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 |
---|---|---|---|---|
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 |
|
Allergic contact dermatitis from undecylenic acid in a commercial antifungal nail solution. | 2002 Feb |
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Undecylenic acid. Monograph. | 2002 Feb |
|
Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. | 2005 Feb |
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Silicon nanoparticles: applications in cell biology and medicine. | 2006 |
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Synthesis and HPLC evaluation of carboxylic acid phases on a hydride surface. | 2006 Apr |
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Natural treatment of chronic rhinosinusitis. | 2006 Sep |
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Grazing angle mirror-backed reflection (GMBR) for infrared analysis of monolayers on silicon. | 2006 Sep 14 |
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Structure and polymer form of poly-3-hydroxyalkanoates produced by Pseudomonas oleovorans grown with mixture of sodium octanoate/undecylenic acid and sodium octanoate/5-phenylvaleric acid. | 2007 Jan 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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Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase. | 2007 Mar |
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Optimizing biosensing properties on undecylenic Acid-functionalized diamond. | 2007 May 8 |
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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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Genomic analysis of post-mating changes in the honey bee queen (Apis mellifera). | 2008 May 19 |
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Oxidation-triggered release of fluorescent molecules or drugs from mesoporous Si microparticles. | 2008 Nov 25 |
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Polymerizable vesicles based on a single-tailed fatty acid surfactant: a simple route to robust nanocontainers. | 2009 Feb 3 |
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Stimulatory effect of undecylenic acid on mouse osteoblast differentiation. | 2010 Apr |
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Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions. | 2010 Jun 14 |
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Simultaneous biosynthesis of two copolymers in Pseudomonas putida GPo1 using a two-stage continuous culture system. | 2010 Jun 14 |
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
Fri Dec 15 15:01:08 UTC 2023
by
admin
on
Fri Dec 15 15:01:08 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
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CFR |
21 CFR 333.210
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |