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
SMILES
OC(=O)C1=CC2=CC=CC=C2C(CC3=C4C=CC=CC4=CC(C(O)=O)=C3O)=C1O.CCN(CCCCOC(=O)C5=CC=C(OC)C(OC)=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)
| 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 |
DescriptionCurator'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
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Alpha-1 adrenergic receptor (guinea pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2442008 |
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Target ID: Muscarinic acetylcholine receptors (guinea pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2442008 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Colofac Approved UseColofac is used to treat symptoms of irritable bowel syndrome and similar problems. Launch Date1978 |
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| Palliative | Colofac Approved UseThis 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 Date1978 |
|||
| Palliative | Colofac Approved UseThis 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 Date1978 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
685.28 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
O-DESMETHYL MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
28.79 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.61 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-BUTANOL, 4-(ETHYL(2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
62.52 ng/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
291.81 ng/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
O-DESMETHYL MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7669.41 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
O-DESMETHYL MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
339.21 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
47.57 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-BUTANOL, 4-(ETHYL(2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
365.85 ng × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2551.74 ng × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
O-DESMETHYL MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
O-DESMETHYL MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
15.78 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.99 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28192719/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-BUTANOL, 4-(ETHYL(2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)- plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.87 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.52 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
O-DESMETHYL MEBEVERINE ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
16.49% |
MEBEVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
||
25.68% |
MEBEVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
||
25% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28435220/ |
MEBEVERINE plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
270 mg 3 times / day multiple, oral Highest studied dose Dose: 270 mg, 3 times / day Route: oral Route: multiple Dose: 270 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Diarrhoea, Anorexia... Other AEs: Diarrhoea (grade 1, 1.7%) Sources: Anorexia (grade 2, 1.7%) Headache (grade 1-2, 3.3%) Menorrhagia (grade 2, 1.7%) Palpitation (grade 2, 1.7%) Alopecia (grade 1, 1.7%) Cystitis (grade 2, 3.3%) |
50 mg single, intravenous Highest studied dose Dose: 50 mg Route: intravenous Route: single Dose: 50 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Faintness, Dizziness... Other AEs: Faintness (7.1%) Sources: Dizziness (14.2%) Vomiting (7.1%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Alopecia | grade 1, 1.7% | 270 mg 3 times / day multiple, oral Highest studied dose Dose: 270 mg, 3 times / day Route: oral Route: multiple Dose: 270 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Diarrhoea | grade 1, 1.7% | 270 mg 3 times / day multiple, oral Highest studied dose Dose: 270 mg, 3 times / day Route: oral Route: multiple Dose: 270 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Headache | grade 1-2, 3.3% | 270 mg 3 times / day multiple, oral Highest studied dose Dose: 270 mg, 3 times / day Route: oral Route: multiple Dose: 270 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Anorexia | grade 2, 1.7% | 270 mg 3 times / day multiple, oral Highest studied dose Dose: 270 mg, 3 times / day Route: oral Route: multiple Dose: 270 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Menorrhagia | grade 2, 1.7% | 270 mg 3 times / day multiple, oral Highest studied dose Dose: 270 mg, 3 times / day Route: oral Route: multiple Dose: 270 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Palpitation | grade 2, 1.7% | 270 mg 3 times / day multiple, oral Highest studied dose Dose: 270 mg, 3 times / day Route: oral Route: multiple Dose: 270 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Cystitis | grade 2, 3.3% | 270 mg 3 times / day multiple, oral Highest studied dose Dose: 270 mg, 3 times / day Route: oral Route: multiple Dose: 270 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Dizziness | 14.2% | 50 mg single, intravenous Highest studied dose Dose: 50 mg Route: intravenous Route: single Dose: 50 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Faintness | 7.1% | 50 mg single, intravenous Highest studied dose Dose: 50 mg Route: intravenous Route: single Dose: 50 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Vomiting | 7.1% | 50 mg single, intravenous Highest studied dose Dose: 50 mg Route: intravenous Route: single Dose: 50 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
|
| Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010-12 |
|
| Management of irritable bowel syndrome in primary care: feasibility randomised controlled trial of mebeverine, methylcellulose, placebo and a patient self-management cognitive behavioural therapy website. (MIBS trial). | 2010-11-18 |
|
