Compound: labetalol
SMILES: O=C(N)c1c(O)ccc(c1)C(O)CNC(CCc2ccccc2)C
InChIKey: SGUAFYQXFOLMHL-UHFFFAOYSA-N
Synonyms: labetalol, 36894-69-6, Labetolol, Ibidomide, Albetol, Labetalolum, 2-Hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)amino)ethyl)benzamide, AH 5158, 5-(1-Hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide, 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide, 3-Carboxamido-4-hydroxy-alpha-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol, AH-5158A FREE BASE, CHEBI:6343, SCH-15719W FREE BASE, 2-Hydroxy-5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)benzamide, R5H8897N95, Benzamide, 2-hydroxy-5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)-, DTXSID2023191, CHEBI:167638, 2-hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]benzamide, Benzamide, 2-hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-, 2-hydroxy-5-{1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl}benzamide, labetalolo, ApoLabetalol, Apo Labetalol, 2-Hydroxy-5-(1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl)benzamide, 2-hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)amino)ethyl)benzene-1-carboximidic acid, 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzene-1-carboximidic acid, RefChem:58510, DTXCID603191, C07AG01, AH5158, 253-258-3, Labetalolum [INN-Latin], 2-hydroxy-5-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]benzamide, Labetalol (INN), MFCD00242941, LABETALOL [INN], Labetalol [INN:BAN], R,S-Labetalol, HSDB 6537, EINECS 253-258-3, UNII-R5H8897N95, 36894-69-6 (free base), Labetalol (Standard), Amipress (Salt/Mix), Trandate (Salt/Mix), Normodyne (Salt/Mix), Spectrum_001607, LABETALOL [MI], LABETALOL [HSDB], Prestwick0_000277, Prestwick1_000277, Prestwick2_000277, Prestwick3_000277, Spectrum2_000863, Spectrum3_001581, Spectrum4_000184, Spectrum5_001010, LABETALOL [VANDF], CHEMBL429, Epitope ID:613438, EC 253-258-3, LABETALOL [WHO-DD], SCHEMBL4582, Lopac0_000687, BSPBio_000154, BSPBio_003142, KBioGR_000727, KBioSS_002087, DivK1c_000474, SPBio_000905, SPBio_002373, BPBio1_000170, GTPL7207, orb1705559, SCHEMBL29687428, BDBM25758, KBio1_000474, KBio2_002087, KBio2_004655, KBio2_007223, KBio3_002642, NINDS_000474, Labetalol hydrochloride (Salt/Mix), IDA16724, IDA16732, AH5158;Sch-15719W free base, EBC-26602, AKOS015908406, CCG-204772, DB00598, DS-4652, HY-121383R, SDCCGSBI-0050665.P004, IDI1_000474, NCGC00015595-03, NCGC00015595-04, NCGC00015595-06, NCGC00015595-07, NCGC00015595-12, NCGC00015595-14, NCGC00015595-19, NCGC00089800-02, AC-18747, SBI-0050665.P003, HY-121383, AB00053659, CS-0081835, NS00008578, C07063, C74903, D08106, AB00053659_13, EN300-1272609, L001344, Q958087, BRD-A07440155-003-05-6, BRD-A07440155-003-16-3, BRD-A07440155-003-25-4, 2-hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenyl-propyl)amino]ethyl]benzamide, 3-Carboxamido-4-hydroxy-.alpha.-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol, 32780-40-8
Theoretical properties:
molecular_formula: C19H24N2O3
molecular_weight: 328.4 g/mol
exact_mass: 328.17869263 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 8
heavy_atom_count: 24
topological_polar_surface_area: 95.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 5.78e-03 g/L
Descriptions:
pubchem: Labetalol is a diastereoisomeric mixture of approximately equal amounts of all four possible stereoisomers ((R,S)-labetolol, (S,R)-labetolol, (S,S)-labetalol and (R,R)-labetalol). It is an adrenergic antagonist used to treat high blood pressure. It has a role as a beta-adrenergic antagonist, an antihypertensive agent, an alpha-adrenergic antagonist and a sympatholytic agent. It contains a (S,S)-labetalol, a (R,S)-labetolol, a (S,R)-labetolol and a (R,R)-labetalol.
chebi: A member of the class of benzamides that is benzamide substituted by a hydroxy group at position 2 and by a 1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl group at position 5.
chembl: LABETALOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Labetalol is a medication used to treat high blood pressure and in long term management of angina. This includes essential hypertension, hypertensive emergencies, and hypertension of pregnancy. In essential hypertension it is generally less preferred than a number of other blood pressure medications. It can be given by mouth or by injection into a vein.
Common side effects include low blood pressure with standing, dizziness, feeling tired, and nausea. Serious side effects may include low blood pressure, liver problems, heart failure, and bronchospasm. Use appears safe in the latter part of pregnancy and it is not expected to cause problems during breastfeeding. It works by blocking the activation of β- and α-adrenergic receptors.
Labetalol was patented in 1966 and came into medical use in 1977. It is available as a generic medication. In 2023, it was the 232nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.