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Also known as: 68786-66-3, Fasinex, Egaten, 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1h-benzo[d]imidazole, Triclabendazol, Triclabendazolum
Molecular Formula
C14H9Cl3N2OS
Molecular Weight
359.7  g/mol
InChI Key
NQPDXQQQCQDHHW-UHFFFAOYSA-N
FDA UNII
4784C8E03O

Triclabendazole
Benzimidazole antiplatyhelmintic agent that is used for the treatment of FASCIOLIASIS and PARAGONIMIASIS.
Triclabendazole is an Anthelmintic. The mechanism of action of triclabendazole is as a Cytochrome P450 2C19 Inhibitor, and Cytochrome P450 1A2 Inhibitor, and Cytochrome P450 2A6 Inhibitor, and Cytochrome P450 2B6 Inhibitor, and Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C9 Inhibitor, and Cytochrome P450 2D6 Inhibitor, and Cytochrome P450 3A Inhibitor.
1 2D Structure

Triclabendazole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-chloro-5-(2,3-dichlorophenoxy)-2-methylsulfanyl-1H-benzimidazole
2.1.2 InChI
InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19)
2.1.3 InChI Key
NQPDXQQQCQDHHW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CSC1=NC2=CC(=C(C=C2N1)Cl)OC3=C(C(=CC=C3)Cl)Cl
2.2 Other Identifiers
2.2.1 UNII
4784C8E03O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6-chloro-5-(2,3-dichlorophenoxy)-2-methylthiobenzimidazole

2. Egaten

3. Fasicare

4. Fasinex

5. Flukare

6. Tremacide

2.3.2 Depositor-Supplied Synonyms

1. 68786-66-3

2. Fasinex

3. Egaten

4. 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1h-benzo[d]imidazole

5. Triclabendazol

6. Triclabendazolum

7. 5-chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1h-benzimidazole

8. Nvp-ega230

9. Ega230b

10. 6-chloro-5-(2,3-dichlorophenoxy)-2-methylsulfanyl-1h-benzimidazole

11. Nsc-759250

12. Cpd000466357

13. Mls001424101

14. Chembl1086440

15. 1h-benzimidazole, 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-

16. Cga89317

17. 4784c8e03o

18. Ncgc00164610-01

19. Smr000466357

20. 5-chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)benzimidazole

21. 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1h-benzimidazole

22. 6-[2,3-bis(chloranyl)phenoxy]-5-chloranyl-2-methylsulfanyl-1h-benzimidazole

23. 5-chloro-6-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1h-1,3-benzodiazole

24. Triclabendazol [inn-spanish]

25. Triclabendazolum [inn-latin]

26. Ccris 8988

27. Cga 89317

28. 5-chloro-6-(2,3-dichlorophenoxy)-2-methylsulfanyl-1h-benzimidazole

29. Unii-4784c8e03o

30. 6-chloro-5-(2,3-dichlorophenoxy)-2-methylthio-benzimidazole

31. Fasinex (tn)

32. Egaten (tn)

33. 1h-benzimidazole, 5-chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-

34. Dsstox_cid_23952

35. Dsstox_rid_80094

36. Triclabendazole [mi]

37. Dsstox_gsid_43952

38. Oprea1_236106

39. Triclabendazole (usan/inn)

40. Triclabendazole [inn]

41. Cid_50248

42. Mls000759473

43. Mls000876812

44. Schembl165712

45. Triclabendazole [usan]

46. Triclabendazole [mart.]

47. Dtxsid7043952

48. Triclabendazole [who-dd]

49. Bdbm58491

50. Chebi:94759

51. Triclabendazole [usan:inn:ban]

52. Hms2051e16

53. Hms2232d14

54. Hms3370h02

55. Hms3393e16

56. Hms3652m16

57. Hms3715p16

58. Hms3744i09

59. Kuc103451n

60. Pharmakon1600-01505786

61. Hy-b0621

62. Zinc1444556

63. Tox21_112231

64. Cga-89317

65. Mfcd00864519

66. Nsc759250

67. S4114

68. Stk332284

69. Triclabendazole [orange Book]

70. Akos005439340

71. Akos015950804

72. Ac-7627

73. At10531

74. Ccg-100881

75. Ccg-268150

76. Db12245

77. Ks-5329

78. Nc00131

79. Nsc 759250

80. Sb17173

81. Ncgc00164610-02

82. Sbi-0207022.p001

83. Triclabendazole 100 Microg/ml In Methanol

84. Cas-68786-66-3

85. Ft-0602564

86. Sw197511-2

87. T2826

88. Triclabendazole 100 Microg/ml In Acetonitrile

89. D07364

90. Ab00639964-10

91. Ab00639964_12

92. Ab00639964_13

93. 786t663

94. A836250

95. Q419739

96. Sr-01000759363

97. Sr-01000759363-4

98. Triclabendazole, Vetranal(tm), Analytical Standard

99. Brd-k81916719-001-05-5

100. 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)benzimidazole

101. Triclabendazole, Europepharmacopoeia (ep) Reference Standard

102. 5-chloro-6-(2',3'-dichlorophenoxy)-2-(methylthio)benzimidazole

103. 5-chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1h-benzo[d]imidazole

