Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C16H23NO2.ClH |
| Molecular Weight | 297.82 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCC1=C2OC(=CC2=CC=C1)C(O)CNC(C)(C)C
InChI
InChIKey=KJBONRGCLLBWCJ-UHFFFAOYSA-N
InChI=1S/C16H23NO2.ClH/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;1H
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 |
|---|---|---|
| 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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| Is cytochrome P450 CYP2D activity present in pig liver? | 2002 Oct |
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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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| Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate. | 2003 |
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| Retention of transporter activities in cryopreserved, isolated rat hepatocytes. | 2003 Apr |
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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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| The relative contribution of monoamine oxidase and cytochrome p450 isozymes to the metabolic deamination of the trace amine tryptamine. | 2003 Feb |
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| Role of glutamic acid 216 in cytochrome P450 2D6 substrate binding and catalysis. | 2003 Feb 11 |
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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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| Downregulation of CYP2D16 by ACTH in the guinea pig adrenal cortex: time course, reversibility, and mechanism of action. | 2003 Mar |
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| 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 |
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| 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 |
|
| Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. | 2004 Aug |
|
| 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 |
|
| 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 |
|
| [Potentiometric detection of beta-adrenolytic and beta-adrenergic drugs in HPLC systems]. | 2005 |
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| 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 |
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| 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 |
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| Role of the conserved threonine 309 in mechanism of oxidation by cytochrome P450 2D6. | 2005 Dec 16 |
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| Identification of human P450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its kinetic parameters and inhibition constants. | 2005 Feb |
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| 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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| 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 |
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| Why is quinidine an inhibitor of cytochrome P450 2D6? The role of key active-site residues in quinidine binding. | 2005 Nov 18 |
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| 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 |
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| 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 |
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ACTIVE MOIETY
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