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.

Brand names

The maleic acid salt of trimebutine is marketed under the trademarks of Antinime, Cineprac, Colospasmyl, Colypan, Crolipsa, Debricol, Debridat, Digedrat, Espabion, Gast Reg, Irritratil, Krisxon, Muttifen, Neotina, Polybutin,^[4] Sangalina, Trebutel, Tribudat, Tributina, Trim, Trimeb, Trimedat, and Trimedine.

References

^ 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.
^ Jhee OH, Lee YS, Shaw LM, Jeon YC, Lee MH, Lee SH, Kang JS (January 2007). "Pharmacokinetic and bioequivalence evaluation of two formulations of 100 mg trimebutine maleate (Recutin and Polybutin) in healthy male volunteers using the LC-MS/MS method". Clinica Chimica Acta; International Journal of Clinical Chemistry. 375 (1–2): 69–75. doi:10.1016/j.cca.2006.06.006. PMID 16854404.

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[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.

[4] Jhee OH, Lee YS, Shaw LM, Jeon YC, Lee MH, Lee SH, Kang JS (January 2007). "Pharmacokinetic and bioequivalence evaluation of two formulations of 100 mg trimebutine maleate (Recutin and Polybutin) in healthy male volunteers using the LC-MS/MS method". Clinica Chimica Acta; International Journal of Clinical Chemistry. 375 (1–2): 69–75. doi:10.1016/j.cca.2006.06.006. PMID 16854404.

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Trimebutine

Brand names

See also

References