CAS 55268-74-1|Biltricide|praziquantel|2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one|Praziquantel|Droncit|Biltricide|Praziquantel|2-(环己基羰基)-1,2,3,6,7-11b-六氢-...

General Information

Structure

Molecular Formula

C₁₉H₂₄N₂O₂

Molecular Mass

312.40606

Exact Mass

312.18377802

Charge

InChI

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

InChIKey

FSVJFNAIGNNGKK-UHFFFAOYSA-N

Canonic Smiles

O=C(N1CC(=O)N2C(C1)c1ccccc1CC2)C1CCCCC1

Isomeric Smiles

O=C(N1CC2N(CCc3c2cccc3)C(=O)C1)C1CCCCC1

Calculated Properties

Provided by Enamine

CLogP

3.36

H Donor

Polar Surface Area

40.62

Rotatable Bonds

JChem

Polar Surface Area

40.62

H Donor

H Acceptors

Rotatable Bonds

Lipinski's Rule of Five

true

Log P

2.30

LogD (pH = 5.5)

2.30

LogD (pH = 7.4)

2.30

Acid pKa

19.38

Molar Refractivity

88.79

Polarizability

34.49

LOG S

-4.59

Data Source

Names and Identifiers

Synonyms

DroncitBiltricidePraziquantelPraziquantel2-(环己基羰基)-1,2,3,6,7-11b-六氢-4H-吡嗪并(2,1a)异喹啉-4-酮吡喹酮BiliricideCesol2-Cyclohexylcarbonyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino(2,1-a) isoquinolin-4-oneAzinoxEmbay 8440Distocide2-(Cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-onePrazinonPyquiton(+/-)-PraziquantelCysticideWarmnil2-(Cyclohexylcarbonyl)-1,2,3,6,7-11b-hexahydro-4H-pyrazino[2,1-aisoquinolin-4-one2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one

IUPAC Traditional name

praziquantel 2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one

IUPAC name

2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one 2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-pyrazino[2,1-a]isoquinolin-4-one

Brand Name

Biltricide

API Name

Praziquantel

Names and Identifiers

Registration numbers

PubChem SID

248703504650708216096439224278635

MDL Number

Beilstein Number

EC Number

CAS Number

PubChem CID

DrugBank ID

Registration numbers

Properties

Product Information

Pharmacology Properties

Mechanism of Action

Causes in susceptible worms: loss of intracellular calcium; disintegration of the schistosome tegument.; vacuolization; musculature paralysis; massive contractions

Membrane permeabilizer

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01058

Drug Groups

approved

Description

An anthelmintic used in most schistosome and many cestode infestations. [PubChem]

Indication

For the treatment of infections due to all species of schistosoma.

Pharmacology

Praziquantel is an anthelmintic used in most schistosome and many cestode infestations. Praziquantel effects the permeability of the cell membrane resulting in the contraction of schistosomes. The drug further causes vacuolization and disintegration of the schistosome tegument. The effect is more marked on adult worms compared to young worms. An increased calcium influx may play an important role. Secondary effects are inhibition of glucose uptake, lowering of glycogen levels and stimulation of lactate release. The action of praziquantel is limited very specifically to trematodes and cestodes; nematodes (including filariae) are not affected.

Biotransformation

renal

Absorption

Rapidly absorbed (80%)

Half Life

0.8-1.5 hours (in serum)

Protein Binding

80 to 85%

References

• Doenhoff MJ, Cioli D, Utzinger J: Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008 Dec;21(6):659-67. [Pubmed]

• McManus DP, Loukas A: Current status of vaccines for schistosomiasis. Clin Microbiol Rev. 2008 Jan;21(1):225-42. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1691

Research Area: Infection
Biological Activity:
Praziquantel(Biltricide, Droncit) is an anthelmintic effective against flatworms. It increases the permeability of the membranes of schistosome cells towards calcium ions. The drug， thereby induces contraction of the parasites, resulting in paralysis in the contracted state. The dying parasites are dislodged from their site of action in the host organism and may enter systemic circulation or may be destroyed by host immune reaction (phagocytosis). Additional mechanisms including focal disintegrations and disturbances of oviposition (laying of eggs) are seen in other types of sensitive parasites. [1]

MP Biomedicals

02156346

Purity: 98.5%

Sigma Aldrich

P4668

Application
Praziquantel is a potent anthelmintic used in against schistosome and many cestode infestations. It is used to study voltage-gated Ca2+ channels and is a potential small molecule neurogenic1.
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

46648

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

TRC

P702095

Anthelmintic, effective against flatworms.

Molecule Details

References

PubChem Literature

From Data Sources

• Doenhoff MJ, Cioli D, Utzinger J: Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008 Dec;21(6):659-67. Pubmed

• McManus DP, Loukas A: Current status of vaccines for schistosomiasis. Clin Microbiol Rev. 2008 Jan;21(1):225-42. Pubmed

• http://en.wikipedia.org/wiki/Praziquantel

• Wang, W., et al.: Parasitol., 137, 1905 (2010)

• Kuhn, I., et al.: Bioorg. Med. Chem., 18, 7900 (2010)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

praziquantel 2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one

IUPAC name

2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one 2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-pyrazino[2,1-a]isoquinolin-4-one

Brand Name

Biltricide

API Name

Praziquantel

Registration numbers

PubChem SID

248703504650708216096439224278635

MDL Number

Beilstein Number

EC Number

CAS Number

PubChem CID

DrugBank ID

Properties

Product Information

Pharmacology Properties

Mechanism of Action

Causes in susceptible worms: loss of intracellular calcium; disintegration of the schistosome tegument.; vacuolization; musculature paralysis; massive contractions

Membrane permeabilizer

Molecule Details

DrugBank

DB01058

Drug Groups

approved

Description

An anthelmintic used in most schistosome and many cestode infestations. [PubChem]

Indication

For the treatment of infections due to all species of schistosoma.

Pharmacology

Biotransformation

renal

Absorption

Rapidly absorbed (80%)

Half Life

0.8-1.5 hours (in serum)

Protein Binding

80 to 85%

References

• Doenhoff MJ, Cioli D, Utzinger J: Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008 Dec;21(6):659-67. [Pubmed]

• McManus DP, Loukas A: Current status of vaccines for schistosomiasis. Clin Microbiol Rev. 2008 Jan;21(1):225-42. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

S1691

Purity: 98.5%

P4668

46648

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

TRC

P702095

Anthelmintic, effective against flatworms.

References

PubChem Literature

From Data Sources

• Doenhoff MJ, Cioli D, Utzinger J: Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008 Dec;21(6):659-67. Pubmed

• McManus DP, Loukas A: Current status of vaccines for schistosomiasis. Clin Microbiol Rev. 2008 Jan;21(1):225-42. Pubmed

• http://en.wikipedia.org/wiki/Praziquantel

• Wang, W., et al.: Parasitol., 137, 1905 (2010)

• Kuhn, I., et al.: Bioorg. Med. Chem., 18, 7900 (2010)

Bioactivity

PubChem BioAssay

Molecule

ID:929