THIABENDAZOLE

US Previously Marketed

First approved in 1967

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H7N3S
Molecular Weight	201.2491
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc2c(c1)[nH]c(-c3cscn3)n2

InChI

InChIKey=WJCNZQLZVWNLKY-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/16096slr033,16097slr026_mintezol_lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22927795

Thiabendazole (TBZ, trade names Mintezol, Tresaderm, and Arbotect) was first introduced in 1962. This drug is a fungicide and parasiticide and is indicated for the treatment of: strongyloidiasis (threadworm), cutaneous larva migrans (creeping eruption), visceral larva migrans, trichinosis: relief of symptoms and fever and a reduction of eosinophilia have followed the use of this drug during the invasion stage of the disease. But usage of this drug was discontinued. The precise mode of action of thiabendazole on the parasite is unknown, but it may inhibit the helminthspecific enzyme fumarate reductase. It was shown, also that thiabendazole reversibly disassembles newly established blood vessels, marking it as vascular disrupting agent (VDA) and thus as a potential complementary therapeutic for use in combination with current anti-angiogenic therapies. Was shown, that vascular disruption by TBZ results from reduced tubulin levels and hyper-active Rho signaling. In addition, was confirmed, that thiabendazole slowed tumor growth and decreased vascular density in preclinical fibrosarcoma xenografts and thus, it could lead directly to the identification of a potential new therapeutic application for an inexpensive drug that is already approved for clinical use in humans.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 65 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22927795	Inhibitor 7728
Fumarate reductase flavoprotein subunit 2 Target ID: O06913 Gene ID: 900116.0 Gene Symbol: frdA Target Organism: Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacter\|\|\|pylori) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11031122	Inhibitor 7728

Conditions

Condition	Modality	Highest Phase	Product
Strongyloidiasis 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/16096slr033,16097slr026_mintezol_lbl.pdf	Curative	Approved 8043	MINTEZOL Approved Use MINTEZOL is indicated for the treatment of: Strongyloidiasis (threadworm) Cutaneous larva migrans (creeping eruption) Visceral larva migrans Trichinosis: Relief of symptoms and fever and a reduction of eosinophilia have followed the use of MINTEZOL during the invasion stage of the disease.Thiabendazole is usually inappropriate as first line therapy for enterobiasis (pinworm). However, when enterobiasis occurs with any of the conditions listed above, additional therapy is not required for most patients. MINTEZOL should be used only in the following infestations when more specific therapy is not available or cannot be used or when further therapy with a second agent is desirable: Uncinariasis (hookworm: Necator americanus and Ancylostoma duodenale); Trichuriasis (whipworm); Ascariasis (large roundworm). Launch Date -8.64E10
Cutaneous larva migrans 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/16096slr033,16097slr026_mintezol_lbl.pdf	Curative	Approved 8043	MINTEZOL Approved Use MINTEZOL is indicated for the treatment of: Strongyloidiasis (threadworm) Cutaneous larva migrans (creeping eruption) Visceral larva migrans Trichinosis: Relief of symptoms and fever and a reduction of eosinophilia have followed the use of MINTEZOL during the invasion stage of the disease.Thiabendazole is usually inappropriate as first line therapy for enterobiasis (pinworm). However, when enterobiasis occurs with any of the conditions listed above, additional therapy is not required for most patients. MINTEZOL should be used only in the following infestations when more specific therapy is not available or cannot be used or when further therapy with a second agent is desirable: Uncinariasis (hookworm: Necator americanus and Ancylostoma duodenale); Trichuriasis (whipworm); Ascariasis (large roundworm). Launch Date -8.64E10
Visceral larva migrans 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/16096slr033,16097slr026_mintezol_lbl.pdf	Curative	Approved 8043	MINTEZOL Approved Use MINTEZOL is indicated for the treatment of: Strongyloidiasis (threadworm) Cutaneous larva migrans (creeping eruption) Visceral larva migrans Trichinosis: Relief of symptoms and fever and a reduction of eosinophilia have followed the use of MINTEZOL during the invasion stage of the disease.Thiabendazole is usually inappropriate as first line therapy for enterobiasis (pinworm). However, when enterobiasis occurs with any of the conditions listed above, additional therapy is not required for most patients. MINTEZOL should be used only in the following infestations when more specific therapy is not available or cannot be used or when further therapy with a second agent is desirable: Uncinariasis (hookworm: Necator americanus and Ancylostoma duodenale); Trichuriasis (whipworm); Ascariasis (large roundworm). Launch Date -8.64E10
Trichinosis 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/16096slr033,16097slr026_mintezol_lbl.pdf	Curative	Approved 8043	MINTEZOL Approved Use MINTEZOL is indicated for the treatment of: Strongyloidiasis (threadworm) Cutaneous larva migrans (creeping eruption) Visceral larva migrans Trichinosis: Relief of symptoms and fever and a reduction of eosinophilia have followed the use of MINTEZOL during the invasion stage of the disease.Thiabendazole is usually inappropriate as first line therapy for enterobiasis (pinworm). However, when enterobiasis occurs with any of the conditions listed above, additional therapy is not required for most patients. MINTEZOL should be used only in the following infestations when more specific therapy is not available or cannot be used or when further therapy with a second agent is desirable: Uncinariasis (hookworm: Necator americanus and Ancylostoma duodenale); Trichuriasis (whipworm); Ascariasis (large roundworm). Launch Date -8.64E10

