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6α-Methylprogesterone

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6α-Methylprogesterone
Clinical data
Other names6α-Methylpregn-4-ene-3,20-dione; 6α-MP; 6-MP; 6MP; NSC-75530
Drug classProgestogen; Progestin
Identifiers
  • (6S,8S,9S,10R,13S,14S,17S)-17-acetyl-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H32O2
Molar mass328.496 g·mol−1
3D model (JSmol)
  • C[C@H]1C[C@H]2[C@@H]3CC[C@@H]([C@]3(CC[C@@H]2[C@@]4(C1=CC(=O)CC4)C)C)C(=O)C
  • InChI=1S/C22H32O2/c1-13-11-16-18-6-5-17(14(2)23)21(18,3)10-8-19(16)22(4)9-7-15(24)12-20(13)22/h12-13,16-19H,5-11H2,1-4H3/t13-,16-,17+,18-,19-,21+,22+/m0/s1
  • Key:GNFABWAPJFOZSF-KTORGGLSSA-N

6α-Methylprogesterone (6α-MP) is a progestin which was never marketed.[1][2][3][4][5][6][7] It has 150% of the progestogenic potency of progesterone.[5] In addition, and in contrast to progesterone, 6α-MP has weak androgenic, antiandrogenic, and synandrogenic actions.[5] 6α-MP is structurally related to medroxyprogesterone acetate (MPA; 6α-methyl-17α-acetoxyprogesterone) and megestrol acetate (MGA; 6-dehydro-6-methyl-17α-acetoxyprogesterone), which possess androgenic and/or antiandrogenic activity to varying degrees similarly.[5] MPA is more androgenic than 6α-MP and MGA.[5]

References

[edit]
  1. ^ Wu YL, Chow WZ, Hou CC (October 1965). "Synthesis of 6-alpha-methylprogesterone from hyodesoxycholic acid". Scientia Sinica. 14 (10): 1533–1535. PMID 5881565.
  2. ^ Brown TR, Bullock LP, Bardin CW (1979). "In Vivo Metabolism and Binding of 6α-Methylprogesterone; A Progestin with Anti-Androgenic and Synandrogenic Activities". Steroid Hormone Receptor Systems. Advances in Experimental Medicine and Biology. Vol. 117. pp. 269–280. doi:10.1007/978-1-4757-6589-2_14. ISBN 978-1-4757-6591-5. PMID 474281.
  3. ^ Brown TR, Bullock LP, Bardin CW (December 1981). "The nuclear uptake of 6 alpha-[3H]methylprogesterone and its 20 alpha-hydroxy metabolite: the requirement for multiple receptors". Endocrinology. 109 (6): 1821–1829. doi:10.1210/endo-109-6-1821. PMID 7308133.
  4. ^ Brown TR, Bullock LP, Bardin CW (December 1981). "The biological actions and metabolism of 6 alpha-methylprogesterone: a progestin that mimics and modifies the effects of testosterone". Endocrinology. 109 (6): 1814–1820. doi:10.1210/endo-109-6-1814. PMID 7308132.
  5. ^ a b c d e Bardin CW, Brown T, Isomaa VV, Jänne OA (1983). "Progestins can mimic, inhibit and potentiate the actions of androgens". Pharmacology & Therapeutics. 23 (3): 443–459. doi:10.1016/0163-7258(83)90023-2. PMID 6371845.
  6. ^ Houben PW, Bullock LP (1985). "Receptor binding of 6 alpha-methylprogesterone in mouse kidney". Hormone Research. 21 (4): 261–269. doi:10.1159/000180059 (inactive 1 November 2024). PMID 4007785.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)
  7. ^ Wayne Bardin C, Janne OA (1986). "Steroids of One Class Can Mimic, Inhibit and Potentiate the Biological Effects of Other Steroid Classes when Administered at High Doses". In Gregoire AT, Blye RP (eds.). Contraceptive Steroids. pp. 123–143. doi:10.1007/978-1-4613-2241-2_6. ISBN 978-1-4612-9313-2.
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