CAS 148-79-8|thiabendazole|2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole|2-(1,3-THIAZOL-4-YL)-1H-BENZIMIDAZOLE|Equizole|Mintezol|Thiabendazole|2-[4-Thiazoly]benzimidazole|2-(4-噻唑基)苯并咪唑|噻菌灵|Thia...

General Information

Structure

Molecular Formula

C₁₀H₇N₃S

Molecular Mass

201.24768

Exact Mass

201.03606824

Charge

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

Canonic Smiles

c1scc(n1)c1nc2c([nH]1)cccc2

Isomeric Smiles

s1cc(nc1)c1[nH]c2c(n1)cccc2

Calculated Properties

JChem

LogD (pH = 7.4)

2.33

LogD (pH = 5.5)

2.31

Log P

2.33

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

10.28

Polar Surface Area

41.57

Polarizability

21.02

Molar Refractivity

64.91

LOG S

-3.10

Data Source

Names and Identifiers

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

Synonyms

2-(1,3-THIAZOL-4-YL)-1H-BENZIMIDAZOLEEquizoleMintezolThiabendazole2-[4-Thiazoly]benzimidazole噻菌灵2-(4-噻唑基)苯并咪唑ThiabendazoleThiabenzazoleThiabendazolThiabendoleTiabendazolTiabendazoleTBDZTBZThiabenzole2-(4-Thiazolyl)benzimidazole4-(2-Benzymidazolyl)thiazoleMK 360Mertect2-(4-Thiazolyl)-1H-benzimidazoleTecto4-(1H-Benzo[d]imidazol-2-yl)thiazoleStoriteTiabendazoleThiprazoleThibendoleThibenzole; MertectTBZthiabendazole4-(2-benzimidazolyl)thiazole2-(1,3-THIAZOL-4-YL)-1H-BENZIMIDAZOLETiabendazole2-(thiazol-4-yl)benzimidazoleMK 3602-(4-thiazolyl)-1H-benzimidazole2-(1,3-thiazol-4-yl)benzimidazoleThiabendazole

Brand Name

TiabendaArbotectTestoBioguardTectoMetasol TK 100OmnizoleMertect lspTBZ 60WSanaizol 100StoriteThiprazoleBovizoleSistesanDrawipasEquivet TZMertect 340fThibendoleTriasoxMertectLombristopRPHMertect 160Thibenzole 200TBZ 6EprofilChemviron TK 100MertecNemacinMintesolThibenzolTebuzateMinzolumTop form wormerTibimix 20PolivalCropasalMycozolMetasol TK 10TobazApl-LusterTecto BHokustar hpThibenzole attTecto 40FThiabenOrmogalThibenzoleNemapanEquizoleMintezolTubazoleTecto 10PTecto 60HymushTecto rph

API Name

Thiabendazole

Names and Identifiers

Registration numbers

CAS Number

MDL Number

EC Number

Beilstein Number

PubChem SID

248692462490029746505131160964074

Registration numbers

Properties

Physical Property

Safety Information

-20°C

Room Temperature (15-30°C)

Refrigerator

Nature polluting (N)

Pharmacology Properties

human ... CYP2C9(1559)

The precise mode of action of thiabendazole on the parasite is unknown, but it most likely inhibits the helminth-specific enzyme fumarate reductase

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

• Kapoor, V.K., et al.: Anal. Profiles Drug Subs., 16, 611 (1964)

• Kates, K.C., et al.: J. Parasitol., 57, 356 (1964)

• Trus, B.L. et al., Acta Cryst. B, 1973, 29, 2298, (cryst struct)

• Brown, H.D. et al., J.A.C.S., 1961, 83, 1764, (synth)

• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A391

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 187C, (nmr)

• Tada, Y. et al., Food Chem. Toxicol., 1989, 27, 307, (rev, tox)

• Fujitani, T. et al., Food Chem. Toxicol., 1991, 29, 265, (rev, tox)

• Tsuchiya, T. et al., Chem. Pharm. Bull., 1987, 35, 2985, (metab, tox)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 54

• Grenda, V.J. et al., J.O.C., 1965, 30, 259, (synth, uv)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1403

• Pesticide Manual, 9th edn., 1991, No. 11500

• 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)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TEX000

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

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

Synonyms

Brand Name

API Name

Thiabendazole

References

PubChem Literature

From Data Sources

• 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)

• Kapoor, V.K., et al.: Anal. Profiles Drug Subs., 16, 611 (1964)

• Kates, K.C., et al.: J. Parasitol., 57, 356 (1964)

• Trus, B.L. et al., Acta Cryst. B, 1973, 29, 2298, (cryst struct)

• Brown, H.D. et al., J.A.C.S., 1961, 83, 1764, (synth)

• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A391

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 187C, (nmr)

• Tada, Y. et al., Food Chem. Toxicol., 1989, 27, 307, (rev, tox)

• Fujitani, T. et al., Food Chem. Toxicol., 1991, 29, 265, (rev, tox)

• Tsuchiya, T. et al., Chem. Pharm. Bull., 1987, 35, 2985, (metab, tox)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 54

• Grenda, V.J. et al., J.O.C., 1965, 30, 259, (synth, uv)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1403

• Pesticide Manual, 9th edn., 1991, No. 11500

• 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)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TEX000

Bioactivity

PubChem BioAssay

Registration numbers

CAS Number

MDL Number

EC Number

Beilstein Number

PubChem SID

248692462490029746505131160964074

Properties

Physical Property

Safety Information

-20°C

Room Temperature (15-30°C)

Refrigerator

Nature polluting (N)

Pharmacology Properties

human ... CYP2C9(1559)

The precise mode of action of thiabendazole on the parasite is unknown, but it most likely inhibits the helminth-specific enzyme fumarate reductase

Molecule Details

DrugBank

DB00730

Drug Groups

approved

Description

Indication

For the treatment of strongyloidiasis (threadworm), cutaneous larva migrans (creeping eruption), visceral larva migrans, and trichinosis.

Pharmacology

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

Half Life

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]

Molecule

ID:611