Enalaprilat

Enalaprilat Basic information
Product Name:Enalaprilat
Synonyms:ENALAPRILAT HYDRATE;ENALAPRILAT USP(CRM STANDARD);Enalaprilat (Enalapril EP Impurity C);Enalapril maleate impurity C;Enalapril acid;L-Proline, 1-[N-(1-carboxy-3-phenylpropyl)-L-alanyl]-, (S)-;N-[1(S)-Carboxy-3-phenylpropyl]-L-alanyl-L-proline;1-[N-[(S)-1-Carboxy-3-phenylpropyl]-L-alanyl]-L-proline
CAS:76420-72-9
MF:C18H24N2O5
MW:348.39
EINECS:278-459-3
Product Categories:Metabolite;Intermediates & Fine Chemicals;Active Pharmaceutical Ingredients;Various Metabolites and Impurities;Metabolites & Impurities;Pharmaceuticals
Mol File:76420-72-9.mol
Enalaprilat Structure
Enalaprilat Chemical Properties
Melting point 148-151°C
alpha D -67.0° (0.1M HCl)
Boiling point 601.0±55.0 °C(Predicted)
density 1.286±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility Very slightly soluble or slightly soluble in water, sparingly soluble in methanol, practically insoluble in acetonitrile.
form neat
pkapKa 2.30 (Uncertain);3.39 (Uncertain)
Water Solubility Soluble in water with heating (~60°C)
CAS DataBase Reference76420-72-9(CAS DataBase Reference)
EPA Substance Registry SystemL-Proline, N-[(1S)-1-carboxy-3-phenylpropyl]-L-alanyl- (76420-72-9)
Safety Information
Hazard Codes Xn
Risk Statements 22
WGK Germany 2
Enalaprilat Usage And Synthesis
DescriptionEnalaprilat is the diacid active metabolite of enalapril. As an injectable ACE inhibitor, it is reportedly useful in the treatment of uncomplicated accelerated hypertension and hypertensive emergencies. Enalaprilat is more effective in reducing blood pressure in the elderly than in the young, despite the fact that renin activity is lower in old age.
Chemical PropertiesWhite Crystalline Solid
OriginatorMerck (USA)
UsesEnalapril is a ACE (angiotensin-converting enzyme) inhibitor, suggested to be more potent than Captopril (sc-200566). Studies indicate that Enalapril downregulates the expression of IL-β, IL-6, and NF-κB. Further studies show that Enalapril upregulates the expression of VEGF and heme oxygenase-1. Enalaprilat reports demonstrate that the compound has some antioxidant activity, which does not include the PKC-NADPH oxidase pathway.
UsesActive metabolite of Enalapril. A nonsulfhydryl dipeptide angiotensin converting enzyme (ACE) inhibitor
Usesprimary hypertension
DefinitionChEBI: Enalapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid. Enalaprilat is an angiotensin-converting enzyme (ACE) inhibitor and is used (often in the form of its prodrug, enalapril) in the treatment of hypertension an heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients. Unlike enalapril, enalaprilat is not absorbed by mouth but is g ven by intravenous injection, usually as the dihydrate.
Brand nameVasotec (Biovail);Renitec.
Enalapril Enalapril maleate Ramipril Propionyl bromide Propyl gallate Enalaprilat ALTRENOGEST Hoe 288 Glycine cis-4-Hydroxy-L-proline Methyl 3-oxovalerate PHENYL VALERATE L-PROLINE-(4-3H(N)) AMINO ACIDS Propyl butyrate Phenylhydrazine L-Alanyl-L-Glutamine Pyrrolidine

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