Compound: lisinopril
SMILES: O=C(O)[C@H]1N(C(=O)[C@@H](N[C@H](C(=O)O)CCc2ccccc2)CCCCN)CCC1
InChIKey: RLAWWYSOJDYHDC-BZSNNMDCSA-N
Synonyms: lisinopril, 76547-98-3, Prinivil, Zestril, Lisinopril anhydrous, Lysinopril, Carace, Novatec, Lisinoprilum, Lisinoprilum [Latin], Qbrelis, 7Q3P4BS2FD, MK-521, [N2-[(S)-1-CARBOXY-3-PHENYLPROPYL]-L-LYSYL-L-PROLINE, N-(1(S)-Carboxy-3-phenylpropyl)-L-lysyl-L-proline, N2-((S)-1-Carboxy-3-phenylpropyl)-L-lysyl-L-proline, (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid, L-Proline, N2-((1S)-1-carboxy-3-phenylpropyl)-L-lysyl-, DTXSID6040537, (S)-1-(N(2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-L-proline, CHEBI:43755, Lisinoprilum (Latin), L-Proline, 1-(N2-(1-carboxy-3-phenylpropyl)-L-lysyl)-, (S)-, NSC-751176, NSC-758151, (2S)-1-[(2S)-6-amino-2-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic acid, L-PROLINE, 1-(N(SUP 2)-(1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL)-, 1-(N(SUP 2)-((S)-1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL)-L-PROLINE, (2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid, (N2-((S)-1-carboxy-3-phenylpropyl)-L-lysyl-L-proline, L-Proline, N2-[(1S)-1-carboxy-3-phenylpropyl]-L-lysyl-, Lisinoril, Lisopress, (2S)-1-((2S)-6-amino-2-(((1S)-1-carboxy-3-phenylpropyl)amino)hexanoyl)pyrrolidine-2-carboxylic acid, (2S)-1-((2S)-6-amino-2-(((2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl)amino)hexanoyl)pyrrolidine-2-carboxylic acid, L-Proline, 1-(N2-(1-carboxy-3-phenylpropyl)-L-lysyl)-, dihydrate, (S)-, RefChem:5952, L-Proline, 1-(N(sup 2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-, dihydrate, (S)-, DTXCID4020537, C09AA03, N2-((1S)-1-Carboxy-3-phenylpropyl)-L-lysyl-L-proline, Dihydrate, 278-488-1, E7199S1YWR, Ranolip, Linopril, Tensopril, Acercomp, Inhibril, Lisipril, Noperten, Presiten, Sinopril, Acerbon, Vivatec, Coric, 83915-83-7, Alapril, Inopril, Lisinal, Lisoril, Lispril, Sinopryl, Cipral, Cipril, Linvas, Lipril, Longes, Loril, Prinil, Tensyn, Tersif, Hipril, Lisinopril (INN), Lisinopril [INN], (S)-1-((S)-6-Amino-2-(((S)-1-carboxy-3-phenylpropyl)amino)hexanoyl)pyrrolidine-2-carboxylic acid, Zestril (TN), MFCD00214086, C21H31N3O5, LPR, (S)-1-(N2-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline, Nanopril, CHEMBL1237, (S)-Lisinopril Dihydrate, N~2~-[(1S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline, Lizinopril, Diroton, Lisitec, Lisopril, Listril, Lizonoton, Optimon, Prinvil, Skopryl, Vitopril, Amicor, Doneka, Irumed, Laaven, MLS002154258, N2-[(1S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline, MK 521, MK 522, SMR000544473, CCRIS 3568, SMR001233519, EINECS 278-488-1, UNII-7Q3P4BS2FD, BRN 4276619, L-Proline, 1-(N2-(1-carboxy-3-phenylpropyl)-L-lysyl)-, lysinopryl, (S)-1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl]-L-proline, Zestoretic;, Acercomp;, Prinivil;, Prinzide;, Acecomb;, Acerbon;, Alapril;, Novatec;, Novazyd;, Vivatec;, Carace;, Longes;, HSDB 6852, Coric;, (S)-1-(N(sup 2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline, (S)-1-[(S)-6-Amino-2-[[(S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic Acid, (S)-1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl]-L-proline dihydrate, Lisinopril (Zestril), 1-(N2-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline, Spectrum_000497, LISINOPRIL [MI], (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid;hydrate, Prestwick0_000301, Prestwick1_000301, Prestwick2_000301, Prestwick3_000301, Spectrum2_001456, Spectrum3_000941, Spectrum4_001040, Spectrum5_000995, LISINOPRIL [WHO-DD], SCHEMBL15680, BSPBio_000262, KBioGR_001599, KBioSS_000977, MLS001306436, MLS001306481, BIDD:GT0755, DivK1c_001037, SPECTRUM1501217, SPBio_001351, SPBio_002481, BPBio1_000290, GTPL6360, ICI-209K, orb1306371, BDBM66979, HMS503O15, KBio1_001037, KBio2_000977, KBio2_003545, KBio2_006113, KBio3_002002, N(2)-[(1S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline, cid_22887897, NINDS_001037, HMS1921B14, HMS2090O14, HMS2092L21, HMS2850N20, Pharmakon1600-01501217, 1-[Nalpha-[(S)-1-Carboxy-3-phenylpropyl]-L-lysyl]-L-proline, BDBM50367879, CCG-39190, DL-434, EBC-02057, NSC751176, NSC758151, s2076, AKOS015836369, AKOS015894970, L-Proline, 1-(N(sup 2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-, (S)-, DB00722, IDI1_001037, NCGC00179623-01, NCGC00179623-07, (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenyl-propyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid, HY-18206, SY468011, SBI-0051692.P002, L0220, NS00009977, C76449, D08131, AB00052250-13, AB00052250_14, AB00052250_15, Q412208, SR-05000001786, SR-05000001786-1, BRD-K67966701-001-10-8, BRD-K67966701-001-11-6, BRD-K67966701-001-12-4, BRD-K67966701-335-03-5, Z1515376765, N-[N2 (1(S)-carboxy-3-phenylpropyl)-L-lysyl]-L-proline, N-[N2 -(1(S)-carboxy-3-phenylpropyl)-L-lysyl]-L-proline, Lisinopril Dihydrate Working Standard (Secondary Reference Standard), (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenyl-propyl]amino]hexanoyl]proline;hydrate, (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]-1-oxohexyl]-2-pyrrolidinecarboxylic acid;hydrate, (2S)-1-[(2S)-6-azanyl-2-[[(2S)-1-oxidanyl-1-oxidanylidene-4-phenyl-butan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic acid;hydrate
Theoretical properties:
molecular_formula: C21H31N3O5
molecular_weight: 405.5 g/mol
exact_mass: 405.22637110 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 12
heavy_atom_count: 29
topological_polar_surface_area: 133 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Lisinopril is a dipeptide. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor. It contains a L-lysine residue and a L-prolino group.
chembl: LISINOPRIL ANHYDROUS is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Lisinopril is a medication belonging to the drug class of angiotensin-converting enzyme (ACE) inhibitors and is used to treat hypertension (high blood pressure), heart failure, and heart attacks. For high blood pressure it is usually a first-line treatment. It is also used to prevent kidney problems in people with diabetes mellitus. Lisinopril is taken orally (swallowed by mouth). Full effect may take up to four weeks to occur.
Common side effects include headache, dizziness, feeling tired, cough, nausea, and rash. Serious side effects may include low blood pressure, liver problems, hyperkalemia (high blood potassium), and angioedema. Use is not recommended during the entire duration of pregnancy as it may harm the baby. Lisinopril works by inhibiting the renin–angiotensin–aldosterone system.
Lisinopril was patented in 1978 and approved for medical use in the United States in 1987. It is available as a generic medication. In 2023, it was the fourth most commonly prescribed medication in the United States, with more than 76 million prescriptions. It is available in combination with amlodipine (as lisinopril/amlodipine) and in combination with hydrochlorothiazide (as lisinopril/hydrochlorothiazide).