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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
Structure of THIABENDAZOLE PAMOATE

SMILES

N1C(=NC2=C1C=CC=C2)C3=CSC=N3.OC(=O)C4=CC5=C(C=CC=C5)C(CC6=C(O)C(=CC7=C6C=CC=C7)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)

HIDE SMILES / InChI

Molecular Formula C10H7N3S
Molecular Weight 201.248
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H16O6
Molecular Weight 388.3695
Charge 0
Count
MOL RATIO
UNSPECIFIED
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MINTEZOL
Curative
MINTEZOL
Curative
MINTEZOL
Curative
MINTEZOL

Cmax

ValueDoseCo-administeredAnalytePopulation
5 μg/mL
25 mg/kg single, oral
THIABENDAZOLE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.9 μg × min/mL
25 mg/kg single, oral
THIABENDAZOLE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.17 h
25 mg/kg single, oral
THIABENDAZOLE serum
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

PubMed

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
Substance Class Chemical
Record UNII
S5BM1I2UKT
Record Status Validated (UNII)
Record Version