U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of GAMOLENIC ACID

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-

HIDE SMILES / InChI
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

Description

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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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

Originator

Osbond, J.M. et al.
2
Curator's Comment: The substance was isolated by Heiduschka A. and Luft K. in 1919 from seed oil of Oenothera biennis and was synthesized by Osbond J.M. in 1961.

Approval Year

2017
422
Targets

Targets

Primary TargetPharmacologyConditionPotency
Interacts
323
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
EFAMAST

Approved Use

Unknown
Primary
Approved
8429
EPOGAM

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
The influence of polyunsaturated fatty acids on probiotic growth and adhesion.
2001 Jan 15
Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy.
2001 Jul
Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses.
2002 May
Characterization of a heart-specific fatty acid transport protein.
2003 May 2
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
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
Metabolic consequences of hypoxia from birth and dexamethasone treatment in the neonatal rat: comprehensive hepatic lipid and fatty acid profiling.
2004 Nov
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
Induction of apoptosis in K562/ADM cells by gamma-linolenic acid involves lipid peroxidation and activation of caspase-3.
2006 Aug 25
Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation.
2006 Nov
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
JNK implication in adipocyte-like cell death induced by chemotherapeutic drug cisplatin.
2015 Feb
Patents

Patents

06432684
3
06664406
3
06858416
3
07241619
3
08143383
3
08143486
3
08765423
2
08778632
3
JPH01132371A
2
JPH0347119A
2
JPH1171260A
2
JPS57144986A
2
JPS61130237A
2
JPS61192292A
2
JPS6314695A
2

Sample Use Guides

In Vivo Use Guide
4–6 capsules (500 mg) twice daily (40 mg gamolenic acid per capsule).
Route of Administration: Oral
In Vitro Use Guide
Sources: www.ncbi.nlm.nih.gov/pubmed/19356705
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 Fri Dec 15 15:13:52 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:52 GMT 2023
Record UNII
78YC2MAX4O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GAMOLENIC ACID
INN   MART.   WHO-DD  
INN  
Official Name English
GLA (GAMMA LINOLENIC ACID) SAFFLOWER OIL [NDI]
Common Name English
Gamolenic acid [WHO-DD]
Common Name English
GLA
Common Name English
(6Z,9Z,12Z-OCTADECATRIENOIC ACID
Common Name English
NDI 609 [FDMS]
Code English
C18:3 (N-6)
Common Name English
GAMOLENIC ACID [MART.]
Common Name English
(6Z,9Z,12Z)-6,9,12-OCTADECATRIENOIC ACID
Systematic Name English
.GAMMA.-LINOLENIC ACID [MI]
Common Name English
GAMMA LINOLENIC ACID
Common Name English
.GAMMA.-LINOLENIC ACID
MI  
Systematic Name English
CIS-6,CIS-9,CIS-12-OCTADECATRIENOIC ACID
Common Name English
.GAMMA.-LINOLENIC ACID (CONSTITUENT OF EVENING PRIMROSE OIL) [DSC]
Common Name English
GAMOLENIC-ACID
Common Name English
CIS,CIS,CIS-6,9,12-OCTADECATRIENOIC ACID
Systematic Name English
SONOVA 400
Brand Name English
(Z,Z,Z)-6,9,12-OCTADECATRIENOIC ACID
Systematic Name English
GAMMA-LINOLENIC ACID (CONSTITUENT OF SPIRULINA) [DSC]
Common Name English
.GAMMA.-LINOLENIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]
Common Name English
GAMMA-LINOLENATE
Systematic Name English
DELTA-LINOLENIC ACID
Common Name English
6,9,12-OCTADECATRIENOIC ACID, (Z,Z,Z)-
Common Name English
gamolenic acid [INN]
Common Name English
GAMMALINOLENIC ACID
Common Name English
GAMMA-LINOLENIC ACID
Systematic Name English
18:3(N-6)
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 82994
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
NCI_THESAURUS C2563
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
DSLD 1290 (Number of products:674)
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
WHO-VATC QD11AX02
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
NCI_THESAURUS C68403
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
WHO-ATC D11AX52
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
WHO-ATC D11AX02
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
WHO-VATC QD11AX52
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
Code System Code Type Description
RXCUI
618453
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
ALTERNATIVE
DRUG BANK
DB13854
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
DRUG CENTRAL
1276
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
NCI_THESAURUS
C68369
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
SMS_ID
100000084515
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL464982
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
EVMPD
SUB07879MIG
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
MERCK INDEX
m6832
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY Merck Index
RXCUI
25605
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
CHEBI
28661
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
RXCUI
283564
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
MESH
D017965
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID7046170
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
INN
2834
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
PUBCHEM
5280933
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
FDA UNII
78YC2MAX4O
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
DAILYMED
78YC2MAX4O
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
CAS
506-26-3
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
WIKIPEDIA
GAMMA-LINOLENIC ACID
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
Related Record Type Details
ALOE VERA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
EVENING PRIMROSE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
RICE BRAN OIL
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
Structure of SODIUM .GAMMA.-LINOLENATE
SALT/SOLVATE -> PARENT
BORAGE SEED OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
SPIRULINA
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Related Record Type Details
Structure of GAMOLENIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966