Progesterone derivatives that bind to the digitalis receptor: synthesis of 14 beta-hydroxyprogesterone. A novel steroid with positive inotropic activity.
The synthesis of 14-hydroxy-14 beta-pregn-4-ene-3,20-dione (14 beta-hydroxyprogesterone) is described. This novel steroid is about 10 times more potent than progesterone and one-tenth as potent as ouabagenin in an [3H]ouabain radioligand binding assay and is the first in a series of progesterone congeners that interact at the cardiac glycoside receptor both to possess the C/D cis ring junction and to enhance contractility of isolated cardiac tissue.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D004285:Dogs; D005260:Female; D006168:Guinea Pigs; D006908:Hydroxyprogesterones / Q000096:biosynthesis / Q000378:metabolism / Q000494:pharmacology*; D008297:Male; D009089:Mucor / Q000378:metabolism; D009200:Myocardial Contraction / Q000187:drug effects*; D010042:Ouabain / Q000031:analogs & derivatives / Q000378:metabolism / Q000494:pharmacology; D011374:Progesterone / Q000378:metabolism; D011955:Receptors, Drug / Q000378:metabolism*; D000254:Sodium-Potassium-Exchanging ATPase; D013268:Stimulation, Chemical
D006908:Hydroxyprogesterones; D011955:Receptors, Drug; C027082:digitalis receptor; C053404:14-hydroxyprogesterone; D011374:Progesterone; D010042:Ouabain; D000254:Sodium-Potassium-Exchanging ATPase; C008721:ouabagenin