Alacepril

Antihypertensive drug of the ACE inhibitor class
  • none
Legal statusLegal status
  • In general: ℞ (Prescription only)
Identifiers
  • (2S)-2-[[(2S)-1-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid
CAS Number
  • 74258-86-9 ☒N
PubChem CID
  • 71992
ChemSpider
  • 64993 checkY
UNII
  • X39TL7JDPF
KEGG
  • D01900 checkY
ChEMBL
  • ChEMBL2103775 ☒N
CompTox Dashboard (EPA)
  • DTXSID3048576 Edit this at Wikidata
Chemical and physical dataFormulaC20H26N2O5SMolar mass406.50 g·mol−13D model (JSmol)
  • Interactive image
  • C[C@H](CSC(=O)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O
InChI
  • InChI=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 checkY
  • Key:FHHHOYXPRDYHEZ-COXVUDFISA-N checkY
 ☒NcheckY (what is this?)  (verify)

Alacepril (INN) is an ACE inhibitor medication indicated as a treatment for hypertension. The medication metabolizes to captopril and desacetylalacepril.[1] 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.[2]

Mechanism of action

In vivo, when alacepril undergoes deacetylation, it loses a molecule similar to the amino acid phenylalanine which transforms it into captopril.[3] 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.[4]

References

  1. ^ "Alacepril". IBM Micromedex. 24 August 2010. Retrieved 23 June 2022.
  2. ^ "Alacepril". DrugCentral online drug compendium. Retrieved 13 April 2024. It is an angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. It used for the treatment of essential or renovascular hypertension (usually administered with other drugs, particularly thiazide diuretics).
  3. ^ Campese VM, Lakdawala RS (2017). "The Challenges of Blood Pressure Control in Dialysis Patients". In Nissenson AR, Fine RN (eds.). Handbook of dialysis therapy (5th ed.). Philadelphia, PA: Elsevier. doi:10.1016/B978-0-323-39154-2.00053-9. ISBN 978-0-323-39154-2. The sulfhydryl agents, such as alacepril, delapril, and moveltopril, are prodrugs and thus are converted to captopril in vivo. These sulfhydryl-containing compounds have a slower onset and longer duration of action than captopril.
  4. ^ Odaka C, Mizuochi T (September 2000). "Angiotensin-converting enzyme inhibitor captopril prevents activation-induced apoptosis by interfering with T cell activation signals". Clinical and Experimental Immunology. 121 (3): 515–522. doi:10.1046/j.1365-2249.2000.01323.x. PMC 1905724. PMID 10971519.

External links

  • Media related to Alacepril at Wikimedia Commons
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ACE inhibitors
("-pril")AIIRAs
("-sartan")Renin inhibitors
("-kiren")Dual ACE/NEP inhibitors
Neprilysin inhibitors
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ATRTooltip Angiotensin receptor
Combinations:
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