104. 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1h-1,3-benzodiazole

105. 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1h-benzimidazole

106. 5-[2,3-bis(chloranyl)phenoxy]-6-chloranyl-2-methylsulfanyl-1h-benzimidazole

107. 6-chloro-5-(2,3-dichlorophenoxy)-2-methylsulfanyl-1h-benzimidazole;triclabendazole

108. Triclabendazole For System Suitability, Europepharmacopoeia (ep) Reference Standard

109. Ja9

2.4 Create Date
2005-07-09
3 Chemical and Physical Properties
Molecular Weight 359.7 g/mol
Molecular Formula C14H9Cl3N2OS
XLogP35.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass357.950117 g/mol
Monoisotopic Mass357.950117 g/mol
Topological Polar Surface Area63.2 Ų
Heavy Atom Count21
Formal Charge0
Complexity365
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

This drug is indicated for the treatment of fascioliasis in patients aged 6 years old and above.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Triclabendazole and its metabolites are active against both the immature and mature worms of _Fasciola hepatica_ and _Fasciola gigantica_ helminths. **Effect on QT interval** This drug may prolong the cardiac QT interval. Monitor ECG in patients with a history of QT prolongation or who are taking medications known to prolong the QT interval.


5.2 MeSH Pharmacological Classification

Antiplatyhelmintic Agents

Agents used to treat cestode, trematode, or other flatworm infestations in man or animals. (See all compounds classified as Antiplatyhelmintic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TRICLABENDAZOLE
5.3.2 FDA UNII
4784C8E03O
5.3.3 Pharmacological Classes
Anthelmintics [CS]; Cytochrome P450 1A2 Inhibitors [MoA]; Cytochrome P450 2A6 Inhibitors [MoA]; Cytochrome P450 2B6 Inhibitors [MoA]; Cytochrome P450 2C19 Inhibitors [MoA]; Cytochrome P450 2C8 Inhibitors [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]; Cytochrome P450 2D6 Inhibitors [MoA]; Cytochrome P450 3A Inhibitors [MoA]; Anthelmintic [EPC]
5.4 ATC Code

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02B - Antitrematodals

P02BX - Other antitrematodal agents

P02BX04 - Triclabendazole


5.5 Absorption, Distribution and Excretion

Absorption

After a single oral dose of 10 mg/kg triclabendazole with a 560-kcal meal to patients diagnosed with fascioliasis, mean peak plasma concentrations (Cmax) for triclabendazole, the sulfoxide, and sulfone metabolites were 1.16, 38.6, and 2.29 mol/L, respectively. The area under the curve (AUC) for triclabendazole, the sulfoxide and sulfone metabolites were 5.72, 386, and 30.5 molh/L, respectively. After the oral administration of a single dose of triclabendazole at 10 mg/kg with a 560 calorie meal to patients with fascioliasis, the median Tmax for the parent compound as well as the active sulfoxide metabolite was 3 to 4 hours. **Effect of Food** Cmax and AUC of triclabendazole and sulfoxide metabolite increased about 2-3 times when triclabendazole was administered as a single dose at 10 mg/kg with a meal containing approximately 560 calories. Additionally, the sulfoxide metabolite Tmax increased from 2 hours in fasting subjects to 4 hours in fed subjects.


Route of Elimination

No data regarding excretion is available in humans. In animals, triclabendazole is primarily excreted by the biliary tract in the feces (90%), together with the sulfoxide and sulfone metabolite. Less than 10% of an oral dose is found excreted in the urine.


Volume of Distribution

The apparent volume of distribution (Vd) of the sulfoxide metabolite in fed patients is about 1 L/kg.


5.6 Metabolism/Metabolites

Based on in vitro studies, triclabendazole is mainly metabolized by CYP1A2 enzyme (approximately 64%) into its active _sulfoxide_ metabolite and to a lesser extent by CYP2C9, CYP2C19, CYP2D6, CYP3A, and FMO (flavin containing monooxygenase). This sulfoxide metabolite is further metabolized mainly by CYP2C9 to the active sulfone metabolite, and to a smaller extent by CYP1A1, CYP1A2, CYP1B1, CYP2C19, CYP2D6, and CYP3A4, _in vitro_.


5.7 Biological Half-Life

The plasma elimination half-life (t1/2) of triclabendazole, the sulfoxide and sulfone metabolites in human is about 8, 14, and 11 hours, respectively.


5.8 Mechanism of Action

Triclabendazole is an anthelmintic agent against _Fasciola_ species. The mechanism of action against Fasciola species is not fully understood at this time. In vitro studies and animal studies suggest that triclabendazole and its active metabolites (_sulfoxide_ and _sulfone_) are absorbed by the outer body covering of the immature and mature worms, causing a reduction in the resting membrane potential, the inhibition of tubulin function as well as protein and enzyme synthesis necessary for survival. These metabolic disturbances lead to an inhibition of motility, disruption of the worm outer surface, in addition to the inhibition of spermatogenesis and egg/embryonic cells. **A note on resistance** In vitro studies, in vivo studies, as well as case reports suggest a possibility for the development of resistance to triclabendazole. The mechanism of resistance may be multifactorial and include changes in drug uptake/efflux mechanisms, target molecules, and changes in drug metabolism. The clinical significance of triclabendazole resistance in humans is not yet elucidated.


API Reference Price

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05-Jan-2021
26-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
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Average Price
(USD/KGS)
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