Pyrantel

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Pyrantel
Accession Number
DB11156
Type
Small Molecule
Groups
Approved, Vet approved
Description

Pyrantel is an anthelmintic agent for the oral treatment of various parasitic worm infections including ascariasis, hookworm infections, enterobiasis (pinworm infection), trichostrongyliasis, and trichinellosis. It resembles the properties of both competitive and depolarizing neuromuscular blocking agents, which explains the paralytic effect of the drug on parasites. Pyrantel is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Pyrantel pamoate81BK194Z5M22204-24-6AQXXZDYPVDOQEE-MXDQRGINSA-N
Pyrantel tartrateSC82VF048033401-94-4VWRCYAZJKNPEQR-NIEARKAZSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jaa Pyral 35 Tablet 35mgTablet35 mgOralJaapharm Canada Inc.1989-12-31Not applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Combantrin Oral Suspension 50mg/mlSuspension50 mgOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1973-12-31Not applicableCanada
Combantrin Tab 125mgTablet125 mgOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1973-12-31Not applicableCanada
CVS Pinworm TreatmentSuspension144 mg/mLOralCVS Health2016-12-15Not applicableUs
Jaa Pyral 125 Tablet 125mgTablet125 mgOralJaapharm Canada Inc.1998-11-27Not applicableCanada
Jaa Pyral P Oral Paste - 125mg/gPaste125 mgOralJaapharm Canada Inc.1995-12-31Not applicableCanada
Jaa Pyral S Suspension 50mg/76Suspension50 mgOralJaapharm Canada Inc.1995-12-31Not applicableCanada
Jamp-pyrantel PamoateTablet125 mgOralJamp Pharma Corporation2013-12-13Not applicableCanada
Jamp-pyrantel Pamoate SuspensionSuspension50 mgOralJamp Pharma Corporation2014-03-25Not applicableCanada
ParasitexxSuspension144 mg/mLOralDannso corp./d.b.a. Essential Products2017-05-01Not applicableUs
ParasitolSuspension144 mg/mLOralMenper Distributors2013-01-01Not applicableUs
Categories
UNII
4QIH0N49E7
CAS number
Not Available
Weight
Average: 206.31
Monoisotopic: 206.087769633
Chemical Formula
C11H14N2S
InChI Key
YSAUAVHXTIETRK-AATRIKPKSA-N
InChI
InChI=1S/C11H14N2S/c1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10/h2,4-6,9H,3,7-8H2,1H3/b6-5+
IUPAC Name
1-methyl-2-[(E)-2-(thiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine
SMILES
[H]\C(=C(\[H])C1=NCCCN1C)C1=CC=CS1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UG-protein coupled receptor 35Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinPyrantel may increase the arrhythmogenic activities of Acetyldigitoxin.Approved
AcetyldigoxinPyrantel may increase the arrhythmogenic activities of Acetyldigoxin.Experimental
AclarubicinAclarubicin may increase the respiratory depressant activities of Pyrantel.Investigational
AldoxorubicinAldoxorubicin may increase the respiratory depressant activities of Pyrantel.Investigational
AmikacinAmikacin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational, Vet Approved
AmodiaquineThe serum concentration of Pyrantel can be decreased when it is combined with Amodiaquine.Approved, Investigational
AmrubicinAmrubicin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational
AnnamycinAnnamycin may increase the respiratory depressant activities of Pyrantel.Investigational
ApramycinApramycin may increase the respiratory depressant activities of Pyrantel.Experimental, Vet Approved
ArbekacinArbekacin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational
BekanamycinBekanamycin may increase the respiratory depressant activities of Pyrantel.Experimental
Botulinum Toxin Type ABotulinum Toxin Type A may increase the neuromuscular blocking activities of Pyrantel.Approved, Investigational
Botulinum Toxin Type BPyrantel may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved, Investigational
BumetanideBumetanide may decrease the neuromuscular blocking activities of Pyrantel.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Pyrantel.Approved
ChloroquineThe serum concentration of Pyrantel can be decreased when it is combined with Chloroquine.Approved, Investigational, Vet Approved
ChlortetracyclineChlortetracycline may increase the neuromuscular blocking activities of Pyrantel.Approved, Investigational, Vet Approved
ClindamycinClindamycin may increase the neuromuscular blocking activities of Pyrantel.Approved, Vet Approved
ColistimethateColistimethate may increase the neuromuscular blocking activities of Pyrantel.Approved, Vet Approved
CyclosporineCyclosporine may increase the neuromuscular blocking activities of Pyrantel.Approved, Investigational, Vet Approved
CymarinPyrantel may increase the arrhythmogenic activities of Cymarin.Experimental
DaunorubicinDaunorubicin may increase the respiratory depressant activities of Pyrantel.Approved
DemeclocyclineDemeclocycline may increase the neuromuscular blocking activities of Pyrantel.Approved
DeslanosidePyrantel may increase the arrhythmogenic activities of Deslanoside.Approved
DibekacinDibekacin may increase the respiratory depressant activities of Pyrantel.Experimental
DigitoxinPyrantel may increase the arrhythmogenic activities of Digitoxin.Approved, Investigational
DigoxinPyrantel may increase the arrhythmogenic activities of Digoxin.Approved
Digoxin Immune Fab (Ovine)Pyrantel may increase the arrhythmogenic activities of Digoxin Immune Fab (Ovine).Approved
DihydrostreptomycinDihydrostreptomycin may increase the respiratory depressant activities of Pyrantel.Investigational, Vet Approved
DoxorubicinDoxorubicin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational
DoxycyclineDoxycycline may increase the neuromuscular blocking activities of Pyrantel.Approved, Investigational, Vet Approved
