6-chloro-5-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-1,3-benzodiazole

• ChemBase ID: 70461
• Molecular Formular: C14H9Cl3N2OS
• Molecular Mass: 359.65806
• Monoisotopic Mass: 357.95011696
• SMILES: c1([nH]c2c(n1)cc(c(c2)Cl)Oc1c(c(ccc1)Cl)Cl)SC
• Canonical SMILES: CSc1[nH]c2c(n1)cc(c(c2)Cl)Oc1cccc(c1Cl)Cl
• InChI: InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19)
• InChIKey: NQPDXQQQCQDHHW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-1,3-benzodiazole; 5-chloro-6-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-1,3-benzodiazole
• IUPAC Traditional name: triclabendazole; 5-chloro-6-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-1,3-benzodiazole
• Synonyms: 6-Chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzo[d]imidazole; 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole; Triclabendazole; Triclabendazole; 6-chloro-5-(2,3-dichlorophenoxy)-2-methylthio-benzimidazole; 5-Chloro-6-(2,3-dichlorophenoxy)-2-methylthiobenzimidazole; CGA-89317, Egaten; Fasinex; 5-氯-6-(2,3-二氯苯氧基)-2-(甲硫基)-1H-苯并咪唑; 三氯苯哒唑

Database IDs

• CAS Number: 68786-66-3
• MDL Number: MFCD00864519; MFCD03147039
• PubChem SID: 162036177
• PubChem CID: 50248
• ATC CODE: P02BX04; QP52AC01
• CHEMBL: 1086440
• Chemspider ID: 45565
• Unique Ingredient Identifier: 4784C8E03O
• Wikipedia Title: Triclabendazole

CALCULATED PROPERTIES

• Acid pKa: 10.456478
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 5.8406267
• LogD (pH = 7.4): 5.8834763
• Log P: 5.8843923
• Molar Refractivity: 87.8559 cm^3
• Polarizability: 35.573475 Å^3
• Polar Surface Area: 37.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Beige Solid
• Melting Point: 175-176°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: DD6747000
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Excretion: >95% in faeces, 2% in urine, and < 1% in milk
• Half Life: 22 - 24 hs
• Metabolism: oxidation to the sulfone and sulfoxide parent compound
• Mechanism of Action: Binds to beta-tubulin and prevent the polymerisation of the microtubules of which they are part

Product Information

• Purity: 95+%; 98%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Description: Tautomers (~1:1)
• Application(s): Anthelmintic (with active sulfoxide metabolite)
• Empirical Formula (Hill Notation): C14H9Cl3N2OS

DETAILS

Sigma Aldrich - 32802

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - T774175

An anthelmintic (fasciola).

REFERENCES

• Wolff, K., et al.: Vet. Parasitol., 13, 145 (1983)
• Ger. Pat., 1978, Ciba-Geigy, 2 815 621; CA, 90, 38919c, (synth, pharmacol)
• Negro, A. et al., J. Chromatogr., 1992, 576, 135, (hplc)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 55
• Stitt, A.W. et al., Parasitol. Res., 1993, 79, 529, (pharmacol)
• Martin, P.A. et al., Vet. Rec., 1993, 133, 300, (tox)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CFL200