Spirapril

Spirapril is an azaspiro compound resulting from the formal condensation of the amino group of (8S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid with the carboxy group of N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanine. It is a prodrug for the antihypertensive drug spiraprilat. Among its listed roles, it functions as a EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an antihypertensive agent and a prodrug. It is a tertiary carboxamide, an ethyl ester, an azaspiro compound, a dicarboxylic acid monoester, a dipeptide, a pyrrolidinecarboxylic acid, a secondary amino compound and a dithioketal. Functionally, it is related to spiraprilat. Spirapril is an ACE inhibitor antihypertensive drug used to treat hypertension. Spirapril is converted to the active spiraprilat after administration. ACE inhibitors are used mainly in treatment of hypertension and congestive heart failure. Spirapril is a prodrug and non-sulfhydryl angiotensin converting enzyme (ACE) inhibitor with antihypertensive activity. Spirapril is converted in the body to its active metabolite spiraprilat. Spiraprilat competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II and results in vasodilation. Spiraprilat also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow. It is grouped under the following drug class(es): ACE Inhibitors. The directory classifies it as a discontinued API with a synthetic source/manufacturing origin. Other names for this substance include Espirapril and Spiraprilum. Its PubChem CID is 5311447.

CAS No 83647-97-6
Molecular Formula C22H30N2O5S2
Molecular Weight 466.6 g/mol
Synonyms (8S)-7-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid

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