Mebeverine

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Mebeverine
Mebeverine.svg
Mebeverine2.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Identifiers
  • (RS)-4-(Ethyl[1-(4-methoxyphenyl)propan-2-yl]amino)butyl 3,4-dimethoxybenzoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.020.756 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H35NO5
Molar mass 429.557 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • O=C(OCCCCN(C(C)Cc1ccc(OC)cc1)CC)c2cc(OC)c(OC)cc2
  • 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 Yes check.svgY
  • Key:VYVKHNNGDFVQGA-UHFFFAOYSA-N Yes check.svgY
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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]

Contents

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]

References

  1. 1 2 3 "Colofac data sheet" (PDF). New Zealand Medicines and Medical Devices Safety Authority. 14 June 2017. Retrieved 21 July 2017.
  2. 1 2 3 4 5 "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. ↑ 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 NM (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. ↑ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 132. ISBN   9780471899792.
  10. ↑ "Mebeverine". druginfosys. Retrieved 1 February 2015.
  11. ↑ "Mebeverine". International. drugs.com. Retrieved 1 February 2015.
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