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.

See full entry for Pyrantel

Accession Number

DBSALT001530

Structure

Similar Structures

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

External Links

KEGG Drug: D00486
KEGG Compound: C07389
ChemSpider: 4444501
ChEBI: 8655
ChEMBL: CHEMBL1599768
Wikipedia: Pyrantel

Predicted Properties

Property	Value	Source
logP	6.05	Chemaxon
pKa (Strongest Acidic)	2.38	Chemaxon
pKa (Strongest Basic)	-6.3	Chemaxon
Physiological Charge	-2	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	115.06 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	107.17 m³·mol^-1	Chemaxon
Polarizability	38.88 Å³	Chemaxon
Number of Rings	6	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Pyrantel pamoateProduct ingredient for Pyrantel

Structure for Pyrantel pamoate (DBSALT001530)