Identification

Name
Befunolol
Accession Number
DB09013
Type
Small Molecule
Groups
Experimental
Description

Befunolol is a beta blocker introduced in 1983 by Kakenyaku Kakko. It is currently in experimental status, and is being tested for the management of open angle glaucoma.

Structure
Thumb
Synonyms
  • (RS)-1-{7-[2-hydroxy-3-(propan-2-ylamino)propoxy]- 1-benzofuran-2-yl}ethanone
Product Ingredients
IngredientUNIICASInChI Key
befunolol hydrochlorideB03Z2VY37I39543-79-8TVVTWOGRPVJKDJ-UHFFFAOYSA-N
International/Other Brands
Benfuran / Bentos (Kakenyaku Kakko) / Betaclar / Glauconex
Categories
UNII
418546MT3A
CAS number
39552-01-7
Weight
Average: 291.347
Monoisotopic: 291.14705816
Chemical Formula
C16H21NO4
InChI Key
ZPQPDBIHYCBNIG-UHFFFAOYSA-N
InChI
InChI=1S/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
IUPAC Name
1-(7-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-1-benzofuran-2-yl)ethan-1-one
SMILES
CC(C)NCC(O)COC1=CC=CC2=C1OC(=C2)C(C)=O

Pharmacology

Indication

Used in the management of open angle glaucoma. PMID: 12480285.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-1 adrenergic receptorNot AvailableHuman
UBeta-2 adrenergic receptorNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limonene(4R)-limonene may decrease the antihypertensive activities of Befunolol.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Befunolol.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Befunolol.
AcebutololThe therapeutic efficacy of Befunolol can be decreased when used in combination with Acebutolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Befunolol.
AcemetacinAcemetacin may decrease the antihypertensive activities of Befunolol.
AcepromazineBefunolol may increase the orthostatic hypotensive activities of Acepromazine.
AceprometazineAceprometazine may increase the hypotensive activities of Befunolol.
AcetohexamideBefunolol may increase the hypoglycemic activities of Acetohexamide.
AcetylcholineThe risk or severity of adverse effects can be increased when Befunolol is combined with Acetylcholine.
Food Interactions
Not Available

References

General References
  1. Reichl S, Muller-Goymann CC: The use of a porcine organotypic cornea construct for permeation studies from formulations containing befunolol hydrochloride. Int J Pharm. 2003 Jan 2;250(1):191-201. [PubMed:12480285]
External Links
KEGG Drug
D07496
PubChem Compound
2309
PubChem Substance
310264971
ChemSpider
2219
ChEBI
135212
ChEMBL
CHEMBL153984
Wikipedia
Befunolol
ATC Codes
S01ED06 — Befunolol

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US3853923No1971-05-131991-05-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)115Ito, K., Mashiko, I.,Kimura, K. and Nakanishi,T.;U.S. Patent 3,853,923; December 10.1974; assigned to Kakenyaku Kakko Co., Ltd.
Predicted Properties
PropertyValueSource
Water Solubility0.108 mg/mLALOGPS
logP1.71ALOGPS
logP1.23ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.92ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area71.7 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity79.5 m3·mol-1ChemAxon
Polarizability32.01 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzofurans
Sub Class
Not Available
Direct Parent
Benzofurans
Alternative Parents
Aryl alkyl ketones / Alkyl aryl ethers / Benzenoids / Heteroaromatic compounds / Furans / Secondary alcohols / 1,2-aminoalcohols / Oxacyclic compounds / Dialkylamines / Organopnictogen compounds
show 2 more
Substituents
Benzofuran / Aryl ketone / Aryl alkyl ketone / Alkyl aryl ether / Benzenoid / Furan / Heteroaromatic compound / 1,2-aminoalcohol / Ketone / Secondary alcohol
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Yamada Y, Takayanagi R, Tsuchiya K, Ito K, Ohtani H, Sawada Y, Iga T: Assessment of systemic adverse reactions induced by ophthalmic beta-adrenergic receptor antagonists. J Ocul Pharmacol Ther. 2001 Jun;17(3):235-48. [PubMed:11436944]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Yamada Y, Takayanagi R, Tsuchiya K, Ito K, Ohtani H, Sawada Y, Iga T: Assessment of systemic adverse reactions induced by ophthalmic beta-adrenergic receptor antagonists. J Ocul Pharmacol Ther. 2001 Jun;17(3):235-48. [PubMed:11436944]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [PubMed:27836712]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [PubMed:14732961]
  3. Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [PubMed:17125412]

Drug created on June 20, 2014 17:23 / Updated on August 02, 2018 07:48