ChemicalBook CAS DataBase List 26095-59-0

26095-59-0

Name	Otilonium bromide
CAS	26095-59-0
EINECS(EC#)	247-457-4
Molecular Formula	C29H43BrN2O4
MDL Number	MFCD00211142
Molecular Weight	563.57
MOL File	26095-59-0.mol

Synonyms

diethyl(2-hydroxyethyl) methylammonium bromide p-(o-(octyloxy)benzamido)-benzoate n,n-diethyl-n-methyl-2-((4-((2-(octyloxy)benzoyl)amino)benzoyl)oxy)-ethanaminium bromide OCTYLONIUM BROMIDE OCTYLONIUM IODIDE otilonium bromide SPASMONEN ammonium,diethyl(2-hydroxyethyl)methyl-,bromide,p-(o-(octyloxy)benzamido)ben diethyl(2-hydroxyethyl)methylammoniumbromidep-(o-(octyloxy)benzamido)benzoa ethanaminium,n,n-diethyl-n-methyl-2-((4-((2-(octyloxy)benzoyl)amino)benzoyl) octylonium ottiloniobromuro Doralin Menoctyl N,N-Diethyl-N-methy-2-[[4-[[2-(octyloxy)benzoyl]amino]benzoyl]oxy]ethanaminium Bromide Pasminox SP-63 Spasen Spasmoctyl Spasmome Otilonium

Chemical Properties

Appearance	White Powder
Melting point	130-133°C
storage temp.	-20°C
solubility	DMSO (Slightly), Methanol (Slightly)
form	powder
color	white to beige
Water Solubility	H2O: 5mg/mL, clear (warmed)
Usage	Inhibits platlet activating factor induced hypotension. Antispasmodic
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
InChIKey	VWZPIJGXYWHBOW-UHFFFAOYSA-N
SMILES	O(C1C=CC=CC=1C(=O)NC1C=CC(C(=O)OCC[N+](C)(CC)CC)=CC=1)CCCCCCCC.[Br-]
CAS DataBase Reference	26095-59-0(CAS DataBase Reference)

Safety Data

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Toxicity	LD50 in mice (mg/kg) 87.0 i.p. less more

Hazard Information

Description

Otilonium is an inhibitor of L-type (IC₅₀ = 2.3 μM) and T-type calcium channels (IC₅₀s = 0.8, 1.1, and 0.4 μM for Ca_v3.1, Ca_v3.2, and Ca_v3.3, respectively). It is also an antagonist of muscarinic acetylcholine receptors (mAChRs; IC₅₀s = 0.054, 0.4, 0.222, and 0.156 μM for M₁, M₂, M₄, and M₅ muscarinic receptors, respectively) and the platelet activating factor (PAF) receptor (IC₅₀ = 0.0552 μM). Otilonium inhibits the inward calcium current in isolated rat colonic smooth muscle cells (EC₅₀ = 885 nM), an effect that can be blocked by the L-type calcium channel inhibitor nifedipine (Item No. 11106). It inhibits contractions induced by the muscarinic acetylcholine receptor (mAChR) agonist methacholine in isolated circular muscle of the guinea pig proximal colon (IC₅₀ = 3.7 μM). Otilonium (4 mg/kg) decreases fecal excretion and wet dog shakes and increases the tail withdrawal latency in the tail-flick test in a rat model of opioid withdrawal syndrome induced by morphine and naloxone.

Chemical Properties

White Powder

Originator

Spasmomen,Minapharm Co.

Manufacturing Process

3 Methods of producing of p-[2-(n-octyloxy)benzoyl]aminobenzoate of Ndiethylammoniumethanol: 1. 21.20 g (0.1 mole) of o-octyloxybenzoyl chloride and aqueous 10% NaOH are added at room temperature, with stirring and by slow dropping to 23.63 g (0.1 mole) of 2-diethylamine-ethyl-p-aminobenzoate in 100 ml of water, in such a manner as to keep the reaction mixture slightly alkaline. After concluding the slow dropping the solution is kept under stirring for 1 h and then the precipitate is collected. This precipitate, p-[2-(n-octyloxy)benzoyl] aminobenzoate of N-diethylammoniumethanol dried and recrystallized from hexane, has a melting point of 81°-82°C.
2. To 31.3 g (0.1 mole) of p-[2-(n-octyloxy)benzoyl]aminobenzoate acid in 300 ml of ethanol, are added 4.0 g (0.1 mole) of finely ground NaOH and the whole is heated to reflux for 1 h. Then 20.25 g (0.15 mol) of 2 Trade diethylaminoethyl chloride are slowly dropped under stirring and the heating is continued for 4 h. After cooling, the sodium chloride formed is filtered off and the solvent is separated by distillation, and the excess of the base, under a reduced pressure. The residue of p-[2-(n-tyloxy)benzoyl]aminobenzoate of Ndiethylammoniumethanol, recrystallized from hexane, has a melting point of 81°-82°C.
3. 11.7 g (0.1 mole) of N-diethylaminoethanol in 200 ml of anhydrous pyridine are added by careful dropping, 34.7 g (0.1 mole) of the chloride of p[2-(n-octyloxy)benzoyl]aminobenzoate acid and the mixture is heated in a water-bath for 3 h. The solvent is then separated by vacuum concentration, the residue is taken up with water, alkalinized and extracted with ether. The collected ether extracts, anhydridised owing to the separation of the solvent, leave a residue of p-[2-(n-tyloxy)benzoyl]aminobenzoate of Ndiethylammoniumethanol which, recrystallized from hexane, has a melting point of 81°-82°C.
p-[2-(n-Octyloxy)benzoyl]aminobenzoate of N-diethylmethylammoniumethyl bromide may be prepared by reaction of the p-[2-(n-octyloxy) benzoylaminobenzoate of N-diethylammoniumethanol with methylating agents such as methylbromide

