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Mebeverine

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.020.756Edit this at Wikidata
Chemical and physical data
FormulaC25H35NO5
Molar mass429.557 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 adrug used to alleviate some of the symptoms ofirritable bowel syndrome. It works by relaxing the muscles in and around the gut.[1]

Medical use

[edit]

Mebeverine is used to alleviate some of the symptoms ofirritable 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

[edit]

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 systemicanticholinergic 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

[edit]

Mebeverine is ananticholinergic but itsmechanism of action is not known; it appears to work directly on smooth muscle within the gastrointestinal tract and may have an anaesthetic effect, may affectcalcium channels, and may affect muscarinic receptors.[2]

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

Mebeverine exists in twoenantiomeric forms. The commercially available product is aracemic mixture of them. A study in rats indicates that the two have differentpharmacokinetic profiles.[8]

History

[edit]

It is a second generationpapaverine analog, and was first synthesized around the same time asverapamil.[9]

It was first registered in 1965.[10]

Availability

[edit]

Mebeverine is ageneric drug and is available internationally under many brand names, such as Duspatalin as sold byAbbott or Mave and Mave SR byOpsonin Pharma [bn].[11]

References

[edit]
  1. ^abc"Colofac data sheet"(PDF). New Zealand Medicines and Medical Devices Safety Authority. 14 June 2017. Retrieved21 July 2017.
  2. ^abcde"Colofac Tablets 135mg - Summary of Product Characteristics (SPC)". UK Electronic Medicines Compendium. 26 August 2016. Retrieved21 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. Retrieved2018-02-07.
  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. Retrieved1 February 2015.
  11. ^"Mebeverine".International. drugs.com. Retrieved1 February 2015.
Drugs for
functional
bowel
disorders
Antimuscarinics
Tertiary
amino group
Quaternary
ammonium

compounds
Phosphodiesterase
inhibitors
Acting on
serotonin receptors
Other
Belladonna
and derivatives
(antimuscarinics)
Propulsives
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
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