C_max

Value	Dose	Co-administered	Analyte	Population
5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7050189/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		THIABENDAZOLE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
0.9 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7050189/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		THIABENDAZOLE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7050189/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		THIABENDAZOLE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
25 mg/kg 2 times / day steady, oral Recommended Dose: 25 mg/kg, 2 times / day Route: oral Route: steady Dose: 25 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/	unhealthy, adult n = 31 Health Status: unhealthy Condition: strongyloidiasis Age Group: adult Sex: M+F Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/	Other AEs: Asthenia, Epigastralgia... Other AEs: Asthenia (3 patients) Epigastralgia (1 patient) Disorientation (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/

AEs

AE	Significance	Dose	Population
Disorientation	1 patient	25 mg/kg 2 times / day steady, oral Recommended Dose: 25 mg/kg, 2 times / day Route: oral Route: steady Dose: 25 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/	unhealthy, adult n = 31 Health Status: unhealthy Condition: strongyloidiasis Age Group: adult Sex: M+F Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/
Epigastralgia	1 patient	25 mg/kg 2 times / day steady, oral Recommended Dose: 25 mg/kg, 2 times / day Route: oral Route: steady Dose: 25 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/	unhealthy, adult n = 31 Health Status: unhealthy Condition: strongyloidiasis Age Group: adult Sex: M+F Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/
Asthenia	3 patients	25 mg/kg 2 times / day steady, oral Recommended Dose: 25 mg/kg, 2 times / day Route: oral Route: steady Dose: 25 mg/kg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/	unhealthy, adult n = 31 Health Status: unhealthy Condition: strongyloidiasis Age Group: adult Sex: M+F Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/15571478/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1383 P-gp 1330 BSEP 376	CYP1A2 972	CYP1A1 98

Drug as perpetrator

Target	Modality	Activity
BSEP 377	inhibitor 3045 Sources: https://onlinelibrary.wiley.com/doi/full/10.1002/jps.23584	no
CYP1A2 1532	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/16261361/	yes [Ki 1.54 uM]
CYP1A1 192	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/11226373/	yes
P-gp 1514	inhibitor 3045 Sources: https://www.phytojournal.com/archives/2019/vol8issue3/PartBH/8-3-541-743.pdf#page=1 Page: 1.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 972	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9565779/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:45979	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45979
ChemicalBook	CB1685813	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1685813
MolPort	MolPort-001-002-054	https://www.molport.com/shop/molecule-link/MolPort-001-002-054
Selleck Chemicals	Thiabendazole	http://www.selleckchem.com/products/Thiabendazole.html
ZINC	ZINC000000073711	http://zinc15.docking.org/substances/ZINC000000073711
eMolecules	510269	https://www.emolecules.com/cgi-bin/more?vid=510269

