Otilonium bromide | CAS#26095-59-0 | Antispasmodic

MedKoo Cat#: 462128 | Name: Otilonium bromide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Otilonium bromide is an antimuscarinic and calcium channel blocker used to relieve spasmodic pain of the gut, especially in irritable bowel syndrome. Otilonium bromide has been identified as an applicable antifungal agent. Otilonium bromide was identified to inhibit USP28's activity with the IC(50) value at 6.90 0.90 muM.

Chemical Structure

Otilonium bromide

CAS#26095-59-0

Theoretical Analysis

MedKoo Cat#: 462128

Name: Otilonium bromide

CAS#: 26095-59-0

Chemical Formula: C29H43BrN2O4

Exact Mass: 562.2406

Molecular Weight: 563.58

Elemental Analysis: C, 61.81; H, 7.69; Br, 14.18; N, 4.97; O, 11.36

Price and Availability

Size	Price	Availability
10mg	USD 465.00	2 Weeks
50mg	USD 875.00	2 Weeks
100mg	USD 1,330.00	2 Weeks
250mg	USD 2,090.00	2 Weeks

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Synonym

Otilonium bromide; Octylonium

IUPAC/Chemical Name

N,N-diethyl-N-methyl-2-[[4-[[2-(octyloxy)benzoyl]amino]benzoyl]oxy]-ethanaminium, monobromide

InChi Key

VWZPIJGXYWHBOW-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C(NC1=CC=C(C(OCC[N+](CC)(C)CC)=O)C=C1)C2=CC=CC=C2OCCCCCCCC.[Br-]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

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

In vitro activity:

Otilonium bromide (OB) inhibited the generation of ACh-induced calcium signals in a dose dependent manner (IC(50)=880 nM). 6. In CHO-M(3) cells, OB inhibited calcium signals induced by ACh, but not ATP. In addition, OB did not inhibit histamine-induced colonic crypt calcium signals. The present studies have demonstrated that OB inhibited M(3) receptor-coupled calcium signals in human colonic crypts and CHO-M(3) cells, but not those induced by stimulation of other endogenous receptor types. Reference: Br J Pharmacol. 2002 Dec;137(7):1134-42. https://pubmed.ncbi.nlm.nih.gov/12429587/

In vivo activity:

Otilonium bromide showed potent antimicrobial activity against V.vulnificus and had a synergistic effect in combination with antibiotics. Field emission transmission electron microscope images revealed that otilonium bromide caused cell division defects in V.vulnificus. To investigate its inhibitory action mechanisms, this study examined the effect of otilonium bromide on the expression levels of several proteins crucial for V.vulnificus growth, motility, and adhesion. In addition, otilonium bromide significantly decreased the expression levels of outer membrane protein TolCV1, thus inhibiting RtxA1 toxin secretion and substantially reducing V.vulnificus cytotoxicity to host cells. Reference: Res Microbiol. 2023 Jan-Feb;174(1-2):103992. https://pubmed.ncbi.nlm.nih.gov/36122890/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	35.49
	DMSO	62.7	111.19
	Ethanol	61.5	109.12
	PBS (pH 7.2)	10.0	17.74
	Water	106.5	188.97

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 563.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Lindqvist S, Hernon J, Sharp P, Johns N, Addison S, Watson M, Tighe R, Greer S, Mackay J, Rhodes M, Lewis M, Stebbings W, Speakman C, Evangelista S, Johnson I, Williams M. The colon-selective spasmolytic otilonium bromide inhibits muscarinic M(3) receptor-coupled calcium signals in isolated human colonic crypts. Br J Pharmacol. 2002 Dec;137(7):1134-42. doi: 10.1038/sj.bjp.0704942. PMID: 12429587; PMCID: PMC1573573. 2. Gandía L, Villarroya M, Lara B, Olmos V, Gilabert JA, López MG, Martínez-Sierra R, Borges R, García AG. Otilonium: a potent blocker of neuronal nicotinic ACh receptors in bovine chromaffin cells. Br J Pharmacol. 1996 Feb;117(3):463-470. doi: 10.1111/j.1476-5381.1996.tb15213.x. PMID: 8821535; PMCID: PMC1909307. 3. Gong Y, Kim YR. Therapeutic potential of otilonium bromide against Vibrio vulnificus. Res Microbiol. 2023 Jan-Feb;174(1-2):103992. doi: 10.1016/j.resmic.2022.103992. Epub 2022 Sep 17. PMID: 36122890. 4. Xu C, Liu C, Chen K, Zeng P, Chan EWC, Chen S. Otilonium bromide boosts antimicrobial activities of colistin against Gram-negative pathogens and their persisters. Commun Biol. 2022 Jun 21;5(1):613. doi: 10.1038/s42003-022-03561-z. PMID: 35729200; PMCID: PMC9213495.

In vitro protocol:

In vivo protocol:

1. Gong Y, Kim YR. Therapeutic potential of otilonium bromide against Vibrio vulnificus. Res Microbiol. 2023 Jan-Feb;174(1-2):103992. doi: 10.1016/j.resmic.2022.103992. Epub 2022 Sep 17. PMID: 36122890. 2. Xu C, Liu C, Chen K, Zeng P, Chan EWC, Chen S. Otilonium bromide boosts antimicrobial activities of colistin against Gram-negative pathogens and their persisters. Commun Biol. 2022 Jun 21;5(1):613. doi: 10.1038/s42003-022-03561-z. PMID: 35729200; PMCID: PMC9213495.

1: Zhen C, Wang L, Feng Y, Whiteway M, Hang S, Yu J, Lu H, Jiang Y. Otilonium Bromide Exhibits Potent Antifungal Effects by Blocking Ergosterol Plasma Membrane Localization and Triggering Cytotoxic Autophagy in Candida Albicans. Adv Sci (Weinh). 2024 Jul 12:e2406473. doi: 10.1002/advs.202406473. Epub ahead of print. PMID: 38995235. 2: Mousavi T, Sharifnia M, Nikfar S, Abdollahi M. Pharmacotherapy for gastric and intestinal cramping pain: ‎ current and emerging therapies. Expert Opin Pharmacother. 2023 Sep-Dec;24(18):2021-2033. doi: 10.1080/14656566.2023.2265830. Epub 2024 Jan 5. PMID: 37788098. 3: Xu Z, Wang H, Meng Q, Ding Y, Zhu M, Zhou H, Zhang N, Shi L. Otilonium Bromide acts as a selective USP28 inhibitor and exhibits cytotoxic activity against multiple human cancer cell lines. Biochem Pharmacol. 2023 Sep;215:115746. doi: 10.1016/j.bcp.2023.115746. Epub 2023 Aug 12. PMID: 37579857. 4: Traini C, Idrizaj E, Biagioni C, Baccari MC, Vannucchi MG. Otilonium Bromide Prevents Cholinergic Changes in the Distal Colon Induced by Chronic Water Avoidance Stress, a Rat Model of Irritable Bowel Syndrome. Int J Mol Sci. 2023 Apr 18;24(8):7440. doi: 10.3390/ijms24087440. PMID: 37108603; PMCID: PMC10139220. 5: Tkach S, Dorofeyev A, Kuzenko I, Sulaieva O, Falalyeyeva T, Kobyliak N. Fecal microbiota transplantation in patients with post-infectious irritable bowel syndrome: A randomized, clinical trial. Front Med (Lausanne). 2022 Oct 20;9:994911. doi: 10.3389/fmed.2022.994911. PMID: 36341232; PMCID: PMC9631772. 6: Gong Y, Kim YR. Therapeutic potential of otilonium bromide against Vibrio vulnificus. Res Microbiol. 2023 Jan-Feb;174(1-2):103992. doi: 10.1016/j.resmic.2022.103992. Epub 2022 Sep 17. PMID: 36122890. 7: Cox JF 3rd. In IBS, a smartphone application for self-managing a FODMAP- lowering diet vs. otilonium bromide reduced symptoms at 8 wk. Ann Intern Med. 2022 Aug;175(8):JC91. doi: 10.7326/J22-0059. Epub 2022 Aug 2. PMID: 35914257. 8: Xu C, Liu C, Chen K, Zeng P, Chan EWC, Chen S. Otilonium bromide boosts antimicrobial activities of colistin against Gram-negative pathogens and their persisters. Commun Biol. 2022 Jun 21;5(1):613. doi: 10.1038/s42003-022-03561-z. PMID: 35729200; PMCID: PMC9213495. 9: Carbone F, Van den Houte K, Besard L, Tack C, Arts J, Caenepeel P, Piessevaux H, Vandenberghe A, Matthys C, Biesiekierski J, Capiau L, Ceulemans S, Gernay O, Jones L, Maes S, Peetermans C, Raat W, Stubbe J, Van Boxstael R, Vandeput O, Van Steenbergen S, Van Oudenhove L, Vanuytsel T, Jones M, Tack J; DOMINO Study Collaborators; Domino Study Collaborators. Diet or medication in primary care patients with IBS: the DOMINO study - a randomised trial supported by the Belgian Health Care Knowledge Centre (KCE Trials Programme) and the Rome Foundation Research Institute. Gut. 2022 Nov;71(11):2226-2232. doi: 10.1136/gutjnl-2021-325821. Epub 2022 Apr 28. PMID: 35483886; PMCID: PMC9554021. 