ChemicalBook CAS DataBase List 75847-73-3

75847-73-3

Name	Enalapril
CAS	75847-73-3
Molecular Formula	C20H28N2O5
MDL Number	MFCD00865774
Molecular Weight	376.45
MOL File	75847-73-3.mol

Synonyms

1-[2-(1-ETHOXYCARBONYL-3-PHENYL-PROPYL)AMINOPROPANOYL]PYRROLIDINE-2-CARBOXYLIC ACID 1-(n-((s)-1-carboxy-3-phenylpropyl)-l-alanyl)-l-proline 1'-ethyl ester ENALAPRIL (s)-1-(n-(1-(ethoxycarbonyl)-3-phenylpropyl)-l-alanyl)-l-proline Renitec Vasotec Enalapril Maleate USP24 L-Proline, 1-[N-[1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-, (S)- L-Proline, N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl- (S)-1-[N-[1-(Ethoxyearbonyl)-3-phenylpropyl]-L-alanyl]-L-proline G1ioten Hipoartd (2S)-1-[(2S)-2-[[(2S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid (S)-N-[1-Ethoxycarbonyl)-3-phenylpropyl]-Ala-Pro (-)-1-[N-[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline 1-[N-[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline N-[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-Ala-L-Pro-OH N-[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-Ala-L-Pro-OH

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.	under inert gas (nitrogen or Argon) at 2-8°C
solubility	Soluble in DMSO
form	Powder
pka	pKa 2.97 (H2O t=25.0)(Approximate);5.35(H2O t=25.0)(Approximate)
color	White to off-white
Water Solubility	Soluble in water at 25mg/ml
BCS Class	3
InChIKey	GBXSMTUPTTWBMN-XIRDDKMYSA-N
SMILES	C(O)(=O)[C@@H]1CCCN1C(=O)[C@H](C)N[C@H](C(OCC)=O)CCC1=CC=CC=C1
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)

Safety Data

Symbol(GHS)	GHS07,GHS08
Signal word	Warning
Hazard statements	H317-H361
Precautionary statements	P280
Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . less more
WGK Germany	3
Hazardous Substances Data	75847-73-3(Hazardous Substances Data)

Raw materials And Preparation Products

Hazard Information

Uses

angiotensin converting enzyme inhibitor

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.

Uses

It is used for hypertension and chronic cardiac insufficiency.

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.

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.

Synthesis_75847-73-3

in vivo

Enalapril (intraperitoneal injection, 0.03 mg/kg, once, 1 hour) reduces infarct volume due to middle cerebral artery occlusion and lower or higher doses are ineffective in Male NMRI mice^[4].

Animal Model:	Male NMRI mice 20-40 g^[4]
Dosage:	0.03 mg/kg
Administration:	Intraperitoneal injection; once
Result:	Reduced the area of middle cerebral artery infarction in mice at 0.03 mg/kg.

storage

Store at -20°C

Material Safety Data Sheet(MSDS)

Well-known Reagent Company Product Information

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