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Usage

Uses

Used in Pharmaceutical Industry:
5-Hydroxy Thiabendazole is used as a major metabolite of Thiabendazole for its potential applications in the development of new anthelmintic drugs. As a metabolite, it can provide insights into the drug's mechanism of action and help in the design of more effective and safer treatments for parasitic infections.
Used in Research and Development:
5-Hydroxy Thiabendazole is used as a research compound for studying the metabolism and pharmacokinetics of Thiabendazole. Understanding the properties and behavior of this metabolite can contribute to the optimization of drug formulations and dosing regimens, as well as the discovery of new therapeutic agents with improved efficacy and safety profiles.

InChI:InChI=1/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)

Upstream product

• 148-79-8 thiabendazole 
• 1614-04-6 4-(6-methoxy-1H-benzo[d]imidazol-2-yl)thiazole 

Relevant academic research and scientific papers

Major involvement of rabbit liver cytochrome P4501A in thiabendazole 5-hydroxylation

1. Thiabendazole is a widely used food preservative and anthelmintic drug for breeding animal species. In order to characterize precisely the cytochrome P450 isozyme(s) involved in its major route of metabolism, a rapid and sensitive spectrofluorimetric method was developed for the simultaneous determination of thiabendazole and its main hepatic metabolite 5-hydroxythiabendazole. 2. The kinetics of thiabendazole 5-hydroxylation were determined in microsomal preparations from control rabbits or animals previously treated with either β-naphthoflavone, isosafrole, phenobarbital, rifampicin or clofibrate. These treatments led to specific induction of CYP1A1, 1A2, 2B4, 3A6 and 4A1 respectively. 3. By considering this panel of characterised microsomal preparations, only those obtained from BNF-treated rabbits exhibited an increase in thiabendazole 5-hydroxylase activity. Ethoxyresorufin O-deethylation in these microsomes was solely inhibited by thiabendazole. These argue for a specific involvement of the CYP1A, subfamily. 4. In the CYP1A subfamily, CYP1A2 appears to be responsible for basal 5-hydroxylation and further unidentified metabolism of thiabendazole in control livers. However, the major involvement of CYP1A1 is supported by the following characteristics of 5-hydroxylation of thiabendazole: (1) the correlation with CYP1A1 expression and (2) the inhibition by ellipticine and not by furafylline, inhibitors of CYP1A1 and CYP1A2 respectively. 5. All these data demonstrated that the rabbit cytochrome P4501A is predominantly involved in thiabendazole 5-hydroxylation which has been suspected to be critical in terms of safety of the parent drug.