10: He L, Yu Z, Geng Z, Huang Z, Zhang C, Dong Y, Gao Y, Wang Y, Chen Q, Sun L, Ma X, Huang B, Wang X, Zhao Y. Structure, gating, and pharmacology of human CaV3.3 channel. Nat Commun. 2022 Apr 19;13(1):2084. doi: 10.1038/s41467-022-29728-0. PMID: 35440630; PMCID: PMC9019099. 11: Zaki SA, Helal ME, Rashid A. Cardiovascular Toxicity Due to Otilonium Bromide Overdose: A Case Report. J Emerg Med. 2022 Mar;62(3):e47-e50. doi: 10.1016/j.jemermed.2021.10.025. Epub 2022 Jan 12. PMID: 35031171. 12: Cunningham AL, Esarte Palomero O, Voss BJ, Trent MS, Davies BW. Irritable Bowel Syndrome Therapeutic Has Broad-Spectrum Antimicrobial Activity. Antimicrob Agents Chemother. 2021 Sep 17;65(10):e0044321. doi: 10.1128/AAC.00443-21. Epub 2021 Jul 19. PMID: 34280019; PMCID: PMC8448155. 13: Traini C, Idrizaj E, Garella R, Faussone-Pellegrini MS, Baccari MC, Vannucchi MG. Otilonium Bromide treatment prevents nitrergic functional and morphological changes caused by chronic stress in the distal colon of a rat IBS model. J Cell Mol Med. 2021 Jul;25(14):6988-7000. doi: 10.1111/jcmm.16710. Epub 2021 Jun 9. PMID: 34109728; PMCID: PMC8278105. 14: Shrivastava A, Mittal A. A Mini Review on Characteristics and Analytical Methods of Otilonium Bromide. Crit Rev Anal Chem. 2022;52(7):1717-1725. doi: 10.1080/10408347.2021.1913983. Epub 2021 May 26. PMID: 34039224. 15: Erdogan A, Erdogan MA, Atasoy O, Erbas O. Effects of the Calcium Channel Blocker Otilonium Bromide on Seizure Activity in Rats With Pentylenetetrazole- Induced Convulsions. Neurochem Res. 2021 Jul;46(7):1717-1724. doi: 10.1007/s11064-021-03310-4. Epub 2021 Apr 3. PMID: 33811624. 16: Cavalluzzi MM, Budriesi R, De Salvia MA, Quintieri L, Piarulli M, Milani G, Gualdani R, Micucci M, Corazza I, Rosato A, Viale M, Caputo L, Franchini C, Lentini G. Lubeluzole: from anti-ischemic drug to preclinical antidiarrheal studies. Pharmacol Rep. 2021 Feb;73(1):172-184. doi: 10.1007/s43440-020-00167-2. Epub 2020 Oct 19. PMID: 33074530. 17: Zhou L, She P, Tan F, Li S, Zeng X, Chen L, Luo Z, Wu Y. Repurposing Antispasmodic Agent Otilonium Bromide for Treatment of Staphylococcus aureus Infections. Front Microbiol. 2020 Jul 31;11:1720. doi: 10.3389/fmicb.2020.01720. PMID: 32849366; PMCID: PMC7410927. 18: Solís-García Del Pozo J, de Cabo C, Solera J. Gastrointestinal manifestations in Satoyoshi syndrome: a systematic review. Orphanet J Rare Dis. 2020 May 19;15(1):115. doi: 10.1186/s13023-020-01395-8. PMID: 32429959; PMCID: PMC7236136. 19: Parisio C, Lucarini E, Micheli L, Toti A, Di Cesare Mannelli L, Antonini G, Panizzi E, Maidecchi A, Giovagnoni E, Lucci J, Ghelardini C. Researching New Therapeutic Approaches for Abdominal Visceral Pain Treatment: Preclinical Effects of an Assembled System of Molecules of Vegetal Origin. Nutrients. 2019 Dec 20;12(1):22. doi: 10.3390/nu12010022. PMID: 31861862; PMCID: PMC7019336. 20: Lee JH, Kim JI, Baeg MK, Sunwoo YY, Do K, Lee JH, Kim HJ, Choi JS, Kim J, Seo CS, Shin HK, Ha H, Park TY. Effect of Samryungbaekchul-san Combined with Otilonium Bromide on Diarrhea-Predominant Irritable Bowel Syndrome: A Pilot Randomized Controlled Trial. J Clin Med. 2019 Sep 27;8(10):1558. doi: 10.3390/jcm8101558. PMID: 31569833; PMCID: PMC6832362.