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P4668

Sigma-Aldrich

Praziquantel

anthelminic, neurogenic

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Synonym(s):
2-(Cyclohexylcarbonyl)-1,2,3,6,7-11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Empirical Formula (Hill Notation):
C19H24N2O2
CAS Number:
Molecular Weight:
312.41
Beilstein/REAXYS Number:
761557
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

form

powder or crystals

antibiotic activity spectrum

parasites

mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

O=C1CN(CC2N1CCc3ccccc23)C(=O)C4CCCCC4

InChI

1S/C19H24N2O2/c22-18-13-20(19(23)15-7-2-1-3-8-15)12-17-16-9-5-4-6-14(16)10-11-21(17)18/h4-6,9,15,17H,1-3,7-8,10-13H2

InChI key

FSVJFNAIGNNGKK-UHFFFAOYSA-N

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Application

Praziquantel is a potent anthelmintic used against schistosome and many cestode infestations. It is used to study voltage-gated Ca2+ channels and is a potential small molecule neurogenic.

Biochem/physiol Actions

Praziquantel increases the permeability of the tegmentum to Ca2+ which results in the contraction of schistosomes and death. Praziquantel causes vacuolization and disintegration of the schistosome tegument. It is more effective on adult worms than young worms. It inhibits glucose uptake, which lowers glycogen levels and stimulates lactate release. Praziquantel is a potent anthelmintic against parasitic flatworms (flukes and tapeworms). Recent studies have indicated that praziquantel binds to a varient of the β-subunit of the voltage gated Ca2+ channel and to actin, which is a component of some Ca2+ channels.

Other Notes

1g,5g,25g
Keep container tightly closed in a dry and well-ventilated place.

hcodes

pcodes

Hazard Classifications

Aquatic Chronic 3

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

ppe

Eyeshields, Gloves, type N95 (US)


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Dan Zhang et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(44), 15983-15995 (2011-11-04)
There is intense interest in developing methods to regulate proliferation and differentiation of stem cells into neuronal fates for the purposes of regenerative medicine. One way to do this is through in vivo pharmacological engineering using small molecules. However, a
Yuxiang Dong et al.
Bioorganic & medicinal chemistry letters, 20(8), 2481-2484 (2010-03-23)
Six amide and four urea derivatives of praziquantel were synthesized and tested for antischistosomal activity against juvenile and adults stages of Schistosoma mansoni in infected mice. Only one of these had significant activity against adult worms, but, unlike praziquantel, six
R J Martin et al.
Parasitology, 114 Suppl, S111-S124 (1997-01-01)
This paper reviews sites of action of anthelmintic drugs including: (1) levamisole and pyrantel, which act as agonists at nicotinic acetylcholine receptors of nematodes; (2) the avermectins, which potentiate or gate the opening of glutamategated chloride channels found only in
Fiona Ronketti et al.
Bioorganic & medicinal chemistry letters, 17(15), 4154-4157 (2007-06-09)
Several analogues of the potent anthelmintic praziquantel were prepared with variation in the aromatic ring. The biological activity of these analogues was evaluated and compared against known analogues. Amination of the ring was tolerated while other variations were not. These
Jean T Coulibaly et al.
PLoS neglected tropical diseases, 7(3), e2109-e2109 (2013-04-05)
The Kato-Katz technique is widely used for the diagnosis of Schistosoma mansoni, but shows low sensitivity in light-intensity infections. We assessed the accuracy of a commercially available point-of-care circulating cathodic antigen (POC-CCA) cassette test for the diagnosis of S. mansoni

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