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.comInternational Drug Names
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • (RS)-4-(Ethyl[1-(4-methoxyphenyl)propan-2-yl]amino)butyl 3,4-dimethoxybenzoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.756
Chemical and physical data
FormulaC25H35NO5
Molar mass429.557 g·mol−1
3D model (JSmol)
ChiralityRacemic 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
  (verify)

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]

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

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.[5]

In a urine drug-screening test, mebeverine can affect a false positive result for amphetamines.[6]

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.[7]

History

It is a second generation papaverine analog, and was first synthesized around the same time as verapamil.[8]

It was first registered in 1965.[9]

Availability

Mebeverine is a generic drug and is available internationally under many brand names.[10]

References
  1. "Colofac data sheet" (PDF). New Zealand Medicines and Medical Devices Safety Authority. 14 June 2017. Retrieved 21 July 2017.
  2. "Colofac Tablets 135mg - Summary of Product Characteristics (SPC)". UK Electronic Medicines Compendium. 26 August 2016. Retrieved 21 July 2017.
  3. Annaházi A, Róka R, Rosztóczy A, Wittmann T (May 2014). "Role of antispasmodics in the treatment of irritable bowel syndrome". World Journal of Gastroenterology. 20 (20): 6031–43. doi:10.3748/wjg.v20.i20.6031. PMC 4033443. PMID 24876726.
  4. Darvish-Damavandi M, Nikfar S, Abdollahi M (February 2010). "A systematic review of efficacy and tolerability of mebeverine in irritable bowel syndrome". World Journal of Gastroenterology. 16 (5): 547–53. doi:10.3748/wjg.v16.i5.547. PMC 2816265. PMID 20128021.
  5. Lachkar Y, Bouassida W (March 2007). "Drug-induced acute angle closure glaucoma". Current Opinion in Ophthalmology. 18 (2): 129–33. doi:10.1097/ICU.0b013e32808738d5. PMID 17301614. S2CID 30903966.
  6. Optimisation, NECS Medicines (2015-07-21). "Misuse of hyoscine butylbromide (Buscopan) |". medicines.necsu.nhs.uk. Retrieved 2018-02-07.
  7. Hatami M, Farhadi K, Tukmechi A (August 2012). "Fiber-based liquid-phase micro-extraction of mebeverine enantiomers followed by chiral high-performance liquid chromatography analysis and its application to pharmacokinetics study in rat plasma". Chirality. 24 (8): 634–9. doi:10.1002/chir.22057. PMID 22700279.
  8. Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 132. ISBN 9780471899792.
  9. "Mebeverine". druginfosys. Retrieved 1 February 2015.
  10. "Mebeverine". International. drugs.com. Retrieved 1 February 2015.
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