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Identification
- Summary
Undecylenic acid is an antifungal used to treat tinea species infections.
- Brand Names
- Fungi-nail, Fungi-nail Toe and Foot, Fungicure Maximum Strength, Sanafitil Antifungal, Terpenicol, Tineacide Antifungal, Ting
- Generic Name
- Undecylenic acid
- DrugBank Accession Number
- DB11117
- Background
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 6. 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 1. 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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Undecylenic acid (DB11117)
- Weight
- Average: 184.2753
Monoisotopic: 184.146329884 - Chemical Formula
- C11H20O2
- Synonyms
- 10-undecenoic acid
- ácido 10-undecenoico
- Undecenoic acid
- Undecylenate
- Undecylenic acid
- External IDs
- Fema no. 3247
Pharmacology
- Indication
Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Ringworm ••• ••• Treatment of Tinea pedis ••• ••• - Contraindications & Blackbox Warnings
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Zinc undecylendate acts as a fungistatic agent but fungicidal activity may be observed with chronic exposure in high concentrations 5. It is effective against Candida albicans 2,3. It is proposed that undecylenic acid exerts antimicrobial actions via interacting with nonspecific components in the cell membrane 4.
- Mechanism of action
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 3. 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 2. Under the drug treatment, hyphal formation related genes, like HWP1, were significantly reduced in transcriptional level leading to poor biofilm formation 2. Both biofilm and hyphae formation are critical virulence factors for the initiation of skin infection and late development of disseminated infection 2. 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 3.
Target Actions Organism ACalpain-1 catalytic subunit other/unknownHumans - Absorption
Undecylenic acid may be absorbed through the skin MSDS.
- Volume of distribution
No information regarding volume of distribution.
- Protein binding
No information regarding protein binding.
- Metabolism
No information regarding metabolism.
- Route of elimination
No information regarding route of elimination.
- Half-life
No information regarding half-life.
- Clearance
No information regarding clearance.
- Adverse Effects
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Acute oral LD50 in rat and mouse are 2500 mg/kg and 8150 mg/kg, respectively MSDS. Acute dermal LD50 in guinea pig and rat are 50 mg/kg and 2000 mg/kg, respectively MSDS. There are no data available on the carcinogenicity, mutagenicity, teratogenicity and developmental toxicity of undecylenate MSDS.
Oral overdosage may lead to gastrointestinal disturbances, and may affect central nervous system (excitement, somnolence, muscle contraction or spasticity, headache, dizziness), and metabolism (loss of appetite). Prolonged or repeated exposure to undecylenate may cause anorexia or weight loss MSDS.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Zinc undecylenate 388VZ25DUR 557-08-4 YMCOHQVWOBMDCZ-UHFFFAOYSA-L - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Anti-Fungal Pen CVS Liquid 25 g/100mL Topical CVS Health 2016-09-15 Not applicable US 
Antifungal Cream 4.8 mg/36.97mL Topical Blaine Labs Inc. 2016-04-01 Not applicable US Athletes Foot Cream 14.77 mg/59.148mL Topical Blaine Labs Inc. 2016-04-01 Not applicable US Botanimedix OnychoRX Antifungal Nail Gel Gel 0.2508 kg/1kg Topical Cosco International, Inc. 2020-01-01 Not applicable US CRYSTAL FLUSH Maximum Strength Anti-Fungal Formula Solution 25 g/100mL Topical Triple Point Group, LLC 2020-09-17 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antifungal Foot Care Undecylenic acid (6 g/100g) + Zinc undecylenate (6 g/100g) Spray Topical Neobourne Pharma Lp 2015-03-16 2017-11-29 US Antifungal Foot Care Undecylenic acid (6 g/100g) + Zinc undecylenate (6 g/100g) Spray Topical Neobourne Pharma Lp 2015-03-16 2017-11-29 US Cruex Antifungal Cream Zinc undecylenate (20 %) + Undecylenic acid (3 %) Cream Topical Ciba Self Medication 1994-12-31 1998-07-06 Canada 
Cruex Antifungal Cream Zinc undecylenate (20 %) + Undecylenic acid (3 %) Cream Topical Ciba Self Medication 1994-12-31 1998-07-06 Canada Cruex Medicated Spray Powder Zinc undecylenate (20 %) + Undecylenic acid (2 %) Aerosol; Powder Topical Ciba Self Medication 1994-12-31 1996-09-09 Canada
Categories
- ATC Codes
- D01AE04 — Undecylenic acid
- D01AE — Other antifungals for topical use
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acids and conjugates
- Direct Parent
- Medium-chain fatty acids
- Alternative Parents
