Page last updated: 2024-11-04

alverine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

alverine : A tertiary amine having one ethyl and two 3-phenylprop-1-yl groups attached to the nitrogen. An antispasmodic that acts directly on intestinal and uterine smooth muscle, it is used (particularly as the citrate salt) in the treatment of irritable bowel syndrome. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID3678
CHEMBL ID253371
CHEBI ID518413
SCHEMBL ID83067
MeSH IDM0056687

Synonyms (88)

Synonym
BRD-K89055274-048-04-5
KBIO1_000312
DIVK1C_000312
SPECTRUM_000028
BSPBIO_000067
profenil
sestron base
hsdb 3284
alverine [inn:ban]
einecs 205-763-5
alverinum [inn-latin]
alverina [inn-spanish]
sestron
n-ethyl-bis(3-phenylpropyl)amin
dipropylin
dipropyline
alverine
PRESTWICK3_000174
PRESTWICK2_000174
IDI1_000312
D07440
alverine (inn)
150-59-4
QTL1_000007
BPBIO1_000075
BSPBIO_001800
n-ethyl-3-phenyl-n-(3-phenylpropyl)propan-1-amine
alverine citrate(usan)
benzenepropanamine, n-ethyl-n-(3-phenylpropyl)-
dipropylamine, n-ethyl-3,3'-diphenyl-
n-ethyl-3,3'-diphenyldipropylamine
AB00053791
n-ethyl-3-phenyl-n-(3-phenylpropyl)-1-propanamine
di(phenylpropyl)ethylamine
bis(gamma-phenylpropyl)ethylamine
DB01616
n-ethyl-n-(3-phenylpropyl)benzenepropanamine
phenopropamine
phenpropamine
n,n-bis(3-phenylpropyl)ethylamine
KBIOSS_000388
KBIO2_000388
KBIO2_005524
KBIO2_002956
NINDS_000312
PRESTWICK0_000174
SPBIO_001988
PRESTWICK1_000174
NCGC00024034-03
NCGC00021122-01
NCGC00024034-04
CHEMBL253371
alverinum
chebi:518413 ,
alverina
NCGC00021122-03
NCGC00021122-04
NCGC00021122-02
NCGC00021122-05
46tir1560o ,
unii-46tir1560o
ethylbis(3-phenylpropyl)amine
AKOS016008801
FT-0622246
alverine [who-dd]
alverine [inn]
alverine [mi]
alverine [hsdb]
S5945
STL483709
SCHEMBL83067
DTXSID0048557
n-ethyl-3-phenyl-n-(3-phenylpropyl)propan-1-amine;2-oxidanylpropane-1,2,3-tricarboxylic acid
n-ethyl-3-phenyl-n-(3-phenylpropyl)-1-propanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
cid_21718
citric acid;ethyl-bis(3-phenylpropyl)amine
bdbm37636
n-ethyl-3-phenyl-n-(3-phenylpropyl)-1-propanamine #
ZPFXAOWNKLFJDN-UHFFFAOYSA-N
bis(.gamma.-phenylpropyl)ethylamine
AB00053791_15
AB00053791_16
J-519578
SBI-0051275.P003
Q4116162
BRD-K89055274-048-14-4
SB82386
EN300-18539591

Research Excerpts

Overview

Alverine citrate is a commonly used smooth muscle relaxant agent. Alverine, which is a gastrointestinal antispasmodic drug, was further validated to display antidepressant-like effects in the learned helplessness and chronic unpredictable stress models.

ExcerptReferenceRelevance
"Alverine, which is a gastrointestinal antispasmodic drug, was further validated to display antidepressant-like effects in the learned helplessness and chronic unpredictable stress models of depression."( Network-based drug repositioning: A novel strategy for discovering potential antidepressants and their mode of action.
An, L; Li, S; Li, YF; Wang, X; Xue, R; Zhang, TT; Zhang, YZ; Zhao, SW, 2018
)
1.2
"Alverine citrate is a commonly used smooth muscle relaxant agent. "( Alverine citrate induced acute hepatitis.
Arhan, M; Kayacetin, E; Koklu, S; Koksal, AS; Koruk, I; Koruk, S; Yolcu, OF, 2004
)
3.21