Therapeutic Function

Anticholinergic, Spasmolytic

General Description

Otilonium bromide is an antispasmodic. It contains a red color ACh (acetylcholine) like moiety bound to an aromatic system that ends with an octyl ether.

Biochem/physiol Actions

Otilonium Bromide is a muscarinic receptor antagonist (antimuscarinic). Otilonium Bromide is a quaternary ammonium salt that exerts spasmolytic action selective on the distal gastrointestinal tract. It is used world-wide for the treatment of irritable bowel syndrome (IBS).

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. When heated to decomposition it emits toxic fumes of Brí and NOx.

References

[1] M T MARTIN M J L Hove Madsen. Otilonium bromide inhibits muscle contractions via L-type calcium channels in the rat colon.[J]. Neurogastroenterology and Motility, 2004, 16 2: 175-183. DOI: 10.1111/j.1365-2982.2004.00518.x
[2] PETER R STREGE. T-type Ca(2+) channel modulation by otilonium bromide.[J]. American journal of physiology. Gastrointestinal and liver physiology, 2010: G706-13. DOI: 10.1152/ajpgi.00437.2009
[3] S. EVANGELISTA. Receptor-binding profile of otilonium bromide, a drug for irritable bowel syndrome[J]. Gastroenterology, 1998, 114 1. DOI: 10.1016/s0016-5085(98)84640-4
[4] P SANTICIOLI. Antimuscarinic, calcium channel blocker and tachykinin NK2 receptor antagonist actions of otilonium bromide in the circular muscle of guinea-pig colon.[J]. Naunyn-Schmiedeberg’s archives of pharmacology, 1999, 359 5: 420-427. DOI: 10.1007/pl00005370
[5] A PINELLI S V S Trivulzio. Effects exerted by otilonium bromide1 administration on precipitated opioid withdrawal syndrome in rats2[J]. Toxicology, 1997, 122 1: Pages 23-37. DOI: 10.1016/s0300-483x(97)00073-5

Questions And Answer

Pharmacological effects
Otilonium bromide is an anticholinergic and antispasmodic drug. Its trade name is Siba Min. It can regulate the flow of calcium between intestinal smooth muscle extracellular and intracellular calcium pools. It is selective to gastrointestinal smooth muscle, and it has strong antispasmodic effect. It is applied to all motor function hyperthyroidism, and spasm reaction for different reasons and different parts as well as smooth muscle fibers pathological atrophy caused spasm reaction. It is also applied to the treatment of gastrointestinal distal intestine irritable bowel syndrome (IBS) or spastic pain, spastic colon, gastroenteritis, stomach, duodenum and esophagus disease, and endoscopic examination preparation (esophagoscopy, gastroscopy, ten finger colonoscopy and proctoscope). The experimental data show that the drug is absorbed very little by oral medication, and the most absorbed drug passed the biliary tract and were excreted via the stool.
The above information is edited by the chemicalbook of Kui Ming. ;
Toxicology
Acute toxicity: Non-lethal dose of oral administration to rats 1500mg/kg, to dogs is 1000mg/kg.
Chronic toxicity: experimental animals according to the program: 180 days of continuous oral administration, 11.44mg/kg/otilonium bromide. We found no abnormal changes in the results of blood biochemical and histological examination.
Teratogenicity: according to 11.44mg/kg, no embryonic and teratogenic toxicity to rats and rabbits in experiments.
Gene mutations: a large number of experiments have shown no mutagenic effect. ;
Side effects
Therapeutic doses of otilonium bromide doesn’t cause side effects, and it doesn’t cause atropine-like effect. ;
Precautions
Patients with glaucoma, prostatic hypertrophy, pyloric stenosis, pregnant or lactating women, and patients known allergic reaction to otilonium bromide should be used with caution. ;
Uses
Treatment of gastrointestinal spasm. ;

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26095-59-0

Chemical Properties

Safety Data

Hazard Information

Description

Chemical Properties

Originator

Manufacturing Process

Therapeutic Function

General Description

Biochem/physiol Actions

Safety Profile

References

Questions And Answer

Pharmacological effects

Toxicology

Side effects

Precautions

Uses

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

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