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

• ChemBase ID: 132773
• Molecular Formular: C14H22N2O3
• Molecular Mass: 266.33608
• Monoisotopic Mass: 266.16304257
• SMILES: CC(C)NC[C@@H](COc1ccc(cc1)CC(=O)N)O
• 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-/m0/s1
• InChIKey: METKIMKYRPQLGS-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}acetamide
• IUPAC Traditional name: (-)-atenolol
• Synonyms: 4-[(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide; (-)-Atenolol; (S)-Atenolol; Esatenolol; S-(-)-Atenolol; (S)-Atenolol; (-)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide; (S)-(-)-Atenolol

Database IDs

• CAS Number: 93379-54-5
• MDL Number: MFCD00074918
• PubChem SID: 162227050; 24277807; 24859922
• PubChem CID: 175540

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble
• Apperance: white to beige powder
• Melting Point: 148-152 °C(lit.)
• Optical Rotation: [α]23/D -10.5°, c = 0.5 in H2O(lit.); [α]25/D -16°, c = 1 in 1 M HCl

Safety Information

• RTECS: CY1488020
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADRB1(153)

Product Information

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

DETAILS

Sigma Aldrich - A143

Biochem/physiol Actions
β1-Adrenergic receptor antagonist; active enantiomer of atenolol.

Sigma Aldrich - 330892

Packaging
100 mg in glass bottle

Toronto Research Chemicals - A790085

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

REFERENCES

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