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Otilonium Bromide

CAS# 26095-59-0

Otilonium Bromide

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Chemical structure

Otilonium Bromide

3D structure

Chemical Properties of Otilonium Bromide

Cas No. 26095-59-0 SDF Download SDF
PubChem ID 72092 Appearance Powder
Formula C29H43BrN2O4 M.Wt 563.57
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Octylonium bromide; SP63
Solubility H2O : ≥ 100 mg/mL (177.44 mM)
DMSO : 50 mg/mL (88.72 mM; Need ultrasonic)
*"≥" means soluble, but saturation unknown.
Chemical Name diethyl-methyl-[2-[4-[(2-octoxybenzoyl)amino]benzoyl]oxyethyl]azanium;bromide
SMILES [Br-].CCCCCCCCOc1ccccc1C(=O)Nc2ccc(cc2)C(=O)OCC[N+](C)(CC)CC
Standard InChIKey VWZPIJGXYWHBOW-UHFFFAOYSA-N
Standard InChI InChI=1S/C29H42N2O4.BrH/c1-5-8-9-10-11-14-22-34-27-16-13-12-15-26(27)28(32)30-25-19-17-24(18-20-25)29(33)35-23-21-31(4,6-2)7-3;/h12-13,15-20H,5-11,14,21-23H2,1-4H3;1H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Otilonium Bromide

DescriptionOtilonium Bromide is an antimuscarinic used as a spasmolytic agent. Target: mAChR Otilonium bromide inhibited the generation of ACh-induced calcium signals in a dose dependent manner (IC50=880 nM) [1]. Otilonium, a clinically useful spasmolytic, behaves as a potent blocker of neuronal nicotinic acetylcholine receptors (AChR). Whole-cell Ba2+ currents (IBa) through Ca2+ channels of voltage-clamped chromaffin cells were blocked by otilonium with an IC50 of 6.4 microM. Otilonium inhibited the secretory responses induced by 10 s pulses of 50 microM DMPP with an IC50 of 7.4 nM [2]. Otilonium bromide may represent an effective treatment for irritable bowel syndrome because it reduces its predominant symptom (abdominal pain/ discomfort) more than placebo does [3]. ilonium bromide (OB) is a spasmolytic agent that blocks L-Type Calcium channels in human colonic smooth muscle. otilonium bromide is safe, well tolerated and superior to placebo in reducing the frequency of abdominal pain, severity of abdominal bloating and protecting from symptom relapse in IBS. These results further confirm that patients with IBS can improve during and following treatment with otilonium bromide [4].

References:
[1]. Battaglia, G., et al., Otilonium bromide in irritable bowel syndrome: a double-blind, placebo-controlled, 15-week study. Aliment Pharmacol Ther, 1998. 12(10): p. 1003-10. [2]. Clave, P., et al., Randomised clinical trial: otilonium bromide improves frequency of abdominal pain, severity of distention and time to relapse in patients with irritable bowel syndrome. Aliment Pharmacol Ther, 2011. 34(4): p. 432-42. [3]. Lindqvist, S., et al., The colon-selective spasmolytic otilonium bromide inhibits muscarinic M(3) receptor-coupled calcium signals in isolated human colonic crypts. Br J Pharmacol, 2002. 137(7): p. 1134-42. [4]. Gandia, L., et al., Otilonium: a potent blocker of neuronal nicotinic ACh receptors in bovine chromaffin cells. Br J Pharmacol, 1996. 117(3): p. 463-470.

Otilonium Bromide Dilution Calculator

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Otilonium Bromide Molarity Calculator

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Preparing Stock Solutions of Otilonium Bromide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7744 mL 8.872 mL 17.744 mL 35.488 mL 44.3601 mL
5 mM 0.3549 mL 1.7744 mL 3.5488 mL 7.0976 mL 8.872 mL
10 mM 0.1774 mL 0.8872 mL 1.7744 mL 3.5488 mL 4.436 mL
50 mM 0.0355 mL 0.1774 mL 0.3549 mL 0.7098 mL 0.8872 mL
100 mM 0.0177 mL 0.0887 mL 0.1774 mL 0.3549 mL 0.4436 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Otilonium Bromide

Otilonium bromide is an antimuscarinic.

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References on Otilonium Bromide

Changes in nitrergic and tachykininergic pathways in rat proximal colon in response to chronic treatment with otilonium bromide.[Pubmed:25930994]

Neurogastroenterol Motil. 2015 Jul;27(7):997-1009.

