1.0 2009-07-30 17:58:59 UTC 2026-05-14 16:43:33 UTC T3D3517 Labetalol SmallMolecule Labetalol belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. This exogenous compound has the formula C19H24N2O3, an average molecular weight of 328.41 g/mol, and exists as a solid at room temperature. It is used as an antihypertensive agent, a sympatholytic agent, an alpha-adrenergic antagonist, and a beta-adrenergic antagonist. In terms of health effects, it is a treatment for hypertension (PMC10298655, PMC1429741) and eclampsia (PMC10298655, PMC8228929). Labetalol targets several proteins, including the alpha-1A, alpha-1B, and alpha-1D adrenergic receptors, as well as the beta-1, beta-2, and beta-3 adrenergic receptors, and heparanase. Labetalol HCl combines nonselective, competitive, beta-adrenergic blocking activity and selective, competitive, alpha-1-adrenergic blocking activity in a single substance. In man, the ratios of alpha- to beta-blockade have been estimated to be approximately 1:3 following oral administration and 1:7 following intravenous administration. Labetalol contains two asymmetric centers and exists as a molecular complex of two diastereoisomeric pairs, with the R,R' stereoisomer, dilevalol, comprising 25% of racemic labetalol. The compound is recorded in 13 sources, including beta blocking agents, drinking water, indoor air, food preservation, tobacco smoke filters, cigar cigarettes, other smoking requisites, and electrical and electronic equipment such as antennas, electrodes, conductive bodies, hybrid capacitors, and electrically stimulated smoking devices. Recorded exposure routes include oral, intravenous, and inhalation. Drug Synthetic Toxin Organic Compound Amine Amide Ester Drug Sympatholytic Sympathomimetic Antihypertensive Agent Adrenergic alpha-Antagonist Metabolite Adrenergic beta-Antagonist Synthetic Compound Adrenergic alpha-1 Receptor Antagonist Human Neurotoxin 3-Carboxamido-4-hydroxy-alpha-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol 5-(1-Hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide Albetol Labetalolum Labetolol Latol Normadate Normodyne Trandate C19H24N2O3 328.4055 328.178692644 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide labetalol 36894-69-6 CC(CCC1=CC=CC=C1)NCC(O)C1=CC(C(N)=O)=C(O)C=C1 InChI=1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24) SGUAFYQXFOLMHL-UHFFFAOYSA-N Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Salicylamides 1,2-aminoalcohols 1-hydroxy-2-unsubstituted benzenoids Amino acids and derivatives Aralkylamines Aromatic alcohols Benzamides Benzoyl derivatives Dialkylamines Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary carboxylic acid amides Secondary alcohols Vinylogous acids 1,2-aminoalcohol 1-hydroxy-2-unsubstituted benzenoid Alcohol Amine Amino acid or derivatives Aralkylamine Aromatic alcohol Aromatic homomonocyclic compound Benzamide Benzoyl Carboxamide group Carboxylic acid derivative Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Primary carboxylic acid amide Salicylamide Secondary alcohol Secondary aliphatic amine Secondary amine Vinylogous acid Aromatic homomonocyclic compounds benzamides secondary amino compound Detected and Not Quantified Exogenous Cytoplasm Extracellular Membrane Labetalol Pathway Labetalol Action Pathway SMP0000368 Labetalol B1-Adrenergic Cardiac Muscle Relaxation Action Pathway SMP0126203 Laβlol Drug Metabolism Pathway SMP0145329 Solid White powder. melting_point 188°C solubility 117 mg/L (at 25°C) logp 3.09 logp 1.73 ALOGPS logs -4.75 ALOGPS solubility 5.78e-03 g/l ALOGPS logp 1.89 ChemAxon pka_strongest_acidic 8.05 ChemAxon pka_strongest_basic 9.8 ChemAxon iupac 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide ChemAxon average_mass 328.4055 ChemAxon mono_mass 328.178692644 ChemAxon smiles CC(CCC1=CC=CC=C1)NCC(O)C1=CC(C(N)=O)=C(O)C=C1 ChemAxon formula C19H24N2O3 ChemAxon inchi InChI=1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24) ChemAxon inchikey SGUAFYQXFOLMHL-UHFFFAOYSA-N ChemAxon polar_surface_area 95.58 ChemAxon refractivity 94.72 ChemAxon polarizability 36.83 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Oral, parenteral (intravenous injection). Completely absorbed (100%) from the gastrointestinal tract with peak plasma levels occurring 1 to 2 hours after oral administration. The absolute bioavailability of labetalol is increased when administered with food. Labetalol has two asymmetric centers and therefore, exists as a molecular complex of two diastereoisomeric pairs. Dilevalol, the R,R' stereoisomer, makes up 25% of racemic labetalol. Labetalol HCl combines both selective, competitive, alpha-1-adrenergic blocking and nonselective, competitive, beta-adrenergic blocking activity in a single substance. In man, the ratios of alpha- to beta- blockade have been estimated to be approximately 1:3 and 1:7 following