Repositioning Candidate Details
| Candidate ID: | R1340 |
| Source ID: | DB11125 |
| Source Type: | approved |
| Compound Type: | small molecule |
| Compound Name: | Benzethonium |
| Synonyms: | -- |
| Molecular Formula: | C27H42NO2 |
| SMILES: | CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1 |
| Structure: |
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| DrugBank Description: | Benzethonium is a synthetic quaternary ammonium salt with surfactant, antiseptic, and broad spectrum antimicrobial properties. Its salt form, benzethonium chloride, is primarily used as a skin disinfectant at concentrations of 0.1-0.2 %, which are safe and effective concentrations for the compound specified by the U.S. Food and Drug Administration (FDA). It is additionally found in cosmetics and toiletries such as mouthwashes and anti-itch ointments. It is shown to be effective in mediating its antimicrobial action against bacteria, fungi, mold and viruses. There is evidence that benzethonium acts as a spermatocide but may cause vaginal irritation . Benzethonium was identified as a novel cancer-specific compound by cell-based small-molecule screen . |
| CAS Number: | 10172-60-8 |
| Molecular Weight: | 412.637 |
| DrugBank Indication: | Indicated as an antiseptic agent. No therapeutic indications for clinical use. |
| DrugBank Pharmacology: | Benzethonium belongs to the family of compounds known as cationic detergents that act by disrupting lipid bilayers. It demonstrated antitumor activity against cancer cell lines in vitro. The effective dose required to decrease cell viability by 50% after 48 hours (ED50) of benzethonium for FaDu (hypopharyngeal squamous cancer) and C666-1 (nasopharyngeal cancer) cell lines were approximately 3.8 and 5.3 μmol/L, respectively . |
| DrugBank MoA: | While exact mechanism of benzethonium is not fully understood, it is proposed that benzethonium acts similarly to other structurally-related quaternary ammonium compounds in disrupting cytoplasmic and outer membrane lipid bilayers of microorganisms . The positively charged quaternary nitrogen associates with the polar head groups of acidic membrane phospholipids, followed by the hydrophobic tail interacting with the hydrophobic membrane core. Benzethonium is thought to form mixed-micelle aggregates with hydrophobic membrane components that solubilize membrane and lyse the cells, leading to leakage of cytoplasmic contents . Based on findings in vitro cell assays, its mode of action on cancer cells may involve cancer cell apoptosis via dysregulating mitochondria or rough endoplasmic reticulum (rER) . It is proposed that intracellular cationic molecules such as benzethonium will create swelling of the rER and damage the organelle. Ultimately, there is a loss in cell membrane integrity and cytosolic Ca2+ levels increase. Dysregulation of mitochondria and rER leads to the activation of caspase-2, caspase-8, caspase-9, and caspase-3 . |
| Targets: | -- |
| Inclusion Criteria: | Therapeutic strategy associated |
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