Structure via PubChem · Public domain (PubChem)
alacepril
Sign in to saveAlacepril (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
via Wikipedia infobox
Chemical data
- Formula
- C20H26N2O5S
- Molecular weight
- 406.5 g/mol
- IUPAC name
- (2S)-2-[[(2S)-1-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid
- SMILES
- C[C@H](CSC(=O)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O
- InChIKey
- FHHHOYXPRDYHEZ-COXVUDFISA-N
- XLogP
- 2.1
- Polar surface area
- 129 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
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
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 406.156
Show 5 more facts
- 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
- subject has role
- ACE inhibitor
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Mechanism of action
- Synthesis
- References
- External links
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.
== 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 ==
Excerpted from Wikipedia’s “alacepril” article, available under the CC BY-SA 4.0 licence.