| Topical piroxicam in vitro release and in vivo anti-inflammatory and analgesic effects from palm oil esters-based nanocream. | 2010-11-04 |
|
| First derivative synchronous fluorescence spectroscopy for the simultaneous determination of sulpiride and mebeverine hydrochloride in their combined tablets and application to real human plasma. | 2010-11 |
|
| Validated HPLC determination of the two fixed dose combinations (chlordiazepoxide hydrochloride and mebeverine hydrochloride; carvedilol and hydrochlorothiazide) in their tablets. | 2010-10-07 |
|
| Autoimmune hepatitis triggered by nitrofurantoin: a case series. | 2010-09-23 |
|
| Presentations of perforated colonic pathology in patients with polymyalgia rheumatica: two case reports. | 2010-09-06 |
|
| Development and validation of stability indicating HPLC and HPTLC methods for determination of sulpiride and mebeverine hydrochloride in combination. | 2010-09 |
|
| Colloids as a sink for certain pharmaceuticals in the aquatic environment. | 2010-05 |
|
| Predictors of treatment outcome after cognitive behavior therapy and antispasmodic treatment for patients with irritable bowel syndrome in primary care. | 2010-04 |
|
| Design and formulation of mebeverine HCl semisolid formulations for intraorally administration. | 2010-03 |
|
| A systematic review of efficacy and tolerability of mebeverine in irritable bowel syndrome. | 2010-02-07 |
|
| [Modern approaches to the therapy of biliary system diseases]. | 2010 |
|
| [A method for non-medicamentous treatment of irritated bowel syndrome]. | 2009-07-30 |
|
| pH-Sensitive Mebeverine Microspheres for Colon Delivery. | 2009-07 |
|
| The four killers of Meckel's diverticulum. | 2009-05 |
|
| 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. | 2009-01-15 |
|
| Development of membrane selective electrode for determination of the antipsychotic sulpiride in pharmaceuticals and urine. | 2009 |
|
| [The effectiveness of spasmolytic therapy in chronic acalculous cholecystitis]. | 2009 |
|
| [How to raise efficacy of gastroesophageal reflux disease treatment]. | 2009 |
|
| Psychological associations of irritable bowel syndrome besides panic disorder: an often overlooked reality. | 2009 |
|
| Drug use in children: cohort study in three European countries. | 2008-11-24 |
|
| Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis. | 2008-11-13 |
|
| Evaluation of the Birmingham IBS symptom questionnaire. | 2008-07-23 |
|
| 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. | 2008-05 |
|
| Cost-effectiveness of cognitive behaviour therapy in addition to mebeverine for irritable bowel syndrome. | 2008-04 |
|
| [Irritable bowel syndrome-an unbeloved problem]. | 2008-03-27 |
|
| Spectrophotometric determination of benzydamine HCl, levamisole HCl and mebeverine HCl through ion-pair complex formation with methyl orange. | 2008-03 |
|
| Serotonin receptor modulators in the treatment of irritable bowel syndrome. | 2008-02 |
|
| [Efficacy of duspatalin in the treatment and prophylaxis of postcholecystectomic syndrome]. | 2008 |
|
| Colon-specific drug delivery for mebeverine hydrochloride. | 2007-12 |
|
| A novel formulation for mebeverine hydrochloride. | 2007-10 |
|
| Improving the detection limits of antispasmodic drugs electrodes by using modified membrane sensors with inner solid contact. | 2007-05-09 |
|
| [Drug treatment of irritable bowel syndrome: an unmet need]. | 2007-03 |
|
| Development of in situ ion selective sensors for dissolution. | 2007-01-02 |
|
| [Chronic abdominal pain syndrome in biliary pathology]. | 2007 |
|
| Health technology assessment and ill-structured problems: a case study concerning the drug mebeverine. | 2007 |
|
| [Assessment of the efficacy of mebeverine in the complex therapy of chronic noncalculolis cholecystitis and biliary dysfunction]. | 2007 |
|
| Formulation of an antispasmodic drug as a topical local anesthetic. | 2006-12-01 |
|
| Cognitive behavioural therapy in addition to antispasmodic therapy for irritable bowel syndrome in primary care: randomised controlled trial. | 2006-06 |
|
| Quality of life of patients with irritable bowel syndrome is low compared to others with chronic diseases. | 2006-05 |
|
| "My patients are the sickest". | 2006-05 |
|
| Mebeverine influences sodium ion transport in the distal colon. | 2006-03-15 |
|
| Investigative implications of the instability and metabolism of mebeverine. | 2006-03 |
|
| [Mebeverine for complex treatment of opisthorchiasis]. | 2006 |
|
| [The pain problem as a historic aspect. Pain at the biliary pathology. Mebeverine hydrochloride as a part of complex therapy]. | 2006 |
|
| Generic and brand-name drugs. Are different criteria sufficiently taken into account before granting market authorisation? | 2006 |
|
| A new RP-HPLC method for analysis of mebeverine hydrochloride in raw materials and tablets. | 2005-04 |
|
| Rapid accurate mass desorption electrospray ionisation tandem mass spectrometry of pharmaceutical samples. | 2005 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.medicines.org.uk/emc/PIL.22522.latest.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2444442
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
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admin
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Edited
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| Record UNII |
LO53AXD8GP
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| Record Status |
Validated (UNII)
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| Record Version |
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302-043-3
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DTXSID90916525
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94088-43-4
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56841405
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LO53AXD8GP
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SUB22697
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ACTIVE MOIETY |