CAS 14255-87-9|Parbendazole
Introduction：Basic information about CAS 14255-87-9|Parbendazole, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Parbendazole | ||
|---|---|---|---|
| CAS Number | 14255-87-9 | Molecular Weight | 247.293 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | / |
| Molecular Formula | C13H17N3O2 | Melting Point | 255-257°C |
| MSDS | ChineseUSA | Flash Point | / |
| Symbol | GHS07, GHS08 | Signal Word | Warning |
Names
| Name | Parbendazole |
|---|---|
| Synonym | More Synonyms |
Parbendazole BiologicalActivity
| Description | Parbendazole is a potent inhibitor of microtubule assembly, destabilizes tubulin, with an EC50 of 8.79 nM, and exhibits a broad-spectrum anthelmintic activity. |
|---|---|
| Related Catalog | Signaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinSignaling Pathways >>Cytoskeleton >>Microtubule/TubulinResearch Areas >>Infection |
| Target | EC50: 8.79 nM (tubulin)[1] |
| In Vitro | Parbendazole is a tubulin destabilizer, with an EC50 of 8.79 nM, and can induce DNA damage[1]. Parbendazole (2-10 μM) inhibits the assembly of microtubules dose-dependently, with an IC50 of 3 μM. Parbendazole (2-20 μM)-treated cells show an complete absence of microtubules in Vero cells[2]. Parbendazole (up to 10 μM) inhibits the growth of CLd-AXE myxamoebae. Parbendazole (2-5 μM) potently inhibits tubulin purified from the wild-type myxamoebae[3]. |
| Kinase Assay | Pure tubulin is obtained from sheep brain by 2 cycles of assembly and disassembly in vitro. Immediately prior to use the protein is centrifuged at 130000 g for 30 min to remove any aggregates. It is used at a protein concentration of 0-2 mg/mL in 0.025 M Pipes buffer, 0-5 mM EGTA, 0-25 mM Mg2SOsup>4, 0.1 mM GTP. Drug binding is determined by equilibrium dialysis using concentrations of parbendazole between 0.1 μM and 4 μM, and 2% (v/v) DMF (dimethyl formamide) as a carrier. Equilibrium is achieved by constant stirring for 2 h at 26°C, bovine serum albumin being used as a standard. 200 μL aliquots are counted in PCS in a 25-200B liquid scintillation counter[2]. |
| Cell Assay | Vero cells, an established cell line derived from monkey kidney are seeded in DMEM supplemented with 10% (v/v) foetal calf serum onto glass coverslips in multiwell dishes. They are allowed to settle, and spread for 2-5 h in a humid atmosphere at 37°C. After this time the medium is changed to DMEM containing 2, 10 or 20 μM parbendazole and 1% (v/v) DMSO controls contained 1 % (v/v) DMSO or had no additions[2]. |
| References | [1]. Lo YC, et al. Computational Cell Cycle Profiling of Cancer Cells for Prioritizing FDA-Approved Drugs with Repurposing Potential. Sci Rep. 2017 Sep 12;7(1):11261. [2]. Lo YC, et al. Computational Cell Cycle Profiling of Cancer Cells for Prioritizing FDA-Approved Drugs with Repurposing Potential. Sci Rep. 2017 Sep 12;7(1):11261. [3]. Havercroft JC, et al. Binding of parbendazole to tubulin and its influence on microtubules in tissue-culture cells as revealed by immunofluorescence microscopy. J Cell Sci. 1981 Jun;49:195-204. [4]. Havercroft JC, et al. Binding of parbendazole to tubulin and its influence on microtubules in tissue-culture cells as revealed by immunofluorescence microscopy. J Cell Sci. 1981 Jun;49:195-204. [5]. Foster KE, et al. A mutant beta-tubulin confers resistance to the action of benzimidazole-carbamate microtubule inhibitors both in vivo and in vitro. Eur J Biochem. 1987 Mar 16;163(3):449-55. [6]. Foster KE, et al. A mutant beta-tubulin confers resistance to the action of benzimidazole-carbamate microtubule inhibitors both in vivo and in vitro. Eur J Biochem. 1987 Mar 16;163(3):449-55. |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Melting Point | 255-257°C |
| Molecular Formula | C13H17N3O2 |
| Molecular Weight | 247.293 |
| Exact Mass | 247.132080 |
| PSA | 67.01000 |
| LogP | 3.57 |
| Index of Refraction | 1.632 |
| InChIKey | YRWLZFXJFBZBEY-UHFFFAOYSA-N |
