Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H23NO2 |
Molecular Weight | 261.3593 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1=C2OC(=CC2=CC=C1)C(O)CNC(C)(C)C
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
Molecular Formula | C16H23NO2 |
Molecular Weight | 261.3593 |
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
Title | Date | PubMed |
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Application of microtiter plate assay to evaluate inhibitory effects of various compounds on nine cytochrome P450 isoforms and to estimate their inhibition patterns. | 2002 |
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Stability of cytochrome P450 enzymes in human liver samples stored in different tissue preservation buffers. | 2002 |
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In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole. | 2003 |
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V79 Chinese hamster cells genetically engineered for polymorphic cytochrome P450 2D6 and their predictive value for humans. | 2003 |
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'Open access' generic method for continuous determination of major human CYP450 probe substrates/metabolites and its application in drug metabolism studies. | 2003 Dec |
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Cytochrome P450 inhibition using recombinant proteins and mass spectrometry/multiple reaction monitoring technology in a cassette incubation. | 2003 Jul |
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Regulation of CYP2D expression in rat brain by toluene. | 2003 Jun |
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Coordinated intrahepatic and extrahepatic regulation of cytochrome p4502D6 in healthy subjects and in patients after liver transplantation. | 2003 May |
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Identification of metabolic pathways involved in the biotransformation of tolperisone by human microsomal enzymes. | 2003 May |
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Stereoselectivity in the oxidation of bufuralol, a chiral substrate, by human cytochrome P450s. | 2003 May 5 |
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Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components. | 2003 Nov |
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Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. | 2003 Nov |
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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 |
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Phe120 contributes to the regiospecificity of cytochrome P450 2D6: mutation leads to the formation of a novel dextromethorphan metabolite. | 2004 Jun 1 |
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Impact of incubation conditions on bufuralol human clearance predictions: enzyme lability and nonspecific binding. | 2004 Mar |
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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 |
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Effects of etodolac on P450 isoform-specific activities in human hepatic microsomes. | 2005 |
|
[Potentiometric detection of beta-adrenolytic and beta-adrenergic drugs in HPLC systems]. | 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 |
|
Role of the conserved threonine 309 in mechanism of oxidation by cytochrome P450 2D6. | 2005 Dec 16 |
|
Identification of human P450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its kinetic parameters and inhibition constants. | 2005 Feb |
|
Cyp2D6 catalyzes 5-hydroxylation of 1-(2-pyrimidinyl)-piperazine, an active metabolite of several psychoactive drugs, in human liver microsomes. | 2005 Feb |
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Change in enantioselectivity in bufuralol 1''-hydroxylation by the substitution of phenylalanine-120 by alanine in cytochrome P450 2D6. | 2005 Jan |
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Determination of phase I metabolic enzyme activities in liver microsomes of Mrp2 deficient TR- and EHBR rats. | 2005 Jul 22 |
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Selective inhibition of dog hepatic CYP2B11 and CYP3A12. | 2005 May |
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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 |
|
A novel approach to perform metabolite screening during the quantitative LC-MS/MS analyses of in vitro metabolic stability samples using a hybrid triple-quadrupole linear ion trap mass spectrometer. | 2005 Oct |
|
The role of phenylalanine 483 in cytochrome P450 2D6 is strongly substrate dependent. | 2005 Oct 15 |
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CYP2D6-dependent bufuralol 1'-hydroxylation assayed by reverse-phase ion-pair high-performance liquid chromatography with fluorescence detection. | 2006 |
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Catalytic roles of CYP2D6.10 and CYP2D6.36 enzymes in mexiletine metabolism: in vitro functional analysis of recombinant proteins expressed in Saccharomyces cerevisiae. | 2006 Apr 28 |
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New cytochrome P450 2D6*56 allele identified by genotype/phenotype analysis of cryopreserved human hepatocytes. | 2006 Aug |
|
Effect of oral administration of clinically relevant doses of dexamethasone on regulation of cytochrome P450 subfamilies in hepatic microsomes from dogs and rats. | 2006 Feb |
|
Roles of phenylalanine at position 120 and glutamic acid at position 222 in the oxidation of chiral substrates by cytochrome P450 2D6. | 2006 Feb |
|
Expression, purification, and characterization of mouse CYP2d22. | 2006 Jul |
|
Binding of bufuralol, dextromethorphan, and 3,4-methylenedioxymethylamphetamine to wild-type and F120A mutant cytochrome P450 2D6 studied by resonance Raman spectroscopy. | 2006 May 12 |
|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6202966
Single dose - 30 mg
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:25:56 UTC 2023
by
admin
on
Thu Jul 06 22:25:56 UTC 2023
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Record UNII |
891H89GFT4
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C72900
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M2755
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891H89GFT4
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |