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Details

Stereochemistry ACHIRAL
Molecular Formula C20H27N
Molecular Weight 281.4351
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALVERINE

SMILES

CCN(CCCC1=CC=CC=C1)CCCC2=CC=CC=C2

InChI

InChIKey=ZPFXAOWNKLFJDN-UHFFFAOYSA-N
InChI=1S/C20H27N/c1-2-21(17-9-15-19-11-5-3-6-12-19)18-10-16-20-13-7-4-8-14-20/h3-8,11-14H,2,9-10,15-18H2,1H3

HIDE SMILES / InChI

Description

Alverine is a smooth muscle relaxant used for the treatment irritable bowel syndrome. Alverine may increase calcium influx during action potentials due to inhibition of the inactivation of L-type calcium channels, but may also suppress evoked activity by inhibiting the sensitivity of contractile proteins to calcium.

CNS Activity

CNS Active
3913
Curator's Comment: Alverine is CNS active in animals. No human data available.

Originator

Külz, F. et al.
3
Sources: Buth W, Kulz F, Rosemund KW. Über Synthesen spasmolytisch wirkendender Stoffe. Ber. Dtsch. Chem. Ges. B. 1939;72:19–28. | Kulz F, Rosenmund KW, Kayser E, Schwarzhaupt O, Sommer H. Über Synthesen spasmolytisch wirkender Stoffe. II. Mitteilung. Berichte der deutschen chemischen Gesellschaft (A and B Series) 1939;72(12):2161–2167.
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/23675775

Approval Year

1947
99
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Alverine

Approved Use

Alverine citrate is an anti-spasmodic medicine. It relaxes the muscles in the intestine (gut) and uterus (womb). This helps stop the pain you feel when the muscles become tense. Alverine citrate is used to help people who have Irritable Bowel Syndrome (IBS). Some of the symptoms of IBS are: abdominal pains like cramp which come and go, diarrhoea, constipation, feeling full and bloated, wanting to go to the toilet urgently. Sometimes these symptoms are worse if you are worried or under stress. Alverine citrate is also used for a condition of the large intestine called painful diverticular disease of the colon. It is also used to relieve period pains.
Primary
Preclinical
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2574 pg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29404023
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALVERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
2841.78 pg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29404023
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PARA HYDROXY ALVERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15562.3 pg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29404023
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALVERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
19755.5 pg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29404023
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PARA HYDROXY ALVERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.37 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29404023
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALVERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
9.84 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29404023
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PARA HYDROXY ALVERINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15259090/
unhealthy, 34 years
n = 1
Health Status: unhealthy
Condition: esophagitis and pangastritis
Age Group: 34 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/15259090/
Disc. AE: Hepatitis acute...
AEs leading to
discontinuation/dose reduction:
Hepatitis acute
Sources:
https://pubmed.ncbi.nlm.nih.gov/15259090/
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day, during 4 weeks)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
unhealthy, mean age 46.5 years
n = 207
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: mean age 46.5 years
Sex: M+F
Population Size: 207
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
Disc. AE: Eye swelling...
Other AEs: Nausea, Abdominal pain upper...
AEs leading to
discontinuation/dose reduction:
Eye swelling (0.5%)
Other AEs:
Nausea (2.9%)
Abdominal pain upper (1.4%)
Headache (3.4%)
Asthenia (0.5%)
Vertigo (1.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
AEs

