ChemicalBook > CAS DataBase List > Acebutolol

Acebutolol

Product Name
Acebutolol
CAS No.
37517-30-9
Chemical Name
Acebutolol
Synonyms
Prent;Sectral;ACEBUTOLOL;Acebuprolol;Acebutololum;Acetobutolol;dl-Acebutolol;Acebutolo HCl;Acebutolol USP/EP/BP;AcebutololDiscontinued. See: A123800
CBNumber
CB5393651
Molecular Formula
C18H28N2O4
Formula Weight
336.43
MOL File
37517-30-9.mol
More
Less

Acebutolol Property

Melting point:
119-123°C
Boiling point:
472.9°C (rough estimate)
Density 
1.1748 (rough estimate)
refractive index 
1.5700 (estimate)
storage temp. 
-20°C Freezer
solubility 
DMF: 10 mg/mL,DMSO: 5 mg/mL,Ethanol: 5 mg/mL,PBS (pH 7.2): 0.3 mg/mL
form 
A solid
pka
pKa 9.40 (Uncertain)
color 
Crystals
Water Solubility 
259 mg/L
CAS DataBase Reference
37517-30-9(CAS DataBase Reference)
NIST Chemistry Reference
Acebutolol(37517-30-9)
EPA Substance Registry System
Butanamide, N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]- (37517-30-9)
More
Less

Safety

Toxicity
TDLo orl-wmn: 152 mg/kg:CVS,BPR JTCTDW 20,69,83
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H362May cause harm to breast-fed children

Precautionary statements

P201Obtain special instructions before use.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P308+P313IF exposed or concerned: Get medical advice/attention.

More
Less

N-Bromosuccinimide Price

AK Scientific
Product number
E887
Product name
Acebutolol
Packaging
1g
Price
$171
Updated
2021/12/16
AK Scientific
Product number
E887
Product name
Acebutolol
Packaging
5g
Price
$411
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0000343
Product name
ACEBUTOLOL
Purity
95.00%
Packaging
1G
Price
$516
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0000343
Product name
ACEBUTOLOL
Purity
95.00%
Packaging
5G
Price
$866.87
Updated
2021/12/16
Crysdot
Product number
CD12077597
Product name
N-(3-Acetyl-4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)butyramide
Purity
97%
Packaging
10g
Price
$250
Updated
2021/12/16
More
Less

Acebutolol Chemical Properties,Usage,Production

Chemical Properties

Crystalline Solid

Originator

Sectral ,May and Baker ,UK ,1975

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.

Uses

Cardioselective ?adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II)

Uses

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

Definition

ChEBI: An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.

Manufacturing Process

Crude 5'-butyramido-2'-(2,3-epoxypropoxy)acetophenone (16 g), isopropylamine (20 g) and ethanol (100 ml) were heated together under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure and the residual oil was dissolved in N hydrochloric acid. The acid solution was extracted with ethyl acetate, the ethyl acetate layers being discarded. The acidic solution was brought to pH 11 with 2 N aqueous sodium hydroxide solution and then extracted with chloroform. The dried chloroform extracts were concentrated under reduced pressure to give an oil which was crystallized from a mixture of ethanol and diethyl ether to give 5'-butyramido- 2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone (3 g), MP 119-123°C.
Crude 5'-butyramido-2'-(2,3-epoxypropoxy)acetophenone used as starting material was prepared as follows: p-butyramidophenol (58 g; prepared according to Fierz-David and Kuster, Helv. Chim. Acta 1939,2282), acetyl chloride (25.4 g) and benzene (500 ml) were heated together under reflux until a solution formed (12 hours). This solution was cooled and treated with water. The benzene layer was separated and the aqueous layer was again extracted with benzene.
The combined benzene extracts were dried and evaporated to dryness under reduced pressure to give p-butyramidophenyl acetate (38 g) as an off-white solid, MP 102-103°C. A mixture of p-butyramidophenyl acetate (38 g), aluminum chloride (80 g) and 1,1,2,2-tetrachloroethane (250 ml) was heated at 140°C for 3 hours. The reaction mixture was cooled and treated with iced water. The tetrachloroethane layer was separated and the aqueous layer was extracted with chloroform. The combined organic layers were extracted with 2 N aqueous sodium hydroxide and the alkaline solution was acidified to pH 5 with concentrated hydrochloric acid. The acidified solution was extracted with chloroform and the chloroform extract was dried and concentrated under reduced pressure to give 5'-butyramido-2'-hydroxyacetophenone (15.6 g), MP 114-117°C. A solution of 5'-butyramido-2'-hydroxyacetophenone (15.6 g) in ethanol (100 ml) was added to an ethanolic solution of sodium ethoxide which was prepared from sodium (1.62 g) and ethanol (100 ml). The resulting solution was evaporated to dryness under reduced pressure and dimethylformamide (100 ml) was added to the solid residue. Approximately 10 ml of dimethylformamide was removed by distillation under reduced pressure. Epichlorohydrin (25 ml) was added and the solution was heated at 100°C for 4 hours. The solution was concentrated under reduced pressure to give a residual oil which was treated with water to give a solid. The solid was dissolved in ethanol and the resulting solution was treated with charcoal, filtered and concentrated under reduced pressure to give crude 5'-butyramido- 2'-(2,3-epoxypropoxy)acetophenone (16 g), MP 110-116°C.
The crude compound may be purified by recrystallization from ethyl acetate, after treatment with decolorizing charcoal, to give pure 5'-butyramido-2'-(2,3- epoxypropoxy)acetophenone, MP 136-138°C.

brand name

Sectral (Dr. Reddy’s).

