Mebeverine

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.^[1]

Mebeverine

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 Y HCl: 2753-45-9 Y
PubChem CID	4031
DrugBank	DB12554 Y
ChemSpider	3891 Y
UNII	7F80CC3NNV HCl: 15VZ5AL4JN Y
KEGG	D04868 Y
ChEMBL	ChEMBL282121 Y
CompTox Dashboard (EPA)	DTXSID6023238
ECHA InfoCard	100.020.756
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 Y Key:VYVKHNNGDFVQGA-UHFFFAOYSA-N Y
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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.^[2]

Historically data from controlled clinical trials have not found a difference from placebo or statistically significant results in the global improvement of IBS.^[3][4] 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. ^[5]

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.^[1]

Adverse effects

Adverse effects include hypersensitivity reactions and allergic reactions, immune system disorders, skin disorders including hives, oedema and widespread rashes.^[2]

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.^[1]

It does not have systemic anticholinergic side effects.^[2]

Mebeverine can, on highly rare occasions, cause drug-induced acute angle closure glaucoma.^[6]

In a urine drug-screening test, mebeverine can affect a false positive result for amphetamines.^[7]

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.^[2]

It is metabolized mostly by esterases, and almost completely. The metabolites are excreted in urine.^[2]

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.^[8]

History

It is a second generation papaverine analog, and was first synthesized around the same time as verapamil.^[9]

It was first registered in 1965.^[10]

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 [bn].^[11]