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-
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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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.
Originator
Approval Year
Doses
AEs
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.