CAS 148-79-8|Thiabendazole

Introduction：Basic information about CAS 148-79-8|Thiabendazole, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Thiabendazole BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles62
8. Synonyms

Common Name	Thiabendazole
CAS Number	148-79-8	Molecular Weight	201.248
Density	1.4±0.1 g/cm3	Boiling Point	446.0±37.0 °C at 760 mmHg
Molecular Formula	C₁₀H₇N₃S	Melting Point	298-301ºC
MSDS	ChineseUSA	Flash Point	226.2±16.9 °C
Symbol	GHS09	Signal Word	Warning

Names

Name	thiabendazole
Synonym	More Synonyms

Thiabendazole BiologicalActivity

Description	Thiabendazole inhibites the mitochondrial helminth-specific enzyme, fumarate reductase, with anthelminthic property. Target: Fumarate ReductaseTiabendazole serves to block angiogenesis in both frog embryos and human cells. It has also been shown to serve as a vascular disrupting agent to reduce newly established blood vessels. Tiabendazole has been shown to effectively do this in certain cancer cells. Thiabendazole works by inhibition of the mitochondrial, helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone [1].Thiabendazole inhibited B16F10 proliferation in vitro in a dose- and time-dependent manner with an IC50 of 532.4 +/- 32.6, 322.9 +/- 28.9, 238.5 +/- 19.8 microM at 24, 48, and 72 h, respectively. Moreover, thiabendazole inhibited the angiogenesis and the migration of B16F10 cells in vitro. Furthermore, thiabendazole restrained transcription and translation of the VEGF gene in B16F10 in vitro, and the apoptotic percentage of B16F10 cells was increased after exposure to thiabendazole [2].
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>Mitochondrial MetabolismResearch Areas >>Infection
References	[1]. Cha, H.J., et al., Evolutionarily repurposed networks reveal the well-known antifungal drug thiabendazole to be a novel vascular disrupting agent. PLoS Biol, 2012. 10(8): p. e1001379. [2]. Zhang, J., et al., Thiabendazole, a well-known antifungal drug, exhibits anti-metastatic melanoma B16F10 activity via inhibiting VEGF expression and inducing apoptosis. Pharmazie, 2013. 68(12): p. 962-8.

Description

Thiabendazole inhibites the mitochondrial helminth-specific enzyme, fumarate reductase, with anthelminthic property. Target: Fumarate ReductaseTiabendazole serves to block angiogenesis in both frog embryos and human cells. It has also been shown to serve as a vascular disrupting agent to reduce newly established blood vessels. Tiabendazole has been shown to effectively do this in certain cancer cells. Thiabendazole works by inhibition of the mitochondrial, helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone [1].Thiabendazole inhibited B16F10 proliferation in vitro in a dose- and time-dependent manner with an IC50 of 532.4 +/- 32.6, 322.9 +/- 28.9, 238.5 +/- 19.8 microM at 24, 48, and 72 h, respectively. Moreover, thiabendazole inhibited the angiogenesis and the migration of B16F10 cells in vitro. Furthermore, thiabendazole restrained transcription and translation of the VEGF gene in B16F10 in vitro, and the apoptotic percentage of B16F10 cells was increased after exposure to thiabendazole [2].

Related Catalog

Signaling Pathways >>Metabolic Enzyme/Protease >>Mitochondrial MetabolismResearch Areas >>Infection

References

[1]. Cha, H.J., et al., Evolutionarily repurposed networks reveal the well-known antifungal drug thiabendazole to be a novel vascular disrupting agent. PLoS Biol, 2012. 10(8): p. e1001379.

