Trimebutine

Trimebutine
Clinical data
Trade names	Debridat, Recutin, Polybutin, others
AHFS/Drugs.com	International Drug Names
ATC code	A03AA05 (WHO) ;
Identifiers
	IUPAC name 2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate;
CAS Number	39133-31-8 ;
PubChem CID	5573;
ChemSpider	5372 ;
UNII	QZ1OJ92E5R;
ChEMBL	ChEMBL190044 ;
CompTox Dashboard (EPA)	DTXSID4023707 ;
ECHA InfoCard	100.049.354
Chemical and physical data
Formula	C22H29NO5
Molar mass	387.476 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(COC(=O)C1=CC(=C(C(=C1)OC)OC)OC)(C2=CC=CC=C2)N(C)C;
	InChI InChI=1S/C22H29NO5/c1-7-22(23(2)3,17-11-9-8-10-12-17)15-28-21(24)16-13-18(25-4)20(27-6)19(14-16)26-5/h8-14H,7,15H2,1-6H3 ; Key:LORDFXWUHHSAQU-UHFFFAOYSA-N ;
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Trimebutine is a drug with antimuscarinic and very weak mu opioid agonist effects.^[1] It is used for the treatment of irritable bowel syndrome and other gastrointestinal disorders.

The major product from drug metabolism of trimebutine in human beings is nortrimebutine,^[2] which comes from removal of one of the methyl groups attached to the nitrogen atom. Trimebutine exerts its effects in part due to causing a premature activation of phase III of the migrating motor complex in the digestive tract.^[3]
Both trimebutine and its metabolite^{[citation needed]} are commercially available.

^ Kaneto H, Takahashi M, Watanabe J (July 1990). "The opioid receptor selectivity for trimebutine in isolated tissues experiments and receptor binding studies". Journal of Pharmacobio-Dynamics. 13 (7): 448–53. doi:10.1248/bpb1978.13.448. hdl:10069/38849. PMID 1963196.
^ Roman FJ, Lanet S, Hamon J, Brunelle G, Maurin A, Champeroux P, et al. (June 1999). "Pharmacological properties of trimebutine and N-monodesmethyltrimebutine". The Journal of Pharmacology and Experimental Therapeutics. 289 (3): 1391–7. PMID 10336531.
^ Hiyama T, Yoshihara M, Tanaka S, Haruma K, Chayama K (April 2009). "Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract" (PDF). Journal of Gastroenterology and Hepatology. 24 (4): 537–46. doi:10.1111/j.1440-1746.2009.05780.x. PMID 19220673. S2CID 25767036.

[1] Kaneto H, Takahashi M, Watanabe J (July 1990). "The opioid receptor selectivity for trimebutine in isolated tissues experiments and receptor binding studies". Journal of Pharmacobio-Dynamics. 13 (7): 448–53. doi:10.1248/bpb1978.13.448. hdl:10069/38849. PMID 1963196.

[2] Roman FJ, Lanet S, Hamon J, Brunelle G, Maurin A, Champeroux P, et al. (June 1999). "Pharmacological properties of trimebutine and N-monodesmethyltrimebutine". The Journal of Pharmacology and Experimental Therapeutics. 289 (3): 1391–7. PMID 10336531.

[Hiyama-2009-3] Hiyama T, Yoshihara M, Tanaka S, Haruma K, Chayama K (April 2009). "Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract" (PDF). Journal of Gastroenterology and Hepatology. 24 (4): 537–46. doi:10.1111/j.1440-1746.2009.05780.x. PMID 19220673. S2CID 25767036.

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