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Details

Stereochemistry RACEMIC
Molecular Formula C22H29NO5
Molecular Weight 387.4694
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMEBUTINE

SMILES

CCC(COC(=O)C1=CC(OC)=C(OC)C(OC)=C1)(N(C)C)C2=CC=CC=C2

InChI

InChIKey=LORDFXWUHHSAQU-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H29NO5
Molecular Weight 387.4694
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Trimebutine [3,4,5-trimethoxybenzoic acid 2-(dimethylamino)-2-phenylbutylester] is a noncompetitive spasmolytic agent. The actions of trimebutine on the gastrointestinal tract are mediated via (i) an agonist effect on peripheral mu, kappa and delta opiate receptors and (ii) release of gastrointestinal peptides such as motilin and modulation of the release of other peptides, including vasoactive intestinal peptide, gastrin and glucagon. Trimebutine attenuated colonic motility mainly through the inhibition of L-type Ca(2+) channels at higher concentrations, whereas, at lower concentrations, it depolarized membrane potentials by reducing BK(ca) currents, resulting in the enhancement of the muscle contractions.Trimebutine accelerates gastric emptying, induces premature phase III of the migrating motor complex in the intestine and modulates the contractile activity of the colon. It is indicated for the treatment and relief of symptoms associated with the irritable bowel syndrome (spastic colon); and in postoperative paralytic ileus in order to accelerate the resumption of the intestinal transit following abdominal surgery.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRIMEBUTINE
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1271.1 ng/mL
100 mg single, oral
NOR-TRIMEBUTINE plasma
Homo sapiens
44.3 ng/mL
100 mg single, oral
TRIMEBUTINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4533.4 ng × h/mL
100 mg single, oral
NOR-TRIMEBUTINE plasma
Homo sapiens
72.1 ng × h/mL
100 mg single, oral
TRIMEBUTINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.9 h
100 mg single, oral
NOR-TRIMEBUTINE plasma
Homo sapiens
1.83 h
100 mg single, oral
TRIMEBUTINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
23%
TRIMEBUTINE serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
The adult recommended dose is up to 600 mg daily in divided doses. It may be administered as two 100 mg tablets three times daily before meals or one 200 mg tablet three times daily before meals.
Route of Administration: Oral
In Vitro Use Guide
0.1 mM trimebutine inhibits proliferation of human LOVO colon cancer cells.
Substance Class Chemical
Record UNII
QZ1OJ92E5R
Record Status Validated (UNII)
Record Version