Compound: Enalaprilat
SMILES: O=C(O)[C@H]1N(C(=O)[C@@H](N[C@H](C(=O)O)CCc2ccccc2)C)CCC1
InChIKey: LZFZMUMEGBBDTC-QEJZJMRPSA-N
Synonyms: Enalaprilat, 76420-72-9, Enalaprilate, Enalaprilatum, Enalapril diacid, Enalaprilat anhydrous, enalaprilat (anhydrous), N-[(1S)-1-carboxy-3-phenylpropyl]-L-alanyl-L-proline, Q508Q118JM, MK 422, CHEBI:4786, N-(1(S)-Carboxy-3-phenylpropyl)-L-alanyl-L-proline, NSC-760053, (2S)-1-[(2S)-2-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid, L-Proline, N-((1S)-1-carboxy-3-phenylpropyl)-L-alanyl-, L-Proline, N-[(1S)-1-carboxy-3-phenylpropyl]-L-alanyl-, CHEBI:59877, Enalapril diacid dihydrate anhydrous, N-((1S)-1-carboxy-3-phenylpropyl)-L-alanyl-L-proline, (2S)-1-((2S)-2-(((2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylic acid, RefChem:136738, MK422, 278-459-3, Enalapril diacid dihydrate, GV0O7ES0R3, Vasotec i.v., Enalapril acid, Enalaprilic acid, (S)-1-((S)-2-(((S)-1-Carboxy-3-phenylpropyl)amino)propanoyl)pyrrolidine-2-carboxylic acid, Enalaprilat [INN], MK-422, MFCD00865786, DTXSID0048975, 1-((2S)-2-{[(1S)-1-CARBOXY-3-PHENYLPROPYL]AMINO}PROPANOYL)-L-PROLINE, ((S)-1-carboxy-3-phenylpropyl)-L-alanyl-L-proline, (2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid, EAL, DTXCID301265905, ENALAPRILAT INHIBITOR, SMR000466359, CAS-76420-72-9, enalaprilat [Spanish], MK 421 diacid, CHEMBL577, Enalaprilate [French], Enalaprilatum [Latin], UNII-Q508Q118JM, NCGC00183129-01, (2S)-1-((2S)-2-(((1S)-1-CARBOXY-3-PHENYLPROPYL)AMINO)PROPANOYL)PYRROLIDINE-2-CARBOXYLIC ACID, (2S)-1-[(2S)-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]propanoyl]pyrrolidine-2-carboxylic acid, EINECS 278-459-3, Enalaprilate; Enalaprilic acid; MK 421 diacid, SCHEMBL37289, MLS000759476, MLS001424138, BIDD:GT0752, GTPL6332, orb1908989, Enalaprilat, analytical standard, Enalapril Maleate EP Impurity C, HY-B0231A, HMS2051H16, HMS2089P04, HMS2232B19, HMS3263O13, Pharmakon1600-01503833, Tox21_113430, Tox21_501036, BDBM50367254, EBC-26684, NSC760053, AKOS015840130, AKOS015892570, Tox21_113430_1, CCG-101042, DB09477, LP01036, NC00292, SDCCGSBI-0633781.P001, NCGC00164593-01, NCGC00164593-02, NCGC00164593-11, NCGC00261721-01, (2S)-1-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]propanoyl]pyrrolidine-2-carboxylic Acid (Enalaprilat), AS-13013, BP-41163, CS-0012359, E1302, NS00015409, EN300-123964, AB00698268-05, AB00698268-07, AB00698268-08, AB00698268_09, AB00698268_10, ENALAPRIL DIACID DIHYDRATE ANHYDROUS [MI], ENALAPRIL MALEATE IMPURITY C [EP IMPURITY], SR-01000763426, Q5375179, SR-01000763426-3, BRD-K99447003-335-02-5, BRD-K99447003-335-03-3, BRD-K99447003-335-04-1, BRD-K99447003-335-05-8, N-[(s)-1-carboxy-3-phenyl-propyl]-l-alanyl-l-proline, 1-(N-((S)-1-CARBOXY-3-PHENYLPROPYL)-L-ALANYL)-L-PROLINE, L-Proline, 1-(N-(1-carboxt-3-phenylpropyl)-L-alanyl)-, (S)-, L-PROLINE, 1-(N-(1-CARBOXY-3-PHENYLPROPYL)-L-ALANYL)-, (S)-, (S)-1-((S)-2-(((S)-1-Carboxy-3-phenylpropyl)amino)propanoyl)pyrrolidine-2-carboxylicacid, (2S)-1-[(2S)-2-[[(1S)-1-CARBOXY-3-PHENYL-PROPYL]AMINO]PROPANOYL]PYRROLIDINE-2-CARBOXYLIC ACID
Theoretical properties:
molecular_formula: C18H24N2O5
molecular_weight: 348.4 g/mol
exact_mass: 348.16852187 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 8
heavy_atom_count: 25
topological_polar_surface_area: 107 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 148 - 151 °C
Descriptions:
{"pubchem": "Enalaprilat (anhydrous) is enalapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid. Enalaprilat is an angiotensin-converting enzyme (ACE) inhibitor and is used (often in the form of its prodrug, enalapril) in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients. Unlike enalapril, enalaprilat is not absorbed by mouth but is given by intravenous injection, usually as the dihydrate. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor and an antihypertensive agent. It is a dicarboxylic acid and a dipeptide.", "chebi": "Enalapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid. Enalaprilat is an angiotensin-converting enzyme (ACE) inhibitor and is used (often in the form of its prodrug, enalapril) in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients. Unlike enalapril, enalaprilat is not absorbed by mouth but is given by intravenous injection, usually as the dihydrate.", "chembl": "ENALAPRILAT ANHYDROUS is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Enalaprilat is the active metabolite of enalapril. It is the first dicarboxylate-containing ACE inhibitor and was developed partly to overcome these limitations of captopril. The thiol functional group of captopril was replaced with a carboxylic acid group, but additional modifications were required to achieve a potency similar to captopril.\nEnalaprilat, however, had a problem of its own. The consequence of the structural modifications was that its ionisation characteristics do not allow for sufficient GI absorption. Thus, enalaprilat was only suitable for intravenous administration. This was overcome by the monoesterification of enalaprilat with ethanol to produce enalapril.\nAs a prodrug, enalapril is hydrolyzed in vivo to the active form enalaprilat by various esterases. Peak plasma enalaprilat concentrations occur 2 to 4 hours after oral enalapril administration. Elimination thereafter is biphasic, with an initial phase which reflects renal filtration (elimination half-life 2 to 6 hours) and a subsequent prolonged phase (elimination half-life 36 hours), the latter representing equilibration of drug from tissue distribution sites.\nThe prolonged phase does not contribute to drug accumulation on repeated administration but is thought to be of pharmacological significance in mediating drug effects. Renal impairment [particularly creatinine clearance <20 mL/min (<1.2 L/h)] results in significant accumulation of enalaprilat and necessitates dosage reduction. Accumulation is probably the cause of reduced elimination in healthy elderly individuals and in patients with concomitant diabetes, hypertension and heart failure."}