Mebeverine

Mebeverine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	A03AA04 (WHO) ;
Legal status
Legal status	UK: P (Pharmacy medicines); US: Not approved; In general: ℞ (Prescription only);
Identifiers
	IUPAC name (RS)-4-(Ethyl[1-(4-methoxyphenyl)propan-2-yl]amino)butyl 3,4-dimethoxybenzoate;
CAS Number	3625-06-7 ; HCl: 2753-45-9 ;
PubChem CID	4031;
DrugBank	DB12554 ;
ChemSpider	3891 ;
UNII	7F80CC3NNV; HCl: 15VZ5AL4JN ;
KEGG	D04868 ;
ChEMBL	ChEMBL282121 ;
CompTox Dashboard (EPA)	DTXSID6023238 ;
ECHA InfoCard	100.020.756
Chemical and physical data
Formula	C25H35NO5
Molar mass	429.557 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic 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 ; Key:VYVKHNNGDFVQGA-UHFFFAOYSA-N ;
	(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 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

^ ^a ^b ^c "Colofac data sheet" (PDF). New Zealand Medicines and Medical Devices Safety Authority. 14 June 2017. Retrieved 21 July 2017.
^ ^a ^b ^c ^d ^e "Colofac Tablets 135mg - Summary of Product Characteristics (SPC)". UK Electronic Medicines Compendium. 26 August 2016. Retrieved 21 July 2017.
^ 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.
^ 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.
^ 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.
^ 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.
^ Optimisation NM (2015-07-21). "Misuse of hyoscine butylbromide (Buscopan) |". medicines.necsu.nhs.uk. Retrieved 2018-02-07.
^ 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.
^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 132. ISBN 9780471899792.
^ "Mebeverine". druginfosys. Retrieved 1 February 2015.
^ "Mebeverine". International. drugs.com. Retrieved 1 February 2015.

[NZlabel2017-1] "Colofac data sheet" (PDF). New Zealand Medicines and Medical Devices Safety Authority. 14 June 2017. Retrieved 21 July 2017.

[UKlabel2016-2] "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] 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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