oral and intravenous (IV) administration, respectively. Beta-2-agonist activity has been demonstrated in animals with minimal beta-1-agonist (ISA) activity detected. In animals, at doses greater than those required for alpha- or beta- adrenergic blockade, a membrane stabilizing effect has been demonstrated. LD50 = 66 mg/kg (Rat, parental-intravenous) Primarily hepatic, undergoes significant first pass metabolism Route of Elimination: These metabolites are present in plasma and are excreted in the urine, and via the bile, into the feces. Half Life: 6-8 hours LD50 = 66 mg/kg (Rat, parental-intravenous) No indication of carcinogenicity to humans (not listed by IARC). For the management of hypertension (alone or in combination with other classes of antihypertensive agents), as well as chronic stable angina pectoris and sympathetic overactivity syndrome associated with severe tetanus. Labetalol is used parenterally for immediate reduction in blood pressure in severe hypertension or in hypertensive crises when considered an emergency, for the control of blood pressure in patients with pheochromocytoma and pregnant women with preeclampsia, and to produce controlled hypotension during anesthesia to reduce bleeding resulting from surgical procedures. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7226b179f8> Side effects or adverse reactions include dizziness when standing up, very low blood pressure, severely slow heartbeat, weakness, diminished sexual function, fatigue DB00598 HMDB14736 3869 CHEMBL429 3734 C07063 6343 Labetalol Labetalol BE0004863 BE0000172 Labetalol has two asymmetric centers and therefore, exists as a molecular complex of two diastereoisomeric pairs. Dilevalol, the R,R' stereoisomer, makes up 25% of racemic labetalol. Labetalol HCl combines both selective, competitive, alpha-1-adrenergic blocking and nonselective, competitive, beta-adrenergic blocking activity in a single substance. In man, the ratios of alpha- to beta- blockade have been estimated to be approximately 1:3 and 1:7 following oral and intravenous (IV) administration, respectively. Beta-2-agonist activity has been demonstrated in animals with minimal beta-1-agonist (ISA) activity detected. In animals, at doses greater than those required for alpha- or beta- adrenergic blockade, a membrane stabilizing effect has been demonstrated. Dissociation 0.0235 uM BindingDB 25758 Dissociation 0.03162 uM BindingDB 25758 BE0000694 Labetalol has two asymmetric centers and therefore, exists as a molecular complex of two diastereoisomeric pairs. Dilevalol, the R,R' stereoisomer, makes up 25% of racemic labetalol. Labetalol HCl combines both selective, competitive, alpha-1-adrenergic blocking and nonselective, competitive, beta-adrenergic blocking activity in a single substance. In man, the ratios of alpha- to beta- blockade have been estimated to be approximately 1:3 and 1:7 following oral and intravenous (IV) administration, respectively. Beta-2-agonist activity has been demonstrated in animals with minimal beta-1-agonist (ISA) activity detected. In animals, at doses greater than those required for alpha- or beta- adrenergic blockade, a membrane stabilizing effect has been demonstrated. BE0001012 Dissociation 0.661 uM BindingDB 25758 BE0001064 Dissociation 1000 uM BindingDB 25758 BE0000501 Labetalol has two asymmetric centers and therefore, exists as a molecular complex of two diastereoisomeric pairs. Dilevalol, the R,R' stereoisomer, makes up 25% of racemic labetalol. Labetalol HCl combines both selective, competitive, alpha-1-adrenergic blocking and nonselective, competitive, beta-adrenergic blocking activity in a single substance. In man, the ratios of alpha- to beta- blockade have been estimated to be approximately 1:3 and 1:7 following oral and intravenous (IV) administration, respectively. Beta-2-agonist activity has been demonstrated in animals with minimal beta-1-agonist (ISA) activity detected. In animals, at doses greater than those required for alpha- or beta- adrenergic blockade, a membrane stabilizing effect has been demonstrated. BE0000575 Labetalol has two asymmetric centers and therefore, exists as a molecular complex of two diastereoisomeric pairs. Dilevalol, the R,R' stereoisomer, makes up 25% of racemic labetalol. Labetalol HCl combines both selective, competitive, alpha-1-adrenergic blocking and nonselective, competitive, beta-adrenergic blocking activity in a single substance. In man, the ratios of alpha- to beta- blockade have been estimated to be approximately 1:3 and 1:7 following oral and intravenous (IV) administration, respectively. Beta-2-agonist activity has been demonstrated in animals with minimal beta-1-agonist (ISA) activity detected. In animals, at doses greater than those required for alpha- or beta- adrenergic blockade, a membrane stabilizing effect has been demonstrated. BE0000715