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

• ChemBase编号: 480
• 分子式: C19H24N2O3
• 平均质量: 328.40546
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide
• IUPAC传统名: labetalolum
• 商标名: Albetol; Ibidomide; Normodyne; Presdate; Trandate
• 别名: Labetolol; Labetalolum [INN-Latin]; Labetalol hydrochloride; Labetalol HCL; Labetalol

登记号

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

理论计算性质

JChem

• Acid pKa: 8.049597
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -0.09246248
• LogD (pH = 7.4): 1.2584062
• Log P: 1.8865051
• 摩尔折射率: 94.7152 cm^3
• 极化性: 36.471325 Å^3
• 极化表面积: 95.58 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.73
• LOG S: -4.75
• 溶解度: 5.78e-03 g/l

分子性质

理化性质

• 溶解度: 20 mg/ml (HCl salt)
• 疏水性(logP): 2.7

详细说明

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