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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
Molecular Formula C20H27N
Molecular Weight 281.4351
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Acute hepatitis caused by alverine associated with anti-lamin A and C autoantibodies.
1997 Aug
Effects of alverine citrate on cat intestinal mechanoreceptor responses to chemical and mechanical stimuli.
1999 Apr
Rectal antinociceptive properties of alverine citrate are linked to antagonism at the 5-HT1A receptor subtype.
2001 Oct
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Chemogenomic profiling predicts antifungal synergies.
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
Alverine citrate, simeticone, and Rome III irritable bowel syndrome.
2010 Apr
Clinical trial: the efficacy of alverine citrate/simeticone combination on abdominal pain/discomfort in irritable bowel syndrome--a randomized, double-blind, placebo-controlled study.
2010 Mar
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:34:04 UTC 2023
Edited
by admin
on Fri Dec 15 16:34:04 UTC 2023
Record UNII
46TIR1560O
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
NCI_THESAURUS C66880
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
WHO-ATC A03AX08
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
WHO-ATC A03AX58
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
WHO-VATC QA03AX08
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
Code System Code Type Description
DRUG BANK
DB01616
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
FDA UNII
46TIR1560O
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
MESH
C010846
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-763-5
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
ChEMBL
CHEMBL253371
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
RXCUI
17627
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY RxNorm
INN
95
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
EVMPD
SUB05384MIG
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
WIKIPEDIA
Alverine
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
CAS
150-59-4
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
DRUG CENTRAL
142
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
NCI_THESAURUS
C76387
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
MERCK INDEX
m1635
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY Merck Index
SMS_ID
100000087661
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID0048557
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
CHEBI
518413
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
HSDB
3284
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
PUBCHEM
3678
Created by admin on Fri Dec 15 16:34:04 UTC 2023 , Edited by admin on Fri Dec 15 16:34:04 UTC 2023
PRIMARY
Related Record Type Details
Structure of ALVERINE CITRATE
SALT/SOLVATE -> PARENT
Structure of ALVERINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ALVERINE
ACTIVE MOIETY
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