Name | Enalapril |
Synonyms | Renitec Amprace Vasotec ENALAPRIL Vaseretic Enalapril Enalapril Maleate USP24 N-[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline (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 N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline (2Z)-but-2-enedioate 1-[2-(1-ETHOXYCARBONYL-3-PHENYL-PROPYL)AMINOPROPANOYL]PYRROLIDINE-2-CARBOXYLIC ACID |
CAS | 75847-73-3 |
InChI | InChI=1/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1 |
Molecular Formula | C20H28N2O5 |
Molar Mass | 376.45 |
Density | 1.204±0.06 g/cm3(Predicted) |
Melting Point | 142-147℃ |
Boling Point | 582.4±50.0 °C(Predicted) |
Flash Point | 306°C |
Water Solubility | Soluble in water at 25mg/ml |
Vapor Presure | 2.1E-14mmHg at 25°C |
Appearance | Powder |
pKa | pKa 2.97 (H2O t=25.0)(Approximate);5.35(H2O t=25.0)(Approximate) |
Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
Refractive Index | 1.549 |
Physical and Chemical Properties | Enalapril Maleate: C20H28N2O5? C4H4O4. [76095-16-4]. White needle crystal or crystalline powder, odorless and tasteless. Soluble in water, slightly soluble in acetonitrile. Melting point 143-144.5 °c. [Α] D25-42.2 °(C = 1, methanol). Ph(1% aqueous solution) = 2.6. pKal3.0,pKa2(25 °c) 5.4. |
Use | Used in the treatment of hypertension, is an ACE inhibitor |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
WGK Germany | 3 |
RTECS | TW3665500 |
a-substituted phenylbutyrate ethyl ester and L-alanyl-L-proline dipeptide are condensed under the action of 4A molecular sieve, and then reduced with sodium cyanoborohydride to obtain enalapril. Enalapril maleate can be obtained by forming a salt with maleic acid. Alternatively, enalapril can be obtained by condensation of ethyl a-phenylbutyrate with L-alanyl-L-proline dipeptide in dimethylformamide solution under the action of triethylamine. It is also possible to acylate benzene with maleic anhydride to form β-benzoylacrylic acid. This was refluxed with absolute ethanol, benzene and concentrated sulfuric acid to give ethyl β-benzoylacrylate. The compound is mixed with alanine benzyl ester p-toluenesulfonate, anhydrous ethanol and triethylamine, stirred at room temperature, and the treated compound is reacted with sulfuric acid, glacial acetic acid and palladium-carbon catalyst, the obtained compound and N-hydroxysuccinimide are dissolved in dimethylformamide, dicyclohexylcarbodiimide is added under cooling in an ice bath, stirred at room temperature, and a dimethylformamide solution of L-proline tetramethylammonium salt is added, the reaction was followed by treatment to enalapril maleate.
developed by Merk Sharp 8L Dohme, Inc., was first launched in Germany in 1984. The angiotensin converting enzyme inhibitor (ACE-1) is the second marketed ACE-I in the world after captopril. The effect of treating hypertension is similar to that of captopril, but better than captopril, and the effect is slow and lasting. For primary, renal hypertension, renal vascular hypertension, malignant hypertension, etc., also applies to congestive heart failure, especially high renin, high blood calcium need long-term medication of hypertensive patients and digitalis, diuretic drug treatment invalid congestive heart failure, it can also be used for patients who cannot tolerate captopril.