11-Dehydroprogesterone

11-Dehydroprogesterone
Clinical data
Other names	Pregna-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	2625-60-7;
PubChem CID	228863;
ChemSpider	199223;
UNII	YUL6GTR69Y;
KEGG	C14646;
ChEBI	CHEBI:34929;
ChEMBL	ChEMBL44282;
CompTox Dashboard (EPA)	DTXSID90180885 ;
Chemical and physical data
Formula	C21H28O2
Molar mass	312.453 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

^ ^a ^b 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.
^ ^a ^b 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.
^ ^a ^b 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.
^ 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.
^ Ferin J (1950). "[Effects of 11-dehydroprogesterone in women]". Annales d'Endocrinologie. 11 (2): 179–182. PMID 14799957. (in Undetermined Language)

[pmid13583809-1] 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.

[pmid13416376-2] 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.

[PfiffnerKamm1942-3] 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.

[pmid13033848-4] 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.

[pmid14799957-5] Ferin J (1950). "[Effects of 11-dehydroprogesterone in women]". Annales d'Endocrinologie. 11 (2): 179–182. PMID 14799957. (in Undetermined Language)

[1]

[2]

[3]

[4]

[5]