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

• ChemBase ID: 154880
• Molecular Formular: C22H26ClF2NO4
• Molecular Mass: 441.8959464
• Monoisotopic Mass: 441.15184244
• SMILES: c1cc2c(cc1F)CC[C@@H](O2)[C@H](CNC[C@@H]([C@@H]1CCc2cc(ccc2O1)F)O)O.Cl
• Canonical SMILES: O[C@H]([C@@H]1CCc2c(O1)ccc(c2)F)CNC[C@@H]([C@H]1CCc2c(O1)ccc(c2)F)O.Cl
• InChI: InChI=1S/C22H25F2NO4.ClH/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;1H/t17-,18-,21-,22+;/m0./s1
• InChIKey: JWEXHQAEWHKGCW-BIISKSHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-[(2R)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-2-{[(2S)-2-[(2S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]-2-hydroxyethyl]amino}ethan-1-ol hydrochloride
• IUPAC Traditional name: l-nebivolol hydrochloride
• Synonyms: Narbivolol; Nebilet; R-65824; rel-(aR,a′R,2R,2′S)-a,a′-[iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] hydrochloride; Nebivolol hydrochloride

Database IDs

• CAS Number: 152520-56-4
• PubChem SID: 162249018
• PubChem CID: 11626384

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H410
• GHS Precautionary statements: P273-P501
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H25F2NO4 · HCl

DETAILS

Sigma Aldrich - N1915

Biochem/physiol Actions
Nebivolol is a competitive, highly selective b1-receptor antagonist with mild vasodialating properties, possibly due to an interaction with the L-arginine/ NO pathway, and is used for treatment of essential hypertension. It is 40-fold selective for β1 vs. β2, and lacks ISA (intrinsic sympathomimetic activity).