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Merck

33818

5-Hydroxythiabendazole

PESTANAL®, analytical standard

Synonym(s):

2-(4-Thiazolyl)-5-benzimidazolol, 5-Hydroxy-2-(4-thiazolyl)benzimidazole

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About This Item

Empirical Formula (Hill Notation):
C10H7N3OS
CAS Number:
948-71-0
Molecular Weight:
217.25
NACRES:
NA.24
PubChem Substance ID:
329754660
UNSPSC Code:
41116107
MDL number:
MFCD00152219

Product Name

5-Hydroxythiabendazole, PESTANAL®, analytical standard

InChI

1S/C10H7N3OS/c14-6-1-2-7-8(3-6)13-10(12-7)9-4-15-5-11-9/h1-5,14H,(H,12,13)

SMILES string

Oc1ccc2[nH]c(nc2c1)-c3cscn3

InChI key

VNENJHUOPQAPAT-UHFFFAOYSA-N

grade

analytical standard

product line

PESTANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

agriculture
environmental
forensics and toxicology
veterinary

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Thiabendazole and its metabolite 5-hydroxythiabendazole can undergo specific binding with monoclonal antibodies and can further undergo immobilization on agarose gels, which can find applications in immunoaffinity chromatography.

General description

5-Hydroxythiabendazole present in excreta, eggs, edible tissues and milk is found to be the major metabolite of thiabendazole, an active ingredient in fungicidal preparations effective for plants. It can also be used as an anthelmintic drug, which is applicable both for humans and animals.

Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H302,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6952
BCCH9374
BCCH0371
BCCG0673
BCCF0006

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M Coulet et al.
Chemico-biological interactions, 127(2), 109-124 (2000-08-11)
Thiabendazole (TBZ), an anthelmintic and fungicide benzimidazole, was recently demonstrated to be extensively metabolized by cytochrome P450 (CYP) 1A2 in man and rabbit, yielding 5-hydroxythiabendazole (5OH-TBZ), the major metabolite furtherly conjugated, and two minor unidentified metabolites (M1 and M2). In
Deepak Dalvie et al.
Drug metabolism and disposition: the biological fate of chemicals, 34(4), 709-717 (2006-01-26)
Thiabendazole (TBZ) is a broad-spectrum antihelmintic used for treatment of parasitic infections in animals and humans and as an agricultural fungicide for postharvest treatment of fruits and vegetables. It is teratogenic and nephrotoxic in mice, and cases of hepatotoxicity have
R V Arenas et al.
Journal of AOAC International, 78(3), 642-646 (1995-05-01)
A novel liquid chromatographic multiresidue method has been developed for quantitation of thiabendazole (TBZ), the metabolite 5-hydroxythiabendazole (5-OH-TBZ), and the sulfate conjugate of 5-hydroxythiabendazole (5-HSO4-TBZ) in raw cow's milk. The 5-HSO4-TBZ is hydrolyzed quantitatively under acidic conditions to 5-OH-TBZ. TBZ
G E Hardee et al.
Research in veterinary science, 43(1), 13-17 (1987-07-01)
Separate high performance liquid chromatographic methods were developed for thiabendazole (TBZ) and 5-hydroxy thiabendazole (5-OH-TBZ) determination in horse plasma using 1-methyl-2-phenyl benzimidazole (MPBZ) as an internal standard. In both methods TBZ and 5-OH-TBZ were extracted from plasma using organic solvents
Joseph D Jamieson et al.
Toxicology in vitro : an international journal published in association with BIBRA, 25(5), 1061-1066 (2011-04-26)
Thiabendazole (TBZ), an antihelminthic and antifungal agent, is associated with a host of adverse effects including nephrotoxicity, hepatotoxicity, and teratogenicity. Bioactivation of the primary metabolite of TBZ, 5-hydroxythiabendazole, has been proposed to yield a reactive intermediate. Here we show that
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