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Details

Stereochemistry ACHIRAL
Molecular Formula C29H43N2O4.Br
Molecular Weight 563.567
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OTILONIUM BROMIDE

SMILES

[Br-].CCCCCCCCOC1=CC=CC=C1C(=O)NC2=CC=C(C=C2)C(=O)OCC[N+](C)(CC)CC

InChI

InChIKey=VWZPIJGXYWHBOW-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C29H43N2O4
Molecular Weight 483.6627
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/otilonium-bromide.html | https://www.ncbi.nlm.nih.gov/pubmed/8867109 | https://www.ncbi.nlm.nih.gov/pubmed/25057296

Otilonium is a musculotropic spasmolytic agent belonging to the family of quaternary ammonium derivatives and successfully used in the treatment of patients affected by Irritable bowel syndrome (IBS) due to its specific pharmacokinetic and pharmacodynamic properties. The positive polarity of the head of the Otilonium molecule determines the main pharmacokinetic property of this drug: a minimal systemic absorption and the consequently high safety profile. Studies on animal models revealed a specific Otilonium accumulation in colonic circular muscle at therapeutic µm concentrations, while its plasma levels were 1000 times lower, together with a poor penetration of the drug in the central nervous system. Consistently, after oral administration to healthy volunteers, the Otilonium plasmatic concentration was very low, less than 1% of the drug was eliminated by urine, and 97% was eliminated by feces. Recent clinical studies showed comparable safety and tolerability for Otilonium and placebo. Otilonium was shown to inhibit the main patterns of human sigmoid motility in vitro, including: the tone of smooth muscle cells (SMCs); the rhythmic phasic contractions induced by the interstitial cells of Cajal; and the strong contractions induced by stimulation of enteric motor neurons mainly by blocking the calcium influx through L-type calcium channels on SMCs. Recent in vitro studies using cultured human colonic SMCs to further assess the musculotropic spasmolytic properties of Otilonium confirmed that this drug causes smooth muscle relaxation through the inhibition of voltage-gated calcium channels (L-type > T-type) and the inhibition of muscarinic and tachykinergic effects.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Obimal

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Otilonium bromide enhances sensory thresholds of volume and pressure in patients with irritable bowel syndrome.
2001 Jan-Dec
Optimisation and validation of a capillary electrophoresis method for the simultaneous determination of diazepam and otilonium bromide.
2001 Oct
Extended analysis of a double-blind, placebo-controlled, 15-week study with otilonium bromide in irritable bowel syndrome.
2002 Dec
The colon-selective spasmolytic otilonium bromide inhibits muscarinic M(3) receptor-coupled calcium signals in isolated human colonic crypts.
2002 Dec
Otilonium bromide inhibits muscle contractions via L-type calcium channels in the rat colon.
2004 Apr
Suppressive activity of tiotropium bromide on matrix metalloproteinase production from lung fibroblasts in vitro.
2008
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.
2008 Nov 13
Determination of the unstable drug otilonium bromide in human plasma by LC-ESI-MS and its application to a pharmacokinetic study.
2010 Oct 15
Patents

Patents

Sample Use Guides

3 tablets (3 × 40 mg) daily before meals (120 mg Otilonium/day)
Route of Administration: Oral
Human circular smooth muscle cells were used for activity evaluation. To determine the effect of Otilonium on ionic conductances in human jejunal circular smooth muscle, we patch clamped enzymatically dissociated cells with Cs+ in the pipette to block outward K+ currents and with NaCl or NMDG-Cl Ringer’s extracellular solution. Electrodes were coated with R6101 (Dow Corning, Midland, MI, USA) and fire polished to a final resistance of 3–5 M. Currents were amplified, digitized and processed using an Axopatch 200B amplifier, a Digidata 1200, and pCLAMP 8 software (Axon Instruments, Foster City, CA, USA). In experiments examining Na+ or Ca2+ current, whole cell records were sampled at 10 kHz and filtered at 4 kHz with an eight-pole Bessel filter. For these experiments, cells were held at -100 mV and pulsed from -80 to +35 mV in 5 mV intervals for 50 ms. Otilonium (0.09–9 mkM) was used as this reproduced clinical intracellular concentrations. In human circular smooth muscle cells, Otilonium inhibited L-type Ca2+ current by 25% at 0.9 mkM and 90% at 9 mkM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:14:54 GMT 2023
Edited
by admin
on Sat Dec 16 17:14:54 GMT 2023
Record UNII
21HN3N72PV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OTILONIUM BROMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
DIETHYL(2-HYDROXYETHYL)METHYLAMMONIUM BROMIDE P-(O-(OCTYLOXY)BENZAMIDO)-BENZOATE
Common Name English
SP63
Code English
otilonium bromide [INN]
Common Name English
OCTYLONIUM BROMIDE
Common Name English
DORALIN
Brand Name English
OTILONIUM BROMIDE [MART.]
Common Name English
OTILONIUM BROMIDE [MI]
Common Name English
SPASMOCTYL 40
Brand Name English
SP-63
Code English
Otilonium bromide [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
WHO-VATC QA03AB06
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
WHO-VATC QA03CA04
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
WHO-ATC A03CA04
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
WHO-ATC A03AB06
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
Code System Code Type Description
MESH
C013934
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
ECHA (EC/EINECS)
247-457-4
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
DRUG CENTRAL
2003
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
WIKIPEDIA
Otilonium bromide
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
FDA UNII
21HN3N72PV
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
EVMPD
SUB09479MIG
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PRIMARY
RXCUI
54216
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PRIMARY RxNorm
PUBCHEM
72092
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PRIMARY
INN
4325
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PRIMARY
MERCK INDEX
m8267
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY Merck Index
DRUG BANK
DBSALT002518
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID0046357
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
CAS
26095-59-0
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL1433361
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
NCI_THESAURUS
C90743
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
SMS_ID
100000083575
Created by admin on Sat Dec 16 17:14:54 GMT 2023 , Edited by admin on Sat Dec 16 17:14:54 GMT 2023
PRIMARY
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