AEs

AESignificanceDosePopulation
Hepatitis acute Disc. AE
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15259090/
unhealthy, 34 years
n = 1
Health Status: unhealthy
Condition: esophagitis and pangastritis
Age Group: 34 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/15259090/
Asthenia 0.5%
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day, during 4 weeks)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
unhealthy, mean age 46.5 years
n = 207
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: mean age 46.5 years
Sex: M+F
Population Size: 207
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
Eye swelling 0.5%
Disc. AE
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day, during 4 weeks)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
unhealthy, mean age 46.5 years
n = 207
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: mean age 46.5 years
Sex: M+F
Population Size: 207
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
Abdominal pain upper 1.4%
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day, during 4 weeks)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
unhealthy, mean age 46.5 years
n = 207
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: mean age 46.5 years
Sex: M+F
Population Size: 207
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
Vertigo 1.9%
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day, during 4 weeks)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
unhealthy, mean age 46.5 years
n = 207
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: mean age 46.5 years
Sex: M+F
Population Size: 207
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
Nausea 2.9%
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day, during 4 weeks)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
unhealthy, mean age 46.5 years
n = 207
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: mean age 46.5 years
Sex: M+F
Population Size: 207
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
Headache 3.4%
60 mg 3 times / day multiple, oral
Recommended
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Co-administed with::
simeticone(300 mg; 3 times per day, during 4 weeks)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
unhealthy, mean age 46.5 years
n = 207
Health Status: unhealthy
Condition: irritable bowel syndrome
Age Group: mean age 46.5 years
Sex: M+F
Population Size: 207
Sources:
https://pubmed.ncbi.nlm.nih.gov/20003095/
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:518413
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:518413
ChemicalBook
CB5333673
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5333673
ZINC
ZINC000001481966
http://zinc15.docking.org/substances/ZINC000001481966
eMolecules
618386
https://www.emolecules.com/cgi-bin/more?vid=618386
PubMed

PubMed

TitleDatePubMed
Effects of alverine on the spontaneous electrical activity and nervous control of the proximal colon of the rabbit.
1992
Effects of alverine citrate on cat intestinal mechanoreceptor responses to chemical and mechanical stimuli.
1999 Apr
Alverine induced toxic hepatitis: a case report.
2002 Dec
Chemical genomics in yeast.
2004
[Dynamics of clinical symptoms and indices of visceral sensitivity in patients with the irritated bowels syndrome treated with meteospasmyl].
2005
Evolving mechanisms of action of alverine citrate on phasic smooth muscles.
2007 Dec
[Irritable bowel syndrome: current treatment options].
2007 Nov
Spasmolytic and anti-inflammatory effects of constituents from Hertia cheirifolia.
2009 Dec
Alverine citrate, simeticone, and Rome III irritable bowel syndrome.
2010 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Determination of pregabalin in human plasma by electrospray ionisation tandem mass spectroscopy.
2010 Jul
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.
2010 Jun
Patents

Patents

US20040147443A1
3
US6335368B1
3

Sample Use Guides

In Vivo Use Guide
Alverine citrate 60 mg capsules: 1 or 2 capsules one to three times daily
Route of Administration: Oral
In Vitro Use Guide
30 μg/ml alverine citrate can enhance the cytotoxic effects of MG132 on breast cancer cells.
Name Type Language
ALVERINE
HSDB   INN   MI   WHO-DD  
INN  
Official Name English
Alverine [WHO-DD]
Common Name English
PHENPROPAMINE
Common Name English
ALVERINE [HSDB]
Common Name English
N-ETHYL-3,3'-DIPHENYLDIPROPYLAMINE
Common Name English
alverine [INN]
Common Name English
ALVERINE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QA03AX58
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
NCI_THESAURUS C66880
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
WHO-ATC A03AX08
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
WHO-ATC A03AX58
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
WHO-VATC QA03AX08
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
Code System Code Type Description
DRUG BANK
DB01616
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
FDA UNII
46TIR1560O
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
MESH
C010846
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-763-5
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
ChEMBL
CHEMBL253371
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
RXCUI
17627
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY RxNorm
INN
95
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
EVMPD
SUB05384MIG
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
WIKIPEDIA
Alverine
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
CAS
150-59-4
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
DRUG CENTRAL
142
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
NCI_THESAURUS
C76387
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
MERCK INDEX
m1635
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY Merck Index
SMS_ID
100000087661
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID0048557
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
CHEBI
518413
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
HSDB
3284
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
PUBCHEM
3678
Created by admin on Fri Dec 15 16:34:04 GMT 2023 , Edited by admin on Fri Dec 15 16:34:04 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of ALVERINE
SALT/SOLVATE (PARENT)
Structure of ALVERINE CITRATE
SALT/SOLVATE (PARENT)
Structure of ALVERINE HYDROCHLORIDE
NIH
NCATS
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