(2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol

• ChemBase ID: 1073
• Molecular Formular: C17H27NO4
• Molecular Mass: 309.40058
• Monoisotopic Mass: 309.19400835
• SMILES: O[C@@H]1[C@H](O)Cc2c(C1)c(OCC(O)CNC(C)(C)C)ccc2
• Canonical SMILES: OC(COc1cccc2c1C[C@H](O)[C@@H](C2)O)CNC(C)(C)C
• InChI: InChI=1S/C17H27NO4/c1-17(2,3)18-9-12(19)10-22-16-6-4-5-11-7-14(20)15(21)8-13(11)16/h4-6,12,14-15,18-21H,7-10H2,1-3H3/t12?,14-,15+/m1/s1
• InChIKey: VWPOSFSPZNDTMJ-UCWKZMIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol
• IUPAC Traditional name: nadolol
• Brand Name: Anabet; Corgard; Solgol
• Synonyms: Nadolol; Nadolol; (2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol; 纳多洛尔

Database IDs

• CAS Number: 42200-33-9
• EC Number: 255-706-3
• MDL Number: MFCD00079476
• PubChem SID: 46505509; 24897535; 160964536
• PubChem CID: 39147
• ATC CODE: C07AA12
• CHEMBL: 649
• Chemspider ID: 35815
• DrugBank ID: DB01203
• IUPHAR ligand ID: 554
• KEGG ID: D00432
• Unique Ingredient Identifier: FEN504330V
• Wikipedia Title: Nadolol
• Medline Plus: a682666

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.586201
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.3368313
• LogD (pH = 7.4): -1.4429477
• Log P: 0.8654279
• Molar Refractivity: 85.5269 cm^3
• Polarizability: 33.76481 Å^3
• Polar Surface Area: 81.95 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.23
• LOG S: -2.14
• Solubility (Water): 2.25e+00 g/l

PROPERTIES

Physical Property

• Solubility: 8330 mg/L
• Hydrophobicity(logP): 0.379; 1.2

Safety Information

• RTECS: QJ4870000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal and fecal (unchanged)
• Half Life: 14-24 hours
• Metabolism: Nil
• Protein Bound: 30%
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: C (US)
• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: 95%
• Grade: analytical standard
• Empirical Formula (Hill Notation): C17H27NO4

DETAILS

DrugBank - DB01203

• Drug Groups: approved
• Description: A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for migraine disorders and for tremor. [PubChem]
• Indication: Used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension.
• Pharmacology: Nadolol is a nonselective beta-adrenergic receptor antagonist with a long half-life, and is structurally similar to propranolol. Clinical pharmacology studies have demonstrated beta-blocking activity by showing (1) reduction in heart rate and cardiac output at rest and on exercise, (2) reduction of systolic and diastolic blood pressure at rest and on exercise, (3) inhibition of isoproterenol-induced tachycardia, and (4) reduction of reflex orthostatic tachycardia. Nadolol has no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, nadolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
• Toxicity: Oral, mouse: LD₅₀ = 4500mg/kg. Symptoms of overdose include abdominal irritation, central nervous system depression, coma, extremely slow heartbeat, heart failure, lethargy, low blood pressure, and wheezing.
• Affected Organisms: Humans and other mammals
• Biotransformation: Not metabolized by the liver and excreted unchanged primarily by the kidneys.
• Absorption: Absorption of nadolol after oral dosing is variable, averaging about 30 percent.
• Half Life: 14-24 hours
• Protein Binding: 30%
• Elimination: Unlike many other beta-adrenergic blocking agents, nadolol is not metabolized by the liver and is excreted unchanged, principally by the kidneys. Nadolol is excreted predominantly in the urine.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - N1892

Biochem/physiol Actions
β-Adrenergic blocker