BUFURALOL

Possibly Marketed Outside US

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

Structure Search

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

HIDE SMILES / InChI

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	( + / - )

Description
Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/bc2ba6731122a2b539616c6929597d18.html | https://www.ncbi.nlm.nih.gov/pubmed/2878678 | https://www.ncbi.nlm.nih.gov/pubmed/12235248 | https://www.ncbi.nlm.nih.gov/pubmed/6202966 | Martindale, W. (1993) The Extra Pharmacopoeia, page 631, retrieved from: https://books.google.ru/books?id=EGZWAAAAYAAJ

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	15618695
Stability of cytochrome P450 enzymes in human liver samples stored in different tissue preservation buffers.	2002	14632311
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole.	2003	15618748
V79 Chinese hamster cells genetically engineered for polymorphic cytochrome P450 2D6 and their predictive value for humans.	2003	12947487
'Open access' generic method for continuous determination of major human CYP450 probe substrates/metabolites and its application in drug metabolism studies.	2003 Dec	14742145
Cytochrome P450 inhibition using recombinant proteins and mass spectrometry/multiple reaction monitoring technology in a cassette incubation.	2003 Jul	12814974
Regulation of CYP2D expression in rat brain by toluene.	2003 Jun	14703099
Coordinated intrahepatic and extrahepatic regulation of cytochrome p4502D6 in healthy subjects and in patients after liver transplantation.	2003 May	12732845
Identification of metabolic pathways involved in the biotransformation of tolperisone by human microsomal enzymes.	2003 May	12695352
Stereoselectivity in the oxidation of bufuralol, a chiral substrate, by human cytochrome P450s.	2003 May 5	12666241
Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components.	2003 Nov	14570772
Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor.	2003 Nov	14570767
Cloning CYP2D21 and CYP3A22 cDNAs from liver of miniature pigs.	2004 Apr	15039288
Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities.	2004 Aug	15258107
Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism.	2004 Dec 1	15498516
Designing safer (soft) drugs by avoiding the formation of toxic and oxidative metabolites.	2004 Feb	14764938
Atomoxetine hydrochloride: clinical drug-drug interaction prediction and outcome.	2004 Feb	14610241
Phe120 contributes to the regiospecificity of cytochrome P450 2D6: mutation leads to the formation of a novel dextromethorphan metabolite.	2004 Jun 1	14992686
Impact of incubation conditions on bufuralol human clearance predictions: enzyme lability and nonspecific binding.	2004 Mar	14977863
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	15474473
Generic three-column parallel LC-MS/MS system for high-throughput in vitro screens.	2004 Nov 26	15595659
Use of a cocktail of probe substrates for drug-metabolizing enzymes for the assessment of the metabolic capacity of hepatocyte preparations.	2004 Nov-Dec	15801540
Metabolism of human cytochrome P450 marker substrates in mouse: a strain and gender comparison.	2004 Sep	15742976
Effects of etodolac on P450 isoform-specific activities in human hepatic microsomes.	2005	16430028
[Potentiometric detection of beta-adrenolytic and beta-adrenergic drugs in HPLC systems].	2005	16407794
Identification and characterization of novel sequence variations in the cytochrome P4502D6 (CYP2D6) gene in African Americans.	2005	15768052
Different effects of desipramine on bufuralol 1''-hydroxylation by rat and human CYP2D enzymes.	2005 Apr	15802801
Substrate specific metabolism by polymorphic cytochrome P450 2D6 alleles.	2005 Aug	15893449
Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.	2005 Aug	15860655
Role of the conserved threonine 309 in mechanism of oxidation by cytochrome P450 2D6.	2005 Dec 16	16269134
Identification of human P450 isoforms involved in the metabolism of the antiallergic drug, oxatomide, and its kinetic parameters and inhibition constants.	2005 Feb	15684493
Cyp2D6 catalyzes 5-hydroxylation of 1-(2-pyrimidinyl)-piperazine, an active metabolite of several psychoactive drugs, in human liver microsomes.	2005 Feb	15507542
Change in enantioselectivity in bufuralol 1''-hydroxylation by the substitution of phenylalanine-120 by alanine in cytochrome P450 2D6.	2005 Jan	15526337
Determination of phase I metabolic enzyme activities in liver microsomes of Mrp2 deficient TR- and EHBR rats.	2005 Jul 22	15913659
Selective inhibition of dog hepatic CYP2B11 and CYP3A12.	2005 May	15677349
Automated assessment of time-dependent inhibition of human cytochrome P450 enzymes using liquid chromatography-tandem mass spectrometry analysis.	2005 Nov	16049126
Why is quinidine an inhibitor of cytochrome P450 2D6? The role of key active-site residues in quinidine binding.	2005 Nov 18	16162505
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: a comparison with SKF-525A.	2005 Oct	16272753
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	16206149
The role of phenylalanine 483 in cytochrome P450 2D6 is strongly substrate dependent.	2005 Oct 15	16135359
CYP2D6-dependent bufuralol 1'-hydroxylation assayed by reverse-phase ion-pair high-performance liquid chromatography with fluorescence detection.	2006	16719382
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	16527257
New cytochrome P450 2D6*56 allele identified by genotype/phenotype analysis of cryopreserved human hepatocytes.	2006 Aug	16679388
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	16454641
Roles of phenylalanine at position 120 and glutamic acid at position 222 in the oxidation of chiral substrates by cytochrome P450 2D6.	2006 Feb	16432914
Expression, purification, and characterization of mouse CYP2d22.	2006 Jul	16595712
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	16563352
Innovative methods to study human intestinal drug metabolism in vitro: precision-cut slices compared with ussing chamber preparations.	2006 Nov	16914511
Effects of individual ginsenosides, ginkgolides and flavonoids on CYP2C19 and CYP2D6 activity in human liver microsomes.	2006 Sep	16922812
Intestinal and hepatic metabolic activity of five cytochrome P450 enzymes: impact on prediction of first-pass metabolism.	2006 Sep	16763093

Sample Use Guides

In Vivo Use Guide

Single dose - 30 mg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Thu Jul 06 22:25:56 UTC 2023` Edited by `admin` on `Thu Jul 06 22:25:56 UTC 2023`
Record UNII	891H89GFT4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUFURALOL

Official Name

English

BUFURALOL [MI]

Common Name

English

bufuralol [INN]

Common Name

English

Bufuralol [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C72900