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Details

Stereochemistry RACEMIC
Molecular Formula C16H23NO2
Molecular Weight 261.3599
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUFURALOL

SMILES

CCc1cccc2cc(C(CNC(C)(C)C)O)oc12

InChI

InChIKey=SSEBTPPFLLCUMN-UHFFFAOYSA-N
InChI=1S/C16H23NO2/c1-5-11-7-6-8-12-9-14(19-15(11)12)13(18)10-17-16(2,3)4/h6-9,13,17-18H,5,10H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C16H23NO2
Molecular Weight 261.3599
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Bufuralol is a non-cardioselective beta-adrenergic blocker with high intrinsic sympathomimetic activity. It has affinity for both β1 and β2-adrenergic receptors. It acts as a potent β-adrenoceptor antagonist with partial agonist activity. Bufuralol is primarily metabolized by cytochrome P450 (CYP) isoform CYP2D6, with CYP1A2 and CYP2C19. Activity of bufuralol has been shown to yield antianginal and antihypertensive effects. It appears to have a higher incidence of adverse eflects than with other beta blockers. Bufuralol has been in phase III clinical trials for the treatment of hypertension. However, this research has been discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Application of microtiter plate assay to evaluate inhibitory effects of various compounds on nine cytochrome P450 isoforms and to estimate their inhibition patterns.
2002
Stability of cytochrome P450 enzymes in human liver samples stored in different tissue preservation buffers.
2002
Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions.
2002 Dec
Is cytochrome P450 CYP2D activity present in pig liver?
2002 Oct
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole.
2003
V79 Chinese hamster cells genetically engineered for polymorphic cytochrome P450 2D6 and their predictive value for humans.
2003
Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate.
2003
Retention of transporter activities in cryopreserved, isolated rat hepatocytes.
2003 Apr
'Open access' generic method for continuous determination of major human CYP450 probe substrates/metabolites and its application in drug metabolism studies.
2003 Dec
The relative contribution of monoamine oxidase and cytochrome p450 isozymes to the metabolic deamination of the trace amine tryptamine.
2003 Feb
Role of glutamic acid 216 in cytochrome P450 2D6 substrate binding and catalysis.
2003 Feb 11
Residues glutamate 216 and aspartate 301 are key determinants of substrate specificity and product regioselectivity in cytochrome P450 2D6.
2003 Feb 7
Catalytic activities of cytochrome P450 enzymes and UDP-glucuronosyltransferases involved in drug metabolism in rat everted sacs and intestinal microsomes.
2003 Jan
High-throughput inhibition screening of major human cytochrome P450 enzymes using an in vitro cocktail and liquid chromatography-tandem mass spectrometry.
2003 Jan 1
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Cytochrome P450 inhibition using recombinant proteins and mass spectrometry/multiple reaction monitoring technology in a cassette incubation.
2003 Jul
Regulation of CYP2D expression in rat brain by toluene.
2003 Jun
Downregulation of CYP2D16 by ACTH in the guinea pig adrenal cortex: time course, reversibility, and mechanism of action.
2003 Mar
Coordinated intrahepatic and extrahepatic regulation of cytochrome p4502D6 in healthy subjects and in patients after liver transplantation.
2003 May
Identification of metabolic pathways involved in the biotransformation of tolperisone by human microsomal enzymes.
2003 May
Stereoselectivity in the oxidation of bufuralol, a chiral substrate, by human cytochrome P450s.
2003 May 5
Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components.
2003 Nov
Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor.
2003 Nov
Cloning CYP2D21 and CYP3A22 cDNAs from liver of miniature pigs.
2004 Apr
Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities.
2004 Aug
Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism.
2004 Dec 1
Designing safer (soft) drugs by avoiding the formation of toxic and oxidative metabolites.
2004 Feb
Atomoxetine hydrochloride: clinical drug-drug interaction prediction and outcome.
2004 Feb
