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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443486376 | verifiedrevid = 448194071
| IUPAC_name = 2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate | IUPAC_name = 2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate
| image = Trimebutine.png | image = Trimebutine.svg
| image_class = skin-invert-image


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Debridat, Recutin, Polybutin, others
| Drugs.com = {{drugs.com|international|trimebutine}} | Drugs.com = {{drugs.com|international|trimebutine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 39133-31-8 | CAS_number = 39133-31-8
| ATC_prefix = A03 | ATC_prefix = A03
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QZ1OJ92E5R | UNII = QZ1OJ92E5R
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 190044
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 5372


<!--Chemical data--> <!--Chemical data-->
| C=22 | H=29 | N=1 | O=5 | C=22 | H=29 | N=1 | O=5
| smiles = CCC(COC(=O)C1=CC(=C(C(=C1)OC)OC)OC)(C2=CC=CC=C2)N(C)C
| molecular_weight = 387.47 g/mol
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = LORDFXWUHHSAQU-UHFFFAOYSA-N
}} }}
'''Trimebutine''' is a drug with ] and weak ] ] ] effects.<ref>Kaneto H, Takahashi M, Watanabe J. The opioid receptor selectivity for trimebutine in isolated tissues experiments and receptor binding studies. ''Journal of Pharmacobiodynamics''. 1990 Jul;13(7):448-53. PMID 1963196</ref> The ] salt of trimebutine is marketed under the ] of Debridat, Recutin, Polybutin,<ref>Ok Hwa Jhee, Yun Sik Lee, Leslie M. Shaw, Yong Cheol Jeon, Min Ho Lee, Seung Hoon Lee and Ju Seop Kang The 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''. 2007 Jan;375(1-2):69-75. PMID 16854404</ref> or Modulon for treatment of ] and other gastrointestinal disorders. The major product from ] of trimebutine in human beings is nor-trimebutine,<ref>F.J. Roman, S. Lanet, J. Hamon, G. Brunelle, A. Maurin, P. Champeroux, S. Richard, N. Alessandri, and M. Gola Pharmacological Properties of Trimebutine and N-Monodesmethyltrimebutine. ''The Journal of Pharmacology and Experimental Therapeutics'' 1999;289:1391–1397. PMID 10336531</ref> which comes from removal of one of the methyl groups attached to nitrogen. Both Trimebutine and its metabolite are commercially available.


'''Trimebutine''' is a drug with ] and very weak ] ] ] effects.<ref>{{cite journal | vauthors = Kaneto H, Takahashi M, Watanabe J | title = The opioid receptor selectivity for trimebutine in isolated tissues experiments and receptor binding studies | journal = Journal of Pharmacobio-Dynamics | volume = 13 | issue = 7 | pages = 448–53 | date = July 1990 | pmid = 1963196 | doi = 10.1248/bpb1978.13.448 | doi-access = free | hdl = 10069/38849 | hdl-access = free }}</ref> It is used for the treatment of ] and other gastrointestinal disorders.
⚫ ==References==

{{reflist}}
The major product from ] of trimebutine in human beings is ],<ref>{{cite journal | vauthors = Roman FJ, Lanet S, Hamon J, Brunelle G, Maurin A, Champeroux P, Richard S, Alessandri N, Gola M | display-authors = 6 | title = Pharmacological properties of trimebutine and N-monodesmethyltrimebutine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 289 | issue = 3 | pages = 1391–7 | date = June 1999 | pmid = 10336531 }}</ref> 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 ] in the digestive tract.<ref name="Hiyama-2009">{{cite journal | vauthors = Hiyama T, Yoshihara M, Tanaka S, Haruma K, Chayama K | title = Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract | journal = Journal of Gastroenterology and Hepatology | volume = 24 | issue = 4 | pages = 537–46 | date = April 2009 | pmid = 19220673 | doi = 10.1111/j.1440-1746.2009.05780.x | s2cid = 25767036 | url = http://onlinelibrary.wiley.com/store/10.1111/j.1440-1746.2009.05780.x/asset/j.1440-1746.2009.05780.x.pdf?v=1&t=hl2d93pj&s=53675e2a2742207be72071a180997b9023ea13ec | doi-access = free }}</ref> <br>
Both trimebutine and its metabolite{{Citation needed|date=January 2018|reason=Only aware trimebutine is marketed. Sources for metabolite please.}} are commercially available.

==Brand names==
The ] salt of trimebutine is marketed under the ]s of Antinime, Cineprac, Colospasmyl, Colypan, Crolipsa, Debricol, Debridat, Digedrat, Espabion, Gast Reg, Irritratil, Krisxon, Muttifen, Neotina, Polybutin,<ref>{{cite journal | vauthors = Jhee OH, Lee YS, Shaw LM, Jeon YC, Lee MH, Lee SH, Kang JS | title = 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 | journal = Clinica Chimica Acta; International Journal of Clinical Chemistry | volume = 375 | issue = 1–2 | pages = 69–75 | date = January 2007 | pmid = 16854404 | doi = 10.1016/j.cca.2006.06.006 }}</ref> Sangalina, Trebutel, Tribudat, Tributina, Trim, Trimeb, Trimedat, and Trimedine.

== See also ==
* ]
* ]

⚫ == References ==
{{Reflist}}


{{Drugs for functional gastrointestinal disorders}} {{Drugs for functional gastrointestinal disorders}}
{{Muscarinic acetylcholine receptor modulators}}
{{Opioids}}
{{Opioid receptor modulators}}


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{{gastrointestinal-drug-stub}} {{gastrointestinal-drug-stub}}

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Latest revision as of 15:22, 11 January 2025

Chemical compound Pharmaceutical compound
Trimebutine
Clinical data
Trade namesDebridat, Recutin, Polybutin, others
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.049.354 Edit this at Wikidata
Chemical and physical data
FormulaC22H29NO5
Molar mass387.476 g·mol
3D model (JSmol)
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
  (what is this?)  (verify)

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.

The major product from drug metabolism of trimebutine in human beings is nortrimebutine, 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.
Both trimebutine and its metabolite 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, Sangalina, Trebutel, Tribudat, Tributina, Trim, Trimeb, Trimedat, and Trimedine.

See also

References

  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.
  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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