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11-Dehydroprogesterone

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Chemical compound Pharmaceutical compound
11-Dehydroprogesterone
Clinical data
Other namesPregna-4,11-diene-3,20-dione
Identifiers
IUPAC name
  • (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-1,2,6,7,8,9,14,15,16,17-decahydrocyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol
3D model (JSmol)
SMILES
  • CC(=O)1CC21(C=C32CCC4=CC(=O)CC34C)C
InChI
  • InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h9,11-12,16-19H,4-8,10H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
  • Key:XMUAORABVRJUDU-LEKSSAKUSA-N

11-Dehydroprogesterone, also known as pregna-4,11-diene-3,20-dione, is a steroidal progestin that was never marketed. It was found to be 2- to 3-fold as potent as progesterone as a progestogen in animal bioassays, although other studies found them to be equivalent in potency. 11-Dehydroprogesterone has been studied in women. It was discovered in the 1930s or 1940s, and was one of the earliest synthetic progestogens.

See also

References

  1. ^ Zarrow MX, Peters LE, Caldwell AL (July 1958). "Comparative potency of several progestogenic compounds in a battery of different biological tests". Annals of the New York Academy of Sciences. 71 (5): 532–541. Bibcode:1958NYASA..71..532Z. doi:10.1111/j.1749-6632.1958.tb54629.x. PMID 13583809.
  2. ^ Zarrow MX, Neher GM, Lazowasem EA, Salhanick HA (May 1957). "Biological activity of certain progesterone-like compounds as determined by the Hooker-Forbes bioassay". The Journal of Clinical Endocrinology and Metabolism. 17 (5): 658–666. doi:10.1210/jcem-17-5-658. PMID 13416376.
  3. ^ Pfiffner JJ, Kamm O (1942). "The Chemistry of the Hormones". Annual Review of Biochemistry. 11 (1): 283–308. doi:10.1146/annurev.bi.11.070142.001435. ISSN 0066-4154.
  4. Tullner WW, Hertz R (March 1953). "High progestational activity of 19-norprogesterone". Endocrinology. 52 (3): 359–361. doi:10.1210/endo-52-3-359. PMID 13033848.
  5. Ferin J (1950). "". Annales d'Endocrinologie. 11 (2): 179–182. PMID 14799957. (in Undetermined Language)
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
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