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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

O=C(C1CCCCC1)N2C[C@H]3N(CCC4=CC=CC=C34)C(=O)C2

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
400 or 800 mg/kg
Route of Administration: Oral
In Vitro Use Guide
(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
Record UNII
88027IXB7M
Record Status Validated (UNII)
Record Version