Pyrvinium
Basic information
- CAS
7187-62-4- Standard SMILES
Cc1cc(/C=C/c2ccc3cc(N(C)C)ccc3[n+]2C)c(C)n1-c1ccccc1- InChIKey
QMHSXPLYMTVAMK-UHFFFAOYSA-N- Molecular formula
- C26H28N3+
- Average molar mass
- 382.5 g/mol
- Monoisotopic mass
- 382.22832291
Overview
Pyrvinium is a quinolinium ion that is 1-methylquinolinium substituted by dimethylamino group at position 6 and a (E)-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl at position 2. It is a anthelminthic drug active against pinworms. The salts of pyrvinium can also be used as anticancer agents. It has a role as an anthelminthic drug and an antineoplastic agent.
Names & identifiers
- Preferred name
- Pyrvinium
- IUPAC
- 2-[(E)-2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine
Names & synonyms
PYRVINIUM7187-62-4pyrvinium (cation)Pyrvinium ionPyrvinium cationPyrvinum (base)CHEBI:86876B9991FLU3Quinolinium, 6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl)-1-methyl-6-(Dimethylamino)-2-(2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl)-1-methylquinoliniumQuinolinium, 6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenylpyrrol-3-yl)vinyl)-1-methyl-DTXSID2043795
Show more names
2-((E)-2-(2,5-dimethyl-1-phenyl-pyrrol-3-yl)vinyl)-N,N,1-trimethyl-quinolin-1-ium-6-amine2-[(E)-2-(2,5-dimethyl-1-phenyl-pyrrol-3-yl)vinyl]-N,N,1-trimethyl-quinolin-1-ium-6-amineRefChem:177975DTXCID0023795PyrvinumHSDB 31782-[(E)-2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-aminepyrvinium-pamoate
Database identifiers
- CAS
7187-62-4- PubChem CID
- 5281035
- ChEMBL
CHEMBL1201303- ChEBI
CHEBI:8687- UNII
- 6B9991FLU3
- Nikkaji
- J257.477B
Properties
Computed structural properties
- XLogP
- 5.9
- Topological polar surface area
- 12.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 4
- Heavy atoms
- 29
- Formal charge
- 1
- Complexity
- 552
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Color/FormDEEP-RED CRYSTALLINE SOLID
Solubility
SPARINGLY SOL IN WATER /CHLORIDE/
SLIGHTLY SOL IN CHLOROFORM & METHOXYETHANOL /PAMOATE/
VERY SLIGHTLY SOL IN ALC /PAMOATE/
PRACTICALLY INSOL IN WATER & ETHER /PAMOATE/
Melting PointMP: 210-215 °C (SOFTENS @ 190 °C); ABSORPTION MAX: 236, 356, 503 NM /PAMOATE/
Stability/Shelf LifeSTABLE TO HEAT, LIGHT & AIR /PAMOATE/
Other Experimental Properties
DECOMP @ 249-251 °C /DIHYDRATE/
BRIGHT ORANGE OR ORANGE-RED TO ALMOST BLACK PPT /PAMOATE/
DEEP-RED POWDER /DIHYDRATE/
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
Human Toxicity Excerpts
SIDE EFFECTS REPORTED IN SMALL PROPORTION OF TREATED PT INCL NAUSEA, VOMITING, & CRAMPING; MAJORITY OF THESE PT WERE OLDER CHILDREN OR ADULTS WHO HAD RECEIVED RELATIVELY LARGE DOSE OF EITHER SUSPENSION OR TABLETS. EMESIS...MOST FREQUENT SIDE EFFECT ASSOC WITH SUSPENSION, BUT...DID NOT OCCUR IN PT...GIVEN TABLETS. /PAMOATE/
...TRANSIENT PHOTOSENSITIZATION.../HAS/ BEEN REPORTED.
Non-Human Toxicity Excerpts
ADMIN OF PYRANTEL PAMOATE (500, 1000, OR 3000 MG/KG, ORALLY FOR 1 MO) DID NOT RESULT IN TOXIC EFFECTS IN RATS. PYRVINIUM PAMOATE WAS MORE TOXIC THAN PYRANTEL PAMOATE; 6 OF 13 FEMALE RATS GIVEN 3000 MG/KG DIED WITHIN 1 MO.
PYRVINIUM EMBONATE WAS ACTIVATED BY RAT LIVER MICROSOMAL PREPN TO MUTAGEN CAPABLE OF CAUSING BOTH BASE-PAIR SUBSTITUTION IN SALMONELLA TYPHIMURIUM TA100 & FRAMESHIFT MUTATIONS IN TA98 STRAIN. MODIFIED AMES TEST WAS USED.
Chemistry & industry
Pharmacology
ATC CodeP - Antiparasitic products, insecticides and repellents
PharmacodynamicsPyrvinium is an anthelmintic agent which acts to kill pinworms.
Mechanism of Action
Pyrvinium is believed to interfere with glucose uptake by pinworms. Pyrvinium is also thought to inhibit mitochondrial respiration complex 1 and suppress the unfolded protein response. It is also believed to supress the Wnt pathway by activating casein kinase 1α. These properties have led to the investigation of pyrvinium's activity against cancers like intestinal polyposis.
INHIBITION OF OXYGEN UPTAKE OF ADULT LITOMOSOIDES IS EFFECTED BY...COMPD CONTAINING AMIDINIUM ION SYSTEM, IN WHICH A QUATERNARY NITROGEN IS SEPARATED FROM A TERTIARY NITROGEN BY RESONATING CARBON CHAIN OF ALTERNATING DOUBLE & SINGLE BONDS. THIS RESP INHIBITION IS ASSOC WITH COMPENSATORY INCR IN AEROBIC GLYCOLYSIS. /PAMOATE/
...ANTHELMINTIC ACTIVITY...IS ASSOC WITH INHIBITION OF RESP IN AEROBES, & INTERFERENCE WITH ABSORPTION OF EXOGENOUS GLUCOSE IN INTESTINAL HELMINTHS. SUCH INTERFERENCE MAY ACCOUNT FOR ANTHELMINTIC EFFECTS OF CYANINES IN TRICHURIASIS & IN OTHER INTESTINAL HELMINTHIASES. /PAMOATE/
MeSH Pharmacological ClassificationAgents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
Absorption, Distribution and Excretion
Pyrvinium is not significantly absorbed from the gastrointestinal tract.
WHEN GIVEN BY ORAL ROUTE, PYRVINIUM PAMOATE IS NOT ABSORBED FROM GI TRACT TO ANY APPRECIABLE EXTENT. /PAMOATE/
Uses & manufacturing
Uses
MEDICATION
Use (kg; approx.) in Germany (2009): >50
Methods of ManufacturingVAN LARE, BROOKER, US PATENT 2,515,912 (1950) /CHLORIDE/ ... ELSLAGER, WORTH, US PATENT, 2,925,417 (1960 TO PARKE, DAVIS). /PAMOATE/
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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