Repositioning Candidate Details
| Candidate ID: | R1338 |
| Source ID: | DB11117 |
| Source Type: | approved; investigational |
| Compound Type: | small molecule |
| Compound Name: | Undecylenic acid |
| Synonyms: | 10-undecenoic acid; Undecenoic acid; Undecylenate; Undecylenic acid |
| Molecular Formula: | C11H20O2 |
| SMILES: | OC(=O)CCCCCCCCC=C |
| Structure: |
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| DrugBank Description: | Undecylenate, or undecylenic acid, is an unsaturated fatty acid with a terminal double bond that is derived from castor oil. Undecylenic acid is also found naturally in the human sweat. It is used as a precursor in the manufacture of aromatic chemicals, polymers or modified silicones . Undecylenic acid was first isolated from the products of distillation of castor oil in 1877 via pyrolysis of ricinoleic acid, and has been polymerized for vinyl production . It it suggested that many organic fatty acids exert fungicidal or fungistatic actions. Undecylenic acid also possesses antifungal properties, but is never used on its own for antifungal purposes. Salts of undecylenate are found in topical over-the-counter or mixture products as antifungal agents. Zinc undecylenate is an example of a topical antifungal agent that treats skin infections such as athlete’s foot and relieves itching, burning, and irritation associated with the skin condition. Due to its bifunctional properties, undecylenate is also used as a linking molecule to conjugate other biomolecules such as proteins. It serves as an acid moiety for anabolic steroid boldenone. |
| CAS Number: | 112-38-9 |
| Molecular Weight: | 184.2753 |
| DrugBank Indication: | Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own. |
| DrugBank Pharmacology: | Zinc undecylendate acts as a fungistatic agent but fungicidal activity may be observed with chronic exposure in high concentrations . It is effective against _Candida albicans_ . It is proposed that undecylenic acid exerts antimicrobial actions via interacting with nonspecific components in the cell membrane . |
| DrugBank MoA: | Undecylenic acid demonstrated effectiveness against _Candida albicans_, which is an opportunistic pathogenic yeast with two cellular morphologies: the round yeast form and the filamentous form with elongated hyphae. Hyphae formation is associated with active infections and virulence . A study proposed that undecylenic acid inhibits biofilm formation of _Candida albicans_ with optimal concentration above 3 mM and disrupts hyphal growth, which is the morphological transition from yeast to filamentous phase, at concentration above 4 mM . Under the drug treatment, hyphal formation related genes, like HWP1, were significantly reduced in transcriptional level leading to poor biofilm formation . Both biofilm and hyphae formation are critical virulence factors for the initiation of skin infection and late development of disseminated infection . Undecylenic acid may also inhibit enzyme involved in lipid metabolism and abolish germ tube formation by carrying protons across the plasma membrane, thus altering cytoplasmic pH . |
| Targets: | -- |
| Inclusion Criteria: | Therapeutic strategy associated |
| Strategy ID | Strategy | Synonyms | Related Targets | Related Drugs | |
|---|---|---|---|---|---|
| S02 | Enhance lipid metabolism | triglyceride-lowering; lipid tolerance; lipid metabolism | 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) inhibitor; Decreases intestinal cholesterol absorption; FXR agonist; ACC inhibitor; FAS inhibitor; DGAT2 inhibitor; SCD-1 inhibitor | Atorvastatin; Ezetimibe; Obeticholic Acid; GS-9674; GS-0976; TVB-2640; IONIS-DGAT2rx; Aramchol; | Details |
| Target ID | Target Name | GENE | Action | Class | UniProtKB ID | Entry Name |
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| Diseases ID | DO ID | Disease Name | Definition | Class |
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