Bromethenmadinone acetate

Bromethenmadinone acetate
Clinical data
Other names	BMMA; Bromsuperlutin; 6-Bromo-16-methylene-17α-hydroxy-Δ6-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;

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.

References

^ Stĕrba R (March 1970). "[Towards a more physiological hormonal contraception]". Zentralbl Gynakol (in German). 92 (10): 303–12. PMID 4096927. Archived from the original on 2018-09-16. Retrieved 2018-09-17.
^ Štěrba, R. (1971). "On the Way to a More Physiological Hormonal Contraception". 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

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[pmid4096927-1] Stĕrba R (March 1970). "[Towards a more physiological hormonal contraception]". Zentralbl Gynakol (in German). 92 (10): 303–12. PMID 4096927. Archived from the original on 2018-09-16. Retrieved 2018-09-17.

[Štěrba1971-2] Štěrba, R. (1971). "On the Way to a More Physiological Hormonal Contraception". 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.

[pmid5107826-3] 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.

[pmid5043870-4] 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.

[Míčková1973-5] 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.

[pmid4845383-6] 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.

[pmid1151979-7] 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.

[pmid171485-8] 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.

[pmid950640-9] 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.

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Bromethenmadinone acetate

See also

References