Thu . 18 Sep 2018

11-Ketoprogesterone

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 It was synthesized in 1940 The steroid has profound effects on carbohydrate metabolism and possesses activities associated with adrenal cortex hormones like cortisone 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 11-Ketoprogesterone may act through membrane glucocorticoid receptors

11-Ketoprogesterone is reportedly devoid of androgenic, estrogenic, and progestogenic activity 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 A halogenated derivative of 11-ketoprogesterone, 9α-bromo-11-ketoprogesterone, possesses relatively high progestogenic activity Similarly to 11α-hydroxyprogesterone and 11β-hydroxyprogesterone, 11-ketoprogesterone is reported to act as an inhibitor of the enzyme 11β-hydroxysteroid dehydrogenase It has also been found to act as a weak negative allosteric modulator of the GABAA receptor

See also

  • 11-Dehydrocorticosterone 11-keto-21-hydroxyprogesterone
  • 21-Deoxycortisone 11-keto-17α-hydroxyprogesterone

References

  1. ^ a b J Elks 14 November 2014 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies Springer pp 1014– ISBN 978-1-4757-2085-3 
  2. ^ a b c Veterinary Medicine American Veterinary Publishing Company 1953 Experimentally, it is reported that ketogestin has a profound effect upon carbohydrate metabolism, accelerating production of glucose from protein gluconegenesis It possesses physiological activities associated with certain hormones of the adrenal cortex Its effect on carbohydrate metabolism is similar to that of cortisone, as proved by deposition of glycogen, increasing glycosuria, and decreasing fat metabolism This compound, however, does not cause certain undesirable activities in ketosis and other conditions as do other adrenocortical hormones, in that it does not cause retention of the sodium ion, nor does it produce hypertension during high sodium ion intake Ketogestin is devoid of androgenic, estrogenic, or progestational activity and is nontoxic in amounts greatly exceeding pharmacological dosage 
  3. ^ Harrison, R W; Balasubramanian, K; Yeakley, J; Fant, M; Svec, F; Fairfield, S 1979 "Heterogeneity of AtT-20 Cell Glucocorticoid Binding Sites: Evidence for a Membrane Receptor" 117: 423–440 doi:101007/978-1-4757-6589-2_23 ISSN 0065-2598 
  4. ^ Ralph I Dorfman 22 October 2013 Steroidal Activity in Experimental Animals and Man Elsevier Science pp 482– ISBN 978-1-4832-7299-3 
  5. ^ a b Otto Hoffmann-Ostenhof 1959 Proceedings of the Fourth International Congress of Biochemistry, Vienna, 1-6 September, 1958 and p 269 In addition, it had been previously reported that 11β-hydroxyprogesterone was devoid of progestational action However, we found that it does possess about 1% of the activity of progesterone This trace activity is substantially enhanced by fluorination, since 9α-fluoro-11β-hydroxyprogesterone is eight times as active as the non-halogenated analogue6 Concomitantly, Fried et al7 described the relatively high progestational activity of 9α-bromo-11-ketoprogesterone as well 
  6. ^ Piwien-Pilipuk G, Galigniana MD 2000 "Oxidative stress induced by L-buthionine-S,R-sulfoximine, a selective inhibitor of glutathione metabolism, abrogates mouse kidney mineralocorticoid receptor function" Biochim Biophys Acta 1495 3: 263–80 PMID 10699465 
  7. ^ Zhong Y, Simmonds MA 1996 "Pharmacological characterisation of multiple components in the enhancement by pregnanolone and propofol of flunitrazepam binding to GABAA receptors" Neuropharmacology 35 9-10: 1193–8 PMID 9014134 


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    29.10.2014


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