ContaminantDB: Triclabendazole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:42:28 UTC

Update Date

2016-11-09 01:15:41 UTC

Accession Number

CHEM017870

Identification

Common Name

Triclabendazole

Class

Small Molecule

Description

Triclabendazole, manufactured by Novartis pharmaceuticals, is an antihelminthic drug that was approved by the FDA in February 2019 for the treatment of fascioliasis in humans.[FDA label, L5452] Fascioliasis is a parasitic infection often caused by the helminth, _Fasciola hepatica_, which is also known as “the common liver fluke” or “the sheep liver fluke” or by _Fasciola gigantica_, another helminth. These parasites can infect humans following ingestion of larvae in contaminated water or food. Triclabendazole was previously used in the treatment of fascioliasis in livestock, but is now approved for human use. This drug is currently the only FDA-approved drug for individuals with fascioliasis, which affects 2.4 million people worldwide.[A174988,L5452]

Contaminant Sources

STOFF IDENT Compounds
Suspected Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Egaten	Kegg
Fasinex	Kegg
6-Chloro-5-(2,3-dichlorophenoxy)-2-methylthiobenzimidazole	MeSH
Fasicare	MeSH
Flukare	MeSH
Tremacide	MeSH
6-chloro-5-(2,3-Dichlorophenoxy)-2-methylsulphanyl-1H-benzimidazole	Generator
Virbac brand OF triclabendazole	MeSH
Triclabendazole	MeSH
Jurox brand OF triclabendazole	MeSH
Novartis brand OF triclabendazole	MeSH
6-Chloro-5-(2,3-dichlorophenoxy)-2-(methylsulphanyl)-1H-1,3-benzodiazole	Generator

Chemical Formula

C₁₄H₉Cl₃N₂OS

Average Molecular Mass

359.650 g/mol

Monoisotopic Mass

357.950 g/mol

CAS Registry Number

68786-66-3

IUPAC Name

6-chloro-5-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-1,3-benzodiazole

Traditional Name

triclabendazole

SMILES

CSC1=NC2=C(N1)C=C(Cl)C(OC1=CC=CC(Cl)=C1Cl)=C2

InChI Identifier

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)

InChI Key

NQPDXQQQCQDHHW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Benzimidazole
Phenoxy compound
Aryl thioether
Phenol ether
1,2-dichlorobenzene
Alkylarylthioether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
Imidazole
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thioether
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00051 g/L	ALOGPS
logP	5.5	ALOGPS
logP	5.88	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	10.46	ChemAxon
pKa (Strongest Basic)	4.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.86 m³·mol⁻¹	ChemAxon
Polarizability	34.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0230-1944000000-0558457f41742a7d656b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0209000000-8ccc98a85688a2a0d3da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-3fbd7829350b3af433e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-2fb79bfda8b99fe8585c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-94c576ac00ee61093edc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-d7b2f78bf0528ede0828	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-4e1a783d7691ad4bd8e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-0009000000-7f1cc56aaa6613e8fe57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-0009000000-e6fec3ad89cc5d90283b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0005-0936000000-920cfafffb0d59c0929a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-0900000000-7c1864f299cbfbfaf0d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-1900000000-e79f0dad86cbb7cb4483	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-3900000000-79b4e72d8d6c11ae38cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-066r-9000000000-6ef46d3a6eaad77f377a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-066r-9000000000-0143c04bcc788d3bacc1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-066r-9000000000-ec03c59296086f67e89a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0bt9-0019000000-8d8f52e04ea79bdcc664	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00dl-0396000000-bbdca10dffc2975f73b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0390000000-19e15a4b196227bf4cd1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4i-0009000000-1c6e57328ce0ce9875db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-fa35ea94dbfe52339d64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1009000000-f1c2fd4280791a245c9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9412000000-3f049c0a597d3add7509	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-a021a50522b671d8a3a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-1009000000-9e98e0b7ca624d2c1716	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-5595000000-a17da5226a34443eca47	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB12245

HMDB ID

HMDB0259181

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Triclabendazole

Chemspider ID

45565

ChEBI ID

Not Available

PubChem Compound ID

50248

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Triclabendazole (CHEM017870)

Structure for CHEM017870: Triclabendazole