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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-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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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
Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids.
1997 Oct
Metabolic consequences of hypoxia from birth and dexamethasone treatment in the neonatal rat: comprehensive hepatic lipid and fatty acid profiling.
2004 Nov
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
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
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
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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
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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
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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