Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H20O2.C2H7NO |
| Molecular Weight | 245.3584 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCO.OC(=O)CCCCCCCCC=C
InChI
InChIKey=GPOFRJKTYRFQLJ-UHFFFAOYSA-N
InChI=1S/C11H20O2.C2H7NO/c1-2-3-4-5-6-7-8-9-10-11(12)13;3-1-2-4/h2H,1,3-10H2,(H,12,13);4H,1-3H2
| Molecular Formula | C11H20O2 |
| Molecular Weight | 184.2753 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C2H7NO |
| Molecular Weight | 61.0831 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | CRUEX Approved UseFor the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm). |
|||
| Curative | CRUEX Approved UseFor the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm). |
|||
| Primary | Unknown Approved UseUnknown |
|||
| 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 |
|
| Application of linear solvation energy relationships to polymeric pseudostationary phases in micellar electrokinetic chromatography. | 2001 Apr |
|
| 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 |
|
| Formation, characterization, and chemistry of undecanoic acid-terminated silicon surfaces: patterning and immobilization of DNA. | 2004 Dec 21 |
|
| X-ray studies of self-assembled organic monolayers grown on hydrogen-terminated Si(111). | 2004 Jul 20 |
|
| UV photodissociation spectroscopy of oxidized undecylenic acid films. | 2006 Mar 16 |
|
| Natural treatment of chronic rhinosinusitis. | 2006 Sep |
|
| Self-assembled monolayers with latent aldehydes for protein immobilization. | 2007 Jan-Feb |
|
| Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis. | 2007 Jun 1 |
|
| Porous silicon for photosensitized formation of singlet oxygen in water and in simulated body fluid: two methods of modification by undecylenic acid. | 2009 Jun |
|
| Stimulatory effect of undecylenic acid on mouse osteoblast differentiation. | 2010 Apr |
|
| Simple surface modification of poly(dimethylsiloxane) for DNA hybridization. | 2010 Dec 6 |
|
| Simultaneous biosynthesis of two copolymers in Pseudomonas putida GPo1 using a two-stage continuous culture system. | 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
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 15:20:39 UTC 2023
by
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on
Fri Dec 15 15:20:39 UTC 2023
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| Record UNII |
89FB3I7256
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| Record Status |
Validated (UNII)
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| Record Version |
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89FB3I7256
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |