Basic information
- CAS
26095-59-0- Standard SMILES
CCCCCCCCOc1ccccc1C(=O)Nc1ccc(C(=O)OCC[N+](C)(CC)CC)cc1.[Br-]- InChIKey
VWZPIJGXYWHBOW-UHFFFAOYSA-N- Molecular formula
- C29H43BrN2O4
- Average molar mass
- 563.6 g/mol
- Monoisotopic mass
- 562.24062
Names & identifiers
- Preferred name
- Otilonium Bromide
- IUPAC
- diethyl-methyl-[2-[4-[(2-octoxybenzoyl)amino]benzoyl]oxyethyl]azanium bromide
- English name
- Otilonium bromide
- Molecular formula
- C29H43BrN2O4
- Molecular weight
- 563.58
Names & synonyms
Otilonium Bromide26095-59-0Octylonium bromideDoralinBromure d'otiloniumBromuro de otilonioSP63Otilonii bromidumSpasmoctyl 40DTXSID0046357SP-6321HN3N72PV
Show more names
OtiloniumSpasmomenSPASMONENSpasenMenoctylPasminoxSpasmome
DTXCID8026357N-diethylmethylammoniummethyl-p-(2-(N-octyloxy)benzoyl)aminobenzoate bromideotilonio bromuroRefChem:168711A03AB06247-457-4Otilonium (bromide)Bromuro de otilonio [INN-Spanish]
Database identifiers
- CAS
26095-59-0- PubChem CID
- 72092
- DTXSID
DTXSID0046357- ChEMBL
CHEMBL2103773- UNII
- 21HN3N72PV
- EC Number
- 247-457-4
Properties
Computed structural properties
- Topological polar surface area
- 64.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 17
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 599
Physicochemical properties
- Melting point
- 130 · 130-133°C
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- powder
- color
- white to beige
- Water Solubility
- 2 O: · H2O: 5mg/mL, clear (warmed)
- 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 · 26095-59-0(CAS DataBase Reference)
- FDA UNII
- 21 HN3N72PV · 21HN3N72PV
- ATC code
- 3 AB06 · A03AB06
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302+H312+H332 (16.7%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (66.7%)
Safety data
- wgk
- WGK 3
- Toxicity
- LD50 in mice (mg/kg) 87.0 i.p.
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
A03AB06
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
MeSH Pharmacological Classification
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.
Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.
Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.
Applications
UsesTreatment of gastrointestinal spasm.
DescriptionOtilonium 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 Cav3.1, Cav3.2, and Cav3.3, 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 . 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.
UsesOtilonium bromide is an antimuscarinic
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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