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 |
|---|---|---|
| Parasitic skin infections in the elderly: recognition and drug treatment. | 2001 |
|
| Developmental toxicity of orally administered thiabendazole in ICR mice. | 2001 Apr |
|
| Thiabendazole induces urinary tract toxicity in male ICR mice. | 2001 Apr 12 |
|
| [Disseminated strongyloidiasis]. | 2001 Apr 28 |
|
| Familial resemblance for free androgens and androgen glucuronides in sedentary black and white individuals: the HERITAGE Family Study. Health, Risk Factors, Exercise Training and Genetics. | 2001 Aug |
|
| Optimization and evaluation of low-pressure gas chromatography-mass spectrometry for the fast analysis of multiple pesticide residues in a food commodity. | 2001 Aug 17 |
|
| Nematocidal activities of thiabendazole and ivermectin against the larvae of Strongyloides ratti and S. venezuelensis. | 2001 Aug 31 |
|
| Prevalence of anthelmintic resistance in gastrointestinal nematodes of dairy goats under extensive management conditions in southwestern France. | 2001 Dec |
|
| Chronic toxicity of thiabendazole (TBZ) in CD-1 mice. | 2001 Dec 28 |
|
| [Anisakiasis of the stomach--a case report from Germany]. | 2001 Feb |
|
| Induction of cytochrome P450 1A1 gene expression, oxidative stress, and genotoxicity by carbaryl and thiabendazole in transfected human HepG2 and lymphoblastoid cells. | 2001 Feb 15 |
|
| Treatment of larva migrans cutanea (creeping eruption): a comparison between albendazole and traditional therapy. | 2001 Jan |
|
| Prurigo in a patient with intestinal strongyloidiasis. | 2001 Jan |
|
| The Aspergillus nidulans bncA1 mutation causes defects in the cell division cycle, nuclear movement and developmental morphogenesis. | 2001 Jan |
|
| Screening for Strongyloides infection among the institutionalized mentally disabled. | 2001 Jan-Feb |
|
| Cutaneous larva migrans contracted in England: a reminder. | 2001 Jul |
|
| Pesticide residues in oranges from Valencia (Spain). | 2001 Jul |
|
| Myosin V-mediated vacuole distribution and fusion in fission yeast. | 2001 Jul 24 |
|
| Analysis of post-harvest fungicides by micellar electrokinetic chromatography. | 2001 Jul 27 |
|
| In vitro study on thiabendazole action on viability of Ascaris lumbricoides (Lineu, 1758) eggs. | 2001 Jul-Aug |
|
| Mixed-mode solid-phase extraction and cleanup procedures for the liquid chromatographic determination of thiabendazole and carbendazim in fruit juices. | 2001 Mar-Apr |
|
| Reproductive and neurobehavioural effects of thiabendazole administered to mice in the diet. | 2001 May |
|
| Treatment of widespread cutaneous larva migrans with thiabendazole. | 2001 Nov |
|
| 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 |
|
| Cutaneous larva migrans: clinical features and management of 44 cases presenting in the returning traveller. | 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 |
|
| 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 |
|
| [Disseminated strongyloidiasis, a rare cause of multiple organ failure]. | 2002 Aug 10 |
|
| Oxidative, heat and anthelminthic stress responses in four species of Trichinella: comparative study. | 2002 Dec 1 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study. | 2002 Jun |
|
| Bud morphogenesis and the actin and microtubule cytoskeletons during budding in the corn smut fungus, Ustilago maydis. | 2002 Nov |
|
| 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 |
|
| 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 |
|
| Simple and rapid determination of thiabendazole, imazalil, and o-phenylphenol in citrus fruit using flow-injection electrospray ionization tandem mass spectrometry. | 2003 Feb 12 |
|
| 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