EpirubicinEpirubicin may increase the respiratory depressant activities of Pyrantel.Approved
Etacrynic acidEtacrynic acid may decrease the neuromuscular blocking activities of Pyrantel.Approved, Investigational
FramycetinFramycetin may increase the respiratory depressant activities of Pyrantel.Approved
FurosemideFurosemide may decrease the neuromuscular blocking activities of Pyrantel.Approved, Vet Approved
GeneticinGeneticin may increase the respiratory depressant activities of Pyrantel.Experimental
GentamicinGentamicin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
GENTAMICIN C1AGENTAMICIN C1A may increase the respiratory depressant activities of Pyrantel.Experimental
GitoformatePyrantel may increase the arrhythmogenic activities of Gitoformate.Experimental
GPX-150GPX-150 may increase the respiratory depressant activities of Pyrantel.Investigational
HydroxychloroquineThe serum concentration of Pyrantel can be decreased when it is combined with Hydroxychloroquine.Approved
Hygromycin BHygromycin B may increase the respiratory depressant activities of Pyrantel.Vet Approved
IdarubicinIdarubicin may increase the respiratory depressant activities of Pyrantel.Approved
IsepamicinIsepamicin may increase the respiratory depressant activities of Pyrantel.Experimental
KanamycinKanamycin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational, Vet Approved
Lanatoside CPyrantel may increase the arrhythmogenic activities of Lanatoside C.Experimental
LincomycinLincomycin may increase the neuromuscular blocking activities of Pyrantel.Approved, Vet Approved
LithiumLithium may increase the neuromuscular blocking activities of Pyrantel.Approved
Magnesium HydroxideMagnesium Hydroxide may increase the neuromuscular blocking activities of Pyrantel.Approved, Investigational
Magnesium oxideMagnesium oxide may increase the neuromuscular blocking activities of Pyrantel.Approved
Magnesium salicylateMagnesium salicylate may increase the neuromuscular blocking activities of Pyrantel.Approved
Magnesium SulfateMagnesium Sulfate may increase the neuromuscular blocking activities of Pyrantel.Approved, Investigational, Vet Approved
MetildigoxinPyrantel may increase the arrhythmogenic activities of Metildigoxin.Experimental
MetrizamideMetrizamide may increase the respiratory depressant activities of Pyrantel.Approved
MicronomicinMicronomicin may increase the respiratory depressant activities of Pyrantel.Experimental
MinocyclineMinocycline may increase the neuromuscular blocking activities of Pyrantel.Approved, Investigational
NeamineNeamine may increase the respiratory depressant activities of Pyrantel.Experimental
NeomycinNeomycin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
NetilmicinNetilmicin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational
OleandrinPyrantel may increase the arrhythmogenic activities of Oleandrin.Experimental, Investigational
OuabainPyrantel may increase the arrhythmogenic activities of Ouabain.Approved
ParomomycinParomomycin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational
PeruvosidePyrantel may increase the arrhythmogenic activities of Peruvoside.Experimental
PirarubicinPirarubicin may increase the respiratory depressant activities of Pyrantel.Investigational
PiretanidePiretanide may decrease the neuromuscular blocking activities of Pyrantel.Experimental
PirlimycinPirlimycin may increase the neuromuscular blocking activities of Pyrantel.Vet Approved
PlazomicinPlazomicin may increase the respiratory depressant activities of Pyrantel.Investigational
PlicamycinPlicamycin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational, Withdrawn
Polymyxin B SulfatePolymyxin B Sulfate may increase the neuromuscular blocking activities of Pyrantel.Approved, Vet Approved
PrimaquineThe serum concentration of Pyrantel can be decreased when it is combined with Primaquine.Approved
ProcainamideProcainamide may increase the neuromuscular blocking activities of Pyrantel.Approved
ProscillaridinPyrantel may increase the arrhythmogenic activities of Proscillaridin.Experimental
PuromycinPuromycin may increase the respiratory depressant activities of Pyrantel.Experimental
QuinidineQuinidine may increase the neuromuscular blocking activities of Pyrantel.Approved, Investigational
QuinineQuinine may increase the neuromuscular blocking activities of Pyrantel.Approved
RibostamycinRibostamycin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational
SabarubicinSabarubicin may increase the respiratory depressant activities of Pyrantel.Investigational
SisomicinSisomicin may increase the respiratory depressant activities of Pyrantel.Investigational
SP1049CSP1049C may increase the respiratory depressant activities of Pyrantel.Investigational
SpectinomycinSpectinomycin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational, Vet Approved
StreptomycinStreptomycin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
StreptozocinStreptozocin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational
TobramycinTobramycin may increase the respiratory depressant activities of Pyrantel.Approved, Investigational
TorasemideTorasemide may decrease the neuromuscular blocking activities of Pyrantel.Approved
ValrubicinValrubicin may increase the respiratory depressant activities of Pyrantel.Approved
VancomycinVancomycin may increase the neuromuscular blocking activities of Pyrantel.Approved
Zoptarelin doxorubicinZoptarelin doxorubicin may increase the respiratory depressant activities of Pyrantel.Investigational
ZorubicinZorubicin may increase the respiratory depressant activities of Pyrantel.Experimental
Food Interactions
Not Available

