Enalaprilat

Base Information

• Chemical Name: Enalaprilat
• CAS No.: 76420-72-9
• Molecular Formula: C18H24N2O5
• Molecular Weight: 348.399
• Hs Code.: 2933990090
• European Community (EC) Number: 278-459-3
• NSC Number: 760053
• UNII: Q508Q118JM
• DSSTox Substance ID: DTXSID0048975
• Nikkaji Number: J21.388H
• Wikipedia: Enalaprilat
• Wikidata: Q5375179
• NCI Thesaurus Code: C76135
• RXCUI: 1545989
• Pharos Ligand ID: NVHP63K624ML
• Metabolomics Workbench ID: 49999
• ChEMBL ID: CHEMBL577
• Mol file: 76420-72-9.mol

Synonyms:1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline dihydrate;Enalaprilat;Enalaprilat Anhydrous;Enalaprilat Citrate, Anhydrous;Enalaprilat Dihydrate;Enalaprilat, (R)-Isomer, Anhydrous;Enalaprilic Acid;MK 422;MK-422;MK422;Pres iv;Vasotec;Xanef

Chemical Property of Enalaprilat

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 2.71E-15mmHg at 25°C
• Melting Point: 148-151 °C
• Boiling Point: 601 °C at 760 mmHg
• PKA: pKa 2.30 (Uncertain);3.39 (Uncertain)
• Flash Point: 317.3 °C
• PSA: 106.94000
• Density: 1.286±0.06 g/cm3(Predicted)
• LogP: 1.45490
• Storage Temp.: 2-8°C
• Solubility.: Very slightly soluble or slightly soluble in water, sparingly soluble in methanol, practically insoluble in acetonitrile.
• Water Solubility.: Soluble in water with heating (~60°C)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 348.16852187
• Heavy Atom Count: 25
• Complexity: 490

Purity/Quality:

98% ^*data from raw suppliers

Enalaprilat analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)N1CCCC1C(=O)O)NC(CCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N[C@@H](CCC2=CC=CC=C2)C(=O)O
• Recent ClinicalTrials: Effect of DPP4 Inhibition on Vasoconstriction
• Description: Enalaprilat 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.
• Uses: Enalapril 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. Active metabolite of Enalapril. A nonsulfhydryl dipeptide angiotensin converting enzyme (ACE) inhibitor primary hypertension

Technology Process of Enalaprilat

There total 12 articles about Enalaprilat which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

enalapril (75847-73-3) → enalaprilate (76420-72-9)

Guidance literature:

With sodium hydroxide; for 24h; Ambient temperature;

DOI:10.1248/cpb.37.280

Reference yield:

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride (84793-24-8) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2,122076-80-6) + enalaprilate (76420-72-9) + enalapril (75847-73-3) + (S)-2-((3S,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid ethyl ester (115729-52-7)

Guidance literature:

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride; L-proline; In water; ethyl acetate; at 19 - 20 ℃; for 5h; pH=10 - 11;

at 30 ℃; for 0.166667h; pH=4.3 - 4.7;

Reference yield:

Amprace (76095-16-4,1356932-13-2) → enalaprilate (76420-72-9)

Guidance literature:

With sodium hydroxide; In water; Ambient temperature;

DOI:10.1021/jo00189a036

upstream raw materials:

Amprace

enalapril

N--L-alanyl>-L-proline tert butyl ester

3-phenyl-propionaldehyde

Refernces

• 1、 Van Antwerpen, Pierre,Legssyer, Ilham,Zouaoui Boudjeltia, Karim,Babar, Sajida,Moreau, Patrick,Moguilevsky, Nicole,Vanhaeverbeek, Michel,Ducobu, Jean,Neve, Jean. "Captopril inhibits the oxidative modification of apolipoprotein B-100 caused by myeloperoxydase in a comparative in vitro assay of angiotensin converting enzyme inhibitors". . p. 31 - 36. Retrieved 2006.
• 2、 -. "Process for preparing pharmacologically acceptable salt of N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl amino acids". Example 1. . Retrieved 2008/06/13.