GAMOLENIC ACID

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 Search

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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
prostanoid metabolic process 2 Target ID: GO:0006692 Sources: http://www.allthingscanid.org/EveningPrimroseOil.pdf	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mastalgia 5 Sources: http://www.quackwatch.org/02ConsumerProtection/gla_withdrawal.html	Primary		Approved 8429	EFAMAST Approved Use Unknown
Atopic dermatitis 43 Sources: http://www.quackwatch.org/02ConsumerProtection/gla_withdrawal.html	Primary		Approved 8429	EPOGAM Approved Use Unknown

PubMed

Title	Date	PubMed
gamma-Carboxyglutamate excretion and warfarin therapy.	1979 May	373941
Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1?	1989 Sep	2550526
Evening primrose oil (Epogam) in the treatment of chronic hand dermatitis: disappointing therapeutic results.	1996	8884146
Plasma and tissue levels of lipids, fatty acids and plasma carnitine in neonates receiving a new fat emulsion.	1997 Jun	9202801
Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids.	1997 Oct	9415022
Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet.	1997 Sep	9306089
Characterization of arachidonic acid-induced apoptosis.	1999	10403056
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.	1999 Jul 14	10403814
Identification of the major intestinal fatty acid transport protein.	1999 Sep	10518211
Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites.	2000 Jan	10617998
Trifluoromethyl-containing 3-alkoxymethyl- and 3-aryloxymethyl-2-pyridinones are potent inhibitors of HIV-1 non-nucleoside reverse transcriptase.	2001 Feb 12	11212098
The influence of polyunsaturated fatty acids on probiotic growth and adhesion.	2001 Jan 15	11164299
Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy.	2001 Jul	11421921
Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses.	2002 May	12010583
Characterization of a heart-specific fatty acid transport protein.	2003 May 2	12556534
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	14569405
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	15318936
Metabolic consequences of hypoxia from birth and dexamethasone treatment in the neonatal rat: comprehensive hepatic lipid and fatty acid profiling.	2004 Nov	15271879
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.	2005 Jan	15619630
Synergistic regulation of endothelial tight junctions by antioxidant (Se) and polyunsaturated lipid (GLA) via Claudin-5 modulation.	2006 Aug 1	16514648
Induction of apoptosis in K562/ADM cells by gamma-linolenic acid involves lipid peroxidation and activation of caspase-3.	2006 Aug 25	16857180
Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation.	2006 Nov	17092368
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids.	2007 Jan 15	17038422
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008 Apr	18324785
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.	2010 Aug	20541177
Antineoplastic effects of gamma linolenic Acid on hepatocellular carcinoma cell lines.	2010 Jul	20664735
JNK implication in adipocyte-like cell death induced by chemotherapeutic drug cisplatin.	2015 Feb	25560393

Patents

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

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 UTC 2023` Edited by `admin` on `Fri Dec 15 15:13:52 UTC 2023`
Record UNII	78YC2MAX4O
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GAMOLENIC ACID

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

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