thiabendazole Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anthelminthics, tiabendazole derivatives 2621 148-79-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • thiabendazole
  • thiabendazol
  • thiabendole
  • thiabenzole
  • thibendole
  • thibenzol
  • thibenzole
  • tiabendazol
  • tiabendazole
  • bovizole
  • equizole
  • mintesol
  • mintezol
  • minzolum
  • omnizole
2-Substituted benzimidazole first introduced in 1962. It is active against a variety of nematodes and is the drug of choice for STRONGYLOIDIASIS. It has CENTRAL NERVOUS SYSTEM side effects and hepatototoxic potential. (From Smith and Reynard, Textbook of Pharmacology, 1992, p919)
  • Molecular weight: 201.25
  • Formula: C10H7N3S
  • CLOGP: 2.36
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 41.57
  • ALOGS: -3.16
  • ROTB: 1

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
3 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.05 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 212.95 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
April 7, 1967 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 9.68 0 3 6 101621 2256455

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Strongyloidiasis 34.81 0 4 4 426 1746347
Drug ineffective 14.83 0 4 4 63797 1682976

Pharmacologic Action:

SourceCodeDescription
ATC D01AC06 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Imidazole and triazole derivatives
ATC P02CA02 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTHELMINTICS
ANTINEMATODAL AGENTS
Benzimidazole derivatives
FDA EPC N0000175481 Antihelminthic
CHEBI has role CHEBI:86328 antifungal agrochemical
CHEBI has role CHEBI:35444 antinematodal drug
MeSH PA D000871 Anthelmintics
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000977 Antiparasitic Agents
FDA EPC N0000175481 Anthelmintic

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Infection by Strongyloides indication 1214006 DOID:10955
Ascariasis indication 2435008 DOID:456
Trichuriasis indication 3752003
Cutaneous larva migrans indication 19362000
Infection by larvae of Trichinella spiralis indication 88264003
Enterobiasis indication 266162007
Infection due to Toxocara indication 406619001
Infection by Uncinaria indication 414490001
Ancylostoma Duodenale Infection indication
Necator Americanus Infection indication
Trichostrongyliasis off-label use 33710003 DOID:1254
Capillaria infection off-label use 52979002 DOID:12474
Infection by Baylisascaris off-label use 91156005
Infection by Dracunculus medinensis off-label use 396334002 DOID:14418
Hepatic failure contraindication 59927004
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.12 acidic
pKa2 4.62 Basic
pKa3 1.83 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Methionine aminopeptidase 2 Enzyme IC50 4.35 CHEMBL
Methionine aminopeptidase 1 Enzyme EC50 5.47 CHEMBL
Peptidyl-prolyl cis-trans isomerase FKBP1A Enzyme Kd 4.22 CHEMBL
Cytochrome P450 1A2 Enzyme IC50 6.10 DRUG MATRIX
Tubulin Structural INHIBITOR CHEMBL CHEMBL
Tubulin Structural INHIBITOR CHEMBL CHEMBL
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Enzyme WOMBAT-PK
Reverse transcriptase/RNaseH Enzyme IC50 4.84 CHEMBL
Methionine aminopeptidase Enzyme IC50 6.33 CHEMBL

External reference:

IDSource
4017955 VUID
N0000146305 NUI
C0039832 UMLSCUI
D00372 KEGG_DRUG
36594001 SNOMEDCT_US
4017955 VANDF
416624006 SNOMEDCT_US
80871 MMSL
10450 RXNORM
5565 MMSL
d00160 MMSL
002985 NDDF
5430 PUBCHEM_CID
CHEBI:45979 CHEBI
CHEMBL625 ChEMBL_ID
DB00730 DRUGBANK_ID
N1Q45E87DT UNII
1436 INN_ID
D013827 MESH_DESCRIPTOR_UI
7304 IUPHAR_LIGAND_ID

Pharmaceutical products:

None