Basic information
- CAS
59995-65-2- Standard SMILES
COc1cc(Br)c(C[N+]2(CCOCCC3CCC4CC3C4(C)C)CCOCC2)cc1OC- InChIKey
DDHUTBKXLWCZCO-UHFFFAOYSA-N- Molecular formula
- C26H41BrNO4+
- Average molar mass
- 511.5 g/mol
- Monoisotopic mass
- 510.2219
Overview
Pinaverium is a monoterpenoid.
Names & identifiers
- Preferred name
- Pinaverium
- IUPAC
- 4-[(2-bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(6,6-dimethyl-2-bicyclo[3.1.1]heptanyl)ethoxy]ethyl]morpholin-4-ium
- English name
- 4-[(2-Bromo-4,5-dimethoxy-phenyl)methyl]-4-[2-[2-(6,6-dimethylnorpinan-2-yl)ethoxy]ethyl]-1-oxa-4-azoniacyclohexane bromide
- Molecular formula
- C26H41Br2NO4
- Molecular weight
- 591.42
Names & synonyms
Pinaverium59995-65-2Pinaverium ionPinaverium cationU2368VVE7OMorpholinium, 4-((2-bromo-4,5-dimethoxyphenyl)methyl)-4-(2-(2-(6,6-dimethylbicyclo(3.1.1)hept-2-yl)ethoxy)ethyl)-RefChem:1743044-[(2-bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(6,6-dimethyl-2-bicyclo[3.1.1]heptanyl)ethoxy]ethyl]morpholin-4-ium4-(2-Bromo-4,5-dimethoxybenzyl)-4-(2-(2-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)ethoxy)ethyl)morpholin-4-iumNCGC00181763-01UNII-U2368VVE7OSCHEMBL312166
Show more names
4-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]ethyl]morpholinium4-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)ethoxy]ethyl]morpholinium4-[(2-Bromo-4,5-dimethoxy-phenyl)methyl]-4-[2-[2-(6,6-dimethylnorpinan-2-yl)ethoxy]ethyl]-1-oxa-4-azoniacyclohexane bromide
CHEMBL1909324DTXSID90860655CHEBI:135811BDBM50101975DB09090Q12361464-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-{2-[2-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)ethoxy]ethyl}morpholin-4-ium
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 36.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 10
- Heavy atoms
- 32
- Formal charge
- 1
- Complexity
- 596
Experimental & physicochemical properties
SolubilitySlightly soluble
Melting Point152-158
Physicochemical properties
- FDA UNII
- 2368 VVE7O · U2368VVE7O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Pinaverium
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Protein BindingPinaverium is highly bound to human plasma proteins with the ratio of 97%.
Pharmacodynamics
Pinaverium is a selective and specific voltage-dependent calcium channel blocker located on intestinal smooth muscle cells to inhibit calcium influx. It mediates various effects on the GI tract: it causes oesophageal, gastric and duodenal relaxation, relaxes the colon and intestines, inhibits colonic motility in response to food, hormonal or pharmacological stimuli, accelerates gastric emptying, and reduces contractions of the gallbladder and phasic contractions of sphincter of Oddi. At higher concentrations, pinaverium also exhibits very weak anticholinergic effects but is not shown to display vasodilatory or anti-arrythmic actions.
Mechanism of Action
Pinaverium interacts with the 1,4-dihydropyridine binding sites on voltage dependent L-type calcium channels located on GI smooth muscle cells in a competitve manner. The binding site is located in the alpha 1S subunit and pinaverium most likely antagonizes the action of calcium ions by stabilizing a non-conducting channel state. Pinaverium inhibits smooth muscle contractions of the GI tract by inhibiting inward calcium current and calcium influx. It is suggested that pinaverium may be able to bind to both closed or inactivates states of the calcium channel with similar affinity.
Biological Half-LifeThe mean elimination half life is approximately 1.5 hours.
Metabolism/MetabolitesHepatic metabolism of pinaverium involves demethylation of one of the methoxy groups, hydroxylation of the norpinanyl ring and elimination of the benzyl group with subsequent opening of the morpholine ring.
MeSH Pharmacological Classification
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Related reactions
0 records
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Compound notes
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