U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of THIABENDAZOLE

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
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O06913
Gene ID: 900116.0
Gene Symbol: frdA
Target Organism: Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacter|||pylori)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Curative
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
Curative
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
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
0.9 μg × min/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.17 h
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

Doses

DosePopulationAdverse 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:
unhealthy, adult
n = 31
Health Status: unhealthy
Condition: strongyloidiasis
Age Group: adult
Sex: M+F
Population Size: 31
Sources:
Other AEs: Asthenia, Epigastralgia...
Other AEs:
Asthenia (3 patients)
Epigastralgia (1 patient)
Disorientation (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, adult
n = 31
Health Status: unhealthy
Condition: strongyloidiasis
Age Group: adult
Sex: M+F
Population Size: 31
Sources:
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:
unhealthy, adult
n = 31
Health Status: unhealthy
Condition: strongyloidiasis
Age Group: adult
Sex: M+F
Population Size: 31
Sources:
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:
unhealthy, adult
n = 31
Health Status: unhealthy
Condition: strongyloidiasis
Age Group: adult
Sex: M+F
Population Size: 31
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Ecchymoses: an unusual manifestation of toxocariasis in children.
2001 Dec
[Toxocariasis].
2001 Dec
Parasitic infections of the intestine.
2001 Oct
Anthelmintics: a review.
2001 Oct-Dec
Evaluation of certain veterinary drug residues in food.
2002
The p21-activated kinase, Shk1, is required for proper regulation of microtubule dynamics in the fission yeast, Schizosaccharomyces pombe.
2002 Apr
Residue uptake and storage responses of Tarocco blood oranges after preharvest thiabendazole spray and postharvest heat treatment.
2002 Apr 10
Loeffler's syndrome and cutaneous larva migrans: a rare association.
2002 Aug
Opinion on the diagnosis and treatment of human trichinellosis.
2002 Aug
Cloning, production and characterisation of a recombinant Cu/Zn superoxide dismutase from Taenia solium.
2002 Aug
[Disseminated strongyloidiasis, a rare cause of multiple organ failure].
2002 Aug 10
The comet assay with 8 mouse organs: results with 39 currently used food additives.
2002 Aug 26
Pesticide residues in biological waste.
2002 Dec
Oxidative, heat and anthelminthic stress responses in four species of Trichinella: comparative study.
2002 Dec 1
Methods for generation of monoclonal antibodies to the very small drug hapten, 5-benzimidazolecarboxylic acid.
2002 Dec 20
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
Hyperinfective strongyloidiasis in the medical ward: review of 27 cases in 5 years.
2002 Jul
[Test treatment with antiparasitic agents for eosinophilia?].
2002 Jul
Induction of aneuploidy in male mouse germ cells detected by the sperm-FISH assay: a review of the present data base.
2002 Jul 25
[A case of toxocariasis with eosinophil-rich pleural effusion].
2002 Jun
[DNA damage in female workers exposed to pesticides in banana plantations at Limón, Costa Rica].
2002 Jun
Yeast RSC function is required for organization of the cellular cytoskeleton via an alternative PKC1 pathway.
2002 Jun
Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study.
2002 Jun
Treatment failure in intestinal strongyloidiasis: an indicator of HTLV-I infection.
2002 Mar
Human strongyloidiasis in AIDS era: its zoonotic importance.
2002 Mar
Analysis of thiabendazole and procymidone in fruits and vegetables by capillary electrophoresis-electrospray mass spectrometry.
2002 Mar 8
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
Bud morphogenesis and the actin and microtubule cytoskeletons during budding in the corn smut fungus, Ustilago maydis.
2002 Nov
Development and validation of a liquid chromatographic-electrospray tandem mass spectrometric multiresidue method for anthelmintics in milk.
2002 Nov 8
Massive infestation of cutanea larva migrans.
2002 Oct
The effects of stage-specific selection on the development of benzimidazole resistance in Haemonchus contortus in sheep.
2002 Oct 16
Characterization of a Schizosaccharomyces pombe strain deleted for a sequence homologue of the human damaged DNA binding 1 (DDB1) gene.
2002 Oct 25
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
Analysis and partial reversal of multidrug resistance to anthelmintics due to P-glycoprotein in Haemonchus contortus eggs using Lens culinaris lectin.
2002 Sep
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
[A case of parasitism by Rhabditis sp in a child from Goiânia, Goiás, Brazil].
2002 Sep-Oct
Photomutagenicity of thiabendazole, a postharvest fungicide, in bacterial assays.
2003
Application of GRAM and TLD to the resolution and quantitation of real complex multicomponent mixtures by fluorescence spectroscopy.
2003 Apr
Treatment of cutaneous larva migrans and Toxocara infection.
2003 Apr
Fission yeast Rad26 responds to DNA damage independently of Rad3.
2003 Apr 3
[Strongyloidiasis].
2003 Feb
Antifungal agents of use in animal health--chemical, biochemical and pharmacological aspects.
2003 Feb
Simple and rapid determination of thiabendazole, imazalil, and o-phenylphenol in citrus fruit using flow-injection electrospray ionization tandem mass spectrometry.
2003 Feb 12
[Selective vs. mass treatment with antihelminthic drugs: experience in two hyperendemic communities].
2003 Jan
Ion trap tandem mass spectrometric identification of thiabendazole phototransformation products on titanium dioxide.
2003 Jan 10
A new role for the transcriptional corepressor SIN3; regulation of centromeres.
2003 Jan 8
A more selective medium for Culicinomyces clavisporus.
2003 Mar
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
Severe drug rashes in three siblings simultaneously.
2003 May
[Toxocariasis: clinical and laboratory features in 54 patients].
2003 May
Patents

Sample Use Guides

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
GREEN BOOK   HSDB   INCI   ISO   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN   INCI  
Official Name English
THIABENDAZOLE [USP MONOGRAPH]
Common Name English
TIABENDAZOLE
EP   INN   JAN   MART.   WHO-DD   WHO-IP  
INN  
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
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 520.2380C
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 520.2380F
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
LIVERTOX 950
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
WHO-ATC D01AC06
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
WHO-VATC QP52AC10
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 520.2380A
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 520.2380D
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 558.600
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
NDF-RT N0000175481
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
EPA PESTICIDE CODE 60101
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
WHO-VATC QD01AC06
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CFR 21 CFR 520.2380E
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 520.2380B
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 520.2380
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 556.730
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
CFR 21 CFR 524.1484G
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
NCI_THESAURUS C250
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
205-725-8
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
INN
1436
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
NCI_THESAURUS
C873
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
THIABENDAZOLE
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY Description: A white to almost white powder; odourless or almost odourless. Solubility: Practically insoluble in water; soluble in 150 parts of ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Anthelmintic. Storage: Tiabendazole should be kept in a well-closed container. Definition: Tiabendazole contains not less than 98.0% and not more than 101.0% of C10H7N3S, calculated with reference to the dried substance.
EVMPD
SUB10996MIG
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
WIKIPEDIA
TIABENDAZOLE
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
MESH
D013827
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
FDA UNII
N1Q45E87DT
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
EPA CompTox
148-79-8
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
MERCK INDEX
M10710
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL625
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
DRUG CENTRAL
2621
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
USP_CATALOG
1655000
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY USP-RS
CAS
148-79-8
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
RXCUI
10450
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY RxNorm
IUPHAR
7304
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
HSDB
2027
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
PUBCHEM
5430
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY
DRUG BANK
DB00730
Created by admin on Fri Jun 25 20:59:05 UTC 2021 , Edited by admin on Fri Jun 25 20:59:05 UTC 2021
PRIMARY