BUFURALOL HYDROCHLORIDE

Possibly Marketed Outside US

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

Structure Search

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

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	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Minipig cytochrome P450 3A, 2A and 2C enzymes have similar properties to human analogs.	2001	11737866
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
Fondaparinux sodium is not metabolised in mammalian liver fractions and does not inhibit cytochrome P450-mediated metabolism of concomitant drugs.	2002	12383041
Designing safer (soft) drugs by avoiding the formation of toxic and oxidative metabolites.	2002	12013781
Effect of alachlor on hepatic cytochrome P450 enzymes in rats.	2002 Feb	11850968
Inhibition kinetics of monoclonal antibodies against cytochromes P450.	2002 Jun	12019198
CYP2D6.10 present in human liver microsomes shows low catalytic activity and thermal stability.	2002 May 10	12051754
Monolithic silica rod liquid chromatography with ultraviolet or fluorescence detection for metabolite analysis of cytochrome P450 marker reactions.	2002 Nov 25	12401345
Diversity in the oxidation of substrates by cytochrome P450 2D6: lack of an obligatory role of aspartate 301-substrate electrostatic bonding.	2002 Sep 10	12206675
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
Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate.	2003	12569440
Residues glutamate 216 and aspartate 301 are key determinants of substrate specificity and product regioselectivity in cytochrome P450 2D6.	2003 Feb 7	12446689
High-throughput inhibition screening of major human cytochrome P450 enzymes using an in vitro cocktail and liquid chromatography-tandem mass spectrometry.	2003 Jan 1	12467917
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003 Jan 1	12464242
Regulation of CYP2D expression in rat brain by toluene.	2003 Jun	14703099
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
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
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 `Fri Dec 16 18:10:44 UTC 2022` Edited by `admin` on `Fri Dec 16 18:10:44 UTC 2022`
Record UNII	G66IY7Q7S4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUFURALOL HYDROCHLORIDE

Common Name

English

BUFURALOL HCL

Common Name

English

ANGIUM

Brand Name

English

RO-3-4787

Code

English

2-BENZOFURANMETHANOL, .ALPHA.,-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-7-ETHYL-, HYDROCHLORIDE, (±)-

Common Name

English

Bufuralol hydrochloride [WHO-DD]

Common Name

English

BUFURALOL HYDROCHLORIDE [MART.]

Common Name

English

RO-3-4787 HYDROCHLORIDE

Code

English

2-BENZOFURANMETHANOL, .ALPHA.-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-7-ETHYL-, HYDROCHLORIDE (1:1)

Systematic Name

English

RO 3-4787 HYDROCHLORIDE

Code

English

BUFURALOL HYDROCHLORIDE [MI]

Common Name

English

Code System Code Type Description

FDA UNII

G66IY7Q7S4