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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	3
Optical Activity	NONE

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 Gamolenic acid was used for the treatment of breast painand atopic dermatitis in Europe, although now the drug is withdrawn from the market (there is no safety issue associated with the withdrawal of the licences).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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
prostanoid metabolic process 2	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mastalgia 5	Primary		Approved 8,429	EFAMAST
Atopic dermatitis 43	Primary		Approved 8,429	EPOGAM

Doses

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Dose	Population	Adverse events
1 mg 1 times / day multiple, intratumoral injection	unhealthy	Other AEs: Deterioration mental (NOS)...

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AEs

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AE	Significance	Dose	Population
Deterioration mental (NOS)	2 patients	1 mg 1 times / day multiple, intratumoral injection	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781			inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461 rCYP3A UMAT 3 CYP19A1 60	CYP2C2 CYP2CAA P-gp 1,537 rOAT1	rCYP2C11 1 rCYP2J CYP2C23 10

Drug as perpetrator

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Target	Modality	Activity
CYP19A1 60	inhibitor 3,277	no
CYP3A4 1,925	inducer 1,573	no
UMAT 3	inhibitor 3,277	no
rCYP3A 3	inhibitor 3,277	yes [Inhibition 50 uM]
CYP2C23 10	inducer 1,573	yes

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Drug as victim

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Target	Modality	Activity
P-gp 1,537	substrate 3,367	no
CYP2C2	substrate 3,367	yes
CYP2CAA	substrate 3,367	yes
rOAT1	substrate 3,367	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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PubMed

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Title	Date	PubMed
gamma-Carboxyglutamate excretion and warfarin therapy.	1979 May	373941
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

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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.