- Unsaturated fatty acids / Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Medium-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- undecenoic acid (CHEBI:35045) / Unsaturated fatty acids (LMFA01030036)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- K3D86KJ24N
- CAS number
- 112-38-9
- InChI Key
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)
- IUPAC Name
- undec-10-enoic acid
- SMILES
- OC(=O)CCCCCCCCC=C
References
- General References
- Ross J, Gebhart AI, Gerecht JF: The Polymerization of Undecylenic Acid Journal of the American Chemical Society. 1945 August 1;67(8):1275-1278. [Article]
- Shi D, Zhao Y, Yan H, Fu H, Shen Y, Lu G, Mei H, Qiu Y, Li D, Liu W: Antifungal effects of undecylenic acid on the biofilm formation of Candida albicans. Int J Clin Pharmacol Ther. 2016 May;54(5):343-53. doi: 10.5414/CP202460. [Article]
- McLain N, Ascanio R, Baker C, Strohaver RA, Dolan JW: Undecylenic acid inhibits morphogenesis of Candida albicans. Antimicrob Agents Chemother. 2000 Oct;44(10):2873-5. [Article]
- Mazu TK, Bricker BA, Flores-Rozas H, Ablordeppey SY: The Mechanistic Targets of Antifungal Agents: An Overview. Mini Rev Med Chem. 2016;16(7):555-78. [Article]
- ZINC COMPOUNDS - National Library of Medicine HSDB ... - Toxnet - NIH [Link]
- Arkema: Oleris® Undecylenic acid [Link]
- DailyMed: Undecylenic Acid topical antifungal liquid [Link]
- External Links
- Human Metabolome Database
- HMDB0033724
- PubChem Substance
- 347911124
- ChemSpider
- 10771160
- BindingDB
- 50248304
- 314881
- ChEBI
- 35045
- ChEMBL
- CHEMBL1276010
- ZINC
- ZINC000001577120
- Wikipedia
- Undecylenic_acid
- MSDS
- Download (48.3 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Topical 25 g/100mL Cream Topical 4.8 mg/36.97mL Spray Topical Cream Topical 14.77 mg/59.148mL Gel Topical 0.2508 kg/1kg Cream Topical Solution Topical 25 g/100mL Oil Topical 10 g/100g Liquid Topical 250 mg/100mL Liquid Topical 25 mg/100mL Liquid Topical 0.25 g/1L Cream Cutaneous 20.360 g Solution Cutaneous Solution Topical 10 g/100g Spray Topical 100 mg/1mL Cream Topical 22.060 g Powder Topical Aerosol; powder Topical Cream Topical 0.1 g/1g Liquid Topical 10 mg/100mL Liquid Topical 0.5 g/2g Film Topical 0.45 g/15mL Liquid Topical 250 mg/1mL Aerosol Topical Aerosol Topical .1 % Solution Topical 250 mg/1mL Liquid Topical 10 % Liquid Topical 250 mg/1g Gel Topical 250 mg/1g Liquid Topical 125 mg/1mL Ointment Topical 10 g/100mL Spray Topical 25 mg/60mL Spray Topical 25 mg/100mL Spray Topical 250 mg/1mL Liquid Topical 110 mg/1mL Solution Topical 1.1 g/10mL Spray Topical 2 mg/10mL Kit; liquid Topical 25 mg/100mL Spray Topical 20 mg/100mL Liquid Topical 200 mg/1mL Liquid Topical 7.5 g/30mL Cream Topical 150 mg/1mL Cream Cream Topical 200 mg/1mL Suppository Vaginal Cream Vaginal Liquid Topical 10 g/100mL Cream Topical 5.7 g/57g Lotion Topical 85 mg/1mL Liquid Topical 0.23125 g/39.01mL Liquid Topical 100 mg/1mL Ointment Topical 100 mg/1g Cream Topical 4.55 g/37.5mL Cream Topical 25 g/100g Cream Topical 10 g/100g Cream Topical 13 g/100g Cream Cutaneous Liquid Topical 25 mg/30mL Liquid Topical 15 g/100mL Liquid Topical 0.25 g/1mL Liquid Topical 25 mg/1.7mL Liquid Topical 25 mg/3mL Liquid Topical 288 mg/1mL Liquid Topical 40 mg/1.7mL Liquid Topical 7.5 g/30g Liquid Topical 0.25 g/1g Ointment Topical Cream Topical 2 mg/20mL Solution Topical 100 mg/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 24.5 MSDS boiling point (°C) Decomposes at 275°C MSDS water solubility Insoluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.0189 mg/mL ALOGPS logP 3.84 ALOGPS logP 3.73 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 5.02 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 54.12 m3·mol-1 Chemaxon Polarizability 22.78 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 157.1896622 predictedDarkChem Lite v0.1.0 [M-H]- 157.6051622 predictedDarkChem Lite v0.1.0 [M-H]- 157.5645622 predictedDarkChem Lite v0.1.0 [M-H]- 148.03365 predictedDeepCCS 1.0 (2019) [M+H]+ 150.65572 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.27473 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Other/unknown
- General Function
- Calcium-regulated non-lysosomal thiol-protease which catalyzes limited proteolysis of substrates involved in cytoskeletal remodeling and signal transduction (PubMed:19617626, PubMed:21531719, PubMed:2400579). Proteolytically cleaves CTBP1 at 'Asn-375', 'Gly-387' and 'His-409' (PubMed:23707407). Cleaves and activates caspase-7 (CASP7) (PubMed:19617626)
- Specific Function
- calcium ion binding
- Gene Name
- CAPN1
- Uniprot ID
- P07384
- Uniprot Name
- Calpain-1 catalytic subunit
- Molecular Weight
- 81889.325 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at December 03, 2015 16:51 / Updated at August 26, 2024 19:24