Small-molecule inhibitor: spirapril

Name

Common name: spirapril
Other names: Quadropril; Renormax; SCH 33844

Inhibition

History: Sprilapril was described by Sybertz et al. (1987).
Peptidases inhibited: Inhibits angiotensin-converting enzyme compound peptidase (ACE). K_i = 0.74 nM for rabbit lung ACE (Sybertz et al., 1987).
Mechanism: Inhibition is reversible.
Pharmaceutical relevance: Spriapril is used clinically as an ACE inhibitor.
DrugBank: DB01348

Chemistry

CID at PubChem: 5311447
ChEBI: 330124
Structure
Chemical/biochemical name: (8S)-7-[(2S)-2-[[(1S)-1-ethoxycarbonyl-3-phenyl-propyl]amino]propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
Formula weight: 466

Properties

Synthesis: Smith et al. (1989)

General

Inhibitor class: This is a compound in the carboxylate class of reversible metallopeptidase inhibitors. In these, the active site zinc of the enzyme is generally coordinated by a carboxylate of the inhibitor, and this interaction contributes to inhibitory potency. Reviewed by Patchett & Cordes (1985) and Powers & Harper (1986), pp. 268 - 277 (who provide a table of K_i values).