Triclabendazole

Modify Date: 2024-01-02 12:14:53

Triclabendazole structure	Common Name	Triclabendazole
	CAS Number	68786-66-3	Molecular Weight	359.658
	Density	1.6±0.1 g/cm3	Boiling Point	495.9±55.0 °C at 760 mmHg
	Molecular Formula	C₁₄H₉Cl₃N₂OS	Melting Point	175-176°C
	MSDS	Chinese USA	Flash Point	253.7±31.5 °C

Use of Triclabendazole

Triclabendazole(CGA89317) is a benzimidazole, it binds to tubulin impairing intracellular transport mechanisms and interferes with protein synthesis.Target: Microtubule/TubulinTriclabendazole treatment produces percentage decreases of the fluke egg output by 15.3%, 4.3% and 36.6%, respectively, in sheep, dairy cows and heifers, these results indicate the presence of TCBZ-resistant Fasciola hepatica in sheep and cattle on this farm [1]. Triclabendazole sulphoxide (50 mg/mL) results in extensive damage to the tegument of triclabendazole-susceptible F. hepatica, whereas triclabendazole-resistant flukes shows only localized and relatively minor disruption of the tegument covering the spines [2].Triclabendazole is metabolized into a number of compounds, depending on the route of administration, plasma levels peak at 18-24 hours (Triclabendazole sulphoxide) and 36-48 hours (Triclabendazole sulphone), neither Triclabendazole nor any toher metabolites can be detected in plasma. Triclabendazole sulphoxide blocks the transport of secretory bodies from the cell body to the tegumental surface, the block occurs at the site of their formation by the Golgi complex in the cell body, in their movement through the cytoplasmic connections to the syncytium, and in their movement from the base to the apex of the syncytium. Triclabendazole binds to the colchicine binding site on the β-tubulin molecule and this has been used at the basis for evaluating the relative acitvity of Triclabendazole [3].

Name	Triclabendazole
Synonym	More Synonyms

Description	Triclabendazole(CGA89317) is a benzimidazole, it binds to tubulin impairing intracellular transport mechanisms and interferes with protein synthesis.Target: Microtubule/TubulinTriclabendazole treatment produces percentage decreases of the fluke egg output by 15.3%, 4.3% and 36.6%, respectively, in sheep, dairy cows and heifers, these results indicate the presence of TCBZ-resistant Fasciola hepatica in sheep and cattle on this farm [1]. Triclabendazole sulphoxide (50 mg/mL) results in extensive damage to the tegument of triclabendazole-susceptible F. hepatica, whereas triclabendazole-resistant flukes shows only localized and relatively minor disruption of the tegument covering the spines [2].Triclabendazole is metabolized into a number of compounds, depending on the route of administration, plasma levels peak at 18-24 hours (Triclabendazole sulphoxide) and 36-48 hours (Triclabendazole sulphone), neither Triclabendazole nor any toher metabolites can be detected in plasma. Triclabendazole sulphoxide blocks the transport of secretory bodies from the cell body to the tegumental surface, the block occurs at the site of their formation by the Golgi complex in the cell body, in their movement through the cytoplasmic connections to the syncytium, and in their movement from the base to the apex of the syncytium. Triclabendazole binds to the colchicine binding site on the β-tubulin molecule and this has been used at the basis for evaluating the relative acitvity of Triclabendazole [3].
Related Catalog	Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Research Areas >> Infection
References	[1]. Moll, L., et al., Resistance of Fasciola hepatica against triclabendazole in cattle and sheep in The netherlands. Vet Parasitol, 2000. 91(1-2): p. 153-8. [2]. Robinson, M.W., et al., Triclabendazole-resistant Fasciola hepatica: beta-tubulin and response to in vitro treatment with triclabendazole. Parasitology, 2002. 124(Pt 3): p. 325-38. [3]. Fairweather, I., Triclabendazole: new skills to unravel an old(ish) enigma. J Helminthol, 2005. 79(3): p. 227-34.

Description

Related Catalog

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

Research Areas >> Infection

References

[1]. Moll, L., et al., Resistance of Fasciola hepatica against triclabendazole in cattle and sheep in The netherlands. Vet Parasitol, 2000. 91(1-2): p. 153-8.

[2]. Robinson, M.W., et al., Triclabendazole-resistant Fasciola hepatica: beta-tubulin and response to in vitro treatment with triclabendazole. Parasitology, 2002. 124(Pt 3): p. 325-38.

[3]. Fairweather, I., Triclabendazole: new skills to unravel an old(ish) enigma. J Helminthol, 2005. 79(3): p. 227-34.

Density	1.6±0.1 g/cm3
Boiling Point	495.9±55.0 °C at 760 mmHg
Melting Point	175-176°C
Molecular Formula	C₁₄H₉Cl₃N₂OS
Molecular Weight	359.658
Flash Point	253.7±31.5 °C
Exact Mass	357.950104
PSA	63.21000
LogP	5.97
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.724
Stability	Stability

Triclabendazole Revision number: 5
SAFETY DATA SHEET

Section1. IDENTIFICATION
Product name:Triclabendazole

Revision number:5

Section2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDSNot classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDSNot classified
GHS label elements, including precautionary statements
Pictograms or hazard symbolsNone
No signal word
Signal word
Hazard statementsNone
None
Precautionary statements:

Section3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture:Substance
Components:Triclabendazole
Percent:>98.0%(LC)(T)
CAS Number:68786-66-3
Synonyms:5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)benzimidazole , 6-Chloro-5-(2,3-
dichlorophenoxy)-2-(methylthio)benzimidazole
C14H9Cl3N2OS
Chemical Formula:

Section4. FIRST AID MEASURES
Inhalation:Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact:Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact:Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion:Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

Section5. FIRE-FIGHTING MEASURES
Suitable extinguishingDry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical:generate poisonous fume.
Triclabendazole

Section5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protectiveWhen extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

Section6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

Section7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions:Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material:Comply with laws.

