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| 1mg |
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| Targets |
Cimetropium bromide targets muscarinic acetylcholine receptors (mAChRs) in visceral smooth muscle, acting as a competitive, reversible antagonist. It selectively blocks M1 and M3 receptors in the gastrointestinal tract, leading to smooth muscle relaxation and reduced gastrointestinal motility. As a quaternary ammonium compound, it acts as a peripheral antimuscarinic, inhibiting acetylcholine at M-receptors.
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| ln Vitro |
Cetyl bromide functions as a competitive antagonist of muscarinic-mediated contractions in isolated colonic preparations of both species, with affinity values (pA2) varying from 7.41 to 7.82 [1]. The contraction of longitudinal muscle preparations is inhibited by ceytropium bromide's strong antimuscarinic properties. Cimetropium bromide decreased the release of labeled acetylcholine generated by electric field stimulation in perfusion tests using preloaded labeled choline preparations under muscarinic autoinhibitory blockade conditions [2].
In vitro, Cimetropium bromide behaves as a competitive antagonist of muscarinic-mediated contractions in isolated colonic preparations from various species, with affinity values (pA2) ranging between 7.41 and 7.82. It demonstrates potent antispasmodic activity by blocking muscarinic receptor-mediated smooth muscle contraction. The compound's quaternary ammonium structure limits its ability to cross the blood-brain barrier, resulting in peripheral selectivity. |
| ln Vivo |
Cetyl bromide is an effective intravenous medication that inhibits both endogenous and external stimuli-induced large intestinal motility in awake dogs with colic-Tirri fistulas. The colonic motor response to neostigmine treatment is counteracted by cetyl bromide (10-100 μg/kg), with an ID50 of 27.9 μg/kg; this affects both the tonic and phasic components of the contractile response. The medication suppresses intraluminal dilatation-induced locomotor activity within a similar dosing range (3-100 μg/kg) [1].
In vivo, Cimetropium bromide is effective in reducing gastrointestinal smooth-muscle spasms and alleviating symptoms of irritable bowel syndrome, including abdominal pain and cramping. It has been used for long-term treatment of irritable bowel syndrome. The compound reduces gastrointestinal motility and spasm without significant central nervous system effects due to its peripheral selectivity as a quaternary ammonium compound. |
| Enzyme Assay |
In vitro receptor binding assays for muscarinic antagonists typically use radioligand binding with [³H]N-methylscopolamine or [³H]quinuclidinyl benzilate (QNB). Membranes prepared from tissues expressing muscarinic receptors (e.g., rat brain or gastrointestinal tissue) or from cells expressing specific mAChR subtypes (M1-M5) are incubated with the radioligand and varying concentrations of Cimetropium bromide. Specific binding is determined by subtracting non-specific binding (defined by excess atropine). Ki values are calculated from competition curves. Functional assays measure inhibition of carbachol-induced contraction in isolated smooth muscle preparations.
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| Cell Assay |
Cellular assays for muscarinic antagonists typically use CHO or HEK293 cells expressing specific mAChR subtypes (M1, M2, M3, etc.). Cells are loaded with calcium-sensitive dyes and stimulated with carbachol or acetylcholine in the presence or absence of varying concentrations of Cimetropium bromide. The reduction in calcium mobilization is measured using fluorescence plate readers. IC50 or pA2 values are calculated from dose-response curves. Atropine is used as a positive control.
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| Animal Protocol |
In vivo animal studies for antispasmodic efficacy typically use rodent or guinea pig models of gastrointestinal motility. Animals are administered Cimetropium bromide orally or intravenously, and gastrointestinal transit is measured using a charcoal meal or radioactive marker. The distance traveled by the marker is measured, and the degree of inhibition of transit is calculated. In models of induced colonic spasm, the compound's ability to reduce spasm and normalize motility is assessed.
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| ADME/Pharmacokinetics |
Cimetropium bromide is administered orally or parenterally for the treatment of gastrointestinal disorders. As a quaternary ammonium compound, it has limited oral bioavailability due to poor absorption from the gastrointestinal tract. It acts locally in the gastrointestinal tract following oral administration or systemically following parenteral administration. The compound is metabolized in the liver and excreted primarily via the kidneys and bile. Detailed PK parameters are available from published pharmacokinetic studies.
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| Toxicity/Toxicokinetics |
Cimetropium bromide is generally well-tolerated at therapeutic doses. As a peripheral antimuscarinic, it has limited central nervous system side effects due to its quaternary ammonium structure, which restricts blood-brain barrier penetration. Common side effects include dry mouth, blurred vision, constipation, and urinary retention, which are class effects of anticholinergic agents. Serious adverse effects are rare.
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| References | |
| Additional Infomation |
Cimetropium bromide (DA-3177) is a semi-synthetic, quaternary ammonium antimuscarinic compound derived from scopolamine. It acts as a competitive, reversible antagonist of muscarinic receptors in visceral smooth muscle, selectively blocking M1 and M3 receptors in the gastrointestinal tract to relieve spasms. The compound is used to treat irritable bowel syndrome, peptic ulcer, and gastroesophageal reflux disease. Its quaternary ammonium structure ensures peripheral selectivity with minimal CNS effects.
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| Molecular Formula |
C21H28BRNO3
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|---|---|
| Molecular Weight |
422.36
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| Exact Mass |
437.12
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| CAS # |
51598-60-8
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| PubChem CID |
20054870
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| Appearance |
White to off-white solid powder
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
27
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| Complexity |
538
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)[C@H](CO)C4=CC=CC=C4)CC5CC5.[Br-]
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| InChi Key |
WDURTRGFUGAJHA-HNHWXVNLSA-M
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| InChi Code |
InChI=1S/C21H28NO4.BrH/c1-22(11-13-7-8-13)17-9-15(10-18(22)20-19(17)26-20)25-21(24)16(12-23)14-5-3-2-4-6-14;/h2-6,13,15-20,23H,7-12H2,1H3;1H/q+1;/p-1/t15?,16-,17-,18+,19-,20+,22?;/m1./s1
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| Chemical Name |
[(1R,2R,4S,5S)-9-(cyclopropylmethyl)-9-methyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate;bromide
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| Synonyms |
Cimetropii bromidum; Alginor; Cimetropium bromide
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~50 mg/mL (~114.06 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (228.12 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3676 mL | 11.8382 mL | 23.6765 mL | |
| 5 mM | 0.4735 mL | 2.3676 mL | 4.7353 mL | |
| 10 mM | 0.2368 mL | 1.1838 mL | 2.3676 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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