Mebeverine

Structural formula
	1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Mebeverine
other names	( RS ) -3,4-Dimethoxybenzoic acid 4- {ethyl- [2- (4-methoxyphenyl) -1-methylethyl] -amino} butyl ester ( IUPAC ); (±) -3,4-Dimethoxybenzoic acid 4- {ethyl- [2- (4-methoxyphenyl) -1-methylethyl] -amino} butyl ester; rac -3,4-dimethoxybenzoic acid 4- {ethyl- [2- (4-methoxyphenyl) -1-methylethyl] -amino} butyl ester;
Molecular formula	C 25 H 35 NO 5
External identifiers / databases
EC number	222-830-4
ECHA InfoCard	100.020.756
PubChem	4031
ChemSpider	3891
Wikidata	Q418167
Drug information
ATC code	A03 AA04
Drug class	Antispasmodic
properties
Molar mass	429.55 g · mol -1
Physical state	firmly
Melting point	129-131 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	995 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mebeverine is an intestinal spasmolytic that relaxes the muscles of the gastrointestinal area and thus has an antispasmodic effect. The drug blocks the transmission of excitation from the nerve fibers of the vegetative nervous system to the gastrointestinal muscles by displacing the messenger substances responsible for this from their binding sites. In addition, mebeverine also works directly in the muscle cells. Because of these properties, the active ingredient mebeverine is mainly administered to patients with irritable bowel syndrome . A meta-analysis included 23 randomized studies with 1852 patients with irritable bowel syndrome in which a smooth muscle relaxant was tested against a placebo ; five of 23 studies concerned mebeverine. There was a general improvement in symptoms in 56% of the treatment cases, but also after placebo in 38% of the cases (P <0.001). A reduction in abdominal pain was reported by 53% of those treated and 41% of the placebo group (P <0.001). The strong effectiveness of the placebo-treated pations suggests a psychological overlay in many patients with irritable bowel syndrome. Differences between different drugs (cimetropium bromide, hyoscine butyl bromide, mebeverine, otilonium bromide, pinaverium bromide and trimebutine) were not reported in the meta-analysis.

Mebeverine also acts as a FIASMA (functional inhibitor of acid sphingomyelinase ).

Trade names

Monopreparations

Colofac (A), Duspatalin (CH, PL), Duspatal (D), Mebemerck (D), Mebeverin dura (D)

Individual evidence

↑ ^a ^b Entry on Mebeverin. In: Römpp Online . Georg Thieme Verlag, accessed on July 7, 2014.
↑ ^a ^b Data sheet Mebeverine hydrochloride from Sigma-Aldrich , accessed on April 9, 2011 ( PDF ).
↑ T Poynard, C Regimbeau, Y Benhamou: Meta-analysis of smooth muscle relaxants in the treatment of irritable bowel syndrome . In: Alimentary Pharmacology & Therapeutics . tape 15 , no. 3 , 2001, p. 355-361 , PMID 11207510 .
↑ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .

[RÖMPP_Online-1] Entry on Mebeverin. In: Römpp Online . Georg Thieme Verlag, accessed on July 7, 2014.

[Sigma-2] Data sheet Mebeverine hydrochloride from Sigma-Aldrich , accessed on April 9, 2011 ( PDF ).

[3] T Poynard, C Regimbeau, Y Benhamou: Meta-analysis of smooth muscle relaxants in the treatment of irritable bowel syndrome . In: Alimentary Pharmacology & Therapeutics . tape 15 , no. 3 , 2001, p. 355-361 , PMID 11207510 .

[pmid18504571-4] Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .