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Enalapril

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Enalapril Basic information

Product Name:
Enalapril
Synonyms:
  • ENALAPRIL
  • (s)-1-(n-(1-(ethoxycarbonyl)-3-phenylpropyl)-l-alanyl)-l-proline
  • 1-(n-((s)-1-carboxy-3-phenylpropyl)-l-alanyl)-l-proline 1'-ethyl ester
  • 1-[2-(1-ETHOXYCARBONYL-3-PHENYL-PROPYL)AMINOPROPANOYL]PYRROLIDINE-2-CARBOXYLIC ACID
  • N-[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline
  • Renitec
  • Vasotec
  • Enalapril Maleate USP24
CAS:
75847-73-3
MF:
C20H28N2O5
MW:
376.45
Product Categories:
  • Angiotensin
Mol File:
75847-73-3.mol
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Enalapril Chemical Properties

Melting point:
142-147℃
Boiling point:
582.4±50.0 °C(Predicted)
Density 
1.204±0.06 g/cm3(Predicted)
RTECS 
TW3665500
storage temp. 
Inert atmosphere,2-8°C
pka
pKa 2.97 (H2O t=25.0)(Approximate);5.35(H2O t=25.0)(Approximate)
Water Solubility 
Soluble in water at 25mg/ml
CAS DataBase Reference
75847-73-3(CAS DataBase Reference)
EPA Substance Registry System
L-Proline, N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl- (75847-73-3)
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Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
Hazardous Substances Data
75847-73-3(Hazardous Substances Data)

MSDS

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Enalapril Usage And Synthesis

Uses

angiotensin converting enzyme inhibitor

Uses

It is used for hypertension and chronic cardiac insufficiency.

Uses

Enalapril is used in the treatment of hypertension, diabetic nephropathy, and some types of chronic heart failure. It has been proven to protect the function of the kidneys in hypertension, heart failure, and diabetes, and may be used in the absence of hypertension for its kidney protective effects. It is widely used in chronic kidney failure.

Definition

ChEBI: A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).

Mechanism of action

Like captopril, enalapril selectively suppresses the rennin–angiotensin–aldosterone system, inhibits angiotensin-converting enzyme, and prevents conversion of angiotensin I into angiotensin II.

Chemical Synthesis

Enalapril, (S)-1-[N-[1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline (22.7.12), is synthesized by reacting the benzyl ester of L-alanyl-L-proline with the ethyl ester of 3-benzoylacrylic acid, which forms the product 22.7.11, the reduction of which with hydrogen using a Raney nickel catalyst removes the protective benzyl group, giving the desired enalapril (22.7.12) [24]. Alternative methods of syntheses have also been proposed.

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