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148-79-8 molecular structure
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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 and InChIs

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

Cite this record

CBID:611 http://www.chembase.cn/molecule-611.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.276095  H Acceptors
H Donor LogD (pH = 5.5) 2.313469 
LogD (pH = 7.4) 2.3282127  Log P 2.3289173 
Molar Refractivity 64.9065 cm3 Polarizability 22.712265 Å3
Polar Surface Area 41.57 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.47  LOG S -3.16 
Solubility (Water) 1.38e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Practically insoluble (50 mg/L at pH 7, 10 at 20°C) expand Show data source
Apperance
light yellow powder expand Show data source
White to Off-White Solid expand Show data source
Melting Point
>300°C (dec.) expand Show data source
295-305°C expand Show data source
Hydrophobicity(logP)
2.2 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
DE0700000 expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
UN Number
3077 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Hazard Class
9 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
50/53 expand Show data source
R:51/53 expand Show data source
Safety Statements
60-61 expand Show data source
S:61 expand Show data source
GHS Pictograms
GHS09 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H410 expand Show data source
GHS Precautionary statements
P273-P501 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Gloves expand Show data source
RID/ADR
UN 3077 9/PG 3 expand Show data source
Gene Information
human ... CYP2C9(1559) expand Show data source
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 expand Show data source
Purity
≥99% expand Show data source
98% expand Show data source
Grade
analytical standard expand Show data source
PESTANAL®, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Packaging
ampule of 1000 mg expand Show data source
Suitability
plant cell culture tested expand Show data source
suitable for 1694 per US EPA expand Show data source
Application(s)
It is a medication that is used in the treatment of a number of parasitic worm infections expand Show data source
Empirical Formula (Hill Notation)
C10H7N3S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02156843 external link
Light yellow powder
DrugBank - DB00730 external link
Item Information
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 external link
Drug information: experimental
Selleck Chemicals - S1739 external link
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 external link
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 external link
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 external link
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH
Toronto Research Chemicals - T344150 external link
A drug used in the treatment of helminthiases.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  http://en.wikipedia.org/wiki/Tiabendazole
  • • Tocco, D.J., et al.: J. Med. Chem., 7, 399 (1964)
  • • 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)
  • • Kapoor, V.K. et al., Anal. Profiles Drug Subst., 1987, 16, 611, (pharmacol)
  • • Tsuchiya, T. et al., Chem. Pharm. Bull., 1987, 35, 2985, (metab, tox)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1403
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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