2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole

• ChemBase ID: 611
• Molecular Formular: C10H7N3S
• Molecular Mass: 201.24768
• Monoisotopic Mass: 201.03606824
• SMILES: s1cc(nc1)c1[nH]c2c(n1)cccc2
• Canonical SMILES: c1scc(n1)c1nc2c([nH]1)cccc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
• IUPAC Traditional name: thiabendazole; testo; 2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
• Brand Name: Apl-Luster; Arbotect; Bioguard; Bovizole; Chemviron TK 100; Cropasal; Drawipas; Eprofil; Equivet TZ; Equizole; Hokustar hp; Hymush; Lombristop; Mertec; Mertect; Mertect 160; Mertect 340f; Mertect lsp; Metasol TK 100; Metasol TK 10; Mintesol; Mintezol; Minzolum; Mycozol; Nemacin; Nemapan; Omnizole; Ormogal; Polival; RPH; Sanaizol 100; Sistesan; Storite; TBZ 6; TBZ 60W; Tebuzate; Tecto; Tecto 10P; Tecto 40F; Tecto 60; Tecto B; Tecto rph; Testo; Thiaben; Thibendole; Thibenzol; Thibenzole; Thibenzole 200; Thibenzole att; Thiprazole; Tiabenda; Tibimix 20; Tobaz; Top form wormer; Triasox; Tubazole
• Synonyms: TBDZ; TBZ; Thiabendazol; Thiabendole; Thiabenzazole; Thiabenzole; Tiabendazol; Tiabendazole; Thiabendazole; 2-(1,3-THIAZOL-4-YL)-1H-BENZIMIDAZOLE; Thiabendazole; Thiprazole; Thibendole; Thibenzole; Mertect; Storite; Tiabendazole; 4-(1H-Benzo[d]imidazol-2-yl)thiazole; 2-[4-Thiazoly]benzimidazole; 2-(4-Thiazolyl)benzimidazole; Mintezol; Equizole; 2-(4-Thiazolyl)-1H-benzimidazole; 4-(2-Benzymidazolyl)thiazole; MK 360; Mertect; Tecto; 2-(4-噻唑基)苯并咪唑; 噻菌灵

Database IDs

• CAS Number: 148-79-8
• EC Number: 205-725-8
• MDL Number: MFCD00005587
• Beilstein Number: 611403
• PubChem SID: 24900297; 24869246; 24899102; 46505131; 160964074; 24900571
• PubChem CID: 5430
• E Number: E233

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.276095
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.313469
• LogD (pH = 7.4): 2.3282127
• Log P: 2.3289173
• Molar Refractivity: 64.9065 cm^3
• Polarizability: 22.712265 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.47
• LOG S: -3.16
• Solubility (Water): 1.38e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Practically insoluble (50 mg/L at pH 7, 10 at 20°C)
• Apperance: light yellow powder; White to Off-White Solid
• Melting Point: >300°C (dec.); 295-305°C
• Hydrophobicity(logP): 2.2

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: DE0700000
• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53; R:51/53
• Safety Statements: 60-61; S:61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Pharmacology Properties

• Gene Information: human ... CYP2C9(1559)
• Mechanism of Action: The precise mode of action of thiabendazole on the parasite is unknown, but it most likely inhibits the helminth-specific enzyme fumarate reductase

Product Information

• Purity: ≥99%; 98%
• Grade: analytical standard; PESTANAL®, analytical standard
• Salt Data: Free Base
• Packaging: ampule of 1000 mg
• Suitability: plant cell culture tested; suitable for 1694 per US EPA
• Application(s): It is a medication that is used in the treatment of a number of parasitic worm infections
• Empirical Formula (Hill Notation): C10H7N3S