BACKGROUND: Otilonium Bromide (OB) is used as a spasmolytic drug in the treatment of the functional bowel disorder irritable bowel syndrome. Although its acute effects on colonic relaxation are well-characterized, little is known about the effects of chronic administration of OB on enteric neurons, neuromuscular transmission, and interstitial cells of Cajal (ICC), key regulators of the gut function. METHODS: Adult Sprague-Dawley rats were treated with OB in drinking water at a dose of 2 mg/kg for 30 days. The colons of OB-treated and age-matched control rats were studied by confocal immunohistochemistry to detect immunoreactivity (IR) in myenteric plexus neurons for nitrergic and tachykininergic markers, and also by microelectrode electrophysiology. KEY RESULTS: Using immunohistochemistry, chronic OB administration did not change total neuron number, assessed by anti-Hu IR, but resulted in a significant increase in NK1 receptor positive neurons, a decrease in neuronal nitric oxide synthase expressing neurons, and a reduction in volume of substance P in nerve fibers in the myenteric plexus. Chronic OB administration potentiated inhibitory and excitatory junction potentials evoked by repetitive electrical field stimulation. The various types of colonic ICC, detected by Kit IR, were not altered nor were slow waves or smooth muscle membrane potential. CONCLUSIONS & INFERENCES: Chronic treatment with OB caused significant changes in the nitrergic and tachykinergic components of the myenteric plexus and in both inhibitory and excitatory neurotransmission in the rat colon.

Efficacy of otilonium bromide in irritable bowel syndrome: a pooled analysis.[Pubmed:28246548]

Therap Adv Gastroenterol. 2017 Mar;10(3):311-322.

BACKGROUND: Otilonium Bromide (OB) is a spasmolytic agent acting as an L-type calcium channel antagonist in intestinal and colonic smooth muscle cells (SMCs). We analyzed three independent clinical trials with homogeneous design on patients with irritable bowel syndrome (IBS). After 2 weeks receiving placebo, patients were randomized to receive OB (3 x 40 mg daily) or placebo for 15 weeks. We aimed to perform a pooled analysis of the data from these homogeneous clinical trials to evaluate the efficacy of OB treatment on symptoms and global response of patients. METHODS: A total of 883 patients with IBS (69.8% women, mean age 46.2 years, 43.8% mixed type) were included, 442 treated with OB and 441 with placebo. The efficacy results from the three studies at weeks 5, 10 and 15 were pooled in an intention-to-treat (ITT) strategy, analyzed with a logistic regression model and described by forest plots. RESULTS: Despite a placebo effect in all efficacy variables, a significant therapeutic effect of OB was observed at weeks 10 and 15 with reference to: (a) intensity and frequency of abdominal pain; (b) rate of responders as evaluated by patients (71.8% at week 10 and 77.2% at week 15); (c) severity of bloating; (d) rate of responders as evaluated by physicians (55% at week 10 and 63.9% at week 15). No significant OB effect was observed in stool frequency and consistency. CONCLUSIONS: OB is more effective than placebo in IBS treatment. Therapeutic benefits are significant after 10 weeks and are maximal after 15 weeks of treatment.

Repeated otilonium bromide administration prevents neurotransmitter changes in colon of rats underwent to wrap restraint stress.[Pubmed:27866394]

J Cell Mol Med. 2017 Apr;21(4):735-745.

Otilonium Bromide (OB) is a spasmolytic drug successfully used for the treatment of irritable bowel syndrome (IBS). Its efficacy has been attributed to the block of L- and T-type Ca(2+) channels and muscarinic and tachykinin receptors in the smooth muscle. Furthermore, in healthy rats, repeated OB administration modified neurotransmitter expression and function suggesting other mechanisms of action. On this basis, we investigated whether repeated OB treatment prevented the functional and neurochemical changes observed in the colon of rats underwent to wrap restrain stress (WRS) a psychosocial stressor considered suitable to reproduce the main IBS signs and symptoms. In control, WRS and OB/WRS rats functional parameters were measured in vivo and morphological investigations were done ex vivo in the colon. The results showed that OB counteracts most of the neurotransmitters changes caused by WRS. In particular, the drug prevents the decrease in SP-, NK1r-, nNOS-, VIP-, and S100beta-immunoreactivity (IR) and the increase in CGRP-, and CRF1r-IR. On the contrary, OB does not affect the increase in CRF2r-IR neurons observed in WRS rats and does not interfere with the mild mucosal inflammation due to WRS. Finally, OB per se increases the Mr2 expression in the muscle wall and decreases the number of the myenteric ChAT-IR neurons. Functional findings show a significantly reduction in the number of spontaneous abdominal contraction in OB treated rats. The ability of OB to block L-type Ca(2+) channels, also expressed by enteric neurons, might represent a possible mechanism through which OB exerts its actions.

A New, More Stable Polymorphic Form of Otilonium Bromide: Solubility, Crystal Structure, and Phase Transformation.[Pubmed:27444388]

J Pharm Sci. 2016 Oct;105(10):3013-3020.

A new polymorphic form of Otilonium Bromide is presented (Form I), and a thorough analysis of its crystal and molecular structure is performed. The compound suffers a temperature-driven first-order phase transition at about 396 K, which transforms it into the polymorph reported by Dapporto P and Sega A (Acta Cryst. 1986;C42:474-478) (Form II). Through thermal analysis and solubility experiments the relative stability of both crystal modifications were determined, confirming that at room temperature this new Form I is the more stable one, Form II existing just in a metastable state.

Description

Octylonium bromide (SP63) is an antimuscarinic used as a spasmolytic agent.

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