Mebeverine

Mebeverine

File:Mebeverine.svg
File:Mebeverine2.png
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	By mouth
ATC code	A03AA04 (WHO)
Legal status
Legal status	UK: P (Pharmacy medicines) US: Not approved In general: ℞ (Prescription only)
Identifiers
IUPAC name (RS)-4-(Ethyl[1-(4-methoxyphenyl)propan-2-yl]amino)butyl 3,4-dimethoxybenzoate
CAS Number	3625-06-7 checkY HCl: 2753-45-9 checkY
PubChem CID	4031
DrugBank	DB12554 checkY
ChemSpider	3891 checkY
UNII	7F80CC3NNV HCl: 15VZ5AL4JN checkY
KEGG	D04868 checkY
ChEMBL	ChEMBL282121 checkY
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C25H35NO5
Molar mass	429.557 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES O=C(OCCCCN(C(C)Cc1ccc(OC)cc1)CC)c2cc(OC)c(OC)cc2
InChI InChI=1S/C25H35NO5/c1-6-26(19(2)17-20-9-12-22(28-3)13-10-20)15-7-8-16-31-25(27)21-11-14-23(29-4)24(18-21)30-5/h9-14,18-19H,6-8,15-17H2,1-5H3 checkY Key:VYVKHNNGDFVQGA-UHFFFAOYSA-N checkY
(verify)

Mebeverine is a drug used to alleviate some of the symptoms of irritable bowel syndrome. It works by relaxing the muscles in and around the gut.

Medical use

Mebeverine is used to alleviate some of the symptoms of irritable bowel syndrome (IBS) and related conditions; specifically stomach pain and cramps, persistent diarrhoea, and flatulence.

Historically data from controlled clinical trials have not found a difference from placebo or statistically significant results in the global improvement of IBS. However, more recent systematic reviews found Mebeverine is an effective treatment option in IBS, with a good safety profile and low frequency of adverse effects.

It has not been tested in pregnant women nor in pregnant animals so pregnant women should not take it; it is expressed at low levels in breast milk, while no adverse effects have been reported in infants, breastfeeding women should not take this drug.

Adverse effects

Adverse effects include hypersensitivity reactions and allergic reactions, immune system disorders, skin disorders including hives, oedema and widespread rashes.

Additionally, the following adverse effects have been reported: heartburn, indigestion, tiredness, diarrhoea, constipation, loss of appetite, general malaise, dizziness, insomnia, headache, and decreased pulse rate.

It does not have systemic anticholinergic side effects.

Mebeverine can, on highly rare occasions, cause drug-induced acute angle closure glaucoma.

In a urine drug-screening test, mebeverine can affect a false positive result for amphetamines.

Mechanism of action

Mebeverine is an anticholinergic but its mechanism of action is not known; it appears to work directly on smooth muscle within the gastrointestinal tract and may have an anaesthetic effect, may affect calcium channels, and may affect muscarinic receptors.

It is metabolized mostly by esterases, and almost completely. The metabolites are excreted in urine.

Mebeverine exists in two enantiomeric forms. The commercially available product is a racemic mixture of them. A study in rats indicates that the two have different pharmacokinetic profiles.

History

It is a second generation papaverine analog, and was first synthesized around the same time as verapamil.

It was first registered in 1965.

Availability

Mebeverine is a generic drug and is available internationally under many brand names, such as Duspatalin as sold by Abbott or Mave and Mave SR by Opsonin Pharma.