3-(3-Hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo(3.2.1)octane bromide monohydrate

Names

[ Name ]:
3-(3-Hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo(3.2.1)octane bromide monohydrate

[Synonym ]:
Ipratropium Bromide Monohydrate
8-Azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropyl)-8-methyl-8-(1-methylethyl)-, bromide, (3-endo), hydrate (1:1:1)
(3-endo)-3-(3-Hydroxy-2-phenylpropanoyl)-8-isopropyl-8-methyl-8-azoniabicyclo[3.2.1]octane bromide hydrate (1:1:1)
3-(3-Hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo(3.2.1)octane bromide monohydrate

Biological Activity

[Description]:

Ipratropium bromide (Sch 1000) hydrate is a muscarinic receptor antagonist, with IC50s of 2.9 nM, 2 nM, and 1.7 nM for M1, M2, and M3 receptors, respectively. Ipratropium bromide hydrate relaxes smooth muscle, can be used in the research for COPD (chronic obstructive pulmonary disease) and asthma[1][2][3][4][5].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> mAChR

Signaling Pathways >> GPCR/G Protein >> mAChR

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

[Target]

muscarinic M1 receptor:2.9 nM (IC50)

muscarinic M2 receptor:2 nM (IC50)

muscarinic M3 receptor:1.7 nM (IC50)

[In Vitro]

Ipratropium bromide hydrate (1 nM, 10 nM, 100 nM; 15 min) exerts its toxic effects via disruption of mitochondrial membrane potential[1]. Ipratropium bromide hydrate (1 nM-1 μM; 4 h) increases infarct size in isolated perfused heart ischaemia/reperfusion experiments with a dose-responsive manner (EC50=22.7 nM)[1]. Ipratropium bromide hydrate (0.001 nM-0.1 mM; 2 h) inhibits adult rat cardiac myocyte growth after 4 h hypoxia treatment[1]. Cell Viability Assay[1] Cell Line: Adult Rat Cardiac Myocyte Concentration: 0.001 nM-0.1 mM Incubation Time: 2 h in dark; prior to 4 h hypoxia Result: Resulted cell viability in a dose-dependent manner, with the inhibition rate of 52.7% at 0.1 mM dose.

[In Vivo]

Ipratropium bromide hydrate (1.0 μg/kg; i.v.; single dose) enhances vagal nerve stimulation induing bronchoconstriction[2]. Ipratropium bromide hydrate (0.04 mg/20 mL and 0.20 mg/20 mL; inhalation for 30 min, rate=30 mL/30 min) can protect the lungs against the cadmium-induced acute neutrophilic inflammation by reducing the parenchyma inflammatory infiltration of neutrophils[4]. Animal Model: Guinea-pigs of the Dunkin Hartley strain[2] Dosage: 0.1-1 μg/kg Administration: Intravenous injection; single dose Result: Resulted little blocking effect on post-junctional muscarinic receptors at 0.3 μg/kg, and inhibited ACh-induced bronchoconstriction at 0.5 μg/kg. Animal Model: Male Sprague-Dawley rats (300-350 g)[4] Dosage: 0.04 mg/20 mL and 0.20 mg/20 mL Administration: Inhalation; atomization rate of 30 mL/30 min; 30 min Result: Had no significant effects on any parameters recorded in healthy rats but exerted a protective effect against the inflammatory reaction elicited by cadmium.

[References]

[1]. Fryer AD, et al. Maclagan, Ipratropium bromide potentiates bronchoconstriction induced by vagal nerve stimulation in the guinea-pig. Eur J Pharmacol, 1987. 139(2): p. 187-91.

[2]. Harvey, et al. Maddock, Ipratropium Bromide-Mediated Myocardial Injury in In Vitro Models of Myocardial Ischaemia/Reperfusion. Toxicol Sci, 2014.

[3]. Maria Prat, et al. Discovery of novel quaternary ammonium derivatives of (3R)-quinuclidinyl amides as potent and long acting muscarinic antagonists. Bioorg Med Chem Lett. 2015 Apr 15;25(8):1736-1741.

[4]. Wenhui Zhang, et al. Anti-inflammatory effects of formoterol and ipratropium bromide against acute cadmium-induced pulmonary inflammation in rats. Eur J Pharmacol. 2010 Feb 25;628(1-3):171-8.

[5]. Venkatasamy R, et al. Novel relaxant effects of RPL554 on guinea pig tracheal smooth muscle contractility. Br J Pharmacol. 2016 Aug;173(15):2335-51.

Chemical & Physical Properties

[ Molecular Formula ]:
C₂₀H₃₂BrNO₃

[ Molecular Weight ]:
414.377

[ Exact Mass ]:
413.156555

[ PSA ]:
46.53000

[ LogP ]:
0.02610

[ Appearance of Characters ]:
white

[ Water Solubility ]:
H2O: soluble10mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302 + H332-H319

[ Precautionary Statements ]:
P261-P301 + P312 + P330-P305 + P351 + P338

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/22-36

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
YM3700000

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

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