ChemicalBook--->CAS DataBase List--->75847-73-3

75847-73-3

75847-73-3 Structure

75847-73-3 Structure
IdentificationMore
[Name]

Enalapril
[CAS]

75847-73-3
[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
[Molecular Formula]

C20H28N2O5
[MDL Number]

MFCD00865774
[Molecular Weight]

376.45
[MOL File]

75847-73-3.mol
Chemical PropertiesBack Directory
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)Health Hazard (GHS08)
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 .
[WGK Germany ]

3
[Hazardous Substances Data]

75847-73-3(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl acetate-->Acetic acid-->Water-->Maleic anhydride-->Bromobenzene-->Formamide-->Propylene-->Ethyl acrylate-->Dicyclohexylcarbodiimide-->Maleic acid-->L-Proline-->Sodium cyanoborohydride-->D-Alanine-->Palladium carbon fine chemical catalyzer-->N-Hydroxysuccinimide-->Dowex(R) 50WX4 hydrogen form-->Ethyl 2-oxo-4-phenylbutyrate-->Enalapril maleate-->L-Alanyl-L-proline
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Enalapril(75847-73-3).msds
Hazard InformationBack Directory
[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
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

75847-73-3(sigmaaldrich)
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