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-
Molecular Formula | C18H30O2 |
Molecular Weight | 278.4296 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 3 |
Optical Activity | NONE |
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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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 |
---|---|---|---|---|
Primary | EFAMAST Approved UseUnknown |
|||
Primary | EPOGAM Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Identification of the major intestinal fatty acid transport protein. | 1999 Sep |
|
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 |
|
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 |
|
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. | 2007 Jan 15 |
|
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008 Apr |
|
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010 Aug |
|
Antineoplastic effects of gamma linolenic Acid on hepatocellular carcinoma cell lines. | 2010 Jul |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:45:24 UTC 2023
by
admin
on
Wed Jul 05 22:45:24 UTC 2023
|
Record UNII |
78YC2MAX4O
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
FDA ORPHAN DRUG |
82994
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
||
|
NCI_THESAURUS |
C2563
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
||
|
DSLD |
1290 (Number of products:674)
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
||
|
WHO-VATC |
QD11AX02
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
||
|
NCI_THESAURUS |
C68403
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
||
|
WHO-ATC |
D11AX52
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
||
|
WHO-ATC |
D11AX02
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
||
|
WHO-VATC |
QD11AX52
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
618453
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
ALTERNATIVE | |||
|
DB13854
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
1276
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
C68369
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
100000084515
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
CHEMBL464982
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
SUB07879MIG
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
M6832
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | Merck Index | ||
|
25605
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
28661
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
283564
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
D017965
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
DTXSID7046170
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
2834
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
5280933
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
78YC2MAX4O
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
78YC2MAX4O
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
506-26-3
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY | |||
|
GAMMA-LINOLENIC ACID
Created by
admin on Wed Jul 05 22:45:24 UTC 2023 , Edited by admin on Wed Jul 05 22:45:24 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
LIPID -> FATTY ACID |
U.S produced rice oil. Values are % of composition.
|
||
|
SALT/SOLVATE -> PARENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |