Repositioning Candidate Details
| Candidate ID: | R1373 |
| Source ID: | DB11386 |
| Source Type: | approved; investigational; vet_approved |
| Compound Type: | small molecule |
| Compound Name: | Chlorobutanol |
| Synonyms: | Chloretone; Chlorobutanol |
| Molecular Formula: | C4H7Cl3O |
| SMILES: | CC(C)(O)C(Cl)(Cl)Cl |
| Structure: |
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| DrugBank Description: | Chlorobutanol, or chlorbutol, is an alcohol-based preservative with no surfactant activity . It also elicits sedative-hypnotic and weak local anesthetic actions in addition to antibacterial and antifungal properties. Similar in nature to chloral hydrate, it is formed by the simple nucleophilic addition of chloroform and acetone. As a long-term stabilizer of multi-ingredient preparations, chlorobutanol is normally used at a concentration of 0.5%. At this concentration, it also conserves its antimicrobial activity. Due to the long terminal half-life of 37 days, the use of chlorobutanol as a sedative is limited because of the considerable accumulation which will occur following multiple dosing . Chlorobutanol is a common detergent preservative in eye drops and other ophthalmic therapeutic formulations . |
| CAS Number: | 57-15-8 |
| Molecular Weight: | 177.45 |
| DrugBank Indication: | No approved therapeutic indications on its own. |
| DrugBank Pharmacology: | Chlorobutanol is a detergent preservative with a broad spectrum of antimicrobial activity . _In vitro_, chlorobutanol demonstrated to inhibit platelet aggregation and release via unknown mechanisms . A study proposes that the antiplatelet effect of chlorobutanol may occur from inhibition of the arachidonic acid pathway . It attenuated thromboxane B2 formation, elevation of cytosolic free calcium, and ATP release, and additionally exhibited a significant inhibitory activity toward several aggregation inducers in a time- and concentration-dependent manner . Chlorobutanol may exert a direct negative inotropic effect on myocardial cells to isometric tension produced by the heart . Chlorobutanol was shown to induce conjunctival and corneal cell toxicity _in vitro_: at a concentration of 0.1%, Cbl caused near depletion of the squamous layer while degeneration of corneal epithelial cells, generation of conspicuous membranous blebs, cytoplasmic swelling, and occasional breaks in the external cell membrane were observed at a concentration of 0.5% . |
| DrugBank MoA: | As a detergent, chlorobutanol disrupts the lipid structure of the cell membrane and increases the cell permeability, leading to cell lysis . It induces conjunctival and corneal cell toxicity via causing cell retraction and cessation of normal cytokines, cell movement, and mitotic activity . It disrupts the barrier and transport properties of the corneal epithelium as well as inhibits the utilization of oxygen by the cornea . Chlorobutanol also inhibits oxygen use by the cornea, which increases susceptibility to infection . |
| Targets: | Potassium voltage-gated channel subfamily H member 2 |
| Inclusion Criteria: | Therapeutic strategy associated |
| Strategy ID | Strategy | Synonyms | Related Targets | Related Drugs |
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| Target ID | Target Name | GENE | Action | Class | UniProtKB ID | Entry Name | |
|---|---|---|---|---|---|---|---|
| T18 | Acetyl-CoA carboxylase 1 | ACACA | inhibitor | Enzyme | Q13085 | ACACA_HUMAN | Details |
| T21 | Diacylglycerol O-acyltransferase 2 | DGAT2 | inhibitor | Enzyme | Q96PD7 | DGAT2_HUMAN | Details |
| T07 | Bile acid receptor | NR1H4 | agonist | Nuclear hormone receptor | Q96RI1 | NR1H4_HUMAN | Details |
| Diseases ID | DO ID | Disease Name | Definition | Class |
|---|