[2]. Zhang, J., et al., Thiabendazole, a well-known antifungal drug, exhibits anti-metastatic melanoma B16F10 activity via inhibiting VEGF expression and inducing apoptosis. Pharmazie, 2013. 68(12): p. 962-8.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	446.0±37.0 °C at 760 mmHg
Melting Point	298-301ºC
Molecular Formula	C₁₀H₇N₃S
Molecular Weight	201.248
Flash Point	226.2±16.9 °C
Exact Mass	201.036072
PSA	69.81000
LogP	2.47
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.740
InChIKey	WJCNZQLZVWNLKY-UHFFFAOYSA-N
SMILES	c1ccc2[nH]c(-c3cscn3)nc2c1
Water Solubility	0.005 g/100 mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DE0700000

CHEMICAL NAME :: Benzimidazole, 2-(4-thiazolyl)-

CAS REGISTRY NUMBER :: 148-79-8

LAST UPDATED :: 199806

DATA ITEMS CITED :: 46

MOLECULAR FORMULA :: C10-H7-N3-S

MOLECULAR WEIGHT :: 201.26

WISWESSER LINE NOTATION :: T56 BM DNJ C- ET5N CSJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 47619 ug/kg/1D-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2080 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1300 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3850 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 4 gm/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - domestic

DOSE/DURATION :: 400 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 22200 mg/kg/60D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 13650 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - other changes Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 36 gm/kg/26W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 24 gm/kg/30D

TOXIC EFFECTS :: Behavioral - general anesthetic Behavioral - food intake (animal) Behavioral - ataxia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3500 mg/kg/7D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - urine volume increased

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 160 gm/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Blood - changes in spleen Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 175 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Reproductive - Tumorigenic effects - testicular tumors Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1250 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10080 mg/kg

SEX/DURATION :: male 6 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2368 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) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5336 mg/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - skin and skin appendages

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 250 mg/kg

SEX/DURATION :: female 9 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 11700 mg/kg

SEX/DURATION :: female 7-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 60 mg/kg

SEX/DURATION :: female 9 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 240 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2400 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 7800 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

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

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: DNA damage

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Sex chromosome loss and nondisjunction

MUTATION DATA

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 50 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 287,29,1993 *** REVIEWS *** TOXICOLOGY REVIEW MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 32,151,1975 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 72430 No. of Facilities: 183 (estimated) No. of Industries: 2 No. of Occupations: 6 No. of Employees: 1746 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 72430 No. of Facilities: 193 (estimated) No. of Industries: 3 No. of Occupations: 12 No. of Employees: 5960 (estimated) No. of Female Employees: 1184 (estimated)

Safety Information

Symbol	GHS09
Signal Word	Warning
Hazard Statements	H410
Precautionary Statements	P273-P501
Personal Protective Equipment	Eyeshields;Gloves
Hazard Codes	N:Dangerousfortheenvironment;
Risk Phrases	R50/53
Safety Phrases	S60-S61
RIDADR	UN 3077
WGK Germany	2
RTECS	DE0700000
Packaging Group	III
Hazard Class	9
HS Code	2934100015

Customs

HS Code	2934100015
Summary	2934100015 2,4-dimethyl-n-phenylthiazole-5-carboxamide。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:20.0%

Articles62

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

Pen-on-paper approach toward the design of universal surface enhanced Raman scattering substrates.

Small 10(15) , 3065-71, (2014)

The translation of a technology from the laboratory into the real world should meet the demand of economic viability and operational simplicity. Inspired by recent advances in conductive ink pens for ...

Synonyms

Arbotect

Tresaderm

2-(thiazol-4-yl)benzimidazole

Mintezol

2-(4-Thiazolyl)benzimidazole,Thiabendazole

2-(4-thiazolyl)-1H-benzimidazole

TBZ

Benzimidazole, 2-(4-thiazolyl)-

2-(4-Thiazolyl)benzimidazole

4-(1H-Benzo[d]imidazol-2-yl)thiazole

2-(4-Thiazoly)benzimidazole

1H-Benzimidazole, 2-(4-thiazolyl)-

EINECS 205-725-8

Tiabendazole

2-(1,3-Thiazol-4-yl)-1H-benzimidazole

2-(1,3-thiazol-4-yl)benzimidazole

MFCD00005587

Thiabendazole

2-(1,3-thiazol-4-yl)-1H-1,3-benzimidazole

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