2-{4-[(2R)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}acetamide

• ChemBase ID: 4640
• Molecular Formular: C14H22N2O3
• Molecular Mass: 266.33608
• Monoisotopic Mass: 266.16304257
• SMILES: O=C(N)Cc1ccc(cc1)OC[C@H](O)CNC(C)C
• Canonical SMILES: O[C@@H](COc1ccc(cc1)CC(=O)N)CNC(C)C
• InChI: InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)/t12-/m1/s1
• InChIKey: METKIMKYRPQLGS-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2R)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}acetamide
• IUPAC Traditional name: (+)-atenolol
• Synonyms: 2-(4-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)PHENYL)ETHANAMIDE; (+)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide; (R)-(+)-Atenolol; 4-[(2R)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide; (+)-(R)-Atenolol; (+)-Atenolol; (R)-(+)-Atenolol; (R)-Atenolol; (+)-4-[2-羟基-3-[(1-甲基乙基)氨基]丙氧基]苯乙酰胺; (R)-(+)-阿替洛尔

Database IDs

• CAS Number: 56715-13-0
• MDL Number: MFCD00074917
• PubChem SID: 160968072; 99443458; 24859921
• PubChem CID: 180559

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.078504
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.7682068
• LogD (pH = 7.4): -1.8002133
• Log P: 0.42502484
• Molar Refractivity: 73.5053 cm^3
• Polarizability: 29.0903 Å^3
• Polar Surface Area: 84.58 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.57
• LOG S: -2.79
• Solubility (Water): 4.29e-01 g/l

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: >6.0 mg/mL; ethanol or 0.1 N HCl: soluble; H2O: insoluble
• Apperance: pale yellow solid
• Melting Point: 148-152 °C(lit.)
• Optical Rotation: [α]25/D +16°, c = 1 in 1 M HCl

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 99%
• Linear Formula: (CH3)2CHNHCH2CH(OH)CH2OC6H4CH2CONH2

DETAILS

DrugBank - DB06987

Drug information: experimental

Sigma Aldrich - A142

Biochem/physiol Actions
Less active enantiomer

Sigma Aldrich - 330884

Packaging
100, 500 mg in glass bottle

Toronto Research Chemicals - A790080

Cardioselective β-adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic (class II).

REFERENCES

• Caplar, V., et al.: Anal. Profiles Drug Subs., 13, 1 (1984)