Section8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection:Protective gloves.
Eye protection:Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

Section9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C):Solid
Form:Crystal- Powder
Colour:White - Slightly pale yellow red
Odour:No data available
pH: No data available
Melting point/freezing point:176°C
No data available
Boiling point/range:
Flash point:No data available
Flammability or explosive
limits:
No data available
Lower:
Upper:No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents]No data available
5.35
Log Pow:
Triclabendazole

Section10. STABILITY AND REACTIVITY
Chemical stability:Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides, Hydrogen
products:chloride

Section11. TOXICOLOGICAL INFORMATION
orl-rat LD50:>8 g/kg
Acute Toxicity:
ihl-rat LC50:>500 mg/m3/4H
skn-rat LD50:>4 g/kg
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: cyt-ctl-lym 25 mg/L/48H
sce-ctl-lym 25 mg/L/48H
Carcinogenicity:
IARC =No data available
No data available
NTP =
Reproductive toxicity:No data available
DD6747000
RTECS Number:

Section12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish:No data available
Crustacea:No data available
Algae:No data available
Persistence / degradability: No data available
BioaccumulativeNo data available
potential(BCF):
Mobility in soil
Log Pow:5.35
Soil adsorption (Koc):No data available
Henry's LawNo data available
constant(PaM3/mol):

Section13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

Section14. TRANSPORT INFORMATION
Hazards Class:Does not correspond to the classification standard of the United Nations
UN-No:Not listed

Section15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
Triclabendazole

SECTION 16 - ADDITIONAL INFORMATION
N/A

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DD6747000

CHEMICAL NAME :: 1H-Benzimidazole, 5-chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-

CAS REGISTRY NUMBER :: 68786-66-3

LAST UPDATED :: 199106

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C14-H9-Cl3-N2-O-S

MOLECULAR WEIGHT :: 359.66

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >500 mg/m3/4H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 206 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 21,227,1985 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 800 mg/kg

SEX/DURATION :: female 8-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 43,283,1987

Hazard Statements	H413
Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	Xn: Harmful;
Risk Phrases	R36/37/38
Safety Phrases	S26-S36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	DD6747000
HS Code	2933990090

5-chloro-6-(2,3...

CAS#:68828-69-3

Dimethyl sulfate

CAS#:77-78-1

~80%

Triclabendazole

CAS#:68786-66-3

Literature: SEQUENT SCIENTIFIC LIMITED; Rane, Ramkrishna Appaji; Verma, Sudhakar; Arulmoli, Thangavel Patent: US2013/303781 A1, 2013 ; Location in patent: Paragraph 0031 ;

5-chloro-6-(2,3...

CAS#:68828-69-3

methyl iodide

CAS#:74-88-4

~65%

6-chloro-5-(2,3...

CAS#:145770-89-4

5-chloro-6-(2,3...

CAS#:145770-88-3

Detail

Literature: Bulletin des Societes Chimiques Belges, , vol. 99, # 9 p. 673 - 701

4-Chloro-5-(2,3...

CAS#:118353-04-1

Triclabendazole

CAS#:68786-66-3

Literature: US2013/303781 A1, ;

2,3-Dichlorophenol

CAS#:576-24-9

Triclabendazole

CAS#:68786-66-3

Literature: US2013/303781 A1, ;

Acetamide,N-(4,...

CAS#:5462-30-6

Triclabendazole

CAS#:68786-66-3

Literature: US2013/303781 A1, ;

4-chloro-5-(2,3...

CAS#:139369-42-9

Triclabendazole

CAS#:68786-66-3

Literature: US2013/303781 A1, ;

Precursor 7
CAS#:68828-69-3 5-chloro-6-(2,3... CAS#:77-78-1 Dimethyl sulfate CAS#:74-88-4 methyl iodide CAS#:118353-04-1 4-Chloro-5-(2,3...
CAS#:576-24-9 2,3-Dichlorophenol CAS#:5462-30-6 Acetamide,N-(4,... CAS#:139369-42-9 4-chloro-5-(2,3...
DownStream 1
CAS#:100648-13-3 Triclabendazole...

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Time-course and accumulation of triclabendazole and its metabolites in bile, liver tissues and flukes collected from treated sheep.

Exp. Parasitol. 136 , 14-9, (2014)

The flukicidal compound triclabendazole (TCBZ) has a complex metabolic pattern that includes the systemic presence of its sulphoxide (TCBZ.SO) and sulphone (TCBZ.SO2) metabolites, usually recovered fr...

The anthelmintic triclabendazole and its metabolites inhibit the membrane transporter ABCG2/BCRP.

Antimicrob. Agents Chemother. 56(7) , 3535-43, (2012)

ABCG2/BCRP is an ATP-binding cassette transporter that extrudes compounds from cells in the intestine, liver, kidney, and other organs, such as the mammary gland, affecting pharmacokinetics and milk s...

Isothermal microcalorimetry to study the activity of triclabendazole and its metabolites on juvenile and adult Fasciola hepatica.

Exp. Parasitol. 133(3) , 265-8, (2013)

Isothermal microcalorimetry (IMC) is an analytical tool that continuously measures the heat flow generated by chemical, physical or biological processes. We have demonstrated that IMC is a useful tool...

Fasinex

MFCD00864519

Triclabendazole

6-Chloro-5-(2,3-dichlorophenoxy)-2-methylthio-benzimidazole

5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-benzimidazole

1H-Benzimidazole, 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-

5-Chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole

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Product Name: Triclabendazole
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