Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C11H19O2.Zn |
Molecular Weight | 431.944 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Zn++].[O-]C(=O)CCCCCCCCC=C.[O-]C(=O)CCCCCCCCC=C
InChI
InChIKey=YMCOHQVWOBMDCZ-UHFFFAOYSA-L
InChI=1S/2C11H20O2.Zn/c2*1-2-3-4-5-6-7-8-9-10-11(12)13;/h2*2H,1,3-10H2,(H,12,13);/q;;+2/p-2
Molecular Formula | Zn |
Molecular Weight | 65.409 |
Charge | 2 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C11H19O2 |
Molecular Weight | 183.2674 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.fda.gov/ohrms/dockets/ac/04/briefing/4036B1_06_OTC%20Monograph%20Topical.htmCurator's Comment: description was created based on several sources, including
http://www.altmedrev.com/publications/7/1/68.pdf |
https://www.ncbi.nlm.nih.gov/pubmed/10991877
Sources: https://www.fda.gov/ohrms/dockets/ac/04/briefing/4036B1_06_OTC%20Monograph%20Topical.htm
Curator's Comment: description was created based on several sources, including
http://www.altmedrev.com/publications/7/1/68.pdf |
https://www.ncbi.nlm.nih.gov/pubmed/10991877
Undecylenic acid is unsaturated fatty acid, which naturally occurs in sweat, and is commercially produced by the vacuum distillation of castor bean oil. It is recognized as GRASE by FDA, and is marketed over the counter to treat skin infections and to relieve itching. Undecylenic acid acts by inhibition of morphogenesis from yeast to hyphae forms.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map00061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10991877 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | CRUEX Approved UseFor the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm). |
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Curative | CRUEX Approved UseFor the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm). |
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Primary | Unknown Approved UseUnknown |
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Primary | CRUEX Approved UseItching, burning, redness, irritation, scaling, soreness and discomfort which may accompany these conditions |
Doses
Dose | Population | Adverse events |
---|---|---|
2.2 g 3 times / day multiple, oral Dose: 2.2 g, 3 times / day Route: oral Route: multiple Dose: 2.2 g, 3 times / day Co-administed with:: nicotinic acid(50 mgm. morning and night) Sources: |
unhealthy, 56 years n = 1 Health Status: unhealthy Condition: psoriasis Age Group: 56 years Sex: M Population Size: 1 Sources: |
Disc. AE: Toxic labyrinthitis... AEs leading to discontinuation/dose reduction: Toxic labyrinthitis (1 patient) Sources: |
1 g 3 times / day multiple, oral Dose: 1 g, 3 times / day Route: oral Route: multiple Dose: 1 g, 3 times / day Sources: |
unhealthy, 8-14 years n = 4 Health Status: unhealthy Condition: psoriasis | NEURODERMATITIS Age Group: 8-14 years Population Size: 4 Sources: |
|
10 g 3 times / day multiple, oral Highest studied dose Dose: 10 g, 3 times / day Route: oral Route: multiple Dose: 10 g, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: psoriasis Age Group: adult Sources: |
|
2 % 1 times / day multiple, topical Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Co-administed with:: zinc undecylenate(0.2) Sources: |
unhealthy n = 29 Health Status: unhealthy Condition: TINEA PEDIS Population Size: 29 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Toxic labyrinthitis | 1 patient Disc. AE |
2.2 g 3 times / day multiple, oral Dose: 2.2 g, 3 times / day Route: oral Route: multiple Dose: 2.2 g, 3 times / day Co-administed with:: nicotinic acid(50 mgm. morning and night) Sources: |
unhealthy, 56 years n = 1 Health Status: unhealthy Condition: psoriasis Age Group: 56 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Screening for new compounds with antiherpes activity. | 1984 Oct |
|
Undecylenic acid inhibits morphogenesis of Candida albicans. | 2000 Oct |
|
Antioxidant and cyclooxygenase activities of fatty acids found in food. | 2002 Apr 10 |
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One-pot sequences of reactions with sol-gel entrapped opposing reagents: an enzyme and metal-complex catalysts. | 2002 Dec 4 |
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Allergic contact dermatitis from undecylenic acid in a commercial antifungal nail solution. | 2002 Feb |
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Undecylenic acid. Monograph. | 2002 Feb |
|
Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability. | 2003 Jan |
|
Silicon nanoparticles: applications in cell biology and medicine. | 2006 |
|
3,3,5-Trimethylcyclohexanols and derived esters: green synthetic procedures, odour evaluation and in vitro skin cytotoxicity assays. | 2006 Dec |
|
