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Details

Stereochemistry RACEMIC
Molecular Formula C25H35NO5.C23H16O6
Molecular Weight 817.9186
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEBEVERINE EMBONATE

SMILES

OC(=O)C1=CC2=C(C=CC=C2)C(CC3=C4C=CC=CC4=CC(C(O)=O)=C3O)=C1O.CCN(CCCCOC(=O)C5=CC(OC)=C(OC)C=C5)C(C)CC6=CC=C(OC)C=C6

InChI

InChIKey=ZOXKMIWKTFNORQ-UHFFFAOYSA-N
InChI=1S/C25H35NO5.C23H16O6/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;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h9-14,18-19H,6-8,15-17H2,1-5H3;1-10,24-25H,11H2,(H,26,27)(H,28,29)

HIDE SMILES / InChI
Molecular Formula C25H35NO5
Molecular Weight 429.5491
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
Molecular Formula C23H16O6
Molecular Weight 388.3695
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con744437.pdf | https://www.ncbi.nlm.nih.gov/pubmed/20128021

Mebeverine is an antispasmodic with a direct action on the smooth muscle of the gastrointestinal tract. The exact mechanism of action is not known, but multiple mechanisms, such as a decrease in ion channel permeabilities, blockade of noradrenaline reuptake, a local anesthetic effects, as well as weak anti-muscarinic and phosphodiesterase inhibitory effect might contribute to the local effects of Mebeverine. This medicine is used to treat symptoms of irritable bowel syndrome (IBS) and similar problems such as chronic irritable colon, spastic constipation, mucous colitis and spastic colitis. Most people will not have problems with Mebeverine, but some may get some side effects, such as: difficulty in breathing, swelling of face, neck, tongue or throat, skin rash, red itchy skin.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Alpha-1 adrenergic receptor (guinea pig)
3
Target ID: Alpha-1 adrenergic receptor (guinea pig)
Inhibitor
8297
Muscarinic acetylcholine receptors (guinea pig)
3
Target ID: Muscarinic acetylcholine receptors (guinea pig)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
Colofac

Approved Use

Colofac is used to treat symptoms of irritable bowel syndrome and similar problems.

Launch Date

2.58595193E11
Palliative
Approved
8429
Colofac

Approved Use

This medicine is used to treat symptoms of irritable bowel syndrome (IBS) and similar problems such as chronic irritable colon, spastic constipation, mucous colitis and spastic colitis.

Launch Date

2.58595193E11
Palliative
Approved
8429
Colofac

Approved Use

This medicine is used to treat symptoms of irritable bowel syndrome (IBS) and similar problems such as chronic irritable colon, spastic constipation, mucous colitis and spastic colitis

Launch Date

2.58595193E11
PubMed

PubMed

TitleDatePubMed
Drug therapy options for patients with irritable bowel syndrome.
2001 Jul
Meta-analysis of smooth muscle relaxants in the treatment of irritable bowel syndrome.
2001 Mar
Identification of mebeverine acid as the main circulating metabolite of mebeverine in man.
2002 Jun 20
A double-blind randomised, placebo-controlled trial evaluating the influence of oral long-acting muscle relaxant (Mebeverine MR), and insufflation with CO(2) on pain associated with barium enema.
2003 Jul
Treatment patterns and health care costs of mebeverine-treated IBS patients: a case-control study.
2004 Nov
[Abdominal migraine as a cause of chronic recurrent abdominal pain in a 9-years-old girl--case report].
2005 Aug
[Determination of placebo effect in irritable bowel syndrome].
2005 Aug 26
Mebeverine influences sodium ion transport in the distal colon.
2006 Sep-Oct
[Drug treatment of irritable bowel syndrome: an unmet need].
2007 Mar
A novel formulation for mebeverine hydrochloride.
2007 Oct
Cost-effectiveness of cognitive behaviour therapy in addition to mebeverine for irritable bowel syndrome.
2008 Apr
Serotonin receptor modulators in the treatment of irritable bowel syndrome.
2008 Feb
Spectrophotometric determination of benzydamine HCl, levamisole HCl and mebeverine HCl through ion-pair complex formation with methyl orange.
2008 Mar
Effects of 5-hydroxytryptamine (serotonin) type 3 antagonists on symptom relief and constipation in nonconstipated irritable bowel syndrome: a systematic review and meta-analysis of randomized controlled trials.
2008 May
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.
2008 Nov 13
Development of membrane selective electrode for determination of the antipsychotic sulpiride in pharmaceuticals and urine.
2009
Psychological associations of irritable bowel syndrome besides panic disorder: an often overlooked reality.
2009
Validated LC-MS/MS method for determination of Alverine and one of its hydroxy metabolites in human plasma along with its application to a bioequivalence study.
2009 Jan 15
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Validated HPLC determination of the two fixed dose combinations (chlordiazepoxide hydrochloride and mebeverine hydrochloride; carvedilol and hydrochlorothiazide) in their tablets.
2010 Jul-Aug
Topical piroxicam in vitro release and in vivo anti-inflammatory and analgesic effects from palm oil esters-based nanocream.
2010 Nov 4
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

EP0393747 A2
3
EP0528076 A1
3

Sample Use Guides

In Vivo Use Guide
One tablet (135 mg) three times a day. This may be gradually reduced after a few weeks when the desired effect has been obtained. The tablets are best taken 20 minutes before meals.
Route of Administration: Oral
In Vitro Use Guide
Mebeverine (10^5-10^4 M) suppressed the amplitude of the action potential and lengthened the time between stimulation and the top of the response in non-myelinated fibres of the vagus nerve.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:59:21 UTC 2023
Edited
by admin
on Sat Dec 16 10:59:21 UTC 2023
Record UNII
LO53AXD8GP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEBEVERINE EMBONATE
WHO-DD  
Common Name English
4-((3-CARBOXY-2-HYDROXYNAPHTHALEN-1-YL)METHYL)-3-HYDROXYNAPHTHALENE-2-CARBOXYLIC ACID;4-(ETHYL-(1-(4-METHOXYPHENYL)PROPAN-2-YL)AMINO)BUTYL 3,4-DIMETHOXYBENZOATE
Systematic Name English
Mebeverine embonate [WHO-DD]
Common Name English
4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHOIC) ACID, COMPOUND WITH 4-(ETHYL(2-(P-METHOXYPHENYL)-1-METHYLETHYL)AMINO)BUTYL VERATRATE (1:1)
Systematic Name English
MEBEVERINE PAMOATE
Common Name English
BENZOIC ACID, 3,4-DIMETHOXY-, 4-(ETHYL(2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)BUTYL ESTER, 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLATE) (1:1)
Common Name English
2-NAPHTHALENECARBOXYLIC ACID, 4,4'-METHYLENEBIS(3-HYDROXY-, COMPD. WITH 4-(ETHYL(2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)BUTYL 3,4-DIMETHOXYBENZOATE (1:1)
Systematic Name English
J290.621J
Code English
Code System Code Type Description
ECHA (EC/EINECS)
302-043-3
Created by admin on Sat Dec 16 10:59:21 UTC 2023 , Edited by admin on Sat Dec 16 10:59:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID90916525
Created by admin on Sat Dec 16 10:59:21 UTC 2023 , Edited by admin on Sat Dec 16 10:59:21 UTC 2023
PRIMARY
CAS
94088-43-4
Created by admin on Sat Dec 16 10:59:21 UTC 2023 , Edited by admin on Sat Dec 16 10:59:21 UTC 2023
PRIMARY
SMS_ID
100000088292
Created by admin on Sat Dec 16 10:59:21 UTC 2023 , Edited by admin on Sat Dec 16 10:59:21 UTC 2023
PRIMARY
PUBCHEM
56841405
Created by admin on Sat Dec 16 10:59:21 UTC 2023 , Edited by admin on Sat Dec 16 10:59:21 UTC 2023
PRIMARY
FDA UNII
LO53AXD8GP
Created by admin on Sat Dec 16 10:59:21 UTC 2023 , Edited by admin on Sat Dec 16 10:59:21 UTC 2023
PRIMARY
EVMPD
SUB22697
Created by admin on Sat Dec 16 10:59:21 UTC 2023 , Edited by admin on Sat Dec 16 10:59:21 UTC 2023
PRIMARY
Related Record Type Details
Structure of MEBEVERINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of MEBEVERINE
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