NAV

Befunolol

Identification

Generic Name
Befunolol
DrugBank Accession Number
DB09013
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 291.347
Monoisotopic: 291.14705816
Chemical Formula
C16H21NO4
Synonyms
  • Befunolol
  • Befunololum
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-1 adrenergic receptorNot AvailableHumans
UBeta-2 adrenergic receptorNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
ClobazamThe serum concentration of Befunolol can be increased when it is combined with Clobazam.
ClozapineThe serum concentration of Befunolol can be increased when it is combined with Clozapine.
DesvenlafaxineThe serum concentration of Befunolol can be increased when it is combined with Desvenlafaxine.
DronedaroneThe metabolism of Befunolol can be decreased when combined with Dronedarone.
EscitalopramThe serum concentration of Befunolol can be increased when it is combined with Escitalopram.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Befunolol hydrochlorideB03Z2VY37I39543-79-8TVVTWOGRPVJKDJ-UHFFFAOYSA-N
International/Other Brands
Bentos (Kakenyaku Kakko) / Bentox / Glauconex

Categories

ATC Codes
S01ED06 — Befunolol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Benzenoid / Benzofuran / Ether
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
418546MT3A
CAS number
39552-01-7
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

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. [Article]
KEGG Drug
D07496
PubChem Compound
2309
PubChem Substance
310264971
ChemSpider
2219
ChEBI
135212
ChEMBL
CHEMBL153984
Wikipedia
Befunolol

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Solution / dropsOphthalmic
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US3853923No1971-05-131991-05-13US flag

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-MSsplash10-00fu-9830000000-9a87a1489789d6caedb2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-98c1ccd91b3238ced181
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-6900000000-7e84069920feee38f790
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dj-9020000000-239ec6529685d64aba4d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-0900000000-eac31262bae94c3e3693
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1900000000-fc50dcea8535571915af
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9810000000-f9acdb018a581857b9ac
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-165.95561
predicted
DeepCCS 1.0 (2019)
[M+H]+168.31361
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.40675
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Beta-1 adrenergic receptor
Kind
Protein
Organism
Humans
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. [Article]
Details2. Beta-2 adrenergic receptor
Kind
Protein
Organism
Humans
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. [Article]

Enzymes

Details1. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
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. [Article]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
  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 . [Article]

Drug created at June 20, 2014 23:23 / Updated at December 02, 2023 07:01