Details of the Drug

General Information of Drug (ID: DM7YCK3)

Drug Name

Thiabendazole

Synonyms

Biogard; Bioguard; Bovizole; Cropasal; Drawipas; Eprofil; Equizole; Hymush; Lombristop; Mertec; Mertect; Mintesol; Mintezol; Mintezole; Minzolum; Mycozol; Nemacin; Nemapan; Omnizole; Ormogal; Pitrizet; Polival; RPH; Sistesan; Storite; Tbdz; Tebuzate; Tecto; Testo; Thiaben; Thiabendazol; Thiabendazolum; Thiabendole; Thiabenzazole; Thiabenzole; Thibendole; Thibenzol; Thibenzole; Thiprazole; Tiabenda; Tiabendazol; Tiabendazole; Tiabendazolum; Tobaz; Tresaderm; Triasox; Tubazole; Captan T; Equivet TZ; Equizole A; Helmindrax octelmin; Hokustar HP; Mertect lsp; RTU Flowable Fungicide; Tecto B; Tecto rph; Thibenzole att; Top Form Wormer; Chemviron TK 100; G 491; MK 360; Mertect 160; Mertect 340f; Metasol TK 100; Metasol tk 10; PS1057_SUPELCO; Sanaizol 100; Syntol M100; TBZ 6; TBZ 60W; Tecto 10P; Tecto 40F; Tecto 60; Thibenzole 200; Tibimix 20; APL-luster; Arbotect (TN); MK-360; Metasol TK-100; Mintezol (TN); TBZ-6; Thiabendazole (USP); Thiabendazole [BSI:ISO]; Thiabendazole [USAN:BAN]; Tiabendazolum [INN-Latin]; Tresaderm (TN); E-Z-Ex; Mintezol, Equizole, Thiabendazole; Tiabendazol [INN-Spanish, French]; Tiabendazole (JAN/INN); 2-(1,3-Thiazol-4-yl)-1H-benzimidazole; 2-(1,3-Thiazol-4-yl)benzimidazole; 2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole; 2-(4'-Thiazolyl)benzimidazole; 2-(4-Thiazolyl)-1H-benzimidazole; 2-(4-Thiazolyl)benzimidazole; 2-(Thiazol-4-yl)benzimidazole; 2-Thiazol-4-yl-1H-benzoimidazole; 2-Thiazole-4-ylbenzimidazole; 2-[4-Thiazoly]benzimidazole; 4-(1H-benzimidazol-2-yl)-1,3-thiazole; 4-(2-Benzimidazolyl)thiazole

Indication

Disease Entry	ICD 11	Status	REF
Ascariasis	1F62	Approved	[1]
Dutch elm disease	8D64	Approved	[2]
Enterobiasis	1F65	Approved	[1]
Helminth infection	1F90.0	Approved	[2]
Leptospira infection	1B91	Approved	[1]
Strongyloidiasis	N.A.	Approved	[1]
Trichuris trichiura infection	1F6G	Approved	[1]
Toxocariasis	N.A.	Investigative	[1]
Trichinellosis	N.A.	Investigative	[1]
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Therapeutic Class

Antinematodal Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

201.25

Logarithm of the Partition Coefficient (xlogp)

2.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Elimination: 0.1% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.2 hours [4]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 212.95326 micromolar/kg/day [5]
Water Solubility: The ability of drug to dissolve in water is measured as 0.05 mg/mL [3]

Chemical Identifiers

Formula: C10H7N3S
IUPAC Name: 4-(1H-benzimidazol-2-yl)-1,3-thiazole
Canonical SMILES: C1=CC=C2C(=C1)NC(=N2)C3=CSC=N3
InChI: InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)
InChIKey: WJCNZQLZVWNLKY-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5430
ChEBI ID: CHEBI:45979
CAS Number: 148-79-8
DrugBank ID: DB00730
TTD ID: D08QCJ
VARIDT ID: DR00867
INTEDE ID: DR1578

