- Undecylenic acid
- Accession Number
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.
- Small Molecule
- Approved, Investigational
- Average: 184.2753
- Chemical Formula
- 10-undecenoic acid
- ácido 10-undecenoico
- Undecenoic acid
- External IDs
- Fema no. 3247
Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.Learn More
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.
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.
No information regarding metabolism.
- Route of elimination
No information regarding route of elimination.
No information regarding half-life.
No information regarding clearance.
- Adverse Effects
Learn about our commercial Adverse Effects data.Learn More
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.
- Affected organisms
- Not Available
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- 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.
- 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 Antifungal Cream 4.8 mg/36.97mL Topical Blaine Labs Inc. 2016-04-01 Not applicable Athletes Foot Cream 14.77 mg/59.148mL Topical Blaine Labs Inc. 2016-04-01 Not applicable Botanimedix OnychoRX Antifungal Nail Gel Gel 0.2508 kg/1kg Topical Cosco International, Inc. 2020-01-01 Not applicable Cure Athletes Foot Oil 10 g/100g Topical R And S Research 2014-09-01 2016-12-31 Cvs Maximum Strength Anti Fungal Pen 25 Liquid 250 mg/100mL Topical CVS PHARMACY 2019-01-09 Not applicable CVS Maximum Strength Anti-Fungal Pen 25% Liquid 25 mg/100mL Topical Denison Pharmaceuticals, Llc 2019-01-09 Not applicable CVS Pharmacy Anti-fungal Pen Maximum Strength Liquid 250 mg/1mL Topical CVS PHARMACY 2012-12-27 Not applicable CVS Pharmacy Maximum Strength Antifungal Liquid with Aloe and Vitamin E Liquid 0.25 g/1L Topical CVS Health 2010-05-01 Not applicable Dermaced Maximum Strength Anti-Fungal Liquid 250 mg/1mL Topical Dermaced, Llc 2017-06-29 Not applicableAdditional Data Available
- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.Learn more
- Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.Learn more
- 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 Antifungal Foot Care Undecylenic acid (6 g/100g) + Zinc undecylenate (6 g/100g) Spray Topical Neobourne Pharma Lp 2015-03-16 2017-11-29 Cruex Antifungal Cream Zinc undecylenate (20 %) + Undecylenic acid (3 %) Cream Topical Ciba Self Medication 1994-12-31 1998-07-06 Cruex Antifungal Cream Zinc undecylenate (20 %) + Undecylenic acid (3 %) Cream Topical Ciba Self Medication 1994-12-31 1998-07-06 Cruex Medicated Spray Powder Zinc undecylenate (20 %) + Undecylenic acid (2 %) Aerosol; Powder Topical Ciba Self Medication 1994-12-31 1996-09-09 Cruex Medicated Spray Powder Zinc undecylenate (20 %) + Undecylenic acid (2 %) Aerosol; Powder Topical Ciba Self Medication 1994-12-31 1996-09-09 Derman Antifungal Undecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g) Cream Topical Compania Internacional De Comercio, S.A.P.I De C.V. 2013-08-12 Not applicable Derman Antifungal Undecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g) Cream Topical Farmaqro S.A. de C.V. 2013-08-12 Not applicable Derman Antifungal Undecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g) Cream Topical Teresa Cecena Dba Genesis 2015-05-14 Not applicable Derman Antifungal Undecylenic acid (2 g/100g) + Zinc undecylenate (20 g/100g) Powder Topical Compania Internacional De Comercio, S.A.P.I. De C.V. 2013-09-30 Not applicable
- 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
- 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.
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- 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
- 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)
- CAS number
- InChI Key
- IUPAC Name
- undec-10-enoic acid
- 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.
- 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. [PubMed:26902505]
- 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. [PubMed:10991877]
- 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. [PubMed:26776224]
- ZINC COMPOUNDS - National Library of Medicine HSDB ... - Toxnet - NIH [Link]
- Arkema: Oleris® Undecylenic acid [Link]
- DailyMed: Undecylenic Acid topical antifungal liquid [Link]
- Download (48.3 KB)
- Not Available
- 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 Oil Topical 10 g/100g Liquid Topical 250 mg/100mL Liquid Topical 25 mg/100mL Liquid Topical 0.25 g/1L Solution Topical 10 g/100g Spray Topical 100 mg/1mL Powder Topical Aerosol; powder Topical Cream Topical 0.1 g/1g Liquid Topical 0.5 g/2g Film Topical 0.45 g/15mL Liquid Topical 250 mg/1mL Aerosol Topical Aerosol Topical Ointment Topical 1.25 g Powder Topical 1.25 g Solution Topical 250 mg/1mL Liquid Topical Liquid Topical 250 mg/1g Gel Topical 250 mg/1g Liquid Topical 125 mg/1mL Ointment Topical 10 g/100mL Spray Topical 25 mg/100mL Spray Topical 25 mg/60mL Spray Topical 250 mg/1mL Liquid Topical 110 mg/1mL Solution Topical 1.1 mL/10mL Spray Topical 2 mg/10mL Liquid Topical 200 mg/1mL Liquid Topical 7.5 g/30mL Cream Topical 150 mg/1mL Powder Topical 2 g Ointment Topical 20 g Cream 20 mg/g Cream Topical 200 mg/1mL Suppository Vaginal Cream Vaginal Lotion Topical 85 mg/1mL Liquid Topical 0.23125 g/39.01mL Liquid Topical 100 mg/1mL Ointment Topical 100 mg/1g Ointment Topical 6 g 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 Powder Topical 200 mg Liquid Topical 0.25 g/1mL Liquid Topical 25 mg/3mL Liquid Topical 25 mg/1.7mL Liquid Topical 288 mg/1mL Liquid Topical 40 mg/1.7mL Liquid Topical 7.5 g/30g Liquid Topical 0.25 g/1g Cream Topical 5 g Ointment Topical Cream Topical 2 mg/20mL Solution Topical 100 mg/1mL
- Not Available
- Not Available
- 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
- Mass Spec (NIST)
- Not Available
Drug created on December 03, 2015 09:51 / Updated on January 07, 2021 18:04