DETAILS

MP Biomedicals - 02156843

Light yellow powder

DrugBank - DB00730

• Drug Groups: approved
• Description: 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 CNS side effects and hepatototoxic potential. (From Smith and Reynard, Textbook of Pharmacology, 1992, p919)
• Indication: For the treatment of strongyloidiasis (threadworm), cutaneous larva migrans (creeping eruption), visceral larva migrans, and trichinosis.
• Pharmacology: Thiabendazole is a fungicide and parasiticide. Thiabendazole is also a chelating agent, which means that it is used medicinally to bind metals in cases of metal poisoning, such as lead poisoning, mercury poisoning or antimony poisoning. Thiabendazole is vermicidal and/or vermifugal against Ascaris lumbricoides ("common roundworm"), Strongyloides stercoralis (threadworm), Necator americanus, Ancylostoma duodenale (hookworm), Trichuris trichiura (whipworm), Ancylostoma braziliense (dog and cat hookworm), Toxocara canis, Toxocara cati (ascarids), and Enterobius vermicularis (pinworm). Thiabendazole also suppresses egg and/or larval production and may inhibit the subsequent development of those eggs or larvae which are passed in the feces.
• Toxicity: Overdosage may be associated with transient disturbances of vision and psychic alterations. The oral LD 50 is 3.6 g/kg, 3.1 g/kg and 3.8 g/kg in the mouse, rat, and rabbit respectively.
• Affected Organisms: Roundworms, hookworms, and other helminth species
• Biotransformation: Hepatic. Metabolized almost completely to the 5-hydroxy form which appears in the urine as glucuronide or sulfate conjugates.
• Absorption: Rapidly absorbed and peak plasma concentration is reached within 1 to 2 hours after the oral administration of a suspension. Some systemic absorption may occur from topical preparations applied to the skin.
• Half Life: The half-life for thiabendazole in both normal and anephric patients is 1.2 hours (range 0.9 to 2 hours). The half-life for the 5-hydroxythiabendazole metabolite in both normal and anephric patients is 1.7 hours (range 1.4 to 2 hours).
• Elimination: It is metabolized almost completely to the 5-hydroxy form which appears in the urine as glucuronide or sulfate conjugates.
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB08630

Drug information: experimental

Selleck Chemicals - S1739

Research Area: Infection
Biological Activity:
Thiabendazole inhibites the mitochondrial helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone. [1]A benzimidazole derivative with anthelminthic property. Thiabendazole inhibits the helminth-specific mitochondrial enzyme fumarate reductase, thereby inhibiting the citric acid cycle, mitochondrial respiration and subsequent production of ATP, ultimately leading to helminth’s death. [2]

Sigma Aldrich - T8904

Application
Thiabendazole (TBZ) is a broad-spectrum antihelminthic and is used to treat parasitic infections in humans. It is used as an agricultural fungicide and as a food preservative1. Thiabendazole has been used as a heavy metal chelating detoxification agent. It is used clinically to treat threadworm, cutaneous larva migrans, visceral larva migrans, and trichinosis2.
Biochem/physiol Actions
Thiabendazole inhibits anaerobic respiration at the level of mitochondrial helminth-specific enzyme. It acts as a quinol-fumarate reductase (QFR) inhibitor in ,C. jejuni and H. pylori, blocking quinol oxidation to quinone. Thiabendazole suppresses egg and larval production and may inhibit the subsequent development of eggs and larvae which are passed in feces2. A proposed route of biotransformation of thiabendazole is the CYP1A2-catalyzed hydroxylation to 5-hydroxythiabendazole, which is metabolized to glucuronide and sulfate conjugates1.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - T5535

Application
Thiabendazole, a metal chelator and helminth-specific fumarate reductase inhibitor, is used primarily as an anthelmintic to control infections by helminth organisms. It is also used to control mold and fungal growth in plants.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 45684

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - T344150

A drug used in the treatment of helminthiases.

REFERENCES

• http://en.wikipedia.org/wiki/Tiabendazole
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• Robinson, H.J., et al.: Toxicol. Appl. Pharmacol., 7, 53 (1964)
• Kates, K.C., et al.: J. Parasitol., 57, 356 (1964)
• Kapoor, V.K., et al.: Anal. Profiles Drug Subs., 16, 611 (1964)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 187C, (nmr)
• Brown, H.D. et al., J.A.C.S., 1961, 83, 1764, (synth)
• Grenda, V.J. et al., J.O.C., 1965, 30, 259, (synth, uv)
• Trus, B.L. et al., Acta Cryst. B, 1973, 29, 2298, (cryst struct)
• Daldrup, T. et al., Fresenius' Z. Anal. Chem., 1981, 308, 413, (detn)
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• Tsuchiya, T. et al., Chem. Pharm. Bull., 1987, 35, 2985, (metab, tox)
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• Tada, Y. et al., Food Chem. Toxicol., 1989, 27, 307, (rev, tox)
• Fujitani, T. et al., Food Chem. Toxicol., 1991, 29, 265, (rev, tox)
• Pesticide Manual, 9th edn., 1991, No. 11500
• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A391
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 54
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TEX000