2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide

• ChemBase ID: 480
• Molecular Formular: C19H24N2O3
• Molecular Mass: 328.40546
• Monoisotopic Mass: 328.17869264
• SMILES: OC(CNC(CCc1ccccc1)C)c1cc(c(O)cc1)C(=O)N
• Canonical SMILES: CC(CCc1ccccc1)NCC(c1ccc(c(c1)C(=O)N)O)O
• 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)
• InChIKey: SGUAFYQXFOLMHL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide
• IUPAC Traditional name: labetalolum
• Brand Name: Albetol; Ibidomide; Normodyne; Presdate; Trandate
• Synonyms: Labetolol; Labetalolum [INN-Latin]; Labetalol hydrochloride; Labetalol HCL; Labetalol

Database IDs

• CAS Number: 36894-69-6
• PubChem SID: 46505511; 160963943
• PubChem CID: 3869

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.049597
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.09246248
• LogD (pH = 7.4): 1.2584062
• Log P: 1.8865051
• Molar Refractivity: 94.7152 cm^3
• Polarizability: 36.471325 Å^3
• Polar Surface Area: 95.58 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.73
• LOG S: -4.75
• Solubility (Water): 5.78e-03 g/l

PROPERTIES

Physical Property

• Solubility: 20 mg/ml (HCl salt)
• Hydrophobicity(logP): 2.7

DETAILS

DrugBank - DB00598

• Drug Groups: approved
• Description: Blocker of both alpha- and beta-adrenergic receptors that is used as an antihypertensive. [PubChem]
• Indication: 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.
• Pharmacology: Labetalol is an selective alpha-1 and non-selective beta adrenergic blocker used to treat high blood pressure. It works by blocking these adrenergic receptors, which slows sinus heart rate, decreases peripheral vascular resistance, and decreases cardiac output. 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.
• Toxicity: LD₅₀ = 66 mg/kg (Rat, IV). Side effects or adverse reactions include dizziness when standing up, very low blood pressure, severely slow heartbeat, weakness, diminished sexual function, fatigue
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic, undergoes significant first pass metabolism
• Absorption: 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.
• Half Life: 6-8 hours
• Protein Binding: 50%
• Elimination: These metabolites are present in plasma and are excreted in the urine, and via the bile, into the feces.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com