Effects

ExcerptReferenceRelevance
"Alverine citrate has been used in the treatment of irritable bowel syndrome for many years."( Alverine citrate fails to relieve the symptoms of irritable bowel syndrome: results of a double-blind, randomized, placebo-controlled trial.
Chapman, RW; Mee, AS; Mitchell, SA; Palmer, KR; Smith, GD, 2002
)
3.2

Actions

ExcerptReferenceRelevance
"Alverine may increase Ca influx during action potentials due to inhibition of the inactivation of L-type Ca channels, but may also suppress evoked activity by inhibiting the sensitivity of contractile proteins to Ca2+. "( Evolving mechanisms of action of alverine citrate on phasic smooth muscles.
Brading, AF; Hashitani, H; Hayase, M; Kohri, K; Suzuki, H, 2007
)
2.06

Pharmacokinetics

ExcerptReferenceRelevance
" This method was successfully applied to a pharmacokinetic study after oral administration of alverine citrate 120 mg capsule in Indian healthy male volunteers."( A rapid and most sensitive liquid chromatography/tandem mass spectrometry method for simultaneous determination of alverine and its major metabolite, para hydroxy alverine, in human plasma: application to a pharmacokinetic and bioequivalence study.
Ahir, R; Chakraborty, BS; Ghosh, C; Jha, V; Shah, S; Shinde, CP, 2010
)
0.79
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antispasmodic drugA drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
tertiary amineA compound formally derived from ammonia by replacing three hydrogen atoms by hydrocarbyl groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID311932Inhibition of ASM in human H4 cells assessed as residual activity at 10 uM2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (35)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (25.71)18.7374
1990's3 (8.57)18.2507
2000's10 (28.57)29.6817
2010's11 (31.43)24.3611
2020's2 (5.71)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 67.22

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index67.22 (24.57)
Research Supply Index3.87 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index112.15 (26.88)
Search Engine Supply Index2.02 (0.95)

This Compound (67.22)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials9 (23.68%)5.53%
Reviews0 (0.00%)6.00%
Case Studies4 (10.53%)4.05%
Observational0 (0.00%)0.25%
Other25 (65.79%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (11)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Multicenter, Randomized, Parallel-group, Open-label, Comparative Clinical Study to Evaluate Efficacy and Safety of Mebeverine+Simethicone Fixed-dose Combination Versus Duspatalin® (Mebeverine) and Versus Espumisan® (Simethicone) in Patients With Functiona [NCT05175131]Phase 3465 participants (Actual)Interventional2020-11-27Completed
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) [NCT00934973]Phase 4135 participants (Actual)Interventional2010-04-30Completed
A Comparative Study to Assess Safety and Effectiveness of Ethosuximide and Pentoxifylline in the Treatment of Abdominal Pain Related to Irritable Bowel Syndrome [NCT04217733]Phase 360 participants (Anticipated)Interventional2019-11-01Recruiting
Efficacy and Safety of Meteospasmyl® in Irritable Bowel Syndrome. a 4-Week, Multicentre, Double-Blind, Randomised, Placebo-Controlled Phase IV Trial [NCT00542295]Phase 4400 participants (Anticipated)Interventional2007-07-31Completed
Pharmacological Enhancement for Nocturnal Incontinence in Orthotopic Bladder Substitute. A Randomised Controlled Trial [NCT04635566]120 participants (Actual)Interventional2019-03-01Completed
Efficacy of the Combination Therapy With Alverine-simeticone and i3.1 Probiotic Formula in the Quality of Life of Patients With IBS-D or IBS-M in Hospital Juarez Mexico [NCT04145856]Phase 455 participants (Actual)Interventional2018-09-03Completed
To Compare the Efficacy of (Rifaximin + Mebeverine), (Rifaximin + Amitriptyline), and (Rifaximin + Psyllium Husk) in Irritable Bowel Syndrome Associated With Diarrhea [NCT05867550]Phase 4162 participants (Actual)Interventional2023-01-03Completed
The Instant Efficacy and Safety of Alverine in Decreasing Portal Hypertension: an Exploratory Pilot Study [NCT05508633]Phase 220 participants (Anticipated)Interventional2022-08-31Not yet recruiting
The Role of Irritable Bowel Syndrome in Lactose Intolerance (LION Trial): Protocol of a Multicentre Randomized Controlled Clinical Trial [NCT05100719]200 participants (Anticipated)Interventional2022-09-30Not yet recruiting
Assessment of On-demand MeteoSpasmyl® Use Effectiveness in Irritable Bowel Syndrome [NCT01404923]Phase 4436 participants (Actual)Interventional2009-12-31Completed
Effectiveness of Duspatalin® (Mebeverine Hydrochloride) 200 mg b.i.d. in Patients With Post-cholecystectomy Gastrointestinal Spasm: a Post Marketing Observational Program in the Russian Federation [NCT02260154]220 participants (Actual)Observational2015-07-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT01404923 (2) [back to overview]Change From Baseline in Irritable Bowel Syndrome Quality Of Life Overall Score
NCT01404923 (2) [back to overview]Percentage of Improvement of the Total IBSQoL Scores
NCT02260154 (11) [back to overview]"Percentage of Responders to Duspatalin® Therapy"
NCT02260154 (11) [back to overview]Health Economics Data 3
NCT02260154 (11) [back to overview]Healths Economic Data 2
NCT02260154 (11) [back to overview]"Percentage of Responders to Duspatalin® Therapy"
NCT02260154 (11) [back to overview]Changes in Abdominal Pain
NCT02260154 (11) [back to overview]Changes in Dyspepsia Symptoms
NCT02260154 (11) [back to overview]Changes in Quality of Life
NCT02260154 (11) [back to overview]Changes in Stool Habits and Percentage of Patients Reporting Abnormal Stool Form
NCT02260154 (11) [back to overview]Changes in Stool Habits and Percentage of Patients Reporting Abnormal Stool Form 2
NCT02260154 (11) [back to overview]Health Economic Data
NCT02260154 (11) [back to overview]Reasons for Continuing Treatment Beyond 2 Weeks

