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
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 |
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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 |
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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: |
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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: |
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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 |
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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 |
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Cometabolic biosynthesis of copolyesters consisting of 3-hydroxyvalerate and medium-chain-length 3-hydroxyalkanoates by Pseudomonas sp. DSY-82. | 2001 Oct |
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Antioxidant and cyclooxygenase activities of fatty acids found in food. | 2002 Apr 10 |
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X-ray studies of self-assembled organic monolayers grown on hydrogen-terminated Si(111). | 2004 Jul 20 |
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Simple methods for the direct assembly, functionalization, and patterning of acid-terminated monolayers on Si111. | 2005 Nov 8 |
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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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Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis. | 2007 Jun 1 |
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Cell adhesion properties on photochemically functionalized diamond. | 2007 May 8 |
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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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A rapid and sensitive screening system for human type I collagen with the aim of discovering potent anti-aging or anti-fibrotic compounds. | 2008 Dec 31 |
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Spectra and kinetic studies of the compound I derivative of cytochrome P450 119. | 2008 Oct 8 |
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The compatibility of hepatocytes with chemically modified porous silicon with reference to in vitro biosensors. | 2009 Jan |
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Fed-batch production of unsaturated medium-chain-length polyhydroxyalkanoates with controlled composition by Pseudomonas putida KT2440. | 2009 Mar |
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C514
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CFR |
21 CFR 333.210
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SUB15763MIG
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C29552
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89748
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD