Enalapril

Base Information

• Chemical Name: Enalapril
• CAS No.: 75847-73-3
• Deprecated CAS: 172964-46-4,77549-58-7
• Molecular Formula: C20H28N2O5
• Molecular Weight: 376.453
• Hs Code.: 2933.90
• European Community (EC) Number: 616-271-9
• UNII: 69PN84IO1A
• DSSTox Substance ID: DTXSID5022982
• Nikkaji Number: J240.110J
• Wikipedia: Enalapril
• Wikidata: Q422185
• NCI Thesaurus Code: C62027
• RXCUI: 3827
• Pharos Ligand ID: K5LQU66Q1KCJ
• Metabolomics Workbench ID: 42915
• ChEMBL ID: CHEMBL578
• Mol file: 75847-73-3.mol

Synonyms:Enalapril;Enalapril Maleate;Maleate, Enalapril;MK 421;MK-421;MK421;Renitec;Renitek

Chemical Property of Enalapril

Chemical Property:

• Vapor Pressure: 2.1E-14mmHg at 25°C
• Melting Point: 143-144.5oC
• Refractive Index: 1.549
• Boiling Point: 582.4 °C at 760 mmHg
• PKA: pKa 2.97 (H2O t=25.0)(Approximate);5.35(H2O t=25.0)(Approximate)
• Flash Point: 306 °C
• PSA: 95.94000
• Density: 1.204 g/cm³
• LogP: 1.93340
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Soluble in water at 25mg/ml
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 376.19982200
• Heavy Atom Count: 27
• Complexity: 519

Purity/Quality:

99% ^*data from raw suppliers

Enalapril AldrichCPR ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Angiotensin-Converting Enzyme Inhibitors
• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CCCC2C(=O)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(=O)O
• Recent ClinicalTrials: Efficacy and Safety of Sacubitril/Valsartan Compared With Enalapril on Morbidity, Mortality, and NT-proBNP Change in Patients With CCC
• Recent EU Clinical Trials: Pulmonary REsistance modification under treatment with Sacubitil/valsartaN in paTients with HeartFailure with reduced ejection fraction
• Recent NIPH Clinical Trials: Study to Evaluate Safety, Tolerability, Pharmacokinetics and Pharmacodynamics of LCZ696 Followed by a 52-week Study of LCZ697 Compared With Enalapril in Pediatric Patients With Heart Failure
• Uses: angiotensin converting enzyme inhibitor It is used for hypertension and chronic cardiac insufficiency. 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.

Technology Process of Enalapril

There total 26 articles about Enalapril 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: 92.9%

N-succinimidyl (2S)-2-{N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propionate (89371-34-6) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → enalapril (75847-73-3)

Guidance literature:

With triethylamine; In ethanol; water; for 16h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00084-2

Reference yield: 85.0%

N--L-alanyl>-L-proline tert butyl ester (108428-39-3) → enalapril (75847-73-3)

Guidance literature:

With trifluoroacetic acid; for 3h; Ambient temperature;

DOI:10.1248/cpb.37.280

Reference yield: 70.0%

2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) + L-alanyl-L-proline (13485-59-1) → enalapril (75847-73-3)

Guidance literature:

With hydrogen; In ethanol; at 45 ℃; under 735.074 - 772.577 Torr; Solvent; Reagent/catalyst; Catalytic behavior; Kinetics;

DOI:10.1007/s11172-020-2979-0

upstream raw materials:

2-oxo-4-phenylbutanoic acid ethyl ester

L-alanyl-L-proline

N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester

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

Downstream raw materials:

(S)-2-((3S,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid ethyl ester

enalaprilic acid

enalapril sodium salt

enalaprilate

Refernces

• 1、 Slavinska,Sile,Chipens,Balodis,Rozenthal,Venteris,Lukevics. "Asymmetric reductive alkylation of alanylproline by the ethyl esters of 4-substituted 2-oxobutenoic acids". . p. 1579 - 1583. Retrieved 2003.
• 2、 Tungler, Antal,Szabados, Erika. "Overcoming Problems at Elaboration and Scale-up of Liquid-Phase Pd/C Mediated Catalytic Hydrogenations in Pharmaceutical Production". . p. 1246 - 1251. Retrieved 2016/07/23.
• 3、 -. "A PROCESS FOR THE PREPARATION OF COMPOUNDS HAVING AN ACE INHIBITORY ACTION". Page 9. . Retrieved 2008/06/13.