PubMed

Title	Date	PubMed
Ecchymoses: an unusual manifestation of toxocariasis in children.	2001 Dec	12164030
[Toxocariasis].	2001 Dec	11908154
Parasitic infections of the intestine.	2001 Oct	11964880
Anthelmintics: a review.	2001 Oct-Dec	11963321
Evaluation of certain veterinary drug residues in food.	2002	12592988
The p21-activated kinase, Shk1, is required for proper regulation of microtubule dynamics in the fission yeast, Schizosaccharomyces pombe.	2002 Apr	11972773
Residue uptake and storage responses of Tarocco blood oranges after preharvest thiabendazole spray and postharvest heat treatment.	2002 Apr 10	11929286
Loeffler's syndrome and cutaneous larva migrans: a rare association.	2002 Aug	12174122
Opinion on the diagnosis and treatment of human trichinellosis.	2002 Aug	12150691
Cloning, production and characterisation of a recombinant Cu/Zn superoxide dismutase from Taenia solium.	2002 Aug	12117500
[Disseminated strongyloidiasis, a rare cause of multiple organ failure].	2002 Aug 10	12212512
The comet assay with 8 mouse organs: results with 39 currently used food additives.	2002 Aug 26	12160896
Pesticide residues in biological waste.	2002 Dec	12489733
Oxidative, heat and anthelminthic stress responses in four species of Trichinella: comparative study.	2002 Dec 1	12410594
Methods for generation of monoclonal antibodies to the very small drug hapten, 5-benzimidazolecarboxylic acid.	2002 Dec 20	12445730
Estimation of concentrations of antifungal agents allowed as food additives in foods and their daily intake based on official inspection results in Japan in fiscal year 1998.	2002 Feb	11998320
Hyperinfective strongyloidiasis in the medical ward: review of 27 cases in 5 years.	2002 Jul	12144076
[Test treatment with antiparasitic agents for eosinophilia?].	2002 Jul	12139832
Induction of aneuploidy in male mouse germ cells detected by the sperm-FISH assay: a review of the present data base.	2002 Jul 25	12106657
[A case of toxocariasis with eosinophil-rich pleural effusion].	2002 Jun	12325335
[DNA damage in female workers exposed to pesticides in banana plantations at Limón, Costa Rica].	2002 Jun	12298281
Yeast RSC function is required for organization of the cellular cytoskeleton via an alternative PKC1 pathway.	2002 Jun	12072455
Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study.	2002 Jun	12031927
Treatment failure in intestinal strongyloidiasis: an indicator of HTLV-I infection.	2002 Mar	12044298
Human strongyloidiasis in AIDS era: its zoonotic importance.	2002 Mar	11922234
Analysis of thiabendazole and procymidone in fruits and vegetables by capillary electrophoresis-electrospray mass spectrometry.	2002 Mar 8	11999753
Validation of a method for the determination of multiclass pesticide residues in fruit juices by liquid chromatography/tandem mass spectrometry after extraction by matrix solid-phase dispersion.	2002 May-Jun	12083266
Bud morphogenesis and the actin and microtubule cytoskeletons during budding in the corn smut fungus, Ustilago maydis.	2002 Nov	12409100
Development and validation of a liquid chromatographic-electrospray tandem mass spectrometric multiresidue method for anthelmintics in milk.	2002 Nov 8	12462609
Massive infestation of cutanea larva migrans.	2002 Oct	12546776
The effects of stage-specific selection on the development of benzimidazole resistance in Haemonchus contortus in sheep.	2002 Oct 16	12383623
Characterization of a Schizosaccharomyces pombe strain deleted for a sequence homologue of the human damaged DNA binding 1 (DDB1) gene.	2002 Oct 25	12181326
Active ammonia excretion across the gills of the green shore crab Carcinus maenas: participation of Na(+)/K(+)-ATPase, V-type H(+)-ATPase and functional microtubules.	2002 Sep	12177142
Analysis and partial reversal of multidrug resistance to anthelmintics due to P-glycoprotein in Haemonchus contortus eggs using Lens culinaris lectin.	2002 Sep	12172813
Cytokinetic actomyosin ring formation and septation in fission yeast are dependent on the full recruitment of the polo-like kinase Plo1 to the spindle pole body and a functional spindle assembly checkpoint.	2002 Sep 15	12186944
[A case of parasitism by Rhabditis sp in a child from Goiânia, Goiás, Brazil].	2002 Sep-Oct	12621674
Photomutagenicity of thiabendazole, a postharvest fungicide, in bacterial assays.	2003	12605377
Application of GRAM and TLD to the resolution and quantitation of real complex multicomponent mixtures by fluorescence spectroscopy.	2003 Apr	12707769
Treatment of cutaneous larva migrans and Toxocara infection.	2003 Apr	12667232
Fission yeast Rad26 responds to DNA damage independently of Rad3.	2003 Apr 3	12697061
[Strongyloidiasis].	2003 Feb	12722295
Antifungal agents of use in animal health--chemical, biochemical and pharmacological aspects.	2003 Feb	12603774
Simple and rapid determination of thiabendazole, imazalil, and o-phenylphenol in citrus fruit using flow-injection electrospray ionization tandem mass spectrometry.	2003 Feb 12	12568539
[Selective vs. mass treatment with antihelminthic drugs: experience in two hyperendemic communities].	2003 Jan	12744797
Ion trap tandem mass spectrometric identification of thiabendazole phototransformation products on titanium dioxide.	2003 Jan 10	12564676
A new role for the transcriptional corepressor SIN3; regulation of centromeres.	2003 Jan 8	12526748
A more selective medium for Culicinomyces clavisporus.	2003 Mar	12676556
Fast and easy multiresidue method employing acetonitrile extraction/partitioning and "dispersive solid-phase extraction" for the determination of pesticide residues in produce.	2003 Mar-Apr	12723926
Severe drug rashes in three siblings simultaneously.	2003 May	12752334
[Toxocariasis: clinical and laboratory features in 54 patients].	2003 May	12724074

