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T8904

Sigma-Aldrich

Thiabendazole

≥99%, powder

Synonyme(s) :

2-(4-Thiazolyl)benzimidazole

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About This Item

Formule empirique (notation de Hill):
C10H7N3S
Numéro CAS:
148-79-8
Poids moléculaire :
201.25
Numéro Beilstein :
611403
Numéro CE :
205-725-8
Numéro MDL:
MFCD00005587
Code UNSPSC :
51453501
ID de substance PubChem :
24900571
Nomenclature NACRES :
NA.85

Niveau de qualité

200

Pureté

≥99%

Forme

powder

Couleur

white to off-white

Solubilité

DMF: soluble 50 mg/mL

Spectre d'activité de l'antibiotique

fungi
parasites

Mode d’action

enzyme | inhibits

Chaîne SMILES 

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)

Clé InChI

WJCNZQLZVWNLKY-UHFFFAOYSA-N

Informations sur le gène

human ... CYP2C9(1559)

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Catégories apparentées

Description générale

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Pictogrammes

Environment
GHS09

Mention d'avertissement

Warning

Mentions de danger

H410

Conseils de prudence

P273 - P391 - P501

Classification des risques

Aquatic Acute 1 - Aquatic Chronic 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves

Certificats d'analyse (COA)

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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.
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
Susanne Rath et al.
Chemosphere, 214, 111-122 (2018-09-28)
Brazil is one of the world's largest producers of animal protein, requiring the large-scale use of veterinary drugs. The administration of antimicrobials and antiparasitics is a common practice. However, there is a lack of information on how these drugs impact
Santosh Soparawalla et al.
The Analyst, 136(21), 4392-4396 (2011-09-06)
We describe a rapid in situ method for detecting agrochemicals on the surface or in the tissue of fruit using a portable mass spectrometer equipped with an ambient ionization source. Two such ionization methods, low temperature plasma (LTP) and paper
Andrew C Kotze et al.
PLoS neglected tropical diseases, 5(6), e1203-e1203 (2011-07-09)
Current efforts to control human soil-transmitted helminths (STHs) involve the periodic mass administration of benzimidazole drugs to school aged children and other at- risk groups. Given that high levels of resistance to these drugs have developed in roundworms of livestock
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