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Clinical data | |
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Trade names | Ketogestin |
Other names | Bio 66; U-1258; 11-Oxoprogesterone; Pregn-4-ene-3,11,20-trione |
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ECHA InfoCard | 100.007.476 |
Chemical and physical data | |
Formula | C21H28O3 |
Molar mass | 328.452 g·mol−1 |
3D model (JSmol) | |
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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]
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 GABAA receptor.[7]