Patents

Sample Use Guides

In Vivo Use Guide

The recommended maximum daily dose of MINTEZOL ((Thiabendazole) is 3 grams. MINTEZOL should be given after meals if possible. Tablets MINTEZOL should be chewed before swallowing. Dietary restriction, complementary medications and cleansing enemas are not needed. The usual dosage schedule for all conditions is two doses per day. The dosage is determined by the patient's weight.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

THIABENDAZOLE

Official Name

English

THIABENDAZOLE [USP MONOGRAPH]

Common Name

English

TIABENDAZOLE

Official Name

English

LOMBRISTOP

Common Name

English

2-(4-THIAZOLYL)BENZIMIDAZOLE

Systematic Name

English

THIABENDAZOLE [INCI]

Common Name

English

THIABENDAZOLE [USP-RS]

Common Name

English

OMNIZOLE

Common Name

English

2-(THIAZOL-4-YL)BENZIMIDAZOLE

Systematic Name

English

MINZOLUM

Common Name

English

TIABENDAZOLE [EP]

Common Name

English

1H-BENZIMIDAZOLE, 2-(4-THIAZOLYL)-

Systematic Name

English

THIABENZOLE

Common Name

English

THIABENDAZOLE [ORANGE BOOK]

Common Name

English

NSC-525040

Code

English

2-(4-THIAZOLYL)-1H-BENZIMIDAZOLE

Systematic Name

English

TIABENDAZOLE [WHO-IP]

Common Name

English

NEMAPAN

Common Name

English

PITRIZET

Common Name

English

THIABENDAZOLE [GREEN BOOK]

Common Name

English

THIABENDAZOLE [USAN]

Common Name

English

TIABENDAZOLE [INN]

Common Name

English

TIABENDAZOLE [MART.]

Common Name

English

THIABENDAZOLE [MI]

Common Name

English

TIABENDAZOLE [JAN]

Common Name

English

TIABENDAZOLE [EP MONOGRAPH]

Common Name

English

TIABENDAZOLE [WHO-DD]

Common Name

English

THIABENDAZOLE [VANDF]

Common Name

English

MK-360

Code

English

THIABENDAZOLE [HSDB]

Common Name

English

MINTEZOL

Brand Name

English

THIABENDAZOLE [ISO]

Common Name

English

NSC-90507

Code

English

Classification Tree Code System Code

WHO-ATC

P02CA02