alacepril

Alacepril (INN) is an ACE inhibitor medication indicated as a treatment for hypertension. The medication metabolizes to captopril and desacetylalacepril. Alacepril is primarily used to treat hypertension, and in some cases, renovascular hypertension. It's often combined with other medications, particularly other blood pressure lowering classes of medications like thiazide diuretics to maximize its effectiveness.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 477316241
Drug.IUPAC_name: (2S)-2-[[(2S)-1-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid | image = Alacepril.svg | image_class = skin-invert-image | tradename = | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = Rx-only | routes_of_administration = Oral | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 74258-86-9 | ATC_prefix = none | ATC_suffix = | ATC_supplemental = | PubChem = 71992 | ChEMBL_Ref = | ChEMBL = 2103775 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 64993 | UNII_Ref = | UNII = X39TL7JDPF | KEGG_Ref = | KEGG = D01900 | chemical_formula = | C=20 | H=26 | N=2 | O=5 | S=1 | smiles = C[C@H](CSC(=O)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O | StdInChI_Ref = | StdInChI = 1S/C20H26N2O5S/c1-13(12-28-14(2)23)19(25)22-10-6-9-17(22)18(24)21-16(20(26)27)11-15-7-4-3-5-8-15/h3-5,7-8,13,16-17H,6,9-12H2,1-2H3,(H,21,24)(H,26,27)/t13-,16+,17+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = FHHHOYXPRDYHEZ-COXVUDFISA-N

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Research

94 papers

Pharmacodynamics of alacepril in healthy cats.Journal of feline medicine and surgery · 2017
Evaluation of Alacepril Administration in Canine Patent Ductus Arteriosus According to Plasma Chymase Activity.Animals : an open access journal from MDPI · 2024
Effects of high-dose alacepril on the renin-angiotensin-aldosterone system and autonomic nervous system function in healthy dogs.Veterinary research communications · 2025
Effects of the angiotensin-converting enzyme inhibitor alacepril in dogs with mitral valve disease.The Journal of veterinary medical science · 2018
Effects of high-dose alacepril on left atrial pressure and central aortic pressure in awake dogs with mitral valve regurgitation.Veterinary journal (London, England : 1997) · 2019

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Wikidata facts

Mass: 406.156

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Commons category: Alacepril
chemical formula: C₂₀H₂₆N₂O₅S
isomeric SMILES: C[C@H](CSC(=O)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O
canonical SMILES: CC(CSC(=O)C)C(=O)N1CCCC1C(=O)NC(CC2=CC=CC=C2)C(=O)O

Sources (2)

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Article

4 sections

Contents

Mechanism of action
Synthesis
References
External links

== Mechanism of action == In vivo, when alacepril undergoes deacetylation, it loses a molecule similar to the amino acid phenylalanine which transforms it into captopril. Captopril then provides its blood pressure lowering effect through two ways. First, it inhibits the conversion of angiotensin 1, a precursor molecule, to angiotensin II, a vasoconstrictor that narrows blood vessels. Secondly, captopril prevents the breakdown of bradykinin, a vasodilator peptide that naturally relaxes blood vessels. ==Synthesis== [[File:Alacepril synthesis.svg|thumb|center|500px|Thieme ChemDrug Synthesis: Patents: ~65%:]] Amide formation between S-Acetylcaptopril [64838-55-7] (1) and (S)-tert-Butyl 2-amino-3-phenylpropanoate [16874-17-2] (2) gives PC86595505 (3). Deprotection with trifluoroacetic acid completed the synthesis of alacepril (4). == References ==