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

• ChemBase ID: 219
• Molecular Formular: C14H22N2O3
• Molecular Mass: 266.33608
• Monoisotopic Mass: 266.16304257
• SMILES: O(CC(O)CNC(C)C)c1ccc(cc1)CC(=O)N
• Canonical SMILES: OC(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)
• InChIKey: METKIMKYRPQLGS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
• IUPAC Traditional name: atenolol
• Brand Name: Aircrit; Alinor; Altol; Anselol; Antipressan; Apo-Atenolol; Atcardil; Atecard; Atehexal; Atenblock; Atendol; Atenet; Ateni; Atenil; Atenol; Atenol 1A Pharma; Atenol Acis; Atenol AL; Atenol Atid; Atenol Cophar; Atenol CT; Atenol Fecofar; Atenol Gador; Atenol Genericon; Atenol GNR; Atenol Heumann; Atenol MSD; Atenol NM Pharma; Atenol Nordic; Atenol PB; Atenol Quesada; Atenol Stada; Atenol Tika; Atenol Trom; Atenol Von CT; Atenol-Mepha; Atenol-Ratiopharm; Atenol-Wolff; Atenolin; Atenomel; Atereal; Aterol; Betablok; Betacard; Betasyn; Betatop GE; Blocotenol; Blokium; Cardaxen; Cardiopress; Corotenol; Cuxanorm; Duraatenolol; Duratenol; Evitocor; Farnormin; Felo-Bits; Hipres; Hypoten; Ibinolo; Internolol; Jenatenol; Juvental; Lo-Ten; Loten; Lotenal; Myocord; Normalol; Normiten; Noten; Oraday; Ormidol; Panapres; Plenacor; Premorine; Prenolol; Prenormine; Prinorm; Scheinpharm Atenol; Seles Beta; Selobloc; Serten; Servitenol; Stermin; Tenidon; Teno-Basan; Tenobloc; Tenoblock; Tenolol; Tenoprin; Tenormin; Tenormine; Tensimin; Tredol; Unibloc; Uniloc; Vascoten; Vericordin; Wesipin; Xaten
• Synonyms: 2-{4-[2-Hydroxy-3-(isopropylamino)propoxy]-phenyl}acetamide; 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxyl]benzeneacetamide; 2-[p-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]acetamide; (RS)-Atenolol; (+/-)-Atenolol; ICI-66082; Atehexal; Atenol; Cuxanorm; Myocord; Normalol; Normiten; Uniloc; Vericordin; Wesipin; Xaten; dl-Atenolol; Atenolol; (±)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide; 4-[2′-Hydroxy-3′-(isopropylamino)propoxy]phenylacetamide; Atenolol; 2-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide; 2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide

Database IDs

• CAS Number: 29122-68-7
• EC Number: 249-451-7
• MDL Number: MFCD00057645
• PubChem SID: 24277748; 160963682; 46506915
• PubChem CID: 2249

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: 13.5 mg/mL; Acetic Acid; Dimethyl Sulfoxide; DMSO: soluble18 mg/mL; ethanol: soluble3.4 mg/mL; H2O: soluble0.3 mg/mL; Methanol
• Apperance: Crystalline Solid; white to off-white powder
• Melting Point: 146-148°C; 148 - 152°C
• Hydrophobicity(logP): -0.109; 0.5

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: AC3600000
• German water hazard class: 2
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADRB1(153)rat ... Adrb1(24925)

Product Information

• Purity: ≥98% (TLC); 95%; 97%

DETAILS

DrugBank - DB00335

• Drug Groups: approved
• Description: A cardioselective beta-adrenergic blocker possessing properties and potency similar to propranolol, but without a negative inotropic effect. [PubChem]
• Indication: For the management of hypertention and long-term management of patients with angina pectoris
• Pharmacology: Atenolol, a competitive beta(1)-selective adrenergic antagonist, has the lowest lipid solubility of this drug class. Although it is similar to metoprolol, atenolol differs from pindolol and propranolol in that it does not have intrinsic sympathomimetic properties or membrane-stabilizing activity. Atenolol is used alone or with chlorthalidone in the management of hypertension and edema.
• Toxicity: LD₅₀=2000-3000 mg/kg(orally in mice). Symptoms of an atenolol overdose include a slow heart beat, shortness of breath, fainting, dizziness, weakness, confusion, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (minimal)
• Absorption: Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces.
• Half Life: 6-7 hours
• Protein Binding: Plasma protein binding is 6-16%
• Elimination: Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces. Unlike propranolol or metoprolol, but like nadolol, atenolol undergoes little or no metabolism by the liver, and the absorbed portion is eliminated primarily by renal excretion.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A7655

Biochem/physiol Actions
Selective β1-adrenoceptor antagonist; antihypertensive; antianginal; antiarrhythmic.
Other Notes
Shelf-life of the solid is at least three years.
Application
Atenolol is a β-adrenergic blocker and used in the management of hypertension. Atenolol has antianginal and antiarrhythmic properties.

Toronto Research Chemicals - A790075

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

REFERENCES

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