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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.


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Looking for 68786-66-3 / Triclabendazole API manufacturers, exporters & distributors?

Triclabendazole manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Triclabendazole API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Triclabendazole manufacturer or Triclabendazole supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Triclabendazole manufacturer or Triclabendazole supplier.

PharmaCompass also assists you with knowing the Triclabendazole API Price utilized in the formulation of products. Triclabendazole API Price is not always fixed or binding as the Triclabendazole Price is obtained through a variety of data sources. The Triclabendazole Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Triclabendazole

Synonyms

68786-66-3, Fasinex, Egaten, 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1h-benzo[d]imidazole, Triclabendazol, Triclabendazolum

Cas Number

68786-66-3

Unique Ingredient Identifier (UNII)

4784C8E03O

About Triclabendazole

Benzimidazole antiplatyhelmintic agent that is used for the treatment of FASCIOLIASIS and PARAGONIMIASIS.

Triclabendazole Manufacturers

A Triclabendazole manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Triclabendazole, including repackagers and relabelers. The FDA regulates Triclabendazole manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Triclabendazole API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Triclabendazole manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Triclabendazole Suppliers

A Triclabendazole supplier is an individual or a company that provides Triclabendazole active pharmaceutical ingredient (API) or Triclabendazole finished formulations upon request. The Triclabendazole suppliers may include Triclabendazole API manufacturers, exporters, distributors and traders.

click here to find a list of Triclabendazole suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Triclabendazole USDMF

A Triclabendazole DMF (Drug Master File) is a document detailing the whole manufacturing process of Triclabendazole active pharmaceutical ingredient (API) in detail. Different forms of Triclabendazole DMFs exist exist since differing nations have different regulations, such as Triclabendazole USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Triclabendazole DMF submitted to regulatory agencies in the US is known as a USDMF. Triclabendazole USDMF includes data on Triclabendazole's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Triclabendazole USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Triclabendazole suppliers with USDMF on PharmaCompass.

Triclabendazole CEP

A Triclabendazole CEP of the European Pharmacopoeia monograph is often referred to as a Triclabendazole Certificate of Suitability (COS). The purpose of a Triclabendazole CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Triclabendazole EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Triclabendazole to their clients by showing that a Triclabendazole CEP has been issued for it. The manufacturer submits a Triclabendazole CEP (COS) as part of the market authorization procedure, and it takes on the role of a Triclabendazole CEP holder for the record. Additionally, the data presented in the Triclabendazole CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Triclabendazole DMF.

A Triclabendazole CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Triclabendazole CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Triclabendazole suppliers with CEP (COS) on PharmaCompass.

Triclabendazole WC

A Triclabendazole written confirmation (Triclabendazole WC) is an official document issued by a regulatory agency to a Triclabendazole manufacturer, verifying that the manufacturing facility of a Triclabendazole active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Triclabendazole APIs or Triclabendazole finished pharmaceutical products to another nation, regulatory agencies frequently require a Triclabendazole WC (written confirmation) as part of the regulatory process.

click here to find a list of Triclabendazole suppliers with Written Confirmation (WC) on PharmaCompass.

Triclabendazole NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Triclabendazole as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Triclabendazole API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Triclabendazole as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Triclabendazole and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Triclabendazole NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Triclabendazole suppliers with NDC on PharmaCompass.

Triclabendazole GMP

Triclabendazole Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Triclabendazole GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Triclabendazole GMP manufacturer or Triclabendazole GMP API supplier for your needs.

Triclabendazole CoA

A Triclabendazole CoA (Certificate of Analysis) is a formal document that attests to Triclabendazole's compliance with Triclabendazole specifications and serves as a tool for batch-level quality control.

Triclabendazole CoA mostly includes findings from lab analyses of a specific batch. For each Triclabendazole CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Triclabendazole may be tested according to a variety of international standards, such as European Pharmacopoeia (Triclabendazole EP), Triclabendazole JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Triclabendazole USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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