Atenolol

Base Information

• Chemical Name: Atenolol
• CAS No.: 29122-68-7
• Deprecated CAS: 60966-51-0,106020-65-9
• Molecular Formula: C14H22N2O3
• Molecular Weight: 266.34
• Hs Code.: 29242995
• European Community (EC) Number: 249-451-7
• NSC Number: 757832
• UNII: 50VV3VW0TI
• DSSTox Substance ID: DTXSID2022628
• Nikkaji Number: J3.170D
• Wikipedia: Atenolol
• Wikidata: Q411325
• NCI Thesaurus Code: C28836
• RXCUI: 1202
• Pharos Ligand ID: MSS9M2PUN1DT
• Metabolomics Workbench ID: 128836
• ChEMBL ID: CHEMBL24
• Mol file: 29122-68-7.mol

Synonyms:Atenolol;ICI 66082;ICI-66082;ICI66082;Tenormin;Tenormine

Chemical Property of Atenolol

Chemical Property:

• Appearance/Colour: white to off-white crystalline solid
• Vapor Pressure: 3.82E-11mmHg at 25°C
• Melting Point: 154 °C
• Refractive Index: 1.5110 (estimate)
• Boiling Point: 508.049 °C at 760 mmHg
• PKA: 9.6(at 25℃)
• Flash Point: 261.059 °C
• PSA: 84.58000
• Density: 1.125 g/cm³
• LogP: 1.54330
• Storage Temp.: Store at RT
• Solubility.: H2O: 0.3 mg/mL
• Water Solubility.: 13.5mg/L(25 oC)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 266.16304257
• Heavy Atom Count: 19
• Complexity: 263

Purity/Quality:

98%min ^*data from raw suppliers

Atenolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,F
• Statements: 22-36/37/38-20/21/22-36-11
• Safety Statements: 22-24/25-36-26-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O
• Recent ClinicalTrials: The Effect of Nitrendipine/Atenolol Combination on Blood Pressure Variability.
• Recent EU Clinical Trials: The RIME-IVF study
• Recent NIPH Clinical Trials: Clinical Significance of Sphingosine-1-Phosphate in the Evaluation of Endothelial Function and Cardiovascular Risk in Hypertension
• Uses: β-blockers. Clinical application in the treatment of hypertension, angina and arrhythmia. Selective b1 adrenergic receptor agonist, anti-hypertensive, anti-anginal, anti-arrhythmic Atenolol is 2-[4′[2-hydroxy-3-(iso-propylamino)propoxy]phenyl]acetamide (12.1.7) [11–13].Atenolol is a selective β1-adrenoblocker, or in other words, a cardioblocker. Like acebutol, atenolol possesses antianginal, antihypotensive, and antiarrhythmic action. It is used for arterial hypotension, preventing attacks of angina, sinus tachycardia, and preventing supraventricular tachyarrhythmia. It is used for preventing angina pectoris.
• Therapeutic Function: Beta-adrenergic blocker
• Clinical Use: Beta-adrenoceptor blocker: Hypertension Angina Arrhythmias
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: NSAIDs antagonise hypotensive effect. Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk of bradycardia, myocardial depression and AV block with amiodarone; increased risk of myocardial depression and bradycardia with flecainide. Antidepressants: enhanced hypotensive effect with MAOIs. Antihypertensives: enhanced hypotensive effect; increased risk of withdrawal hypertension with clonidine; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin. Antimalarials: increased risk of bradycardia with mefloquine. Antipsychotics enhanced hypotensive effect with phenothiazines. Calcium-channel blockers: increased risk of bradycardia and AV block with diltiazem; hypotension and heart failure possible with nifedipine and nisoldipine; asystole, severe hypotension and heart failure with verapamil. Cytotoxics: possible increased risk of bradycardia with crizotinib. Diuretics: enhanced hypotensive effect. Fingolimod: possibly increased risk of bradycardia. Moxisylyte: possible severe postural hypotension. Sympathomimetics: severe hypertension with adrenaline and noradrenaline and possibly with dobutamine.

Technology Process of Atenolol

There total 12 articles about Atenolol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1--3-chloropropan-2-ol (115538-83-5) + isopropylamine (75-31-0) → (RS)-atenolol (29122-68-7)

Guidance literature:

In water; at 10 ℃; for 12h;

DOI:10.1039/c4ra16365f

Reference yield: 94.3%

→ (RS)-atenolol (29122-68-7) + isopropylamine (75-31-0)

Guidance literature:

Reference yield: 93.0%

1-(4'-cyanomethylphenoxy)-2-hydroxy-3-(isopropylamino)propane (29277-73-4) → (RS)-atenolol (29122-68-7)

Guidance literature:

With bis(dimethylphosphinous acid-_kP)dimethylphosphinyl-_kP-hydridoplatinum(II); In ethanol; water; for 72h; Reflux;

DOI:10.1021/op9800313

upstream raw materials:

(S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane

isopropylamine

(4-hydroxyphenyl)methanol

2-(4-hydroxyphenyl)acetamide

Downstream raw materials:

(S)-atenolol O-acetyl ester

N-methylpropan-2-amine

4-carboxy methoxy phenyl acetic acid

C₂₀H₃₈N₂O₃Si₂

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE". . . Retrieved 2015/02/05.
• 2、 Pathare, Sagar P.,Akamanchi, Krishnacharya G.. "An efficient protocol for regioselective ring opening of epoxides using sulfated tungstate: Application in synthesis of active pharmaceutical ingredients atenolol, propranolol and ranolazine". . p. 6455 - 6459. Retrieved 2013/11/19.