Change From Baseline in Irritable Bowel Syndrome Quality Of Life Overall Score

Irritable Bowel Syndrome Quality of Life total score (IBSQoL) is a health-related Quality of Life (QoL) disease-specific scale adapted for French patients. Total score ranges from minimum=0 to maximum = 100 representing the best outcome. (NCT01404923)
Timeframe: Baseline and 6 months

Interventionunits on a scale (Mean)
Meteospasmyl13.8
Standard of Care8.4

[back to top]

Percentage of Improvement of the Total IBSQoL Scores

Improvement of the total IBSQoL scores from baseline to month 6 calculated in percentage (NCT01404923)
Timeframe: Baseline and 6 Months

Intervention% of improvement of IBSQoL total scores (Mean)
Meteospasmyl28.5
Standard of Care18.6

[back to top]

"Percentage of Responders to Duspatalin® Therapy"

(NCT02260154)
Timeframe: Up to 6 weeks

Interventionpercentage of participants (Number)
Post-cholecystectomy Gastrointestinal Spasms79.0

[back to top]

Health Economics Data 3

Number of days missed from work for currently employed subjects. Change is calculated as Week 6 value minus Baseline value. Negative change means less number of days missed from work. (NCT02260154)
Timeframe: change from baseline at Week 6

InterventionNumber of days (Mean)
Post-cholecystectomy Gastrointestinal Spasms-2.1

[back to top]

Healths Economic Data 2

Number of visits to clinic for currently employed subjects. Change is calculated as Week 6 value minus Baseline value. Negative change means less number of visits to clinic. (NCT02260154)
Timeframe: from baseline at Week 6

Interventionnumber of visits (Mean)
Post-cholecystectomy Gastrointestinal Spasms-0.9

[back to top]

"Percentage of Responders to Duspatalin® Therapy"

Patients indicating being 'symptom-free' or 'markedly improved'on Global Patient Assessment (NCT02260154)
Timeframe: 2 weeks

Interventionpercentage of participants (Number)
Symptom-free or markedly improvedOther values (slightly improved, unchanged, worse)
Post-cholecystectomy Gastrointestinal Spasms63.636.4

