Compound: enalapril
SMILES: O=C(O)[C@H]1N(C(=O)[C@@H](N[C@H](C(=O)OCC)CCc2ccccc2)C)CCC1
InChIKey: GBXSMTUPTTWBMN-XIRDDKMYSA-N
Synonyms: enalapril, 75847-73-3, Enalaprila, Enalaprilum, Bonuten, Olinapril, 69PN84IO1A, DTXSID5022982, C09AA02, (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, CHEBI:4784, DTXCID202982, (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid, L-Proline, N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-, (2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid, (S)-1-{(S)-2-[1-((S)-Ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid, L-Proline, N-((1S)-1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl-, Renitek, L-Proline, 1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-, (S)-, (2S)-1-((2S)-2-(((2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylic acid, (S)-1-((S)-2-(1-((S)-Ethoxycarbonyl)-3-phenyl-propylamino)-propionyl)-pyrrolidine-2-carboxylic acid, RefChem:6425, 616-271-9, Kinfil, Enalaprilum [INN-Latin], Enalaprila [INN-Spanish], Enalapril (INN), CHEMBL578, N-[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline, NCGC00021569-04, ENALAPRIL [INN], N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-L-proline, Enalapril Richet, Gadopril, HSDB 6529, CAS-75847-73-3, Enalapril [INN:BAN], analapril, UNII-69PN84IO1A, Enaladex, Enalapril, AldrichCPR, Spectrum_001307, ENALAPRIL [MI], SCHEMBL18, Prestwick3_000314, Spectrum2_001455, Spectrum3_001478, Spectrum4_000008, Spectrum5_001107, ENALAPRIL [VANDF], ENALAPRIL [MART.], ENALAPRIL [WHO-DD], BSPBio_000308, BSPBio_003035, KBioGR_000355, KBioSS_001787, BIDD:GT0751, DivK1c_000408, SPBio_001349, BPBio1_000340, GTPL6322, orb1308046, KBio1_000408, KBio2_001787, KBio2_004355, KBio2_006923, KBio3_002535, NINDS_000408, ((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl-L-proline, HMS2090E08, HY-B0331, Tox21_110872, BDBM50017129, EBC-26849, N-{(1S)-1-[(ethyloxy)carbonyl]-3-phenylpropyl}-L-alanyl-L-proline, AKOS025310615, Tox21_110872_1, DB00584, IDI1_000408, NCGC00016932-01, NCGC00021569-05, NCGC00021569-06, NCGC00021569-09, SBI-0051691.P002, CAS-76095-16-4, NS00008385, C06977, D07892, H10947, AB00053615-17, AB00053615-18, AB00053615_19, AB00053615_20, EN300-7481394, F808738, Q422185, BRD-K57545991-050-16-5, BRD-K57545991-050-23-1, BRD-K57545991-050-24-9, N-(1(S)-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline, N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-L-proline, N-[(2S)-1-Ethoxy-1-oxo-4-phenyl-2-butanyl]-L-alanyl-L-proline, Nalpha -[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-L-proline, (S)-1-[N-[1-(ethoxycarbonyl)-3- phenylpropyl]-L-alanyl]-L-proline, (SSS)1-[2-(1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid, 1-[2-(1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid, (2S)-1-[(2S)-2-[[(1S)-1-ethoxycarbonyl-3-phenyl-propyl]amino]propanoyl]pyrrolidine-2-carboxylic acid, (S)-1-((S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylic acid, (S)-1-((S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylicacid, (S)-1-((S)-2-((R)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)propanoyl)pyrrolidine-2-carboxylic acid, (S)-1-[(R)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid, (S,S,S)-1-[2-(1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid, 1-[2-(1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid (Enalapril), 1-[2-(1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid(enalapril), 2-[2-(1-Carboxy-3-phenyl-propylamino)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid(enalapril)
Theoretical properties:
molecular_formula: C20H28N2O5
molecular_weight: 376.4 g/mol
exact_mass: 376.19982200 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 10
heavy_atom_count: 27
topological_polar_surface_area: 95.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 143-144.5
Descriptions:
pubchem: Enalapril is 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). It has a role as a geroprotector, an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an antihypertensive agent and a prodrug. It is a dicarboxylic acid monoester and a dipeptide. It is functionally related to an enalaprilat (anhydrous).
chebi: A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen α to the carboxy group is substituted by the amino group of <small>L</small>-alanyl-<small>L</small>-proline (<i>S</i>-configuration).
chembl: ENALAPRIL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Enalapril, sold under the brand name Vasotec among others, is an ACE inhibitor medication used to treat high blood pressure, diabetic kidney disease, and heart failure. For heart failure, it is generally used with a diuretic, such as furosemide. It is given by mouth or by injection into a vein. Onset of effects are typically within an hour when taken by mouth and last for up to a day.
Common side effects include headache, tiredness, feeling lightheaded with standing, and cough. Serious side effects include angioedema and low blood pressure. Use during pregnancy is believed to result in harm to the baby. It is in the angiotensin-converting-enzyme (ACE) inhibitor family of medications.
Enalapril was patented in 1978, and came into medical use in 1984. It is on the World Health Organization's List of Essential Medicines. In 2023, it was the 195th most commonly prescribed medication in the United States, with more than 2 million prescriptions. It is available as a generic medicine.