Undecylenic acid

Identification

Name
Undecylenic acid
Accession Number
DB11117  (DBSALT001514)
Type
Small Molecule
Groups
Approved, Investigational
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 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.

Structure
Thumb
Synonyms
  • 10-undecenoic acid
  • ácido 10-undecenoico
  • Undecenoic acid
  • Undecylenate
External IDs
Fema no. 3247
Product Ingredients
IngredientUNIICASInChI Key
Zinc undecylenate388VZ25DUR557-08-4YMCOHQVWOBMDCZ-UHFFFAOYSA-L
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Anti-Fungal Pen CVSLiquid25 g/100mLTopicalCVS Health2016-09-15Not applicableUs
AntifungalCream4.8 mg/36.97mLTopicalBlaine Labs Inc.2016-04-01Not applicableUs
Athletes FootCream14.77 mg/59.148mLTopicalBlaine Labs Inc.2016-04-01Not applicableUs
Botanimedix OnychoRX Antifungal Nail GelGel0.2508 kg/1kgTopicalCosco International, Inc.2020-01-01Not applicableUs
Cure Athletes FootOil10 g/100gTopicalR And S Research2014-09-012016-12-31Us
Cvs Maximum Strength Anti Fungal Pen 25Liquid250 mg/100mLTopicalCVS PHARMACY2019-01-09Not applicableUs
CVS Maximum Strength Anti-Fungal Pen 25%Liquid25 mg/100mLTopicalDenison Pharmaceuticals, Llc2019-01-09Not applicableUs
CVS Pharmacy Anti-fungal Pen Maximum StrengthLiquid250 mg/1mLTopicalCVS PHARMACY2012-12-27Not applicableUs
CVS Pharmacy Maximum Strength Antifungal Liquid with Aloe and Vitamin ELiquid0.25 g/1LTopicalCVS Health2010-05-01Not applicableUs
Dermaced Maximum Strength Anti-FungalLiquid250 mg/1mLTopicalDermaced, Llc2017-06-29Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antifungal Foot CareUndecylenic acid (6 g/100g) + Zinc undecylenate (6 g/100g)SprayTopicalNeobourne Pharma Lp2015-03-162017-11-29Us
Antifungal Foot CareUndecylenic acid (6 g/100g) + Zinc undecylenate (6 g/100g)SprayTopicalNeobourne Pharma Lp2015-03-162017-11-29Us
Cruex Antifungal CreamZinc undecylenate (20 %) + Undecylenic acid (3 %)CreamTopicalCiba Self Medication1994-12-311998-07-06Canada
Cruex Antifungal CreamZinc undecylenate (20 %) + Undecylenic acid (3 %)CreamTopicalCiba Self Medication1994-12-311998-07-06Canada
Cruex Medicated Spray PowderZinc undecylenate (20 %) + Undecylenic acid (2 %)Aerosol; PowderTopicalCiba Self Medication1994-12-311996-09-09Canada
Cruex Medicated Spray PowderZinc undecylenate (20 %) + Undecylenic acid (2 %)Aerosol; PowderTopicalCiba Self Medication1994-12-311996-09-09Canada
Derman AntifungalUndecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g)CreamTopicalTeresa Cecena Dba Genesis2015-05-14Not applicableUs
Derman AntifungalUndecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g)CreamTopicalFarmaqro S.A. de C.V.2013-08-12Not applicableUs
Derman AntifungalUndecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g)CreamTopicalTeresa Cecena Dba Genesis2015-05-14Not applicableUs
Derman AntifungalUndecylenic acid (5 g/100g) + Zinc undecylenate (18 g/100g)CreamTopicalFarmaqro S.A. de C.V.2013-08-12Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Nu CalmarUndecylenic acid (200 mg/1mL)CreamTopicalNu Calmar Pty Ltd2020-01-29Not applicableUs
Categories
UNII
K3D86KJ24N
CAS number
112-38-9
Weight
Average: 184.2753
Monoisotopic: 184.146329884
Chemical Formula
C11H20O2
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

Pharmacology

Indication

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

Pharmacodynamics

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.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

Toxicity

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
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
Not Available

References

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.
  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. [PubMed:26902505]
  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. [PubMed:10991877]
  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. [PubMed:26776224]
  5. ZINC COMPOUNDS - National Library of Medicine HSDB ... - Toxnet - NIH [Link]
  6. Arkema: Oleris® Undecylenic acid [Link]
External Links
Human Metabolome Database
HMDB0033724
PubChem Substance
347911124
ChemSpider
10771160
RxNav
314881
ChEBI
35045
ChEMBL
CHEMBL1276010
ZINC
ZINC000001577120
Wikipedia
Undecylenate
ATC Codes
D01AE04 — Undecylenic acidD01AE54 — Undecylenic acid, combinations
MSDS
Download (48.3 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidTopical25 g/100mL
CreamTopical4.8 mg/36.97mL
SprayTopical
CreamTopical14.77 mg/59.148mL
GelTopical0.2508 kg/1kg
CreamTopical
OilTopical10 g/100g
LiquidTopical250 mg/100mL
LiquidTopical25 mg/100mL
LiquidTopical0.25 g/1L
SolutionTopical10 g/100g
SprayTopical100 mg/1mL
PowderTopical
Aerosol; powderTopical
CreamTopical0.1 g/1g
LiquidTopical0.5 g/2g
FilmTopical0.45 g/15mL
LiquidTopical250 mg/1mL
AerosolTopical
AerosolTopical
SolutionTopical250 mg/1mL
LiquidTopical
LiquidTopical250 mg/1g
GelTopical250 mg/1g
LiquidTopical125 mg/1mL
LiquidTopical100 mg/1mL
OintmentTopical10 g/100mL
SprayTopical25 mg/60mL
SprayTopical25 mg/100mL
SprayTopical250 mg/1mL
LiquidTopical1.1 mL/10mL
SolutionTopical1.1 mL/10mL
SprayTopical2 mg/10mL
LiquidTopical200 mg/1mL
LiquidTopical7.5 g/30mL
CreamTopical150 mg/1mL
CreamTopical200 mg/1mL
SuppositoryVaginal
CreamVaginal
LotionTopical85 mg/1mL
LiquidTopical0.23125 g/39.01mL
OintmentTopical100 mg/1g
CreamTopical4.55 g/37.5mL
CreamTopical25 g/100g
CreamTopical10 g/100g
CreamTopical13 g/100g
CreamCutaneous
LiquidTopical25 mg/30mL
LiquidTopical0.25 g/1mL
LiquidTopical25 mg/1.7mL
LiquidTopical25 mg/3mL
LiquidTopical288 mg/1mL
LiquidTopical40 mg/1.7mL
LiquidTopical7.5 g/30g
LiquidTopical0.25 g/1g
OintmentTopical
CreamTopical2 mL/20mL
SolutionTopical100 mg/1mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)24.5MSDS
boiling point (°C)Decomposes at 275°CMSDS
water solubilityInsolubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.0189 mg/mLALOGPS
logP3.84ALOGPS
logP3.73ChemAxon
logS-4ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
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

Taxonomy

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
Medium-chain fatty acid / Unsaturated fatty acid / Straight chain fatty acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
undecenoic acid (CHEBI:35045) / Unsaturated fatty acids (LMFA01030036)

Drug created on December 03, 2015 09:51 / Updated on March 01, 2020 23:36

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