Pyrantel pamoateProduct ingredient for Pyrantel

Name
Pyrantel pamoate
Drug Entry
Pyrantel

Pyrantel is a pyrimidine-derivative anthelmintic agent for the oral treatment of various parasitic worm infections including ascariasis, hookworm infections, enterobiasis (pinworm infection), trichostrongyliasis, and trichinellosis 17.

Pyrantel was initially described in 1965 by researchers from Pfizer who sought cyclic amidines with suitable pharmacokinetic properties (specifically, duration of action) for use as an anthelmintic drug. Pyrantel is mainly available in formulations for dogs and cats as the embonate salt, containing a 34.7% pyrantel base 14.

Pyrantel is on the World Health Organization's List of Essential Medicines, which are the safest and most effective medicines required in a functioning health system 15, 16.

A depolarizing neuromuscular-blocking agent causing longstanding nicotinic receptor activation, resulting in spastic paralysis of susceptible nematodes (worms). Pyrantel has shown to be effective after a single dose 18.

In humans, it is administered as pyrantel pamoate 3,4,8,12.

Accession Number
DBSALT001530
Structure
Synonyms
Pyrantel embonate / Pyrantel pamoate
External IDs
CP-10,423-16
UNII
81BK194Z5M
CAS Number
22204-24-6
Weight
Average: 594.68
Monoisotopic: 594.182457868
Chemical Formula
C34H30N2O6S
InChI Key
AQXXZDYPVDOQEE-MXDQRGINSA-N
InChI
InChI=1S/C23H16O6.C11H14N2S/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10/h1-10,24-25H,11H2,(H,26,27)(H,28,29);2,4-6,9H,3,7-8H2,1H3/b;6-5+
IUPAC Name
1-methyl-2-[(1E)-2-(thiophen-2-yl)ethenyl]-1,4,5,6-tetrahydropyrimidine; 4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid
SMILES
CN1CCCN=C1\C=C\C1=CC=CS1.OC(=O)C1=CC2=C(C=CC=C2)C(CC2=C(O)C(=CC3=C2C=CC=C3)C(O)=O)=C1O
KEGG Drug
D00486
KEGG Compound
C07389
ChemSpider
4444501
ChEBI
8655
ChEMBL
CHEMBL1599768
Wikipedia
Pyrantel
Predicted Properties
PropertyValueSource
logP6.05Chemaxon
pKa (Strongest Acidic)2.38Chemaxon
pKa (Strongest Basic)-6.3Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area115.06 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity107.17 m3·mol-1Chemaxon
Polarizability38.88 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon