Pyrantel pamoate

Pyrantel pamoate

Names
IUPAC name 4-[(3-Carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid; 1-methyl-2-[(E)-2-thiophen-2-ylethenyl]-5,6-dihydro-4H-pyrimidine
Identifiers
CAS Number	22204-24-6
ChEMBL	ChEMBL1599768
ChemSpider	4444501
Jmol interactive 3D	Image
MeSH	Pyrantel+pamoate
PubChem	5281033
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+ Key: AQXXZDYPVDOQEE-MXDQRGINSA-N InChI=1/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+ Key: AQXXZDYPVDOQEE-MXDQRGINBZ
SMILES O=C(O)c2cc1c(cccc1)c(c2O)Cc3c4c(cc(C(=O)O)c3O)cccc4.N\2=C(/C=C/c1sccc1)N(C)CCC/2
Properties
Chemical formula	C34H30N2O6S
Molar mass	594.6768 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pyrantel pamoate (under US Pharmacopoeia) or pyrantel embonate (under European Pharmacopoeia), is used as a deworming agent in the treatment of hookworms (all species) and roundworms (Ascaris lumbricoides, aka ascarids in humans) in domesticated animals such as horses, cattle, sheep, pigs, cats, dogs, and many other species. It is a combination of pyrantel and pamoic acid. Some drug companies pair pyrantel pamoate with praziquantel for tapeworms, and sometimes febantel for whipworms in order to provide more complete treatment for intestinal parasites in one dose.

It is also used for pinworm treatment. There are a number of brands, including "Reese's Pinworm Medicine", "Pin-X", "Pin-Rid","PYRANTRIN" formally called "COMBANTRIN", "Anthel", "Helmintox", "Helmex" and Drontal Cat.

Pyrantel pamoate is also commonly included in monthly administered chewable heartworm preventative tablets for dogs.

Toxicity

Pyrantel pamoate is considered a Pregnancy category C drug for use during pregnancy for humans, but is in category A for canines and felines. Pyrantel is considered safe to use in nursing animals. ^[1]

Drug action

Pyrantel pamoate acts as a depolarizing neuromuscular blocking agent, thereby causing sudden contraction, followed by paralysis, of the helminths. This has the result of causing the worm to "lose its grip" on the intestinal wall and be passed out of the system by natural process. Since Pyrantel is poorly absorbed by the host's intestine, the host is unaffected by the small dosage of medication used. Spastic (tetanic) paralyzing agents, in particular pyrantel pamoate, may induce complete intestinal obstruction in a heavy worm load.^[2] This obstruction is usually in the form of a worm impaction and happens when a very small, but heavily parasitized animal is treated and tries to pass a large number of dislodged worms at once. Worms usually pass in normal stool or with diarrhea, straining, and occasional vomiting.

See also

• Pyrantel

References

1. Plumb, D. C. (2005). Plumb's veterinary drug handbook. Stockholm, Wis: PharmaVet. ISBN 0-8138-0518-X.
2. Salman, A. B. (1997). "Management of intestinal obstruction caused by ascariasis". Journal of Pediatric Surgery 32 (4): 585–587. doi:10.1016/S0022-3468(97)90712-0. PMID 9126759.