Phe120 contributes to the regiospecificity of cytochrome P450 2D6: mutation leads to the formation of a novel dextromethorphan metabolite.
2004 Jun 1
Impact of incubation conditions on bufuralol human clearance predictions: enzyme lability and nonspecific binding.
2004 Mar
The roles of amino acid residues at positions 43 and 45 in microsomal contents and enzymatic functions of rat CYP2D1 and CYP2D2.
2004 Nov 12
Generic three-column parallel LC-MS/MS system for high-throughput in vitro screens.
2004 Nov 26
Use of a cocktail of probe substrates for drug-metabolizing enzymes for the assessment of the metabolic capacity of hepatocyte preparations.
2004 Nov-Dec
Metabolism of human cytochrome P450 marker substrates in mouse: a strain and gender comparison.
2004 Sep
Effects of etodolac on P450 isoform-specific activities in human hepatic microsomes.
2005
Identification and characterization of novel sequence variations in the cytochrome P4502D6 (CYP2D6) gene in African Americans.
2005
Different effects of desipramine on bufuralol 1''-hydroxylation by rat and human CYP2D enzymes.
2005 Apr
Substrate specific metabolism by polymorphic cytochrome P450 2D6 alleles.
2005 Aug
Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.
2005 Aug
Cyp2D6 catalyzes 5-hydroxylation of 1-(2-pyrimidinyl)-piperazine, an active metabolite of several psychoactive drugs, in human liver microsomes.
2005 Feb
Change in enantioselectivity in bufuralol 1''-hydroxylation by the substitution of phenylalanine-120 by alanine in cytochrome P450 2D6.
2005 Jan
Automated assessment of time-dependent inhibition of human cytochrome P450 enzymes using liquid chromatography-tandem mass spectrometry analysis.
2005 Nov
Why is quinidine an inhibitor of cytochrome P450 2D6? The role of key active-site residues in quinidine binding.
2005 Nov 18
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: a comparison with SKF-525A.
2005 Oct
CYP2D6-dependent bufuralol 1'-hydroxylation assayed by reverse-phase ion-pair high-performance liquid chromatography with fluorescence detection.
2006
New cytochrome P450 2D6*56 allele identified by genotype/phenotype analysis of cryopreserved human hepatocytes.
2006 Aug
Roles of phenylalanine at position 120 and glutamic acid at position 222 in the oxidation of chiral substrates by cytochrome P450 2D6.
2006 Feb
Innovative methods to study human intestinal drug metabolism in vitro: precision-cut slices compared with ussing chamber preparations.
2006 Nov
Effects of individual ginsenosides, ginkgolides and flavonoids on CYP2C19 and CYP2D6 activity in human liver microsomes.
2006 Sep
Intestinal and hepatic metabolic activity of five cytochrome P450 enzymes: impact on prediction of first-pass metabolism.
2006 Sep

Sample Use Guides

Single dose - 30 mg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:07:24 UTC 2021
Edited
by admin
on Sat Jun 26 03:07:24 UTC 2021
Record UNII
891H89GFT4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUFURALOL
INN   MI   WHO-DD  
INN  
Official Name English
BUFURALOL [MI]
Common Name English
BUFURALOL [WHO-DD]
Common Name English
BUFURALOL [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C72900
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
Code System Code Type Description
CAS
54340-62-4
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
MERCK INDEX
M2755
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY Merck Index
MESH
C010831
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
PUBCHEM
71733
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
FDA UNII
891H89GFT4
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
WIKIPEDIA
BUFURALOL
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
DRUG CENTRAL
424
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
NCI_THESAURUS
C72613
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
DRUG BANK
DB06726
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
EVMPD
SUB05967MIG
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
INN
3539
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
ECHA (EC/EINECS)
259-112-5
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL296035
Created by admin on Sat Jun 26 03:07:24 UTC 2021 , Edited by admin on Sat Jun 26 03:07:24 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY