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Details

Stereochemistry ACHIRAL
Molecular Formula C20H27N.C6H8O7
Molecular Weight 473.5586
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALVERINE CITRATE

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCN(CCCC1=CC=CC=C1)CCCC2=CC=CC=C2

InChI

InChIKey=RYHCACJBKCOBTJ-UHFFFAOYSA-N
InChI=1S/C20H27N.C6H8O7/c1-2-21(17-9-15-19-11-5-3-6-12-19)18-10-16-20-13-7-4-8-14-20;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-8,11-14H,2,9-10,15-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI
Molecular Formula C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
Sterculia bulk-forming agent with smooth-muscle relaxant versus bran in diverticular disease.
1976 Feb 7
Acute hepatitis caused by alverine associated with anti-lamin A and C autoantibodies.
1997 Aug
Rectal antinociceptive properties of alverine citrate are linked to antagonism at the 5-HT1A receptor subtype.
2001 Oct
Alverine citrate fails to relieve the symptoms of irritable bowel syndrome: results of a double-blind, randomized, placebo-controlled trial.
2002 Jun
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
[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
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.
2008 Nov 13
Alverine citrate plus simethicone reduces cecal intubation time in colonoscopy - a randomized study.
2008 Sep
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
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
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
[A case report of alverine-citrate-induced acute hepatitis].
2010 Mar
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 15:09:08 UTC 2023
Edited
by admin
on Fri Dec 15 15:09:08 UTC 2023
Record UNII
9JFB58YK1E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALVERINE CITRATE
EP   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
SPASMAVERINE
Brand Name English
ALVERINE CITRATE [MI]
Common Name English
PROFENIL CITRATE
Brand Name English
SPACOLIN
Brand Name English
ALVERINE CITRATE [EP MONOGRAPH]
Common Name English
DIPROPYLAMINE, N-ETHYL-3,3'-DIPHENYL-, CITRATE (1:1)
Common Name English
Alverine citrate [WHO-DD]
Common Name English
ALVERINE CITRATE [MART.]
Common Name English
PHENPROPAMINE CITRATE
Common Name English
ANTISPASMIN
Brand Name English
GAMATRAN CITRATE
Brand Name English
N-ETHYL-3,3'-DIPHENYLDIPROPYLAMINE CITRATE (1:1)
Common Name English
ALVERINE CITRATE [USAN]
Common Name English
SPASMONAL
Brand Name English
BENZENEPROPANAMINE, N-ETHYL-N-(3-PHENYLPROPYL)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
PROVERINE
Brand Name English
PROFENINE
Brand Name English
CALMABEL
Brand Name English
NSC-35459
Code English
PROPHELAN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C66880
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
Code System Code Type Description
PUBCHEM
21718
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
MERCK INDEX
m1635
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY Merck Index
DRUG BANK
DBSALT000008
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
CAS
5560-59-8
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
SMS_ID
100000092379
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL253371
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
NCI_THESAURUS
C72692
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
FDA UNII
9JFB58YK1E
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
NSC
35459
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
RXCUI
71767
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID3045562
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
EVMPD
SUB00421MIG
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
ECHA (EC/EINECS)
226-929-3
Created by admin on Fri Dec 15 15:09:08 UTC 2023 , Edited by admin on Fri Dec 15 15:09:08 UTC 2023
PRIMARY
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