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 | C18H29O2 |
| Molecular Weight | 277.4217 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 3 |
| Optical Activity | NONE |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Gamolenic acid also known as gamma-linolenic 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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 mg 1 times / day multiple, intratumoral injection Dose: 1 mg, 1 times / day Route: intratumoral injection Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M Food Status: UNKNOWN Sources: |
Other AEs: Deterioration mental (NOS)... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Deterioration mental (NOS) | 2 patients | 1 mg 1 times / day multiple, intratumoral injection Dose: 1 mg, 1 times / day Route: intratumoral injection Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| yes [Inhibition 50 uM] | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| JNK implication in adipocyte-like cell death induced by chemotherapeutic drug cisplatin. | 2015-02 |
|
| Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010-08 |
|
| Antineoplastic effects of gamma linolenic Acid on hepatocellular carcinoma cell lines. | 2010-07 |
|
| Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008-04 |
|
| TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. | 2007-01-15 |
|
| Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. | 2006-11 |
|
| Induction of apoptosis in K562/ADM cells by gamma-linolenic acid involves lipid peroxidation and activation of caspase-3. | 2006-08-25 |
|
| Synergistic regulation of endothelial tight junctions by antioxidant (Se) and polyunsaturated lipid (GLA) via Claudin-5 modulation. | 2006-08-01 |
|
| Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005-01 |
|
| Metabolic consequences of hypoxia from birth and dexamethasone treatment in the neonatal rat: comprehensive hepatic lipid and fatty acid profiling. | 2004-11 |
|
| A retinoid X receptor (RXR)-selective retinoid reveals that RXR-alpha is potentially a therapeutic target in breast cancer cell lines, and that it potentiates antiproliferative and apoptotic responses to peroxisome proliferator-activated receptor ligands. | 2004 |
|
| Fatty acid profiles, antioxidant status, and growth of preterm infants fed diets without or with long-chain polyunsaturated fatty acids. A randomized clinical trial. | 2003-10 |
|
| Characterization of a heart-specific fatty acid transport protein. | 2003-05-02 |
|
| Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses. | 2002-05 |
|
| Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy. | 2001-07 |
|
| Trifluoromethyl-containing 3-alkoxymethyl- and 3-aryloxymethyl-2-pyridinones are potent inhibitors of HIV-1 non-nucleoside reverse transcriptase. | 2001-02-12 |
|
| The influence of polyunsaturated fatty acids on probiotic growth and adhesion. | 2001-01-15 |
|
| Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites. | 2000-01 |
|
| Identification of the major intestinal fatty acid transport protein. | 1999-09 |
|
| Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999-07-14 |
|
| Characterization of arachidonic acid-induced apoptosis. | 1999 |
|
| Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. | 1997-10 |
|
| Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet. | 1997-09 |
|
| Plasma and tissue levels of lipids, fatty acids and plasma carnitine in neonates receiving a new fat emulsion. | 1997-06 |
|
| Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results. | 1996 |
|
| Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? | 1989-09 |
|
| gamma-Carboxyglutamate excretion and warfarin therapy. | 1979-05 |
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
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Edited
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on
Mon Mar 31 23:38:33 GMT 2025
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| Record UNII |
L4WFA9KRB5
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| Record Status |
Validated (UNII)
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86761-55-9
Created by
admin on Mon Mar 31 23:38:33 GMT 2025 , Edited by admin on Mon Mar 31 23:38:33 GMT 2025
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L4WFA9KRB5
Created by
admin on Mon Mar 31 23:38:33 GMT 2025 , Edited by admin on Mon Mar 31 23:38:33 GMT 2025
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|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
