1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethan-1-ol

• ChemBase ID: 4390
• Molecular Formular: C22H25F2NO4
• Molecular Mass: 405.4350064
• Monoisotopic Mass: 405.17516473
• SMILES: Fc1cc2CCC(Oc2cc1)C(O)CNCC(O)C1Oc2c(CC1)cc(F)cc2
• Canonical SMILES: OC(C1CCc2c(O1)ccc(c2)F)CNCC(C1CCc2c(O1)ccc(c2)F)O
• InChI: InChI=1S/C22H25F2NO4/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2
• InChIKey: KOHIRBRYDXPAMZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethan-1-ol
• IUPAC Traditional name: nebivolol hydrochloride
• Brand Name: Nebilet; Nebicard-5; Nubeta; Nebipill; Bystolic; Nebilong; Nodon; Lobivon; PI-21858
• Synonyms: Nebivololum [latin]; nebivolol; Nebivolol

Database IDs

• CAS Number: 99200-09-6
• PubChem SID: 99443225; 160967822
• PubChem CID: 71301

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.520145
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.19658114
• LogD (pH = 7.4): 1.7054241
• Log P: 3.208403
• Molar Refractivity: 103.3172 cm^3
• Polarizability: 40.23752 Å^3
• Polar Surface Area: 70.95 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.44
• LOG S: -4.0
• Solubility (Water): 4.03e-02 g/l

DETAILS

DrugBank - DB04861

• Drug Groups: approved; investigational
• Description: Nebivolol is a highly cardioselective vasodilatory beta1 receptor blocker used in treatment of hypertension. In most countries, this medication is available only by prescription. [Wikipedia]
• Indication: For the treatment of essential hypertension.
• Pharmacology: Nebivolol is a competitive and highly selective beta-1 receptor antagonist with mild vasodilating properties, possibly due to an interaction with the L-arginine/nitric oxide pathway. In preclinical studies, nebivolol has been shown to induce endothelium-dependent arterial relaxation in a dose dependent manner, by stimulation of the release of endothelial nitric oxide. Nitric oxide acts to relax vascular smooth muscle cells and inhibits platelet aggregation and adhesion.
• Toxicity: The most common signs and symptoms associated with nebivolol overdosage are bradycardia and hypotension. Other important adverse events reported with nebivolol overdose include cardiac failure, dizziness, hypoglycemia, fatigue and vomiting. Other adverse events associated with β-blocker overdose include bronchospasm and heart block. The largest known ingestion of nebivolol worldwide involved a patient who ingested up to 500 mg of nebivolol along with several 100 mg tablets of acetylsalicylic acid in a suicide attempt. The patient experienced hyperhydrosis, pallor, depressed level of consciousness, hypokinesia, hypotension, sinus bradycardia, hypoglycemia, hypokalemia, respiratory failure and vomiting. The patient recovered.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (CYP2D6-mediated)
• Absorption: The absorption of nebivolol is rapid and not affected by food.
• Half Life: 10 hours
• Protein Binding: 98%
• References: Gielen W, Cleophas TJ, Agrawal R: Nebivolol: a review of its clinical and pharmacological characteristics. Int J Clin Pharmacol Ther. 2006 Aug;44(8):344-57. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Gielen W, Cleophas TJ, Agrawal R: Nebivolol: a review of its clinical and pharmacological characteristics. Int J Clin Pharmacol Ther. 2006 Aug;44(8):344-57. Pubmed