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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H41BrNO4
Molecular Weight 511.512
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of PINAVERIUM

SMILES

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=DDHUTBKXLWCZCO-BVSLBCMMSA-N
InChI=1S/C26H41BrNO4/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/q+1/t19-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H41BrNO4
Molecular Weight 511.512
Charge 1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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
[Current approaches to the diagnosis and treatment of irritable bowel syndrome].
2001 Sep-Dec
[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 fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.
2008 Nov 13
Effect of four medications associated with gastrointestinal motility on Oddi sphincter in the rabbit.
2009
Irritable bowel syndrome: a mild disorder; purely symptomatic treatment.
2009 Apr
[Tiaohe Ganpi Hexin Decoction in treatment of irritable bowel syndrome with diarrhea: a randomized controlled trial].
2009 Sep
Effect of probiotic Lactobacillus (Lacidofil® cap) for the prevention of antibiotic-associated diarrhea: a prospective, randomized, double-blind, multicenter study.
2010 Dec
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:52:41 UTC 2023
Edited
by admin
on Sat Dec 16 01:52:41 UTC 2023
Record UNII
U2368VVE7O
Record Status Validated (UNII)
Record Version
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Name Type Language
PINAVERIUM
WHO-DD  
Common Name English
Pinaverium [WHO-DD]
Common Name English
MORPHOLINIUM, 4-((2-BROMO-4,5-DIMETHOXYPHENYL)METHYL)-4-(2-(2-(6,6-DIMETHYLBICYCLO(3.1.1)HEPT-2-YL)ETHOXY)ETHYL)-
Systematic Name English
PINAVERIUM ION
Common Name English
PINAVERIUM CATION
Common Name English
Classification Tree Code System Code
WHO-ATC A03AX04
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
WHO-VATC QA03AX04
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
Code System Code Type Description
RXCUI
33724
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY RxNorm
EVMPD
SUB03826MIG
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID90860655
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
PUBCHEM
40479674
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
DRUG BANK
DB09090
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
WIKIPEDIA
PINAVERIUM
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
CAS
59995-65-2
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
SMS_ID
100000085286
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
CAS
1970218-69-9
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
ALTERNATIVE
DRUG CENTRAL
2174
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
MESH
C013199
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
FDA UNII
U2368VVE7O
Created by admin on Sat Dec 16 01:52:41 UTC 2023 , Edited by admin on Sat Dec 16 01:52:41 UTC 2023
PRIMARY
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