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P7549

Sigma-Aldrich

Pyrantel citrate salt

Synonym(s):

1-Methyl-2-(2-[2-thienyl]ethenyl)-1,4,5,6-tetrahydropyrimidine

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About This Item

Empirical Formula (Hill Notation):
C11H14N2S · C6H8O7
CAS Number:
5685-86-9
Molecular Weight:
398.43
EC Number:
227-154-3
MDL number:
MFCD00079269
UNSPSC Code:
51101500
PubChem Substance ID:
329820311

antibiotic activity spectrum

parasites

mode of action

enzyme | inhibits

SMILES string

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN1CCCN=C1\C=C\c2cccs2

InChI

1S/C11H14N2S.C6H8O7/c1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10;7-3(8)1-6(13,5(11)12)2-4(9)10/h2,4-6,9H,3,7-8H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b6-5+;

InChI key

YJGGCARNRYGSPA-IPZCTEOASA-N

Application

Pyrantel is an antinematodal thiophene. It is commonly used by veterinarians to treat and prevent intestinal parasites in small animals. It has been used to phenotypically characterize Ancylostoma caninum isolates[1] and is used to distinguish cholinergic receptor subtypes in Ascaris muscle[2].

Biochem/physiol Actions

Pyrantel is a nematode muscle cell-associated nicotinic agonist for the acetylcholine (ACh) receptor. Cholinesterase inhibitor.
Pyrantel is a nematode muscle cell-associated nicotinic agonist for the acetylcholine (ACh) receptor. This is a cholinesterase inhibitor. It causes muscle paralysis in parasitic worms due to prolonged activation of the excitatory nicotinic acetylcholine (nACh) receptors[3].

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Storage class (TRGS 510): Non Combustible Solids

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
089F0470

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H Bjørn et al.
International journal for parasitology, 26(12), 1375-1380 (1996-12-01)
The pharmacokinetic disposition of pyrantel after intravenous (i.v.) and oral (p.o.) administration as the citrate and p.o. administration as the pamoate salt was determined in pigs. Following i.v. administration pyrantel was quickly cleared from the bloodstream, exhibiting a terminal half-life
J Aceves et al.
British journal of pharmacology, 38(3), 602-607 (1970-05-01)
1. Tetramisole (100 mug/ml) paralysed live Ascaris in 3 min.2. Tetramisole (10 mug/ml) caused a sustained contraction of the isolated somatic muscles of the worm. This contraction was not blocked by curare nor by piperazine.3. Tetramisole reduced the resting potential
Alan P Robertson et al.
The Journal of pharmacology and experimental therapeutics, 302(3), 853-860 (2002-08-17)
Paraherquamide is a novel natural anthelmintic product with a mode of action that is incompletely characterized. Nicotine and cholinergic-anthelmintic agonists of different chemical classes were used to produce contraction in Ascaris muscle strips. Paraherquamide and a semisynthetic derivative, 2-deoxy-paraherquamide, antagonized
S E Pratt et al.
American journal of veterinary research, 42(5), 871-872 (1981-05-01)
The relative efficacies of pyrantel tartrate and of pyrantel citrate against Oesophagostomum sp in swine were evaluated in a controlled-critical study and the efficacy of pyrantel citrate in a field trial. In the controlled-critical study, pigs naturally infected with Oesophagostomum
Sarah A Habibi et al.
Molecular and biochemical parasitology, 237, 111276-111276 (2020-04-09)
The ACC-1 family of cys-loop receptors are ligand-gated chloride channels sensitive to acetylcholine (ACh), and are only present in invertebrates. Studies of this family of inhibitory receptors has provided insight into how they bind and respond to ACh in a
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