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2D Structure
Also known as: 55268-74-1, Biltricide, Droncit, Pyquiton, Cesol, Embay 8440
Molecular Formula
C19H24N2O2
Molecular Weight
312.4  g/mol
InChI Key
FSVJFNAIGNNGKK-UHFFFAOYSA-N
FDA UNII
6490C9U457

An anthelmintic used in most schistosome and many cestode infestations.
Praziquantel is an Anthelmintic.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one
2.1.2 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
2.1.3 InChI Key
FSVJFNAIGNNGKK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CCC(CC1)C(=O)N2CC3C4=CC=CC=C4CCN3C(=O)C2
2.2 Other Identifiers
2.2.1 UNII
6490C9U457
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Biltricide

2. Cesol

3. Cisticid

4. Cysticide

5. Droncit

6. Drontsit

7. Embay 8440

8. Prasiquantel

9. Praziquantel, (+-)-isomer

10. Praziquantel, (r)-isomer

11. Praziquantel, (s)-isomer

12. Pyquiton

13. Traziquantel

2.3.2 Depositor-Supplied Synonyms

1. 55268-74-1

2. Biltricide

3. Droncit

4. Pyquiton

5. Cesol

6. Embay 8440

7. Praziquantelum

8. Azinox

9. 2-(cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one

10. 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4h-pyrazino[2,1-a]isoquinolin-4-one

11. Embay-8440

12. Mls000038419

13. Praziquantel (biltricide)

14. Mfcd00058531

15. 135526-78-2

16. Nsc-757285

17. Smr000037139

18. 2-(cyclohexanecarbonyl)-1,2,3,6,7,11b-hexahydro-4h-pyrazino[2,1-a]isoquinolin-4-one

19. 2-(cyclohexanecarbonyl)-2,3,6,7-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4(11bh)-one

20. 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4h-pyrazino(2,1-a)isoquinolin-4-one

21. 4h-pyrazino(2,1-a)isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-

22. Cysticide

23. Cutter Tape Tabs

24. 2-cyclohexanecarbonyl-1h,2h,3h,4h,6h,7h,11bh-piperazino[2,1-a]isoquinolin-4-one

25. Distocide

26. Prazinon

27. 6490c9u457

28. Dsstox_cid_1182

29. Dsstox_rid_75995

30. Dsstox_gsid_21182

31. Praziquantelum [inn-latin]

32. Cutter

33. 4h-pyrazino[2,1-a]isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-

34. Biltricide (tn)

35. Ccris 4114

36. (+/-)-praziquantel

37. Sr-01000003100

38. Einecs 259-559-6

39. Brn 0761557

40. Bay-8440

41. Praziquantel (jan/usp/inn)

42. Praziquantel,(s)

43. Unii-6490c9u457

44. Ncgc00016877-01

45. Prestwick_402

46. Cas-55268-74-1

47. Praziquantel 100 Microg/ml In Acetonitrile

48. (+-)-praziquantel

49. Praziquantel [usan:usp:inn:ban:jan]

50. Spectrum_001119

51. Opera_id_378

52. Prestwick0_000260

53. Prestwick1_000260

54. Prestwick2_000260

55. Prestwick3_000260

56. Spectrum2_001288

57. Spectrum3_000550

58. Spectrum4_000482

59. Spectrum5_001064

60. Praziquantel [mi]

61. Praziquantel [inn]

62. Praziquantel [jan]

63. Chembl976

64. P 4668

65. Praziquantel [usan]

66. Cid_4891

67. Praziquantel [vandf]

68. Lopac0_000909

69. Oprea1_163497

70. Schembl44153

71. Bspbio_000080

72. Bspbio_002199

73. Kbiogr_000963

74. Kbioss_001599

75. Praziquantel [mart.]

76. 5-24-03-00361 (beilstein Handbook Reference)

77. Mls000028528

78. Mls001201812

79. Mls001304085

80. Mls002548849

81. Mls006011880

82. Divk1c_000130

83. Praziquantel [usp-rs]

84. Praziquantel [who-dd]

85. Praziquantel [who-ip]

86. Spectrum1500494

87. Spbio_001295

88. Spbio_002299

89. Praziquantel-(cyclohexyl-d11)

90. Bpbio1_000088

91. Dtxsid9021182

92. Schembl16019896

93. Bdbm74574

94. Chebi:91583

95. Hms500g12

96. Kbio1_000130

97. Kbio2_001599

98. Kbio2_004167

99. Kbio2_006735

100. Kbio3_001699

101. Praziquantel [green Book]

102. Ninds_000130

103. Glxc-26256

104. Hms1568d22

105. Hms1920j06

106. Hms2090j19

107. Hms2092a09

108. Hms2095d22

109. Hms3259k07

110. Hms3262f20

111. Hms3655o19

112. Hms3712d22

113. Pharmakon1600-01500494

114. Praziquantel [orange Book]

115. Praziquantel For System Suitability

116. Praziquantel [ep Monograph]

117. Praziquantel [usp Impurity]

118. Amy16524

119. Bcp17829

120. Bcp28525

121. Bcp30228

122. Hy-b0244

123. Wzb34336

124. Praziquantel [usp Monograph]

125. Tox21_110660

126. Tox21_201950

127. Tox21_302927

128. Tox21_500909

129. Ccg-39773

130. Nsc757285

131. Praziquantel, Anthelminic, Neurogenic

132. S1691

133. Stk030186

134. Praziquantelum [who-ip Latin]

135. Akos000541869

136. Akos016398525

137. Broadline Component Praziquantel

138. Profender Component Praziquantel

139. Tox21_110660_1

140. Ac-8426

141. Db01058

142. Lp00909

143. Nc00468

144. Nsc 757285

145. Sb49202

146. Sdccgsbi-0050884.p005

147. 2-(cyclohexylcarbonyl)-1,2,3,6,7-11b-hexahydro-4h-pyrazinoe(2,1a)isoquinolin-4-one

