11-Ketoprogesterone

11-Ketoprogesterone (brand name Ketogestin; former developmental code names Bio 66, U-1258), or 11-oxoprogesterone, also known as pregn-4-ene-3,11,20-trione, is a pregnane steroid related to cortisone (11-keto-17α,21-dihydroxyprogesterone) that was formerly used in veterinary medicine in the treatment of bovine ketosis.^[1] It was synthesized in 1940.^[1] The steroid has profound effects on carbohydrate metabolism and possesses activities associated with adrenal cortex hormones like cortisone.^[2] However, it is non-toxic even in high dosages, suggesting that it lacks conventional glucocorticoid activity, and it does not possess mineralocorticoid activity, unlike other adrenocortical hormones.^[2] 11-Ketoprogesterone may act through membrane glucocorticoid receptors.^[3]

Trade namesKetogestin

Other namesBio 66; U-1258; 11-Oxoprogesterone; Pregn-4-ene-3,11,20-trione

CAS Number

• 516-15-4

PubChem CID

• 94166

Quick facts Clinical data, Trade names ...

11-Ketoprogesterone

Clinical data
Trade names	Ketogestin
Other names	Bio 66; U-1258; 11-Oxoprogesterone; Pregn-4-ene-3,11,20-trione
Identifiers
IUPAC name (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
CAS Number	516-15-4
PubChem CID	94166
ChemSpider	84982
UNII	9Y1Y86O4T5
ChEMBL	ChEMBL284253
CompTox Dashboard (EPA)	DTXSID101031475
ECHA InfoCard	100.007.476
Chemical and physical data
Formula	C21H28O3
Molar mass	328.452 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC(=O)[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChI InChI=1S/C21H28O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-17,19H,4-9,11H2,1-3H3/t15-,16+,17-,19+,20-,21+/m0/s1 Key:WKAVAGKRWFGIEA-DADBAOPHSA-N

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11-Ketoprogesterone is reportedly devoid of androgenic, estrogenic, and progestogenic activity.^[2][4] 11β-Hydroxyprogesterone has also been reported to be devoid of progestogenic activity, but has subsequently been reported to possess about 1% of the progestogenic activity of progesterone.^[5] A halogenated derivative of 11-ketoprogesterone, 9α-bromo-11-ketoprogesterone, possesses relatively high progestogenic activity.^[5] Similarly to 11α-hydroxyprogesterone and 11β-hydroxyprogesterone, 11-ketoprogesterone is reported to act as an inhibitor of the enzyme 11β-hydroxysteroid dehydrogenase.^[6] It has also been found to act as a weak negative allosteric modulator of the GABA_A receptor.^[7]