Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H29O2.Na |
| Molecular Weight | 300.4114 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 3 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCCCC\C=C/C\C=C/C\C=C/CCCCC([O-])=O
InChI
InChIKey=MQLYJTAVSNRQGM-HPFCUAHCSA-M
InChI=1S/C18H30O2.Na/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);/q;+1/p-1/b7-6-,10-9-,13-12-;
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C18H29O2 |
| Molecular Weight | 277.4217 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 3 |
| Optical Activity | NONE |
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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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
PubMed
| Title | Date | PubMed |
|---|---|---|
| gamma-Carboxyglutamate excretion and warfarin therapy. | 1979 May |
|
| Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? | 1989 Sep |
|
| Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results. | 1996 |
|
| Plasma and tissue levels of lipids, fatty acids and plasma carnitine in neonates receiving a new fat emulsion. | 1997 Jun |
|
| Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. | 1997 Oct |
|
| Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet. | 1997 Sep |
|
| Characterization of arachidonic acid-induced apoptosis. | 1999 |
|
| Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999 Jul 14 |
|
| Identification of the major intestinal fatty acid transport protein. | 1999 Sep |
|
| Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites. | 2000 Jan |
|
| Trifluoromethyl-containing 3-alkoxymethyl- and 3-aryloxymethyl-2-pyridinones are potent inhibitors of HIV-1 non-nucleoside reverse transcriptase. | 2001 Feb 12 |
|
| Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy. | 2001 Jul |
|
| Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
|
| Synergistic regulation of endothelial tight junctions by antioxidant (Se) and polyunsaturated lipid (GLA) via Claudin-5 modulation. | 2006 Aug 1 |
|
| Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008 Apr |
|
| JNK implication in adipocyte-like cell death induced by chemotherapeutic drug cisplatin. | 2015 Feb |
Sample Use Guides
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:06:00 GMT 2023
by
admin
on
Sat Dec 16 11:06:00 GMT 2023
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| Record UNII |
L4WFA9KRB5
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| Record Status |
Validated (UNII)
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| Record Version |
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86761-55-9
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L4WFA9KRB5
Created by
admin on Sat Dec 16 11:06:00 GMT 2023 , Edited by admin on Sat Dec 16 11:06:00 GMT 2023
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PARENT -> SALT/SOLVATE |