[back to top]

Changes in Abdominal Pain

Measured by 11-items Numerous Rating Scale where 0 represents no pain and 10 represents the worst pain. Negative change corresponds to better result. Changes are calculated as Week 2 value minus Baseline value and Week 6 value minus Baseline value. (NCT02260154)
Timeframe: Baseline, 2 weeks and up to 6 weeks

Interventionunits on a scale (Mean)
change from baseline at Week 2change from baseline at Week 6
Post-cholecystectomy Gastrointestinal Spasms-3.7-4.4

[back to top]

Changes in Dyspepsia Symptoms

Measured by 11-items Numerous Rating Scale where 0 represents no symptoms and 10 represents the worst symptoms. Negative change corresponds to better result. Changes are calculated as Week 2 value minus Baseline value and Week 6 value minus Baseline value. (NCT02260154)
Timeframe: Baseline, 2 weeks and up to 6 weeks

Interventionunits on a scale (Mean)
change from baseline at Week 2change from baseline at Week 6
Post-cholecystectomy Gastrointestinal Spasms-2.0-2.3

[back to top]

Changes in Quality of Life

Gastrointestinal Quality of Life Index contains 36 questions with 4 possible answers per each (most desirable option returns 4 points, and least desirable option returns 0 points). Total score of the GIQLI is calculated as sum of all items. The source scores are transformed and scaled from 0 to 100. The high score corresponds to better result. Changes are calculated as Week 2 value minus Baseline value and Week 6 value minus Baseline value. (NCT02260154)
Timeframe: Baseline, 2 weeks and up to 6 weeks

Interventionunits on a scale (Mean)
change from baseline at Week 2change from baseline at Week 6
Post-cholecystectomy Gastrointestinal Spasms16.80221.737

[back to top]

Changes in Stool Habits and Percentage of Patients Reporting Abnormal Stool Form

"Changes in Stool Habits: The change is presented as the proportion of patients whose Changes in Stool Habits from 'Abnormal' to 'Normal' and vice versa were registered. Positive is defined as Change from 'Abnormal stool form at BL' to 'Normal stool form at Week 2'. Negative is defined as Change from 'Normal stool form at BL' to 'Abnormal stool form at Week 2'." (NCT02260154)
Timeframe: Baseline to Week 2

Interventionpercentage of participants (Number)
PositiveNegative
Post-cholecystectomy Gastrointestinal Spasms38.252.30

[back to top]

Changes in Stool Habits and Percentage of Patients Reporting Abnormal Stool Form 2

"Changes in Stool Habits: The change is presented as the proportion of patients whose Changes in Stool Habits from 'Abnormal' to 'Normal' and vice versa were registered. Positive is defined as Change from 'Abnormal stool form at BL' to 'Normal stool form at Week 6'. Negative is defined as Change from 'Normal stool form at BL' to 'Abnormal stool form at Week 6'." (NCT02260154)
Timeframe: Baseline to Week 6

Interventionpercentage of participants (Number)
PositiveNegative
Post-cholecystectomy Gastrointestinal Spasms40.002.00

[back to top]

Health Economic Data

Relevant concomitant medication (NCT02260154)
Timeframe: Baseline, up to 6 weeks

Interventionpercentage of participants (Number)
ACE inhibitorsAlpha adrenoreceptor antagonistAluminium compoundsAngiotensine II antagonistAnti arrhythmicsAnti diarrhealAnti inflammatoryBarbituratesBeta blocking against agents, selectiveBiguanigesBile acid preparationsBioflavonoidsBlood transfusion, auxilary productsBeta blocking agents, and other antihypertensivesBeta blocking agents, thiazides
Post-cholecystectomy Gastrointestinal Spasms9.60.52.31.40.51.40.50.54.10.910.10.50.50.50.5

[back to top]

Reasons for Continuing Treatment Beyond 2 Weeks

List and rate of reasons (NCT02260154)
Timeframe: 2 weeks

Interventionpercentage of participants (Number)
Expectation in higher effectivenessTend to treat beyond 2 weeksMaintenance of achieved effect
Post-cholecystectomy Gastrointestinal Spasms84.24.011.9

[back to top]