spirapril   Click here for help

GtoPdb Ligand ID: 6575

Synonyms: Renormax® | SCH-33844
Approved drug
spirapril is an approved drug (FDA (1994))
Compound class: Synthetic organic
Comment: ACE inhibitor prodrug metabolised to spiraprilat
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 146.54
Molecular weight 466.16
XLogP 2.97
No. Lipinski's rules broken 0
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Canonical SMILES CCOC(=O)C(NC(C(=O)N1CC2(CC1C(=O)O)SCCS2)C)CCc1ccccc1
Isomeric SMILES CCOC(=O)[C@@H](N[C@H](C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2)C)CCc1ccccc1
InChI InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18-/m0/s1
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Summary of Clinical Use Click here for help
Used in the treatment of hypertension and congestive heart failure. Marketing authorisation by the US FDA has been discontinued. There is no information regarding approval for clinical use of this drug on the European Medicines Agency website. Other national approval agencies may continue to grant marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Metabolised to the active form spiraprilat, which inhibits angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. This in turn reduces the vasoconstrictive effects of angiotensin II leading to a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms leading to decreased vasopressor activity and decreased aldosterone secretion.