Synthesis and antimineralocorticoid activities of some 6-substituted 7 alpha-carboalkoxy steroidal spirolactones. 1977

R M Weier, and L M Hofmann

Several analogues of the previously reported steroidal spirolactone 1a were synthesized. These analogues bear C-6 substituents and include the 6beta-deuterio (1c), the 6beta-bromo (1d), the 6beta-methyl (1e), and the 6alpha-methyl (7) compounds. The 6beta-hydroxy compound 1b, a human and animal metabolite of 1a, was also synthesized. On subcutaneous administration to adrenalectomized rats, all these compounds exhibited the ability to block the effects of administered deoxycorticosterone acetate (DCA) (MED less than or equal to 0.58 mg). Only 7 failed to show anti-DCA effects at the standard test level on oral administration. None was significantly superior in potency to the parent compound 1a.

UI MeSH Term Description Entries
D008297 Male Males
D003900 Desoxycorticosterone A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE 21-Hydroxyprogesterone,Cortexone,Deoxycorticosterone,Desoxycortone,11-Decorticosterone,21-Hydroxy-4-pregnene-3,20-dione,11 Decorticosterone,21 Hydroxy 4 pregnene 3,20 dione,21 Hydroxyprogesterone
D003903 Deuterium The stable isotope of hydrogen. It has one neutron and one proton in the nucleus. Deuterons,Hydrogen-2,Hydrogen 2
D000315 Adrenalectomy Excision of one or both adrenal glands. (From Dorland, 28th ed) Adrenalectomies
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013148 Spironolactone A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827) Spirolactone,Aldactone,Aldactone A,Aquareduct,Duraspiron,Espironolactona Alter,Espironolactona Mundogen,Flumach,Frumikal,Jenaspiron,Novo-Spiroton,Practon,SC-9420,Spiractin,Spiro L.U.T.,Spiro Von Ct,Spirobeta,Spirogamma,Spirolang,Spirono-Isis,Spironone,Spirospare,Veroshpiron,Verospiron,Verospirone,Ct, Spiro Von,Novo Spiroton,NovoSpiroton,SC 9420,SC9420,Spirono Isis,Von Ct, Spiro
D051381 Rats The common name for the genus Rattus. Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus

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