Bufuralol hydrochloride

Names

[ Name ]:
Bufuralol hydrochloride

[Synonym ]:
1-(7-Ethyl-1-benzofuran-2-yl)-2-[(2-methyl-2-propanyl)amino]ethan ol hydrochloride (1:1)

Biological Activity

[Description]:

Bufuralol hydrochloride (Ro 3-4787 hydrochloride) is a potent non-selective, orally active β-adrenoreceptor antagonist with partial agonist activity. Bufuralol hydrochloride is a CYP2D6 probe substrate[1][2].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Research Areas >> Endocrinology

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

[In Vitro]

Bufuralol is widely used in the characterization of CYP2D6 activity, and possesses aromatic rings and a basic nitrogen that are characteristic of CYP2D6 substrates[3].

[In Vivo]

Bufuralol metabolism mediated by NADPH exhibits biphasic kinetics and is less efficient than that observed in the presence of cumene hydroperoxide (CuOOH) in and monkey intestines, in agreement with the observations in the livers[4].

[References]

[1]. T H Pringle, et al. Pharmacodynamic and pharmacokinetic studies on bufuralol in man. Br J Clin Pharmacol. 1986 Nov;22(5):527-34.

[2]. Jie Cai, et al. Effects of 22 Novel CYP2D6 Variants Found in the Chinese Population on the Bufuralol and Dextromethorphan Metabolisms In Vitro. Basic Clin Pharmacol Toxicol. 2016 Mar;118(3):190-9.

[3]. Sarah M Glass, et al. CYP2D6 Allelic Variants *34, *17-2, *17-3, and *53 and a Thr309Ala Mutant Display Altered Kinetics and NADPH Coupling in Metabolism of Bufuralol and Dextromethorphan and Altered Susceptibility to Inactivation by SCH 66712. Drug Metab Dispos. 2018 Aug;46(8):1106-1117.

[4]. T Prueksaritanont, et al. (+)-bufuralol 1'-hydroxylation activity in human and rhesus monkey intestine and liver. Biochem Pharmacol. 1995 Oct 26;50(9):1521-5.

Chemical & Physical Properties

[ Boiling Point ]:
393.2ºC at 760 mmHg

[ Melting Point ]:
143-146ºC

[ Molecular Formula ]:
C₁₆H₂₄ClNO₂

[ Molecular Weight ]:
297.82000

[ Flash Point ]:
191.6ºC

[ Exact Mass ]:
297.15000

[ PSA ]:
45.40000

[ LogP ]:
4.60960

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Binding of bufuralol, dextromethorphan, and 3,4-methylenedioxymethylamphetamine to wild-type and F120A mutant cytochrome P450 2D6 studied by resonance Raman spectroscopy.

Biochem. Biophys. Res. Commun. 343(3) , 772-9, (2006)

Cytochrome P450 2D6 (CYP2D6) is one of the most important drug-metabolizing enzymes in humans. Resonance Raman data, reported for the first time for CYP2D6, show that the CYP2D6 heme is found to be in...

The ability of cytochrome P450 2D isoforms to synthesize dopamine in the brain: An in vitro study.

Eur. J. Pharmacol. 626(2-3) , 171-8, (2010)

The present study was aimed at determining which rat cytochrome P450 (CYP) isoforms are involved in the hydroxylation of tyramine to dopamine and at determining whether the reaction can take place in ...

Predictions of cytochrome P450-mediated drug-drug interactions using cryopreserved human hepatocytes: comparison of plasma and protein-free media incubation conditions.

Drug Metab. Dispos. 40(4) , 706-16, (2012)

Cryopreserved human hepatocytes suspended in human plasma (HHSHP) have previously provided accurate CYP3A drug-drug interaction (DDI) predictions from a single IC(50) that captures both reversible and...