References

General References
  1. Aubry ML, Cowell P, Davey MJ, Shevde S: Aspects of the pharmacology of a new anthelmintic: pyrantel. Br J Pharmacol. 1970 Feb;38(2):332-44. [PubMed:5417856]
  2. Rayes D, De Rosa MJ, Spitzmaul G, Bouzat C: The anthelmintic pyrantel acts as a low efficacious agonist and an open-channel blocker of mammalian acetylcholine receptors. Neuropharmacology. 2001 Aug;41(2):238-45. [PubMed:11489460]
External Links
KEGG Compound
C07409
PubChem Compound
708857
PubChem Substance
347827925
ChemSpider
618121
ChEBI
8654
ChEMBL
CHEMBL1626223
Wikipedia
Pyrantel
ATC Codes
P02CC01 — Pyrantel
AHFS Codes
  • 08:08.00 — Anthelmintics

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentHookworm Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral125 mg
TabletOral35 mg
PasteOral125 mg
Tablet, chewableOral250 mg/1
SuspensionOral144 mg/mL
LiquidOral5 mL/250mL
SuspensionOral5 g/100mL
SuspensionOral50 mg/mL
TabletOral180 mg/1
SuspensionOral50 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.118 mg/mLALOGPS
logP2.69ALOGPS
logP1.96ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)10.71ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.81 m3·mol-1ChemAxon
Polarizability23.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydropyrimidines. These are compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Hydropyrimidines
Alternative Parents
Imidolactams / Thiophenes / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Hydropyrimidine / 1,4,5,6-tetrahydropyrimidine / Imidolactam / Thiophene / Heteroaromatic compound / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Amidine / Carboxylic acid amidine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
carboxamidine, thiophenes, 1,4,5,6-tetrahydropyrimidines (CHEBI:8654)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
G-protein coupled receptor activity
Specific Function
Acts as a receptor for kynurenic acid, an intermediate in the tryptophan metabolic pathway. The activity of this receptor is mediated by G-proteins that elicit calcium mobilization and inositol pho...
Gene Name
GPR35
Uniprot ID
Q9HC97
Uniprot Name
G-protein coupled receptor 35
Molecular Weight
34071.89 Da
References
  1. Zhao P, Sharir H, Kapur A, Cowan A, Geller EB, Adler MW, Seltzman HH, Reggio PH, Heynen-Genel S, Sauer M, Chung TD, Bai Y, Chen W, Caron MG, Barak LS, Abood ME: Targeting of the orphan receptor GPR35 by pamoic acid: a potent activator of extracellular signal-regulated kinase and beta-arrestin2 with antinociceptive activity. Mol Pharmacol. 2010 Oct;78(4):560-8. doi: 10.1124/mol.110.066746. Epub 2010 Jul 22. [PubMed:20826425]

Drug created on December 03, 2015 09:51 / Updated on February 13, 2018 09:53