Structure via PubChem · Public domain (PubChem)
trimebutine
Sign in to saveAlso known as 2-Dimethylamino-2-phenylbutyl 3,4,5-trimethoxybenzoat, Trimebutino, Trimébutine
Trimebutine is a drug with antimuscarinic and very weak mu opioid agonist effects. It is used for the treatment of irritable bowel syndrome and other gastrointestinal disorders. It is sometimes combined with simethicone as a combination drug. Trimebutine is formulated as a tablet or granules for oral suspension.
Chemical data
- Formula
- C22H29NO5
- Molecular weight
- 387.5 g/mol
- IUPAC name
- [2-(dimethylamino)-2-phenylbutyl] 3,4,5-trimethoxybenzoate
- SMILES
- CCC(COC(=O)C1=CC(=C(C(=C1)OC)OC)OC)(C2=CC=CC=C2)N(C)C
- InChIKey
- LORDFXWUHHSAQU-UHFFFAOYSA-N
- XLogP
- 4
- Polar surface area
- 57.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- irritable bowel syndrome, gastrointestinal disease
via ChEMBL · EBI
Research
282 papers- Trimebutine: a state-of-the-art review.Minerva gastroenterologica e dietologica · 2019
- The trimebutine effect on Helicobacter pylori-related gastrointestinal tract and brain disorders: A hypothesis.Neurochemistry international · 2021
- Gastric ulcer, motility, and trimebutine.Journal of gastroenterology · 1998
- Probiotics Combined With Trimebutine for the Treatment of Irritable Bowel Syndrome Patients: A Systematic Review and Meta-Analysis.Journal of gastroenterology and hepatology · 2025
- Trimebutine suppresses Toll-like receptor 2/4/7/8/9 signaling pathways in macrophages.Archives of biochemistry and biophysics · 2021
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 387.204573
- Has use
- medication
Show 6 more facts
- subject has role
- parasympatholytic
- chemical formula
- C₂₂H₂₉NO₅
- canonical SMILES
- CCC(COC(=O)C1=CC(=C(C(=C1)OC)OC)OC)(C2=CC=CC=C2)N(C)C
- defined daily dose
- 0.6
- medical condition treated
- irritable bowel syndrome
- Commons category
- Trimebutine
via Wikidata · CC0
~7 min read
Encyclopedic overview
15 sectionsContents
- Pharmacology
- Pharmacokinetics
- Metabolism and excretion
- Carcinogenicity
- Interactions
- Adverse effects
- Synthesis
- Research
- Novel salts of trimebutine
- Acute ulcerative colitis
- Cancer
- Alkaline corneal burns
- Brand names
- See also
- References
Trimebutine is a drug with antimuscarinic and very weak mu opioid agonist effects. It is used for the treatment of irritable bowel syndrome and other gastrointestinal disorders. It is sometimes combined with simethicone as a combination drug. Trimebutine is formulated as a tablet or granules for oral suspension.
== Pharmacology == Trimebutine is a multimodal drug that acts on many receptors in the body. Its main effects are mediated through inhibition of voltage-gated L-type calcium channels, thereby decreasing calcium influx in smooth muscle in the gut. This mechanism explains its ability to slow peristalsis, which in turn helps with diarrhoea management in IBS patients. Antispasmodic effect is mediated through inhibition of inward rectifier potassium channels and calcium-dependend potassium channels. Moreover, trimebutine and its metabolite N-desmethyltrimebutine exert non-selective antagonistic effect on mAChRs, which is believed to potentiate its antispasmodic effects, as do many other drugs in this class.
Excerpted from Wikipedia’s “trimebutine” article, available under the CC BY-SA 4.0 licence.