6α-Methylprogesterone

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]

6α-Methylprogesterone
Clinical data
Other names6α-Methylpregn-4-ene-3,20-dione; 6α-MP; 6-MP; 6MP; NSC-75530
Drug classProgestogen; Progestin
Identifiers
IUPAC name
  • (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
Chemical and physical data
FormulaC22H32O2
Molar mass328.496 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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

References
  1. Wu YL, Chow WZ, Hou CC, Huang-minlon (October 1965). "Synthesis of 6-alpha-methylprogesterone from hyodesoxycholic acid". Sci. Sin. 14 (10): 1533–5. PMID 5881565.
  2. Brown TR, Bullock LP, Bardin CW (1979). "In vivo metabolism and binding of 6 alpha-methylprogesterone; a progestin with anti-androgenic and synandrogenic activities". Adv. Exp. Med. Biol. Advances in Experimental Medicine and Biology. 117: 269–80. 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): 1821–9. 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): 1814–20. doi:10.1210/endo-109-6-1814. PMID 7308132.
  5. Bardin CW, Brown T, Isomaa VV, Jänne OA (1983). "Progestins can mimic, inhibit and potentiate the actions of androgens". Pharmacol. Ther. 23 (3): 443–59. 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". Horm. Res. 21 (4): 261–9. doi:10.1159/000180059. PMID 4007785.
  7. Wayne Bardin, C.; Janne, Olli A. (1986). "Steroids of One Class Can Mimic, Inhibit and Potentiate the Biological Effects of Other Steroid Classes When Administered at High Doses". Contraceptive Steroids. pp. 123–143. doi:10.1007/978-1-4613-2241-2_6. ISBN 978-1-4612-9313-2.


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