Bromethenmadinone acetate

Last updated
Bromethenmadinone acetate
Bromethenmadinone acetate.svg
Clinical data
Other namesBMMA; 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
  • [(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
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C24H29BrO4
Molar mass 461.396 g·mol−1
3D model (JSmol)
  • 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=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.

See also

Related Research Articles

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<span class="mw-page-title-main">DU-41164</span> Chemical compound

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<span class="mw-page-title-main">Methenmadinone acetate</span> Progestin

Methenmadinone acetate (MMA), also known as methylenedehydroacetoxyprogesterone (MDAP) and sold under the brand names Superlutin and Antigest, is a progestin medication which was developed in Czechoslovakia in the 1960s. It is the C17α acetate ester of methenmadinone.

<span class="mw-page-title-main">Methenmadinone</span> Chemical compound

Methenmadinone, also known as deacetylsuperlutin or as 16-methylene-6-dehydro-17α-hydroxyprogesterone, is a pregnane steroid which was never marketed. It is a parent compound of methenmadinone acetate, melengestrol, and chlormethenmadinone.

<span class="mw-page-title-main">Chlormethenmadinone acetate</span> Chemical compound

Chlormethenmadinone acetate (CMMA), also known as chlorsuperlutin, is a progestin medication which was developed in Czechoslovakia in the 1960s. It has been used in combination with mestranol in birth control pills under the brand names Biogest, Sterolibrin, and Antigest B, and in veterinary medicine under the brand name Agelin. Analogues of CMMA include bromethenmadinone acetate (bromsuperlutin), which was assessed but was never marketed, and melengestrol acetate (methylsuperlutin), which is used in veterinary medicine.

<span class="mw-page-title-main">Methenmadinone caproate</span> Chemical compound

Methenmadinone caproate is a progestin medication which was developed in Czechoslovakia in the 1960s and was studied for potential use in combined injectable contraceptives in the 1970s but was never marketed. It was studied as a combined injectable contraceptive in combination with estradiol valerate at doses of 60 mg and 10 mg, respectively, once a month by intramuscular injection. MMC is the C17α caproate (hexanoate) ester of methenmadinone and an analogue of methenmadinone acetate. In addition to MMA, analogues of MMC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and megestrol caproate.

<span class="mw-page-title-main">16-Methylene-17α-hydroxyprogesterone acetate</span> Chemical compound

16-Methylene-17α-hydroxyprogesterone acetate is a progestin of the 17α-hydroxyprogesterone group which was never marketed. Given orally, it shows about 2.5-fold the progestogenic activity of parenteral progesterone in animal bioassays. It is a parent compound of the following clinically used progestins:

References

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  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.
  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.