Mebeverine

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by The Nth User (talk | contribs) at 00:37, 23 July 2019 (→‎References: Replaced one category with subcategory). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Mebeverine
Clinical data
AHFS/Drugs.comInternational 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
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.756 Edit this at Wikidata
Chemical and physical data
FormulaC25H35NO5
Molar mass429.6 g/mol g·mol−1
3D model (JSmol)
ChiralityRacemic 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 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.[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 diarrhea, and flatulence.[2]

Data from controlled clinical trials have not found a difference from placebo in the alleviating stomach pain in people with 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, edema and widespread rashes.[2]

Additionally, the following adverse effects have been reported: heartburn, indigestion, tiredness, diarrhea, 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]

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 anesthetic 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.[6]

History

It is a second generation papaverine analog, and was first synthesized around the same time as verapamil.[7]

It was first registered in 1965.[8]

Availability

Mebeverine is a generic drug and is available internationally under many brand names.[9]

References

  1. ^ a b c "Colofac data sheet" (PDF). New Zealand Medicines and Medical Devices Safety Authority. 14 June 2017. Retrieved 21 July 2017.
  2. ^ a b c d e "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 (28 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  4. ^ Darvish-Damavandi, M; Nikfar, S; Abdollahi, M (7 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  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.
  6. ^ Hatami, Mehdi; Farhadi, Khalil; Tukmechi, Amir (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): 634–639. doi:10.1002/chir.22057. PMID 22700279.
  7. ^ Sneader, Walter (2005). Drug Discovery: A History. John Wiley & Sons. p. 132. ISBN 9780471899792.
  8. ^ Mebeverine page at druginfosys Page accessed Feb 1, 2015
  9. ^ International page at drugs.com for Mebeverine Page accessed Feb 1, 2015
Retrieved from "https://en.wikipedia.org/w/index.php?title=Mebeverine&oldid=907452501"