Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H20O2 |
Molecular Weight | 184.2753 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCCCCCCCC=C
InChI
InChIKey=FRPZMMHWLSIFAZ-UHFFFAOYSA-N
InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)
Molecular Formula | C11H20O2 |
Molecular Weight | 184.2753 |
Charge | 0 |
Count |
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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 |
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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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Screening for new compounds with antiherpes activity. | 1984 Oct |
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Undecylenic acid inhibits morphogenesis of Candida albicans. | 2000 Oct |
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Application of linear solvation energy relationships to polymeric pseudostationary phases in micellar electrokinetic chromatography. | 2001 Apr |
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Convenient formation of 4-hydroxyalk-2-en-1-one functionality via A knoevenagel-type carbon chain elongation reaction of aldehyde with 1-arylsulfinylalkan-2-one. | 2001 Feb 23 |
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Determination of undecylenic and sorbic acids in cosmetic preparations by high performance liquid chromatography with electrochemical detection. | 2002 Nov 7 |
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Formation, characterization, and chemistry of undecanoic acid-terminated silicon surfaces: patterning and immobilization of DNA. | 2004 Dec 21 |
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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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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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Simple fluorimetric liquid chromatographic method for the analysis of undecylenic acid and zinc undecylenate in pharmaceutical preparations. | 2006 Jun 30 |
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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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Effects of insemination quantity on honey bee queen physiology. | 2007 Oct 3 |
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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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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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Bioconjugate functionalization of thermally carbonized porous silicon using a radical coupling reaction. | 2010 Dec 7 |
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Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions. | 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
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Edited
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Record UNII |
K3D86KJ24N
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
2995 (Number of products:4)
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WHO-VATC |
QD01AE54
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DSLD |
3453 (Number of products:1)
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WHO-VATC |
QD01AE04
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JECFA EVALUATION |
10-UNDECENOIC ACID
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WHO-ATC |
D01AE04
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CFR |
21 CFR 333.210
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WHO-ATC |
D01AE54
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EPA PESTICIDE CODE |
85501
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NCI_THESAURUS |
C514
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112-38-9
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UNDECYLENIC ACID
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1705505
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C538763
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C29530
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m11303
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CHEMBL1276010
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2013
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DB11117
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