Undecylenic acid



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

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
Monoisotopic: 184.146329884
Chemical Formula
  • 10-undecenoic acid
  • ácido 10-undecenoico
  • Undecenoic acid
  • Undecylenate
  • Undecylenic acid
External IDs
  • Fema no. 3247



Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own.

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Associated Conditions
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.


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
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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.

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.


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Product Ingredients
IngredientUNIICASInChI Key
Zinc undecylenate388VZ25DUR557-08-4YMCOHQVWOBMDCZ-UHFFFAOYSA-L
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Anti-Fungal Pen CVSLiquid25 g/100mLTopicalCVS Health2016-09-15Not applicableUS flag
AntifungalCream4.8 mg/36.97mLTopicalBlaine Labs Inc.2016-04-01Not applicableUS flag
Athletes FootCream14.77 mg/59.148mLTopicalBlaine Labs Inc.2016-04-01Not applicableUS flag
Botanimedix OnychoRX Antifungal Nail GelGel0.2508 kg/1kgTopicalCosco International, Inc.2020-01-01Not applicableUS flag
CRYSTAL FLUSH Maximum Strength Anti-Fungal FormulaSolution25 g/100mLTopicalTriple Point Group, LLC2020-09-17Not applicableUS flag
Cure Athletes FootOil10 g/100gTopicalR And S Research2014-09-012016-12-31US flag
Cvs Maximum Strength Anti Fungal Pen 25Liquid250 mg/100mLTopicalCVS PHARMACY2019-01-09Not applicableUS flag
CVS Maximum Strength Anti-Fungal Pen 25%Liquid25 mg/100mLTopicalDenison Pharmaceuticals, Llc2019-01-09Not applicableUS flag
CVS Pharmacy Anti-fungal Pen Maximum StrengthLiquid250 mg/1mLTopicalCVS PHARMACY2012-12-27Not applicableUS flag
CVS Pharmacy Maximum Strength Antifungal Liquid with Aloe and Vitamin ELiquid0.25 g/1LTopicalCVS Health2010-05-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Antifungal Foot CareUndecylenic acid (6 g/100g) + Zinc undecylenate (6 g/100g)SprayTopicalNeobourne Pharma Lp2015-03-162017-11-29US flag
Antifungal Foot CareUndecylenic acid (6 g/100g) + Zinc undecylenate (6 g/100g)SprayTopicalNeobourne Pharma Lp2015-03-162017-11-29US flag
Cruex Antifungal CreamZinc undecylenate (20 %) + Undecylenic acid (3 %)CreamTopicalCiba Self Medication1994-12-311998-07-06Canada flag
Cruex Antifungal CreamZinc undecylenate (20 %) + Undecylenic acid (3 %)CreamTopicalCiba Self Medication1994-12-311998-07-06Canada flag
Cruex Medicated Spray PowderZinc undecylenate (20 %) + Undecylenic acid (2 %)Aerosol; PowderTopicalCiba Self Medication1994-12-311996-09-09Canada flag
Cruex Medicated Spray PowderZinc undecylenate (20 %) + Undecylenic acid (2 %)Aerosol; PowderTopicalCiba Self Medication1994-12-311996-09-09Canada flag
Derman AntifungalUndecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g)CreamTopicalCompania Internacional De Comercio, S.A.P.I De C.V.2013-08-12Not applicableUS flag
Derman AntifungalUndecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g)CreamTopicalTeresa Cecena Dba Genesis2015-05-14Not applicableUS flag
Derman AntifungalUndecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g)CreamTopicalFarmaqro S.A. de C.V.2013-08-12Not applicableUS flag
Derman AntifungalUndecylenic acid (2 g/100g) + Zinc undecylenate (20 g/100g)PowderTopicalCompania Internacional De Comercio, S.A.P.I. De C.V.2013-09-30Not applicableUS flag


ATC Codes
D01AE04 — Undecylenic acidD01AE54 — Undecylenic acid, combinations
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)
Affected organisms
Not Available

Chemical Identifiers

CAS number
InChI Key
undec-10-enoic acid


General References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. ZINC COMPOUNDS - National Library of Medicine HSDB ... - Toxnet - NIH [Link]
  6. Arkema: Oleris® Undecylenic acid [Link]
  7. DailyMed: Undecylenic Acid topical antifungal liquid [Link]
Human Metabolome Database
PubChem Substance
Download (48.3 KB)

Clinical Trials

Clinical Trials


Not Available
Not Available
Dosage Forms
LiquidTopical25 g/100mL
CreamTopical4.8 mg/36.97mL
CreamTopical14.77 mg/59.148mL
GelTopical0.2508 kg/1kg
SolutionTopical25 g/100mL
OilTopical10 g/100g
LiquidTopical250 mg/100mL
LiquidTopical25 mg/100mL
LiquidTopical0.25 g/1L
CreamCutaneous20.360 g
SolutionTopical10 g/100g
SprayTopical100 mg/1mL
CreamTopical22.060 g
Aerosol; powderTopical
CreamTopical0.1 g/1g
LiquidTopical10 mg/100mL
LiquidTopical0.5 g/2g
FilmTopical0.45 g/15mL
LiquidTopical250 mg/1mL
AerosolTopical.1 %
SolutionTopical250 mg/1mL
LiquidTopical10 %
LiquidTopical250 mg/1g
GelTopical250 mg/1g
LiquidTopical125 mg/1mL
OintmentTopical10 g/100mL
SprayTopical25 mg/60mL
SprayTopical25 mg/100mL
SprayTopical250 mg/1mL
LiquidTopical110 mg/1mL
SolutionTopical1.1 g/10mL
SprayTopical2 mg/10mL
Kit; liquidTopical25 mg/100mL
SprayTopical20 mg/100mL
LiquidTopical200 mg/1mL
LiquidTopical7.5 g/30mL
CreamTopical150 mg/1mL
CreamTopical200 mg/1mL
LiquidTopical10 g/100mL
CreamTopical5.7 g/57g
LotionTopical85 mg/1mL
LiquidTopical0.23125 g/39.01mL
LiquidTopical100 mg/1mL
OintmentTopical100 mg/1g
CreamTopical4.55 g/37.5mL
CreamTopical25 g/100g
CreamTopical10 g/100g
CreamTopical13 g/100g
LiquidTopical25 mg/30mL
LiquidTopical15 g/100mL
LiquidTopical0.25 g/1mL
LiquidTopical25 mg/3mL
LiquidTopical25 mg/1.7mL
LiquidTopical288 mg/1mL
LiquidTopical40 mg/1.7mL
LiquidTopical7.5 g/30g
LiquidTopical0.25 g/1g
CreamTopical2 mg/20mL
SolutionTopical100 mg/1mL
Not Available
Not Available


Experimental Properties
melting point (°C)24.5MSDS
boiling point (°C)Decomposes at 275°CMSDS
water solubilityInsolubleMSDS
Predicted Properties
Water Solubility0.0189 mg/mLALOGPS
pKa (Strongest Acidic)5.02Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity54.12 m3·mol-1Chemaxon
Polarizability22.78 Å3Chemaxon
Number of Rings0Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available


Mass Spec (NIST)
Not Available
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a6u-9100000000-50cef3280113666a9e23
GC-MS Spectrum - EI-BGC-MSsplash10-0a7l-9000000000-830e35fcbdcb4ba9b574
GC-MS Spectrum - EI-BGC-MSsplash10-056u-9200000000-5b8c18292287532e1deb
GC-MS Spectrum - EI-BGC-MSsplash10-00ls-9600000000-b0c6c3ec0da35153ca5d
Mass Spectrum (Electron Ionization)MSsplash10-0apl-9100000000-c392a15a3cd57ccae148
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-0900000000-d8a5d703a9d2aebb6b99
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-4900000000-270e01bbabb57dca4ec2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05nf-9100000000-aa66183f7300eea3b4b4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-e0832ba35c6a39bb8de0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00m0-1900000000-7c7091c9da9db8d3bd82
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9300000000-bb79df7af5aab06986f0
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-001i-0900000000-b90f772663028aa6c273
13C NMR Spectrum1D NMRNot Applicable

Drug created at December 03, 2015 16:51 / Updated at February 21, 2021 18:52