11-Dehydroprogesterone

11-Dehydroprogesterone, also known as pregna-4,11-diene-3,20-dione, is a steroidal progestin that was never marketed.[1][2][3] It was found to be 2- to 3-fold as potent as progesterone as a progestogen in animal bioassays,[1][4] although other studies found them to be equivalent in potency.[2] 11-Dehydroprogesterone has been studied in women.[5] It was discovered in the 1930s or 1940s and was one of the earliest synthetic progestogens.[3]

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-decahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(C=C[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)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

See also

References
  1. ZARROW MX, PETERS LE, CALDWELL AL (1958). "Comparative potency of several progestogenic compounds in a battery of different biological tests". Ann. N. Y. Acad. Sci. 71 (5): 532–41. Bibcode:1958NYASA..71..532Z. doi:10.1111/j.1749-6632.1958.tb46783.x. PMID 13583809.
  2. ZARROW MX, NEHER GM, LAZOWASEM EA, SALHANICK HA (1957). "Biological activity of certain progesterone-like compounds as determined by the Hooker-Forbes bioassay". J. Clin. Endocrinol. Metab. 17 (5): 658–66. doi:10.1210/jcem-17-5-658. PMID 13416376.
  3. Pfiffner, J J; 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 (1953). "High progestational activity of 19-norprogesterone". Endocrinology. 52 (3): 359–61. doi:10.1210/endo-52-3-359. PMID 13033848.
  5. FERIN J (1950). "[Effects of 11-dehydroprogesterone in women]". Ann. Endocrinol. Paris. 11 (2): 179–82. PMID 14799957. (in Undetermined Language)


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