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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H41BrNO4.Br
Molecular Weight 591.416
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PINAVERIUM BROMIDE

SMILES

[Br-].COC1=C(OC)C=C(C[N+]4(CCOCC[C@@H]2CC[C@H]3C[C@@H]2C3(C)C)CCOCC4)C(Br)=C1

InChI

InChIKey=IKGXLCMLVINENI-QOXGANSBSA-M
InChI=1S/C26H41BrNO4.BrH/c1-26(2)21-6-5-19(22(26)16-21)7-11-31-12-8-28(9-13-32-14-10-28)18-20-15-24(29-3)25(30-4)17-23(20)27;/h15,17,19,21-22H,5-14,16,18H2,1-4H3;1H/q+1;/p-1/t19-,21-,22-;/m0./s1

HIDE SMILES / InChI
Pinaverium, known under the brand name DICETEL, is a spasmolytic agent used for functional gastrointestinal disorders. It is a quaternary ammonium compound that acts as an atypical calcium antagonist to restore normal bowel function. It is shown to relieve GI spasm and pain, transit disturbances and other symptoms related to motility disorders and may be considered as effective first-lline therapy for patients with irritable bowel syndrome (IBS). Pinaverium is also used to help relieve symptoms caused by certain disorders of the gallbladder associated with secretion of bile. Pinaverium bromide is the common ingredient in formulations, mostly as oral tablets. Although it is not a currently approved drug by the FDA, pinaverium is available in over 60 countries including Canada. DICETEL® (pinaverium bromide) is a calcium antagonist which inhibits the calcium influx by blocking the voltage-dependent calcium channel at the smooth muscle cell level. It possesses a high degree of selectivity for the intestinal smooth muscle.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Dicetel

Approved Use

DICETEL® (pinaverium bromide) is indicated: - for the treatment and relief of symptoms associated with irritable bowel syndrome (IBS): abdominal pain, bowel disturbances and intestinal discomfort. - for the treatment of symptoms related to functional disorders of the biliary tract.
Palliative
Dicetel

Approved Use

DICETEL® (pinaverium bromide) is indicated: - for the treatment and relief of symptoms associated with irritable bowel syndrome (IBS): abdominal pain, bowel disturbances and intestinal discomfort. - for the treatment of symptoms related to functional disorders of the biliary tract.
PubMed

PubMed

TitleDatePubMed
Contraction of human colonic circular smooth muscle cells is inhibited by the calcium channel blocker pinaverium bromide.
2001 Jun
Increased calcium influx is responsible for the sustained mechanical tone in colon from dystrophic (mdx) mice.
2001 May
[Effects of dicetel on gastrointestinal motility and vegetative dysfunction in patients with duodenal ulcer].
2003
Effect of pinaverium bromide on stress-induced colonic smooth muscle contractility disorder in rats.
2003 Mar
[Randomized controlled clinical study on effect of Chinese compound changjitai in treating diarrheic irritable bowel syndrome].
2003 Nov
Quaternary ammonium derivatives as spasmolytics for irritable bowel syndrome.
2004
[New approaches to diagnosing and treating hyperkinetic biliary dyskinesia associated with chronic acalculous cholecystitis].
2004
[Drug treatment of irritable bowel syndrome: an unmet need].
2007 Mar
[Pinaverium bromide-induced esophageal ulcerations].
2008 Jan-Feb
Effect of four medications associated with gastrointestinal motility on Oddi sphincter in the rabbit.
2009
Patents

Patents

Sample Use Guides

The usual adult dosage is 50 mg three times a day (total daily dose of 150 mg). The dosage may be increased up to a maximum of 100 mg taken three times a day (maximum total daily dose of 300 mg). It is recommended that the tablet be taken with a glass of water during meals or snacks. The tablet should not be swallowed when in the lying position or just before bedtime.
Route of Administration: Oral
In inflamed human colons, pinaverium (1 uM) display a significant higher efficacy than diltiazem or nicardipine to reduce cell contraction induced by CCK-8 or by KCl.
Name Type Language
PINAVERIUM BROMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
DICETEL
Brand Name English
PINAVERIUM BROMIDE [MART.]
Common Name English
4-(6-BROMOVERATRYL)-4-(2-(2-(6,6-DIMETHYL-2-NORPINYL)ETHOXY)ETHYL)MORPHOLINIUM BROMIDE
Systematic Name English
Pinaverium bromide [WHO-DD]
Common Name English
LAT-1717
Code English
MORPHOLINIUM, 4-((2-BROMO-4,5-DIMETHOXYPHENYL)METHYL)-4-(2-(2-(6,6-DIMETHYLBICYCLO(3.1.1)HEPT-2-YL)ETHOXY)ETHYL)-, BROMIDE (1:1)
Systematic Name English
pinaverium bromide [INN]
Common Name English
PINAVERIUM BROMIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Sat Dec 16 17:43:51 GMT 2023 , Edited by admin on Sat Dec 16 17:43:51 GMT 2023
Code System Code Type Description
PUBCHEM
145721938
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PRIMARY
EPA CompTox
DTXSID2048614
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PRIMARY
NCI_THESAURUS
C116775
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PRIMARY
RXCUI
54743
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PRIMARY RxNorm
FDA UNII
7SCF54H12J
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PRIMARY
DRUG BANK
DBSALT001130
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PRIMARY
CAS
53251-94-8
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PRIMARY
ChEMBL
CHEMBL1909324
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PRIMARY
SMS_ID
100000081977
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PRIMARY
CAS
1970218-70-2
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ALTERNATIVE
WIKIPEDIA
Pinaverium bromide
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PRIMARY
EVMPD
SUB09851MIG
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PRIMARY
INN
3696
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PRIMARY
ECHA (EC/EINECS)
258-450-0
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PRIMARY
MERCK INDEX
m8822
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PRIMARY Merck Index