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P4668

Sigma-Aldrich

Praziquantel

anthelminic, neurogenic

Synonyme(s) :

2-(Cyclohexylcarbonyl)-1,2,3,6,7-11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one

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About This Item

Formule empirique (notation de Hill):
C19H24N2O2
Numéro CAS:
55268-74-1
Poids moléculaire :
312.41
Numéro Beilstein :
761557
Numéro CE :
259-559-6
Numéro MDL:
MFCD00058531
Code UNSPSC :
51452701
ID de substance PubChem :
24278635
Nomenclature NACRES :
NA.85

Forme

powder or crystals

Spectre d'activité de l'antibiotique

parasites

Mode d’action

cell membrane | interferes

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Mentions de danger

H412

Conseils de prudence

P273 - P501

Classification des risques

Aquatic Chronic 3

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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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
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
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
Malay Patra et al.
Journal of medicinal chemistry, 56(22), 9192-9198 (2013-11-14)
In vitro metabolic behavior was investigated for two chromium tricarbonyl derivatives of the antischistosomal drug praziquantel (PZQ) with the formula (η(6)-PZQ)Cr(CO)3 (1 and 2), by use of human liver microsomes. The metabolic profiles of the derivatives differ significantly. The optically
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