| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
| Targets |
Tubulin (microtubule destabilizer) - No IC50/Ki reported. Parbendazole free base binds to tubulin and inhibits polymerization.[1]
DNA damage induction - Not a direct target, but compound induces DNA damage response (fold change >5 in ATAD5-luciferase assay).[1] |
|---|---|
| ln Vitro |
DNA damage can be caused by the tubulin destabilizer palbendazole, which has an EC50 of 530 nM [1]. With an IC50 of 3 μM, parbendazool (2-10 μM) inhibits microtubule assembly in a dose-dependent manner. Vero cells treated with palbendazole (2–20 μM) had no microtubules at all [2]. Palbendazole, at concentrations up to 10 μM, stops CLd-AXE myxamoeba from growing. Effectively inhibiting tubulin isolated from wild-type Myxamoeba is palbendazole (2–5 μM) [3].
Parbendazole free base (EC50 = 0.53 μM) reduced HeLa cell viability in a dose-dependent manner. It was among 14 known anticancer drugs identified as tubulin targeting agents (microtubule destabilizer).[1] Parbendazole free base induced a potent DNA damage response (>5 fold increase in luciferase activity relative to DMSO control) in a HEK293T ATAD5-luciferase genotoxicity reporter assay after 18 h treatment at 50 μM.[1] In HeLa and U2OS cells treated with Parbendazole free base at its EC90 for 4 h, immunofluorescence staining showed increased percentage of non-mitotic cells with >5 pH2AX foci and pCHK2 foci, indicating DNA damage. The compound also destabilized cytoplasmic microtubules, as evidenced by lack of polymerized microtubules.[1] Cell cycle profiling of HeLa cells treated with 10 μM Parbendazole free base for 20 h showed a distinct cell cycle fingerprint (as part of the 36 most potent compounds) that clustered with other tubulin destabilizers and DNA damaging agents.[1] |
| ln Vivo |
Wild-type myxamoebae (CLd-AXE) of Physarum polycephalum were sensitive to all concentrations of Parbendazole free base tested, with complete growth inhibition at 2 μM. Mutant myxamoebae (BEN210-AXE) were able to grow in at least 10 μM parbendazole. Both strains reached the same stationary phase density (3×10⁷ cells/ml), with doubling times of 18 h for wild-type and 24 h for mutant.[3]
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| Cell Assay |
Cell cycle profiling: HeLa cells were plated in 384-well plates (1500 cells/well) and treated with 10 μM Parbendazole free base for 20 h. Cells were fixed, stained with 5 μM Vybrant DyeCycle Green, and scanned with an Acumen eX3 fluorescence cytometer (488 nm laser). Cell cycle histogram profiles were generated for each well, and percentages of cells in G1, S, G2/M, and subG1 phases were calculated. A cell cycle index (CCI) based on Euclidean distance from DMSO control was computed.[1]
Cell viability assay: HeLa cells (5×10⁴ cells/ml) were treated with Parbendazole free base at 50 μM final concentration in 384-well plates for 72 h. Cell viability was measured using CellTiterGlo reagent (Promega) and luminescence recorded. An 8-point serial dilution (from 50,000 μM to 4 μM) was used to determine EC50 (0.53 μM). The same assay was performed on HCT116, U2OS, and A549 cells for selected compounds.[1] High-throughput genotoxicity assay: HEK293T ATAD5-luciferase cells (1500 cells/well) were treated with Parbendazole free base at 50 μM for 18 h. ATAD5-luciferase activity was measured using ONE-Glo luciferase assay system. Fold change in luciferase activity per cell was calculated relative to DMSO control.[1] Immunofluorescence microscopy: HeLa and U2OS cells were treated with Parbendazole free base at its EC90 for 4 h, then fixed and stained with antibodies against α-tubulin, phospho-Ser139-histone H2A.X (pH2AX), and phospho-Thr68-Chk2 (pCHK2). Cells were imaged and the percentage of non-mitotic cells with >5 pH2AX or pCHK2 foci was quantified from three independent triplicate experiments.[1] |
| Toxicity/Toxicokinetics |
No specific toxicity data reported. The drug is FDA-approved for anthelmintic use with established safety profile. In this study, at concentrations up to 50 μM in cell culture, no overt cytotoxicity beyond the antiproliferative effect was noted beyond the EC50 determination.[1]
|
| 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]. 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. [3]. 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 |
| Additional Infomation |
Crystals or white fine powder. (NTP, 1992)
Methyl N-(6-butyl-1H-benzimidazole-2-yl)carbamate is a carbamate belonging to the benzimidazole class of compounds. Parbendazole free base is an FDA-approved anthelmintic drug that was found to have unexpected anticancer activity. It destabilizes microtubules and induces DNA damage, as shown by increased pH2AX and pCHK2 foci. Its cell cycle profile clustered with other tubulin destabilizers (colchicine, fenbendazole, mebendazole) and also with DNA damaging agents (chlorambucil, etoposide). The 3D chemical similarity network showed parbendazole linked to chlorambucil, and fragment enrichment analysis identified methoxy and carbonyl groups as common motifs in compounds with dual microtubule and DNA damaging activities.[1] |
| Molecular Formula |
C13H17N3O2
|
|---|---|
| Molecular Weight |
247.298
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| Exact Mass |
247.132
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| CAS # |
14255-87-9
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| Related CAS # |
Parbendazole-d3;1613439-58-9
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| PubChem CID |
26596
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| Appearance |
White to light yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Melting Point |
255-257°C
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| Index of Refraction |
1.632
|
| LogP |
3.57
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
5
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| Heavy Atom Count |
18
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| Complexity |
285
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O(C([H])([H])[H])C(N([H])C1=NC2C([H])=C([H])C(=C([H])C=2N1[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
|
| InChi Key |
YRWLZFXJFBZBEY-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H17N3O2/c1-3-4-5-9-6-7-10-11(8-9)15-12(14-10)16-13(17)18-2/h6-8H,3-5H2,1-2H3,(H2,14,15,16,17)
|
| Chemical Name |
methyl N-(6-butyl-1H-benzimidazol-2-yl)carbamate
|
| Synonyms |
ParbendazoleHelatacPBZ SKF 29044 PBZ (fungicide) HelmatacSKF-29044 SKF29044
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~4 mg/mL (~16.18 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 0.4 mg/mL (1.62 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 4.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 0.4 mg/mL (1.62 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 4.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 0.4 mg/mL (1.62 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0437 mL | 20.2184 mL | 40.4367 mL | |
| 5 mM | 0.8087 mL | 4.0437 mL | 8.0873 mL | |
| 10 mM | 0.4044 mL | 2.0218 mL | 4.0437 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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