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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

Description

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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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

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
411
Targets

Targets

Primary TargetPharmacologyConditionPotency
Interacts
323
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
EFAMAST

Approved Use

Unknown
Primary
Approved
8583
EPOGAM

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/12679162/
unhealthy
Health Status: unhealthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/12679162/
Other AEs: Deterioration mental (NOS)...
Other AEs:
Deterioration mental (NOS) (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12679162/
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/12679162/
unhealthy
Health Status: unhealthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/12679162/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
1087
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1741

rCYP3A
6

UMAT
30

CYP19A1
429
CYP2C2
2

CYP2CAA
2

P-gp
2052

rOAT1
2
rCYP2C11
3

rCYP2J
2

CYP2C23
12
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP19A1
430
 no
CYP3A4
2633
 no
UMAT
30
 no
rCYP3A
10
 yes [Inhibition 50 uM]
CYP2C23
12
 yes
P-gp
1932
 yes
rCYP2C11
4
 yes
rCYP2J
2
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
CYP2C2
2
 yes
CYP2CAA
2
 yes
rOAT1
2
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
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
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.
Name Type Language
.GAMMA.-LINOLENIC ACID
MI  
Preferred Name English
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
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 Mon Mar 31 17:51:02 GMT 2025 , Edited by admin on Mon Mar 31 17:51:02 GMT 2025
NCI_THESAURUS C2563
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DSLD 1290 (Number of products:674)
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WHO-VATC QD11AX02
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NCI_THESAURUS C68403
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WHO-ATC D11AX52
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WHO-ATC D11AX02
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WHO-VATC QD11AX52
Created by admin on Mon Mar 31 17:51:02 GMT 2025 , Edited by admin on Mon Mar 31 17:51:02 GMT 2025
Code System Code Type Description
RXCUI
618453
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ALTERNATIVE
DRUG BANK
DB13854
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PRIMARY
DRUG CENTRAL
1276
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PRIMARY
NCI_THESAURUS
C68369
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PRIMARY
SMS_ID
100000084515
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PRIMARY
ChEMBL
CHEMBL464982
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PRIMARY
EVMPD
SUB07879MIG
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PRIMARY
MERCK INDEX
m6832
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PRIMARY Merck Index
RXCUI
25605
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PRIMARY
CHEBI
28661
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PRIMARY
RXCUI
283564
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PRIMARY
MESH
D017965
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PRIMARY
EPA CompTox
DTXSID7046170
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PRIMARY
INN
2834
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PRIMARY
PUBCHEM
5280933
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PRIMARY
FDA UNII
78YC2MAX4O
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PRIMARY
DAILYMED
78YC2MAX4O
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PRIMARY
CAS
506-26-3
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PRIMARY
WIKIPEDIA
GAMMA-LINOLENIC ACID
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PRIMARY
ACTIVE MOIETY
Structure of GAMOLENIC ACID
SALT/SOLVATE (PARENT)
Structure of SODIUM .GAMMA.-LINOLENATE
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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