39552-01-7

Basic information

• Product Name: Befunolol
• Synonyms: Befunolol;2-Acetyl-7-(2-hydroxy-3-isopropylaminopropoxy)benzofuran;Ethanone, 1-[7-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-2-benzofuranyl]-;1-(7-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2-benzofuranyl)-ethanon;1-(7-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2-benzofuranyl)ethanone;1-[7-[2-Hydroxy-3-[(1-methylethyl)-amino]propoxy]-2-benzofuranyl]ethanone;2-acetyl-7-(2-hyroxy-3-isopropylaminopropoxy)benzofuran;7-(2-hydroxy-3-(isopropylamino)propoxy)-2-benzofuranyl methyl ketone
• CAS NO: 39552-01-7
• Molecular Formula: C16H21NO4
• Molecular Weight: 291.38
• Product Categories: Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 39552-01-7.mol

Chemical Properties

• Melting Point: 115°
• Boiling Point: 433.35°C (rough estimate)
• Appearance: /
• Density: 1.1049 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated)
• CAS DataBase Reference: Befunolol(CAS DataBase Reference)
• NIST Chemistry Reference: Befunolol(39552-01-7)
• EPA Substance Registry System: Befunolol(39552-01-7)

Safety Data

• Hazardous Substances Data: 39552-01-7(Hazardous Substances Data)

Usage

Uses

Used in Ophthalmology:
Befunolol is used as an antiglaucoma agent in ophthalmic solutions. It helps in reducing intraocular pressure, which is a common issue in glaucoma patients. By acting as a β-adrenergic blocker, it effectively manages the symptoms and prevents further damage to the optic nerve.
Used in Cardiovascular Applications:
As a β-adrenergic blocker, Befunolol is also utilized in the treatment of various cardiovascular conditions. It helps in managing heart rate, blood pressure, and reducing the workload on the heart. This makes it a valuable tool in the management of conditions such as hypertension, angina, and certain arrhythmias.
Used in Isolated Organ Studies:
In research and laboratory settings, Befunolol is used as a β-adrenergic partial agonist in isolated organs. This allows scientists to study the effects of the compound on specific organ systems and gain a better understanding of its mechanisms of action and potential applications in various medical fields.

Originator

Bentos,Kakenyaku Kako,Japan,1983

Manufacturing Process

To 8.8 g of 2-acetyl-7-hydroxybenzofuran were added 80 ml of epichlorohydrin and 0.2 g of piperidine hydrochloride and the mixture was heated at 105°C for 3 hours. After the reaction, the excess of epichlorohydrin was evaporated and the resultant was distilled under reduced pressure to give 9.3 g of 2-acetyl-7-(2,3-epoxypropoxy)benzofuranhaving a boiling point of 175° to 176°C/0.7 mm Hg. 6 g of the product was dissolved in 30 ml of ethanol and to the solution was added 10 ml of isopropylamine. After refluxing the mixture for 40 minutes, the solvent was evaporated from the reaction mixture. The resulting residue was recrystallized from cyclohexane-acetone to give 6 g of 2-acetyl-7-(2-hydroxy-3-isopropylaminopropoxy)benzofuran having a melting point of 115°C.

Therapeutic Function

Beta-adrenergic blocker

Contact allergens

Befunolol was implicated in allergic contact dermatitis due to beta-blocker agents in eye-drops. Crosssensitivity has been described with levobunolol.

InChI:InChI=1/C16H21NO4/c1-10(2)17-8-13(19)9-20-14-6-4-5-12-7-15(11(3)18)21-16(12)14/h4-7,10,13,17,19H,8-9H2,1-3H3

Upstream product

• 39543-77-6 2-acetyl-7-glycidyloxybenzofuran 
• 75-31-0 isopropylamine 
• 55636-92-5 dihydrobufenolol 
• 39552-00-6 2-acetyl-7-hydroxybenzofuran potassium salt 
• 106-89-8 epichlorohydrin 
• 39552-12-0 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran 
• 75-26-3 isopropyl bromide 
• 40020-87-9 2-acetyl-7-hydroxybenzofuran 
• 53943-39-8 3-isopropyl-5-(2-acetyl-7-benzofuranoxymethyl)oxazolidone 
• 39552-17-5 2-phenyl-3-isopropyl-5-(2-acetyl-7-benzofuranoxymethyl)oxazolidine 
• 39552-18-6 2-acetyl-7-[2-hydroxy-3-(N-acetyl-N-isopropyl)aminopropoxy]benzofuran 

Downstream Products

• 55636-92-5 dihydrobufenolol 

Relevant articles and documents

THERAPY FOR COMPLICATIONS OF DIABETES

A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

Method for treating resistant hypertension

A method is provided for lowering blood pressure in a patient having clinically diagnosed resistant hypertension. The method comprises administering darusentan to the patient adjunctively with a baseline antihypertensive regimen that comprises administration of at least one diuretic and at least two antihypertensive drugs selected from at least two of (a) ACE inhibitors and angiotensin II receptor blockers, (b) beta-adrenergic receptor blockers and (c) calcium channel blockers. The darusentan is orally administered at a dose and frequency effective, in combination with the baseline regimen, to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures.

Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver

In this study, we compared the enzymatic reduction of 10 drugs with a ketone group by homogeneous carbonyl reductase, aldehyde reductase and three dihydrodiol dehydrogenases of human liver cytosol. At least one and in some cases all of the three dihydrodi

Reaction of Epichlorohydrin with Hydroxybenzofuran

Epichlorohydrin (4) was condensed with 2-acetyl-7-hydroxybenzofuran potassium salt (3) to give two radiochemical regio-isomeric 2-acetyl-7-glycidyloxybenzofurans (5a and 5b).The ratio, 5a/5b, was determined to be 5/7 by using 14C-radioisotopic tracer techniques.The present results showed that the reaction proceeds through two different paths in which the phenolate (3) attacks at C-1 of 4 to give 5a and at C-3 to give 5b, the latter path being more favorable than the former.Keywords - epichlorohydrin; nucleophilic substitution; 2-acetyl-7-glycidyloxybenzofuran; radiochemical regio-isomer; 14C-radioisotopic tracer technique; cleavage of carbon chain; reaction mechanism

PHARMACEUTICAL COMPOSITION CONTAINING BENZOFURAN DERIVATIVE

A pharmaceutical composition containing as the essential active ingredient a benzofuran derivative of the formula: STR1 wherein A is--COR', STR2 or ethyl group; B is hydrogen atom when A is--COR' STR3 or--COR" substituted at the 3 or 4 position of the ben