Mebeverine
Watchedfieldschanged
Verifiedrevid443346749
Iupac name(RS)-4-(Ethyl[1-(4-methoxyphenyl)propan-2-yl]amino)butyl 3,4-dimethoxybenzoate
Width300
ChiralityRacemic mixture
Legal ukP
Legal usNot approved
Legal statusRx-only
Routes of administrationBy mouth
Index2 labelHCl
Cas number 22753-45-9
Unii 215VZ5AL4JN
Cas number3625-06-7
Atc prefixA03
Atc suffixAA04
Pubchem4031
DrugbankDB12554
Chemspiderid3891
Unii7F80CC3NNV
KeggD04868
Chembl282121
C25
H35
N1
O5
SmilesO=C(OCCCCN(C(C)Cc1ccc(OC)cc1)CC)c2cc(OC)c(OC)cc2
Stdinchi1S/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
StdinchikeyVYVKHNNGDFVQGA-UHFFFAOYSA-N

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]

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, a 2022 systematic review found that 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]

Pharmacology

Mechanism of action

Mebeverine is an antispasmodic 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]

Pharmacokinetics

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]

The drug contains the psychoactive drugs moiety such as para-methoxy-N-ethylamphetamine (PMEA) and para-methoxyamphetamine (PMA) within its chemical structure and can form these drugs as minor active metabolites.[9] This can result in false positives for "ecstasy" on drug tests.[9]

History

It is a second generation papaverine analog, and was first synthesized around the same time as verapamil.[10]

It was first registered in 1965.[11]

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.[12]

References

  1. ^ "Colofac data sheet". 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. Archived from the original on 22 September 2022. 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. ^ Daniluk J, Malecka-Wojciesko E, Skrzydlo-Radomanska B, Rydzewska G (February 2022). "The Efficacy of Mebeverine in the Treatment of Irritable Bowel Syndrome-A Systematic Review". Journal of Clinical Medicine. 11 (4): 1044. doi:10.3390/jcm11041044. PMC 8879004. PMID 35207315
  6. ^ 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
  7. ^ Optimisation, NECS Medicines (2015-07-21). "Misuse of hyoscine butylbromide (Buscopan) |". medicines.necsu.nhs.uk. Retrieved 2018-02-07.
  8. ^ 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
  9. ^ "Мебеверин (Mebeverine)" (in Russian). АИПСИН. Retrieved 2 January 2026.
  10. ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 132. ISBN 9780471899792.
  11. ^ "Mebeverine". druginfosys. Retrieved 1 February 2015.
  12. ^ "Mebeverine". International. drugs.com. Retrieved 1 February 2015.