Therapeutic Function

beta-Adrenergic blocker

General Description

Acebutolol is one of the very few β-blockers whosemetabolite plays a significant role in its pharmacological actions.This drug is absorbed well from the gastrointestinaltract, but it undergoes extensive first-pass metabolic conversionto diacetolol by hydrolytic conversion of the amidegroup to the amine, followed by acetylation of the amine. After oral administration, plasma levels of diacetololare higher than those of acebutolol. Diacetolol is also aselective β1-blocker with partial agonistic activity; it has littlemembrane-stabilizing activity. It has a longer half-life (8–12hours) than the parent drug and is excreted by the kidneys.

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.

Side effects

Adverse effects include bradycardia, gastrointestinal upset, dizziness, and headache.

Safety Profile

Moderately toxic by intravenousroute. Human systemic effects by ingestion: developmentalabnormalities of the cardiovascular and respiratory systems;effects on newborn in biochemical and metabolicabnormalities and reduced growth statistics. A humanter

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.

Metabolism

About half of an orally administered dose of acebutolol (Sectral) is absorbed. Approximately 25% of the drug is bound to plasma proteins, and its plasma halflife is about 4 hours.Metabolism of acebutolol produces a metabolite with -blocking activity whose half-life is 10 hours.

Precautions

Acebutolol should not be administered in cardiogenic shock, uncontrolled heart failure, or severe bradycardia or to patients with known hypersensitivity to the drug.

Acebutolol Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Acebutolol Suppliers

LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
Advantage
57
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
Advantage
57
Shanghai HuanChuan Industry Co.,Ltd.
Tel
021-61478794
Fax
021-61478794
Email
sales@hcshhai.com
Country
China
ProdList
9793
Advantage
50
Chizhou Kailong Import and Export Trade Co., Ltd.
Tel
Fax
-
Email
xg01_gj@163.com
Country
China
ProdList
9484
Advantage
50
Shanghai Chaolan Chemical Technology Center
Tel
021-QQ:65489617 15618227136
Fax
21-5161 9052
Email
Sales@ATKchemical.com
Country
China
ProdList
7295
Advantage
58
Amadis Chemical Company Limited
Tel
571-89925085
Fax
0086-571-89925065
Email
sales@amadischem.com
Country
China
ProdList
131957
Advantage
58
Shenzhen Polymeri Biochemical Technology Co., Ltd.
Tel
+86-400-002-6226 +86-13028896684;
Email
sales@rrkchem.com
Country
China
ProdList
57423
Advantage
58
Shenzhen Botel Biotechnology Co. Ltd.
Tel
0755-22202135 13316968096
Email
1979313431@qq.com
Country
China
ProdList
9020
Advantage
58
Hangzhou Synstar pharmaceutical Technology CO.,Ltd
Tel
0571-85361029
Fax
0571-85361029
Email
synstar518@163.com
Country
China
ProdList
1990
Advantage
58
More
Less

View Lastest Price from Acebutolol manufacturers

Career Henan Chemical Co
Product
Acebutolol 37517-30-9
Price
US $1.00/ASSAYS
Min. Order
1ASSAYS
Purity
85.0-99.8%
Supply Ability
20tons
Release date
2020-01-08

37517-30-9, AcebutololRelated Search:


  • (.+/-.)-3'-Acetyl-4'-[2-hydroxy-3-(1-methylethylamino)propoxy]butyranilide
  • (.+/-.)-3'-Acetyl-4'-[2-hydroxy-3-(isopropylamino)propoxy]butyranilide
  • (.+/-.)-N-(3-Acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)butanamide
  • 1-(2-Acetyl-4-n-butyramidophenoxy)-2-hydroxy-3-isopropylaminopropane
  • 3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide
  • 5'-Butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone
  • Butanamide, N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]-, (.+/-.)-
  • dl-Acebutolol
  • N-(3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide
  • Prent
  • Sectral
  • ACEBUTOLOL
  • n-[3-acetyl-4-(2-hydroxy-3-propan-2-ylamino-propoxy)-phenyl]butanamide
  • Acebutolo HCl
  • Acebutololum
  • AcebutololDiscontinued. See: A123800
  • Acetobutolol
  • N-(3-acetyl-4-(2-hydroxy-3-(isopropylaMino)propoxy)phenyl)butyraMide
  • Acebutolol USP/EP/BP
  • Acebutolol D7Q: What is Acebutolol D7 Q: What is the CAS Number of Acebutolol D7 Q: What is the storage condition of Acebutolol D7
  • Acebuprolol
  • 37517-30-9
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Adrenoceptor