148. Idi1_000130

149. Ncgc00015818-04

150. Ncgc00015818-05

151. Ncgc00015818-06

152. Ncgc00015818-07

153. Ncgc00015818-08

154. Ncgc00015818-11

155. Ncgc00015818-12

156. Ncgc00015818-14

157. Ncgc00015818-15

158. Ncgc00015818-26

159. Ncgc00089733-02

160. Ncgc00089733-03

161. Ncgc00089733-04

162. Ncgc00089733-05

163. Ncgc00256422-01

164. Ncgc00259499-01

165. Ncgc00261594-01

166. As-12459

167. Bp166192

168. Praziquantel Component Of Broadline

169. Praziquantel Component Of Profender

170. Sy052322

171. Sbi-0050884.p004

172. Db-052707

173. Praziquantel (ema Epar: Veterinary)

174. (s)-praziquantel; Praziquantel, (s)-isomer

175. Ab00052075

176. Eu-0100909

177. Ft-0630676

178. P2125

179. Sw196645-3

180. 1h-pyrazino[2,1-a]isoquinolin-4(11bh)-one

181. 2-(cyclohexanecarbonyl)-2,3,6,7-tetrahydro-

182. C07367

183. D00471

184. Ab00052075-13

185. Ab00052075-15

186. Ab00052075_16

187. Ab00052075_17

188. Praziquantel, Vetranal(tm), Analytical Standard

189. 268p741

190. A830562

191. Q424145

192. Praziquantel, Antibiotic For Culture Media Use Only

193. Q-201612

194. Sr-01000003100-3

195. Sr-01000003100-5

196. Sr-01000003100-7

197. Brd-a21858158-001-05-2

198. Brd-a21858158-001-16-9

199. Sr-01000003100-16

200. F0037-0136

201. Z1563145961

202. Praziquantel, European Pharmacopoeia (ep) Reference Standard

203. Praziquantel, United States Pharmacopeia (usp) Reference Standard

204. 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro- 4h-pyrazino[2,1-a]-isoquinolin-4-one

205. 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4h-pyrazino-[2,1- A]isoquinolin-4-one

206. 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one

207. 2-cyclohexylcarbonyl-1,2,3,6,7,11b-hexahydro-4h-pyrazino(2,1-a)isoquinolin-4-one

208. Praziquantel For System Suitability, European Pharmacopoeia (ep) Reference Standard

209. Praziquantel, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 312.4 g/mol
Molecular Formula C19H24N2O2
XLogP32.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass312.183778013 g/mol
Monoisotopic Mass312.183778013 g/mol
Topological Polar Surface Area40.6 Ų
Heavy Atom Count23
Formal Charge0
Complexity472
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameBiltricide
PubMed HealthPraziquantel (By mouth)
Drug ClassesAnthelmintic
Drug LabelBILTRICIDE (praziquantel) is a trematodicide provided in tablet form for the oral treatment of schistosome infections and infections due to liver fluke.BILTRICIDE (praziquantel) is 2-(cyclohexylcarbonyl)-1,2,3,6,7, 11b-hexahydro-4H-pyrazino [2, 1...
Active IngredientPraziquantel
Dosage FormTablet
RouteOral
Strength600mg
Market StatusPrescription
CompanyBayer Hlthcare

2 of 2  
Drug NameBiltricide
PubMed HealthPraziquantel (By mouth)
Drug ClassesAnthelmintic
Drug LabelBILTRICIDE (praziquantel) is a trematodicide provided in tablet form for the oral treatment of schistosome infections and infections due to liver fluke.BILTRICIDE (praziquantel) is 2-(cyclohexylcarbonyl)-1,2,3,6,7, 11b-hexahydro-4H-pyrazino [2, 1...
Active IngredientPraziquantel
Dosage FormTablet
RouteOral
Strength600mg
Market StatusPrescription
CompanyBayer Hlthcare

4.2 Drug Indication

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


FDA Label


5 Pharmacology and Biochemistry
5.1 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.


5.2 MeSH Pharmacological Classification

Anthelmintics

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PRAZIQUANTEL
5.3.2 FDA UNII
6490C9U457
5.3.3 Pharmacological Classes
Anthelmintic [EPC]
5.4 ATC Code

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02B - Antitrematodals

P02BA - Quinoline derivatives and related substances

P02BA01 - Praziquantel


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed (80%)


5.6 Metabolism/Metabolites

renal


5.7 Biological Half-Life

0.8-1.5 hours (in serum)


5.8 Mechanism of Action

Praziquantel works by causing severe spasms and paralysis of the worms' muscles. This paralysis is accompanied - and probably caused - by a rapid Ca 2+ influx inside the schistosome. Morphological alterations are another early effect of praziquantel. These morphological alterations are accompanied by an increased exposure of schistosome antigens at the parasite surface. The worms are then either completely destroyed in the intestine or passed in the stool. An interesting quirk of praziquantel is that it is relatively ineffective against juvenile schistosomes. While initially effective, effectiveness against schistosomes decreases until it reaches a minimum at 3-4 weeks. Effectiveness then increases again until it is once again fully effective at 6-7 weeks. Glutathione S-transferase (GST), an essential detoxification enzyme in parasitic helminths, is a major vaccine target and a drug target against schistosomiasis. Schistosome calcium ion channels are currently the only known target of praziquantel.