Well-defined carboxyl-terminated alkyl monolayers grafted onto H-Si(111): packing density from a combined AFM and quantitative IR study. | 2006 Jan 3 |
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Controlling electroosmotic flow in poly(dimethylsiloxane) separation channels by means of prepolymer additives. | 2006 Jul 1 |
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Simple fluorimetric liquid chromatographic method for the analysis of undecylenic acid and zinc undecylenate in pharmaceutical preparations. | 2006 Jun 30 |
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UV photodissociation spectroscopy of oxidized undecylenic acid films. | 2006 Mar 16 |
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Grazing angle mirror-backed reflection (GMBR) for infrared analysis of monolayers on silicon. | 2006 Sep 14 |
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Nanovectors for anticancer agents based on superparamagnetic iron oxide nanoparticles. | 2007 |
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Covalent biofunctionalization of silicon nitride surfaces. | 2007 May 22 |
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Optimizing biosensing properties on undecylenic Acid-functionalized diamond. | 2007 May 8 |
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Effect of double bonds in the formation of sodium dodecanoate and sodium 10-undecenoate mixed micelles in water. | 2007 Oct 11 |
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Effects of insemination quantity on honey bee queen physiology. | 2007 Oct 3 |
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Determination of nateglinide in human plasma by high-performance liquid chromatography with pre-column derivatization using a coumarin-type fluorescent reagent. | 2007 Sep 5 |
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A new concept in the topical treatment of onychomycosis with cyanoacrylate, undecylenic acid, and hydroquinone. | 2008 Apr |
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Topographical and functional characterization of the ssDNA probe layer generated through EDC-mediated covalent attachment to nanocrystalline diamond using fluorescence microscopy. | 2008 Aug 19 |
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Comparison of the skin sensitizing potential of unsaturated compounds as assessed by the murine local lymph node assay (LLNA) and the guinea pig maximization test (GPMT). | 2008 Jun |
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Genomic analysis of post-mating changes in the honey bee queen (Apis mellifera). | 2008 May 19 |
|
Oxidation-triggered release of fluorescent molecules or drugs from mesoporous Si microparticles. | 2008 Nov 25 |
|
Spectra and kinetic studies of the compound I derivative of cytochrome P450 119. | 2008 Oct 8 |
|
Undecylenic acid: a valuable and physiologically active renewable building block from castor oil. | 2009 |
|
The compatibility of hepatocytes with chemically modified porous silicon with reference to in vitro biosensors. | 2009 Jan |
|
Porous silicon for photosensitized formation of singlet oxygen in water and in simulated body fluid: two methods of modification by undecylenic acid. | 2009 Jun |
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Electrochemical behavior of gold colloidal alkyl modified silicon surfaces. | 2009 Nov |
|
Simple surface modification of poly(dimethylsiloxane) for DNA hybridization. | 2010 Dec 6 |
|
Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions. | 2010 Jun 14 |
|
Production of functionalized polyhydroxyalkanoates by genetically modified Methylobacterium extorquens strains. | 2010 Sep 16 |
Patents
Sample Use Guides
Undecylenic acid antifungal liquid should be applied to affected area topically.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10991877
To investigate effect of undecylenic acid on Candida albicans morphogenesis, cells were grown overnight at 30°C on YPD agar and harvested by scraping the cells from the plate and suspending in YPD broth. Two milliliters of cells at 106 cells/ml was distributed into tubes containing liner, approximately 0.5 g of liner per tube. The cultures were incubated at 39°C with agitation for 2 h; planktonic cells were analyzed microscopically to determine the percentage of cells with germ tubes. The presence of Undecylenic acid inhibited the appearance of germ tubes, with 10 μM UDA causing a sevenfold reduction.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:33:13 UTC 2023
by
admin
on
Wed Jul 05 22:33:13 UTC 2023
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Record UNII |
388VZ25DUR
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C514
Created by
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CFR |
21 CFR 333.210
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |