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All Photos(3)

T8904

Sigma-Aldrich

Thiabendazole

≥99%, powder

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

Quality Level

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.

Packaging

100, 500 g in glass bottle

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

13 - Non 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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Stuart Dashper et al.
Antimicrobial agents and chemotherapy, 54(3), 1311-1314 (2009-12-30)
Porphyromonas gingivalis is a major pathogen of chronic periodontitis and exists in a biofilm on the surface of the tooth root. Oxantel, a cholinergic anthelmintic and fumarate reductase inhibitor, significantly inhibited biofilm formation by P. gingivalis and disrupted established biofilms
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
W H Gera Hol et al.
Ecology, 96(8), 2042-2048 (2015-09-26)
The contribution of low-abundance microbial species to soil ecosystems is easily overlooked because there is considerable overlap between metabolic abilities (functional redundancy) of dominant and subordinate microbial species. Here we studied how loss of less abundant soil bacteria affected the
Lili He et al.
Food chemistry, 148, 42-46 (2013-11-23)
We developed a rapid and simple method which combines a surface swab capture method and surface-enhanced Raman spectroscopy for recovery and quantitative detection of thiabendazole on apple surfaces. The whole apple surface was swabbed and the swab was vortexed in
Andrea Peano et al.
Veterinary dermatology, 23(2), 131-135 (2012-02-09)
In this study, we evaluated the antifungal susceptibility of Malassezia pachydermatis to clotrimazole (CTZ), miconazole (MCZ), and thiabendazole (TBD), azole derivatives employed in aural formulations labeled for treatment of canine otitis. The procedure for in vitro testing was based on

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