| SMILES | CCCCc1ccc2nc(NC(=O)OC)[nH]c2c1 |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Water Solubility | <0.1 g/100 mL at 18 ºC |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >40 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1700 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Bird - chicken
- DOSE/DURATION :
- >40 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - domestic
- DOSE/DURATION :
- 660 mg/kg
- TOXIC EFFECTS :
- Gastrointestinal - ulceration or bleeding from stomach
- TYPE OF TEST :
- LD - Lethal dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Mammal - cattle
- DOSE/DURATION :
- >1200 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Mammal - cattle
- DOSE/DURATION :
- 450 mg/kg/6D-I
- TOXIC EFFECTS :
- Gastrointestinal - other changes
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 1200 mg/kg
- SEX/DURATION :
- female 7-18 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - gastrointestinal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 80 mg/kg
- SEX/DURATION :
- female 8-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 80 mg/kg
- SEX/DURATION :
- female 8-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 150 mg/kg
- SEX/DURATION :
- female 8-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 80 mg/kg
- SEX/DURATION :
- female 8-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 4 gm/kg
- SEX/DURATION :
- female 6-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - respiratory system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 90 mg/kg
- SEX/DURATION :
- female 13 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 400 mg/kg
- SEX/DURATION :
- female 6-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 10 gm/kg
- SEX/DURATION :
- female 6-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 16 gm/kg
- SEX/DURATION :
- female 6-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - urogenital system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 130 mg/kg
- SEX/DURATION :
- female 6-18 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - abortion Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 780 mg/kg
- SEX/DURATION :
- female 6-18 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 60 mg/kg
- SEX/DURATION :
- female 21 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - physical
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 30 mg/kg
- SEX/DURATION :
- female 12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - other measures of fertility
MUTATION DATA - TYPE OF TEST :
- Mutation test systems - not otherwise specified
- TEST SYSTEM :
- Mammal - domestic Leukocyte
- DOSE/DURATION :
- 1 mg/L
- REFERENCE :
- THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 31,505,1976
- TYPE OF TEST :
- Mutation test systems - not otherwise specified
- TEST SYSTEM :
- Mammal - domestic Leukocyte
- DOSE/DURATION :
- 1 mg/L
- REFERENCE :
- THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 31,505,1976
Safety Information
| Symbol | GHS07, GHS08 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H361 |
| Precautionary Statements | P280-P301 + P312 + P330 |
| Hazard Codes | Xn |
| Risk Phrases | R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . R36/37/38:Irritating to eyes, respiratory system and skin . |
| Safety Phrases | S26-S36/37/39 |
| RIDADR | 2811 |
| RTECS | DD6495000 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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Synonyms
| methyl5-butyl-2-benzimidazolecarbamate |
| SKandF 29044 |
| TCMDC-131798 |
| Methyl (5-butyl-1H-benzimidazol-2-yl)carbamate |
| Carbamic acid, N-(5-butyl-1H-benzimidazol-2-yl)-, methyl ester |
| EINECS 238-133-3 |
| SK&F 29044 |
| 5-butyl-2-benzimidazolecarbamicacimethylester |
| Methyl (5-butyl-1H-benzoimidazol-2-yl)carbamate |
| helmatac |
| pbdz |
| Methyl (5-butyl-1H-benzo[d]imidazol-2-yl)carbamate |
| Parbendazole |
| verminum |
