Acebutolol

Base Information

• Chemical Name: Acebutolol
• CAS No.: 37517-30-9
• Deprecated CAS: 28197-63-9
• Molecular Formula: C18H28N2O4
• Molecular Weight: 336.431
• Hs Code.: 2924299090
• European Community (EC) Number: 253-539-0
• UNII: 67P356D8GH
• DSSTox Substance ID: DTXSID2048539
• Nikkaji Number: J29.383K
• Wikipedia: Acebutolol
• Wikidata: Q418857
• NCI Thesaurus Code: C61525
• RXCUI: 149
• Pharos Ligand ID: FUGALDKJKWLA
• Metabolomics Workbench ID: 43409
• ChEMBL ID: CHEMBL642
• Mol file: 37517-30-9.mol

Synonyms:Acebutolol;Acebutolol Hydrochloride;Acetobutolol;Apo Acebutolol;Apo-Acebutolol;ApoAcebutolol;M and B 17803 A;M and B 17803A;M and B-17803 A;M and B17803 A;Monitan;Neptal;Novo Acebutolol;Novo-Acebutolol;NovoAcebutolol;Prent;Rhotral;Sectral

Chemical Property of Acebutolol

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 1.45E-13mmHg at 25°C
• Melting Point: 119-123 °C
• Refractive Index: 1.542
• Boiling Point: 564.1 °C at 760 mmHg
• PKA: pKa 9.40 (Uncertain)
• Flash Point: 295 °C
• PSA: 87.66000
• Density: 1.118 g/cm³
• LogP: 2.82940
• Storage Temp.: -20°C Freezer
• Water Solubility.: 259 mg/L
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 336.20490738
• Heavy Atom Count: 24
• Complexity: 401

Purity/Quality:

99% ^*data from raw suppliers

N-(3-Acetyl-4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)butyramide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: CCCC(=O)NC1=CC(=C(C=C1)OCC(CNC(C)C)O)C(=O)C
• Recent ClinicalTrials: Efficacy and Safety of Propranolol Versus Acebutolol on the Proliferative Phase of Infantile Hemangioma
• Recent EU Clinical Trials: Efficacy and safety of acebutolol versus propranolol in the proliferative phase of infantile hemangiomas
• Recent NIPH Clinical Trials: An open-label, single-dose, two-treatment, randomized, cross-over study to investigate the effects of the SLCO2B1 c.1457C>T polymorphism and apple juice on the pharmacokinetics and pharmacodynamics of acebutolol in healthy Korean and Japanese volunteers
• Uses: Acebutol is 3′-acetyl-4′-[2-hydroxy-3-(iso-propylamino)propoxy] butyranilide (12.1.6) [9,10].Acebutol is a selective β1-adrenoblocker. It possesses antianginal, antihypotensive, and antiarrhythmic action. It is used for arterial hypertension, preventing attacks of angina, and cardiac rhythm disturbances.
• Therapeutic Function: beta-Adrenergic blocker
• Clinical Use: Acebutolol (Sectral) is a cardioselective 1-adrenoceptor blocking agent that also has some minor membrane stabilizing effects on the action potential. Acebutolol is effective in the management of the patient with essential hypertension, angina pectoris, and ventricular arrhythmias. Antiarrhythmic effects are observed with the patient both at rest and taking exercise.
• 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 Acebutolol

There total 2 articles about Acebutolol 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:

cyclopropanecarboxylic acid 2-(2-acetyl-4-butyrylamino-phenoxy)-1-(isopropylamino-methyl)-ethyl ester → Acebutolol (37517-30-9,68107-82-4) + cyclopropanecarboxylic acid (1759-53-1)

Guidance literature:

With water; at 37 ℃; pH=1 - 12; Further Variations:; Reagents; Kinetics;

DOI:10.1023/A:1016204602471

Reference yield:

→ Acebutolol (37517-30-9,68107-82-4)

Guidance literature:

DOI:10.1021/jm00225a012 DOI:10.1007/BF01957813

Reference yield:

Acebutolol (37517-30-9,68107-82-4) → (R)-acebutolol (68107-82-4) + (S)-acebutolol (68107-82-4)

Guidance literature:

With AmyCoat (150x46 mm, 3 μm size silica particle); In ethanol; n-heptane; diethylamine; at 27 ℃; Resolution of racemate;

DOI:10.1002/chir.20697

Downstream raw materials:

N-[3-Acetyl-4-(2-hydroxy-3-isopropylamino-propoxy)-phenyl]-3-iodo-benzamide

(R)-acebutolol

(S)-acebutolol

acetolol

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE". . . Retrieved 2015/02/05.
• 2、 -. "ANTIHYPERTENSIVE THERAPY". . . Retrieved 2009/09/08.