed.^{[1][2][3][4][5][6][7][8][9]} Analogues of BMMA include chlormethenmadinone acetate, melengestrol acetate, and methenmadinone acetate.

Bromethenmadinone acetate

Clinical data
Other names	BMMA; Bromsuperlutin; 6-Bromo-16-methylene-17α-hydroxy-Δ^6-progesterone acetate; 6-Bromo-16-methylene-17α-acetoxypregna-4,6-diene-3,20-dione
Drug class	Progestogen; Progestin; Progestogen ester
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17R)-17-Acetyl-6-bromo-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number	24431-75-2
PubChem CID	90679394
ChemSpider	34249907
ChEMBL	ChEMBL3276152
Chemical and physical data
Formula	C24H29BrO4
Molar mass	461.396 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)CC[C@]34C)Br)C)OC(=O)C
InChI InChI=1S/C24H29BrO4/c1-13-10-19-17-12-21(25)20-11-16(28)6-8-22(20,4)18(17)7-9-23(19,5)24(13,14(2)26)29-15(3)27/h11-12,17-19H,1,6-10H2,2-5H3/t17-,18+,19+,22-,23+,24+/m1/s1 Key:GIUDLKYATCHBDT-USYNNDFZSA-N

See also

• List of progestogen esters § Esters of 17α-hydroxyprogesterone derivatives
• 16-Methylene-17α-hydroxyprogesterone acetate

References

1. Stĕrba R (March 1970). . Zentralbl Gynakol (in German). 92 (10): 303–12. PMID 4096927. Archived from the original on 2018-09-16. Retrieved 2018-09-17.
2. Štěrba, R. (1971). . Current Problems in Fertility. pp. 154–158. doi:10.1007/978-1-4615-8651-7_28. ISBN 978-1-4615-8653-1. Archived from the original on 2018-09-16. Retrieved 2018-09-17.
3. Cekan Z, Horesovský O (February 1971). "Elimination and metabolism of 6-chloro-17-alpha-hydroxy-16-methylene-4,6-pregnadiene-3,20-dione acetate and its analogues in rats". Acta Endocrinol. 66 (2): 303–16. doi:10.1530/acta.0.0660303. PMID 5107826.
4. Shapiro EL, Weber L, Harris H, Miskowicz C, Neri R, Herzog HL (July 1972). "Synthesis and biological activity of 17-esters of 6-dehydro-16-methylene-17 -hydroxyprogesterones". J. Med. Chem. 15 (7): 716–20. doi:10.1021/jm00277a006. PMID 5043870.
5. Míčková, R. (1973). "Steroid derivatives. LXXV. The preparation of polyhalogenated derivatives of progestational hormones and the determination of their conformation by circular dichroism spectra". Collection of Czechoslovak Chemical Communications. 38 (8): 2492–2503. doi:10.1135/cccc19732492. ISSN 0010-0765.
6. Wolff ME (August 1974). "A quantitative reexamination of structure-activity relationships in the delta6-6-substituted progesterone series". J. Med. Chem. 17 (8): 898–900. doi:10.1021/jm00254a025. PMID 4845383.
7. Topliss JG, Shapiro EL (June 1975). "Quantitative structure-activity relationships in the delta6-6-substituted progesterone series. A reappraisal". J. Med. Chem. 18 (6): 621–3. doi:10.1021/jm00240a020. PMID 1151979.
8. Wolff ME, Hansch C, Giannini DD, Kollman PA, Duax WL, Baxter J (1975). "Correlation of glucocorticoid and progestational activity with steric, electronic and hydrophobic parameters". J. Steroid Biochem. 6 (3–4): 211–4. doi:10.1016/0022-4731(75)90134-X. PMID 171485.
9. Coburn RA, Solo AJ (June 1976). "Quantitative structure-activity relationships among steroids. Investigations of the use of steric parameters". J. Med. Chem. 19 (6): 748–54. doi:10.1021/jm00228a002. PMID 950640.