Pyrvinium
Explore a selection of our essential drug information below, or:
Identification
- Summary
Pyrvinium is an anthelmintic agent used for the treatment of pinworm infestations.
- Generic Name
- Pyrvinium
- DrugBank Accession Number
- DB06816
- Background
Pyrvinium is an anthelmintic effective for pinworms. Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate. Pyrvinum's anti-cancer properties are currently under investigation.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 382.53
Monoisotopic: 382.227774334 - Chemical Formula
- C26H28N3
- Synonyms
- Not Available
Pharmacology
- Indication
Pyrvinium was once used in the treatment of pinworm infestations 3.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Enterobius vermicularis infection •••••••••••• •••••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Pyrvinium is an anthelmintic agent which acts to kill pinworms 3.
- Mechanism of action
Pyrvinium is believed to interfere with glucose uptake by pinworms 3.
Pyrvinium is also thought to inhibit mitochondrial respiration complex 1 and suppress the unfolded protein response 1. 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 2.
- Absorption
Pyrvinium is not significantly absorbed from the gastrointestinal tract 4.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Pyrvinium pamoate 310X6S84LW 3546-41-6 OOPDAHSJBRZRPH-UHFFFAOYSA-N - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vanquin Suspension 50mg/5ml Suspension 50 mg / 5 mL Oral Pfizer Canada Inc., Consumer Healthcare Division 1994-12-31 2005-02-17 Canada
Categories
- ATC Codes
- P02CX01 — Pyrvinium
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyrroles
- Sub Class
- Substituted pyrroles
- Direct Parent
- Phenylpyrroles
- Alternative Parents
- Aminoquinolines and derivatives / Dialkylarylamines / Pyridinium derivatives / Benzene and substituted derivatives / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Organic cations
- Substituents
- 1-phenylpyrrole / Amine / Aminoquinoline / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Dialkylarylamine / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- quinolinium ion (CHEBI:8687)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 6B9991FLU3
- CAS number
- 7187-62-4
- InChI Key
- QMHSXPLYMTVAMK-UHFFFAOYSA-N
- InChI
- InChI=1S/C26H28N3/c1-19-17-21(20(2)29(19)24-9-7-6-8-10-24)11-13-23-14-12-22-18-25(27(3)4)15-16-26(22)28(23)5/h6-18H,1-5H3/q+1
- IUPAC Name
- 2-[(E)-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-6-(dimethylamino)-1-methylquinolin-1-ium
- SMILES
- CN(C)C1=CC2=C(C=C1)[N+](C)=C(\C=C\C1=C(C)N(C(C)=C1)C1=CC=CC=C1)C=C2
References
- General References
- Ishii I, Harada Y, Kasahara T: Reprofiling a classical anthelmintic, pyrvinium pamoate, as an anti-cancer drug targeting mitochondrial respiration. Front Oncol. 2012 Oct 2;2:137. doi: 10.3389/fonc.2012.00137. eCollection 2012. [Article]
- Li B, Flaveny CA, Giambelli C, Fei DL, Han L, Hang BI, Bai F, Pei XH, Nose V, Burlingame O, Capobianco AJ, Orton D, Lee E, Robbins DJ: Repurposing the FDA-approved pinworm drug pyrvinium as a novel chemotherapeutic agent for intestinal polyposis. PLoS One. 2014 Jul 8;9(7):e101969. doi: 10.1371/journal.pone.0101969. eCollection 2014. [Article]
- Sheth UK (1975). Mechanisms of Anthelmintic Action. In Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Volume 19 (pp. 152). Birkhäuser Basel. [ISBN:978-3-0348-7090-0]
- HSDB: Pyrvinium [Link]
- External Links
- Human Metabolome Database
- HMDB0240273
- KEGG Compound
- C07412
- PubChem Compound
- 5281035
- PubChem Substance
- 310264894
- ChemSpider
- 21125
- 35163
- ChEBI
- 8687
- ChEMBL
- CHEMBL1201303
- ZINC
- ZINC000003831401
- Wikipedia
- Pyrvinium
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Not Yet Recruiting Treatment Gastric Intestinal Metaplasia / Gastric Precancer 1 somestatus stop reason just information to hide 1 Recruiting Treatment Resectable Pancreatic Ductal Adenocarcinoma (PDAC) / Stage 0 Pancreatic Cancer AJCC v8 / Stage I Pancreatic Cancer AJCC v8 / Stage IA Pancreatic Cancer AJCC v8 / Stage IB Pancreatic Cancer AJCC v8 / Stage II Pancreatic Cancer AJCC v8 / Stage IIA Pancreatic Cancer AJCC v8 / Stage IIB Pancreatic Cancer AJCC v8 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suspension Oral 50 ml Suspension Oral Pill Suspension Oral 50 mg / 5 mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000288 mg/mL ALOGPS logP 2.04 ALOGPS logP 1.41 Chemaxon logS -6.2 ALOGPS pKa (Strongest Basic) 1.48 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.05 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 136.12 m3·mol-1 Chemaxon Polarizability 47.31 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 224.8478663 predictedDarkChem Lite v0.1.0 [M-H]- 226.6672663 predictedDarkChem Lite v0.1.0 [M-H]- 192.22743 predictedDeepCCS 1.0 (2019) [M+H]+ 225.1501663 predictedDarkChem Lite v0.1.0 [M+H]+ 227.4937663 predictedDarkChem Lite v0.1.0 [M+H]+ 194.623 predictedDeepCCS 1.0 (2019) [M+Na]+ 224.6546663 predictedDarkChem Lite v0.1.0 [M+Na]+ 226.6432663 predictedDarkChem Lite v0.1.0 [M+Na]+ 200.53552 predictedDeepCCS 1.0 (2019)
Drug created at September 14, 2010 16:21 / Updated at June 02, 2024 21:56