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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H24N2O2
Molecular Weight 312.4061
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAZIQUANTEL, (S)-

SMILES

[H][C@]12CN(CC(=O)N1CCC3=C2C=CC=C3)C(=O)C4CCCCC4

InChI

InChIKey=FSVJFNAIGNNGKK-QGZVFWFLSA-N
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/t17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H24N2O2
Molecular Weight 312.4061
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Praziquantel, (+)- is the dextrorotated (+) isomer of Praziquantel. Praziquantel (PZQ) is the drug of choice against schistosomiasis. Since exposure of schistosomes to the drug is associated with calcium influx and muscular contraction, calcium channels have been suggested as the target. It is a specific pharmacological effect seen exclusively with the active levo-R(-)stereo isomer of the drug. Praziquantel, (+)- apparently contributes little to the therapeutic efficacy of Praziquantel. In vivo, single 400-mg/kg oral doses of Praziquantel, (-)- and Praziquantel, (+)- achieved worm burden reductions of 100 and 19%, respectively. Moreover, worms treated in vivo with Praziquantel, (+)- displayed an only transient hepatic shift and returned to the mesenteric veins within 24 h.

Originator

Curator's Comment: # Bayer AG.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Comparative in vitro and in vivo activity of racemic praziquantel and its levorotated isomer on Schistosoma mansoni.
1989 Mar
Light and scanning electron microscopy studies on the effects of the enantiomers of praziquantel and its main metabolite on Schistosoma mansoni in vitro.
1992
Enantioselective analysis of praziquantel and trans-4-hydroxypraziquantel in human plasma by chiral LC-MS/MS: Application to pharmacokinetics.
2009 Oct 1
Metabolic profiling of praziquantel enantiomers.
2014 Jul 15
Activity of praziquantel enantiomers and main metabolites against Schistosoma mansoni.
2014 Sep
Patents

Patents

Sample Use Guides

400 or 800 mg/kg
Route of Administration: Oral
(S)-Praziquantel showed higher toxicity against L-02 cell line (IC50 =80.4±1.9 μM and 106±2.0 μM, respectively) than (R)-Praziquantel.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:12:01 UTC 2023
Edited
by admin
on Sat Dec 16 09:12:01 UTC 2023
Record UNII
88027IXB7M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRAZIQUANTEL, (S)-
Common Name English
PRAZIQUANTEL, (+)-
Common Name English
(+)-PRAZIQUANTEL
Common Name English
(S)-(+)-PRAZIQUANTEL
Common Name English
4H-PYRAZINO(2,1-A)ISOQUINOLIN-4-ONE, 2-(CYCLOHEXYLCARBONYL)-1,2,3,6,7,11B-HEXAHYDRO-, (11BS)-
Systematic Name English
(S)-PRAZIQUANTEL
Common Name English
Code System Code Type Description
FDA UNII
88027IXB7M
Created by admin on Sat Dec 16 09:12:01 UTC 2023 , Edited by admin on Sat Dec 16 09:12:01 UTC 2023
PRIMARY
CAS
57452-97-8
Created by admin on Sat Dec 16 09:12:01 UTC 2023 , Edited by admin on Sat Dec 16 09:12:01 UTC 2023
PRIMARY
PUBCHEM
1917817
Created by admin on Sat Dec 16 09:12:01 UTC 2023 , Edited by admin on Sat Dec 16 09:12:01 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER