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T8904

Sigma-Aldrich

Thiabendazole

≥99%, powder

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Synonym(s):
2-(4-Thiazolyl)benzimidazole
Empirical Formula (Hill Notation):
C10H7N3S
CAS Number:
148-79-8
Molecular Weight:
201.25
Beilstein:
611403
EC Number:
205-725-8
MDL number:
MFCD00005587
PubChem Substance ID:
24900571
NACRES:
NA.85

Quality Level

200

Assay

≥99%

form

powder

color

white to off-white

solubility

DMF: soluble 50 mg/mL

antibiotic activity spectrum

fungi
parasites

Mode of action

enzyme | inhibits

SMILES string

c1ccc2[nH]c(nc2c1)-c3cscn3

InChI

1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)

InChI key

WJCNZQLZVWNLKY-UHFFFAOYSA-N

Gene Information

human ... CYP2C9(1559)

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General description

Chemical structure: imidazole

Application

Thiabendazole (TBZ) is a broad-spectrum antihelminthic and is used to treat parasitic infections in humans. It is used as an agricultural fungicide and as a food preservative. Thiabendazole has been used as a heavy metal chelating detoxification agent. It is used clinically to treat threadworm, cutaneous larva migrans, visceral larva migrans, and trichinosis.

Biochem/physiol Actions

Thiabendazole inhibits anaerobic respiration at the level of mitochondrial helminth-specific enzyme. It acts as a quinol-fumarate reductase (QFR) inhibitor in ,C. jejuni and H. pylori, blocking quinol oxidation to quinone. Thiabendazole suppresses egg and larval production and may inhibit the subsequent development of eggs and larvae which are passed in feces. A proposed route of biotransformation of thiabendazole is the CYP1A2-catalyzed hydroxylation to 5-hydroxythiabendazole, which is metabolized to glucuronide and sulfate conjugates.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.Storage class (TRGS 510): Non Combustible Solids

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

农药列管产品

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Roslyn S Thelingwani et al.
Drug metabolism and disposition: the biological fate of chemicals, 37(6), 1286-1294 (2009-03-21)
Thiabendazole (TBZ) and its major metabolite 5-hydroxythiabendazole (5OH-TBZ) were screened for potential time-dependent inhibition (TDI) against CYP1A2. Screen assays were carried out in the absence and presence of NADPH. TDI was observed with both compounds, with k(inact) and K(I) values
Stuart Dashper et al.
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