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Fumarate reductase flavoprotein (Bact frdA)	TTHDSE2	FRDA_HELPY	Inhibitor	[6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 1A2 (CYP1A2)_{Main DME}	DEJGDUW	CP1A2_HUMAN	Substrate	[7]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[8]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[9]
Cytochrome P450 2B6 (CYP2B6)	OTOYO4S7	CP2B6_HUMAN	Gene/Protein Processing	[9]
Cytochrome P450 2C9 (CYP2C9)	OTGLBN29	CP2C9_HUMAN	Gene/Protein Processing	[10]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[9]
Myeloperoxidase (MPO)	OTOOXLIN	PERM_HUMAN	Regulation of Drug Effects	[11]
Nuclear receptor subfamily 1 group I member 2 (NR1I2)	OTC5U0N5	NR1I2_HUMAN	Gene/Protein Processing	[12]
Utrophin	OT7TZ637	UTRN_HUMAN	Gene/Protein Processing	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Thiabendazole (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Aminophylline	DML2NIB	Moderate	Decreased metabolism of Thiabendazole caused by Aminophylline.	Asthma [CA23]	[14]
Roflumilast	DMPGHY8	Moderate	Decreased metabolism of Thiabendazole caused by Roflumilast mediated inhibition of CYP450 enzyme.	Asthma [CA23]	[15]
Obeticholic acid	DM3Q1SM	Moderate	Decreased metabolism of Thiabendazole caused by Obeticholic acid mediated inhibition of CYP450 enzyme.	Autoimmune liver disease [DB96]	[16]
Levobupivacaine	DM783CH	Moderate	Decreased metabolism of Thiabendazole caused by Levobupivacaine mediated inhibition of CYP450 enzyme.	Corneal disease [9A76-9A78]	[15]
Oxtriphylline	DMLHSE3	Moderate	Decreased metabolism of Thiabendazole caused by Oxtriphylline.	Cough [MD12]	[14]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Thiabendazole caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[17]
PMID28870136-Compound-49	DMTUC9E	Moderate	Decreased metabolism of Thiabendazole caused by PMID28870136-Compound-49 mediated inhibition of CYP450 enzyme.	Discovery agent [N.A.]	[18]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Thiabendazole caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[15]
Teriflunomide	DMQ2FKJ	Moderate	Increased metabolism of Thiabendazole caused by Teriflunomide mediated induction of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[19]
Pirfenidone	DM6VZFQ	Moderate	Decreased metabolism of Thiabendazole caused by Pirfenidone mediated inhibition of CYP450 enzyme.	Idiopathic interstitial pneumonitis [CB03]	[15]
Givosiran	DM5PFIJ	Moderate	Decreased metabolism of Thiabendazole caused by Givosiran mediated inhibition of CYP450 enzyme.	Inborn porphyrin/heme metabolism error [5C58]	[20]
Ramelteon	DM7IW9J	Moderate	Decreased metabolism of Thiabendazole caused by Ramelteon mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[21]
Tasimelteon	DMLOQ1V	Moderate	Decreased metabolism of Thiabendazole caused by Tasimelteon mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[22]
Alosetron	DML2A03	Moderate	Decreased metabolism of Thiabendazole caused by Alosetron mediated inhibition of CYP450 enzyme.	Irritable bowel syndrome [DD91]	[23]
Capmatinib	DMYCXKL	Moderate	Decreased metabolism of Thiabendazole caused by Capmatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[24]
Vemurafenib	DM62UG5	Moderate	Decreased metabolism of Thiabendazole caused by Vemurafenib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[25]
Exjade	DMHPRWG	Moderate	Decreased metabolism of Thiabendazole caused by Exjade mediated inhibition of CYP450 enzyme.	Mineral absorption/transport disorder [5C64]	[26]
Olaparib	DM8QB1D	Moderate	Increased metabolism of Thiabendazole caused by Olaparib mediated induction of CYP450 enzyme.	Ovarian cancer [2C73]	[19]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Thiabendazole caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[27]
Rasagiline	DM3WKQ4	Major	Decreased metabolism of Thiabendazole caused by Rasagiline mediated inhibition of CYP450 enzyme.	Parkinsonism [8A00]	[19]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Thiabendazole caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[28]
Asenapine	DMSQZE2	Moderate	Decreased metabolism of Thiabendazole caused by Asenapine mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[29]
Pimozide	DMW83TP	Moderate	Decreased metabolism of Thiabendazole caused by Pimozide mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[30]
Pomalidomide	DMTGBAX	Moderate	Decreased clearance of Thiabendazole due to the transporter inhibition by Pomalidomide.	Systemic sclerosis [4A42]	[19]
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References

1	Thiabendazole FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7304).
3	BDDCS applied to over 900 drugs
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Fumarate reductase is essential for Helicobacter pylori colonization of the mouse stomach. Microb Pathog. 2000 Nov;29(5):279-87.
7	Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.
8	Induction of cytochrome P450 1A1 gene expression, oxidative stress, and genotoxicity by carbaryl and thiabendazole in transfected human HepG2 and lymphoblastoid cells. Biochem Pharmacol. 2001 Feb 15;61(4):399-407.
9	Effect of butylated hydroxytoluene, curcumin, propyl gallate and thiabendazole on cytochrome P450 forms in cultured human hepatocytes. Xenobiotica. 2008 Jun;38(6):574-86.
10	Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.
11	Myeloperoxidase-mediated bioactivation of 5-hydroxythiabendazole: a possible mechanism of thiabendazole toxicity. Toxicol In Vitro. 2011 Aug;25(5):1061-6. doi: 10.1016/j.tiv.2011.04.007. Epub 2011 Apr 12.
12	Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
13	Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. PLoS One. 2011;6(10):e26169. doi: 10.1371/journal.pone.0026169. Epub 2011 Oct 20.
14	Lew G, Murray WE, Lane JR, Haeger E "Theophylline-thiabendazole drug interaction." Clin Pharm 8 (1989): 225-7. [PMID: 2706897]
15	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
16	Product Information. Ocaliva (obeticholic acid). Intercept Pharmaceuticals, Inc., New York, NY.
17	Product Information. Isturisa (osilodrostat). Recordati Rare Diseases Inc, Lebanon, NJ.
18	Magnusson M, Bergstrand IC, Bjorkman S, Heijl A, Roth B, Hoglund P "A placebo-controlled study of retinal blood flow changes by pentoxifylline and metabolites in humans." Br J Clin Pharmacol 61 (2006): 138-47. [PMID: 16433868]
19	Cerner Multum, Inc. "Australian Product Information.".
20	Product Information. Givlaari (givosiran). Alnylam Pharmaceuticals, Cambridge, MA.
21	Product Information. Rozerem (ramelteon). Takeda Pharmaceuticals America, Lincolnshire, IL.
22	Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD.
23	Product Information. Lotronex (alosetron). Glaxo Wellcome, Research Triangle Park, NC.
24	Product Information. Tabrecta (capmatinib). Novartis Pharmaceuticals, East Hanover, NJ.
25	Product Information. Zelboraf (vemurafenib). Genentech, South San Francisco, CA.
26	Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
27	EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
28	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
29	Product Information. Saphris (asenapine). Schering-Plough Corporation, Kenilworth, NJ.
30	Krahenbuhl S, Sauter B, Kupferschmidt H, Krause M, Wyss PA, Meier PJ "Case report: reversible QT prolongation with torsades de pointes in a patient with pimozide intoxication." Am J Med Sci 309 (1995): 315-6. [PMID: 7771501]