Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H16O6.C10H7N3S |
| Molecular Weight | 589.617 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N1C2=CC=CC=C2N=C1C3=CSC=N3.OC(=O)C4=CC5=CC=CC=C5C(CC6=C(O)C(=CC7=CC=CC=C67)C(O)=O)=C4O
InChI
InChIKey=PTPIORXVQZURBP-UHFFFAOYSA-N
InChI=1S/C23H16O6.C10H7N3S/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-10,24-25H,11H2,(H,26,27)(H,28,29);1-6H,(H,12,13)
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 |
|---|---|---|
| Ecchymoses: an unusual manifestation of toxocariasis in children. | 2001 Dec |
|
| [Toxocariasis]. | 2001 Dec |
|
| Treatment of widespread cutaneous larva migrans with thiabendazole. | 2001 Nov |
|
| Anthelmintics: a review. | 2001 Oct-Dec |
|
| Evaluation of certain veterinary drug residues in food. | 2002 |
|
| 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 |
|
| [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 |
|
| 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 |
|
| Thiabendazole uptake and storage performance of cactus pear [Opuntia ficus-indica (L.) Mill. Cv Gialla] fruit following postharvest treatments with reduced doses of fungicide at 52 degrees C. | 2002 Feb 13 |
|
| Prevalence of levamisole and benzimidazole resistance in oesophagostomum populations of pig-breeding farms in North Rhine-Westphalia, Germany. | 2002 Jan |
|
| Contact dermatitis caused by pesticides among banana plantation workers in Panama. | 2002 Jan-Mar |
|
| [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 |
|
| 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
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67232-46-6
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S5BM1I2UKT
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154731567
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10101-24-3
Created by
admin on Fri Dec 15 16:17:58 GMT 2023 , Edited by admin on Fri Dec 15 16:17:58 GMT 2023
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NON-SPECIFIC STOICHIOMETRY |
SUBSTANCE RECORD
