Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H7N3S.ClH |
| Molecular Weight | 237.709 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.N1C(=NC2=C1C=CC=C2)C3=CSC=N3
InChI
InChIKey=XRBJCVRLNRBXHG-UHFFFAOYSA-N
InChI=1S/C10H7N3S.ClH/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9;/h1-6H,(H,12,13);1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C10H7N3S |
| Molecular Weight | 201.248 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|---|
Target ID: CHEMBL2095182 |
|||
Target ID: O06913 Gene ID: 900116.0 Gene Symbol: frdA Target Organism: Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacter|||pylori) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | MINTEZOL Approved UseMINTEZOL 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 Date1967 |
|||
| Curative | MINTEZOL Approved UseMINTEZOL 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 Date1967 |
|||
| Curative | MINTEZOL Approved UseMINTEZOL 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 Date1967 |
|||
| Curative | MINTEZOL Approved UseMINTEZOL 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 Date1967 |
Cmax
| 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 |
T1/2
| 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: |
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) Sources: Epigastralgia (1 patient) Disorientation (1 patient) |
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: |
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
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes [Ki 1.54 uM] | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Toxocariasis]. | 2001 Dec |
|
| Prevalence of anthelmintic resistance in gastrointestinal nematodes of dairy goats under extensive management conditions in southwestern France. | 2001 Dec |
|
| Capillary zone electrophoresis for the determination of thiabendazole, prochloraz and procymidone in grapes. | 2001 Dec |
|
| Determination of levamisole in animal tissues using liquid chromatography with ultraviolet detection. | 2001 Dec |
|
| [Strongyloides stercoralis infestation in patients with chronic obstructive lung disease in Vega del Segura (Murcia). 3 case reports]. | 2001 Feb |
|
| Myosin V-mediated vacuole distribution and fusion in fission yeast. | 2001 Jul 24 |
|
| Bob1, a Gim5/MM-1/Pfd5 homolog, interacts with the MAP kinase kinase Byr1 to regulate sexual differentiation in the fission yeast, Schizosaccharomyces pombe. | 2001 Jun |
|
| Mixed-mode solid-phase extraction and cleanup procedures for the liquid chromatographic determination of thiabendazole and carbendazim in fruit juices. | 2001 Mar-Apr |
|
| Case study: Fatal strongyloidiasis associated with human T-cell lymphotropic virus type 1 infection. | 2001 Nov |
|
| An in vivo evaluation of induction of abnormal sperm morphology by some anthelmintic drugs in mice. | 2001 Oct 18 |
|
| Anthelmintics: a review. | 2001 Oct-Dec |
|
| PKC1, a protein kinase C homologue of Saccharomyces cerevisiae, participates in microtubule function through the yeast EB1 homologue, BIM1. | 2001 Sep |
|
| Application of a mixed-mode solid-phase extraction and cleanup procedure for LC/MS determination of thiabendazole and carbendazim in apple juice. | 2001 Sep-Oct |
|
| Evaluation of certain veterinary drug residues in food. | 2002 |
|
| 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 |
|
| Oxidative, heat and anthelminthic stress responses in four species of Trichinella: comparative study. | 2002 Dec 1 |
|
| 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 |
|
| One confirmed and six suspected cases of cutaneous larva migrans caused by overseas infection with dog hookworm larvae. | 2002 Feb |
|
| Nematocidal activity of isoquinoline alkaloids against a species of diplogastridae. | 2002 Feb |
|
| Involvement of Nst1p/YNL091w and Msl1p, a U2B'' splicing factor, in Saccharomyces cerevisiae salt tolerance. | 2002 Feb |
|
| Prevalence of levamisole and benzimidazole resistance in oesophagostomum populations of pig-breeding farms in North Rhine-Westphalia, Germany. | 2002 Jan |
|
| Complexation of several benzimidazole-type fungicides with alpha- and beta-cyclodextrins. | 2002 Jan 2 |
|
| Contact dermatitis caused by pesticides among banana plantation workers in Panama. | 2002 Jan-Mar |
|
| 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 |
|
| 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 |
|
| The effects of stage-specific selection on the development of benzimidazole resistance in Haemonchus contortus in sheep. | 2002 Oct 16 |
|
| 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 |
|
| 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 |
|
| Fission yeast Rad26 responds to DNA damage independently of Rad3. | 2003 Apr 3 |
|
| [Strongyloidiasis]. | 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:50:53 GMT 2023
by
admin
on
Fri Dec 15 19:50:53 GMT 2023
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| Record UNII |
N3B9AKC0T9
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| Record Status |
Validated (UNII)
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| Record Version |
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