Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H30O2 |
Molecular Weight | 278.4296 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 3 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O
InChI
InChIKey=VZCCETWTMQHEPK-QNEBEIHSSA-N
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
DescriptionSources: http://www.allthingscanid.org/EveningPrimroseOil.pdf
Sources: http://www.allthingscanid.org/EveningPrimroseOil.pdf
Gamolenic acid also known as gamma-lonolenic acid is a natural component of Oenothera biennis L. (Evening Primrose). Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences). The mechanism of action of gamolenic acid is connected with its interaction with prostanoid pathway.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0006692 Sources: http://www.allthingscanid.org/EveningPrimroseOil.pdf |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | EFAMAST Approved UseUnknown |
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Primary | EPOGAM Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results. | 1996 |
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Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. | 1997 Oct |
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The influence of polyunsaturated fatty acids on probiotic growth and adhesion. | 2001 Jan 15 |
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Characterization of a heart-specific fatty acid transport protein. | 2003 May 2 |
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Fatty acid profiles, antioxidant status, and growth of preterm infants fed diets without or with long-chain polyunsaturated fatty acids. A randomized clinical trial. | 2003 Oct |
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Synergistic regulation of endothelial tight junctions by antioxidant (Se) and polyunsaturated lipid (GLA) via Claudin-5 modulation. | 2006 Aug 1 |
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TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. | 2007 Jan 15 |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.allthingscanid.org/EveningPrimroseOil.pdf
4–6 capsules (500 mg) twice daily (40 mg gamolenic acid per capsule).
Route of Administration:
Oral
The cells were treated with various concentrations of gamolenic acid for 24 h and cell viability was determined by the MTT assay. Treatment of the K562 cells with gamolenic concentrations less
than 50 uM did not inhibit cell viability, but treatment
with concentrations of 50-150 uM caused a dosedependent decrease, and the concentration of gamolenic acid inducing 50% cell inhibition (IC50) after 24 h was 101.59 uM.
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FDA ORPHAN DRUG |
82994
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NCI_THESAURUS |
C2563
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DSLD |
1290 (Number of products:674)
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WHO-VATC |
QD11AX02
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NCI_THESAURUS |
C68403
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WHO-ATC |
D11AX52
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D11AX02
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QD11AX52
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C68369
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GAMMA-LINOLENIC ACID
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)