2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-4-phenylbutan-2-yl]amino}(2H3)ethyl]benzamide

• ChemBase ID: 172150
• Molecular Formular: C19H24N2O3
• Molecular Mass: 328.40546
• Monoisotopic Mass: 328.17869264
• SMILES: c1([C@H](CN[C@@H](CCc2ccccc2)C)O)cc(c(cc1)O)C(=O)N
• Canonical SMILES: C[C@H](CCc1ccccc1)NC[C@@H](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)/t13-,18+/m1/s1
• InChIKey: SGUAFYQXFOLMHL-ACJLOTCBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-4-phenylbutan-2-yl]amino}(^2H₃)ethyl]benzamide
• IUPAC Traditional name: 2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-4-phenylbutan-2-yl]amino}(^2H₃)ethyl]benzamide
• Synonyms: 2-Hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-1-methyl-3-phenylpropyl]amino]ethyl]benzamide-d3; Dilevalol-d3; Dilevalon-d3; Levadil-d3; Sch 19927-d3; Unicard-d3; (R,R)-Labetalol-d3

Database IDs

• PubChem SID: 164228060
• PubChem CID: 71749708

CALCULATED PROPERTIES

• 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: 36.4726 Å^3
• Polar Surface Area: 95.58 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L096502

Labelled (R,R)-Labetalol (L096500). (R,R)-Labetalol is a specific competitive antagonist at both α-and β-adrenergic receptor sites. (R,R)-Labetalol is used as an antihypertensive.

REFERENCES

• Sybertz, E.J., et al.: J. Pharmacol. Exp. Ther., 218, 435 (1981)
• Clifton, J.E., et al.: J. Med. Chem., 25, 670 (1981)
• Goa, K.L., et al.: Drugs, 37, 583 (1981)