Zinterol hydrochloride

Names

[ Name ]:
Zinterol hydrochloride

[Synonym ]:
N-[2-hydroxy-5-[1-hydroxy-2-[(2-methyl-1-phenylpropan-2-yl)amino]ethyl]phenyl]methanesulfonamide,hydrochloride

Biological Activity

[Description]:

Zinterol hydrochloride (MJ 9184 hydrochloride) is a potent and selective β2-adrenoceptor agonist[1]. Zinterol hydrochloride increases ICa in a concentration-dependent manner with an EC50 of 2.2 nM[2]. Zinterol hydrochloride induces ventricular arrhythmias in conscious heart failure rabbits[3].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

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

[Target]

β2-adrenoceptor[1]

[In Vivo]

Zinterol (2.5 μg/kg i.v. bolus over 5 s) leads to ventricular arrhythmias including premature ventricular complexes (PVCs) and runs of ventricular tachycardia (VT) in heart failure (HF) rabbits. Zinterol at a lower dose (1 μg/kg i.v, n=4) does not induce ventricular arrhythmias in HF rabbits[3]. Animal Model: In New Zealand White HF rabbits of either sex[3] Dosage: 1.0 or 2.5 μg/kg Administration: Intravenous bolus administration; over 5 seconds Result: 2.5 μg/kg did not significantly alter heart rate or mean arterial blood pressure in either control or HF rabbits. 2.5 μg/kg led to ventricular arrhythmias including premature ventricular complexes (PVCs) and runs of VT (up to 13 beats long) in 4 of 6 HF rabbits (vs 0 of 5 controls, p<0.01). 1 μg/kg did not induce ventricular arrhythmias in HF rabbits.

[References]

[1]. Gwee MC, et al. Pharmacological actions of a new -adrenoceptor agonist, MJ-9184-1, in anaesthetized cats. Br J Pharmacol. 1972 Nov;46(3):375-85.

[2]. Skeberdis VA, et al. Beta-2 adrenergic activation of L-type Ca²⁺ current in cardiac myocytes. J Pharmacol Exp Ther. 1997 Nov;283(2):452-61.

[3]. Desantiago J, et al. Arrhythmogenic effects of beta2-adrenergic stimulation in the failing heart are attributable to enhanced sarcoplasmic reticulum Ca load. Circ Res. 2008 Jun 6;102(11):1389-97.

Chemical & Physical Properties

[ Boiling Point ]:
574.3ºC at 760 mmHg

[ Molecular Formula ]:
C₁₉H₂₇ClN₂O₄S

[ Molecular Weight ]:
414.94700

[ Flash Point ]:
301.1ºC

[ Exact Mass ]:
414.13800

[ PSA ]:
107.04000

[ LogP ]:
4.75470

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: PB0512953

CHEMICAL NAME :: Methanesulfonanilide, 5'-(2-((alpha,alpha-dimethylphenethyl)amino)-1-hydrox yethyl)-2'- hydroxy-, monohydrochloride

CAS REGISTRY NUMBER :: 38241-28-0

LAST UPDATED :: 199007

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C19-H26-N2-O4-S.Cl-H

MOLECULAR WEIGHT :: 414.99

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 19,626,1976

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Articles

The beta3-adrenoceptor agonist 4-[[(Hexylamino)carbonyl]amino]-N-[4-[2-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-phenyl]-benzenesulfonamide (L755507) and antagonist (S)-N-[4-[2-[[3-[3-(acetamidomethyl)phenoxy]-2-hydroxypropyl]amino]-ethyl]phenyl]benzenesulfonamide (L748337) activate different signaling pathways in Chinese hamster ovary-K1 cells stably expressing the human beta3-adrenoceptor.

Mol. Pharmacol. 74(5) , 1417-28, (2008)

This study identifies signaling pathways activated by the beta(2)-/beta(3)-adrenoceptor (AR) agonist zinterol, the selective beta(3)-AR agonist L755507, and the selective beta(3)-AR antagonist L748337...

Multiple signalling pathways involved in beta2-adrenoceptor-mediated glucose uptake in rat skeletal muscle cells.

Br. J. Pharmacol. 147(4) , 446-54, (2006)

1. Beta-adrenoceptor (AR) agonists increase 2-deoxy-[3H]-D-glucose uptake (GU) via beta2-AR in rat L6 cells. The beta-AR agonists, zinterol (beta2-AR) and (-)-isoprenaline, increased cAMP accumulation...

Rapid turnover of glycogen in memory formation.

Neurochem. Res. 37(11) , 2456-63, (2012)

The influence of noradrenaline acting at α(2)-AR and β(2)-ARs on the turnover of glycogen after learning has been investigated. The role of glycogen turnover in memory formation was examined using wea...

Related Compounds

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