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Drug-Target Interaction

Drug

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PubChem ID:444899
Structure:
Synonyms:
(14C)Arachidonic acid
(5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid
(5Z,8Z,11Z,14Z)-Eicosatetraenoic acid
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
(5Z,8Z,11Z,14Z)-Icosatetraenoic acid
(5Z,8Z,11Z,14Z)icosa-5,8,11,14-tetraenoic acid
10931_FLUKA
10931_SIGMA
1adl
1gnj
1vyg
5,8,11,14-Eicosatetraenoic acid
5,8,11,14-Eicosatetraenoic acid, (all-Z)-
5,8,11,14-Eicosatetraenoic acid, labeled with carbon-14, (all-Z)-
5,8,11,14-Icosatetraenoic Acid
506-32-1
5Z,8Z,11Z,14Z-icosatetraenoic acid
93444-49-6
A0781
A3555_SIGMA
A3925_SIGMA
A9673_SIGMA
AA
AB1004494
AC-14348
AC1L9H30
ACD
AG-F-70356
AIDS-045704
AIDS045704
all-cis-5,8,11,14-eicosatetraenoic acid
ARA
Arachidonate
Arachidonic acid
ARACHIDONIC ACID (20:4 n-6)
Arachidonsaeure
BML3-B03
BRD-K03070961-001-02-8
BSPBio_001539
C00219
CHEBI:15843
CHEMBL15594
cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid
cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid;
cis-5,8,11,14-Eicosatetraenoic acid
cis-Delta(5,8,11,14)-eicosatetraenoic acid
D18DBC10-379C-4E78-9A50-8B791A2F4E68
Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid
HMS1361M21
HMS1791M21
HMS1989M21
Icosa-5,8,11,14-tetraenoic acid
IDI1_034009
LMFA01030001
MLS001361328
MolPort-003-666-529
NCGC00094608-01
NCGC00094608-02
NCGC00094608-03
NCGC00094608-04
NCGC00094608-05
NCGC00094608-06
nchembio.129-comp13
nchembio.86-comp6
SMR000857374
Spectrum5_001910
ST069383
[1-14C]Arachidonic acid

Target

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Uniprot ID:CP1A2_HUMAN
Synonyms:
CYPIA2
Cytochrome P450 1A2
P(3)450
P450 4
P450-P3
EC-Numbers:1.14.14.1
Organism:Homo sapiens
Human
PDB IDs:2HI4
Structure:
2HI4

Binding Affinities:

Ki: Kd:Ic 50:Ec50/Ic50:
----

References:

16978661
The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes.. Hsien-Tsung Yao; Yi-Wei Chang; Shih-Jung Lan; Chiung-Tong Chen; John T A Hsu; Teng-Kuang Yeh (2006) Life sciences display abstract
The inhibitory effect of saturated fatty acids (SFAs): palmitic acid (PA), stearic acid (SA) and polyunsaturated fatty acids (PUFAs): linoleic acid (LA), linolenic acid (LN), arachidonic acid (AA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) on six human drug-metabolizing enzymes (CYP1A2, 2C9, 2C19, 2D6, 2E1 and 3A4) was studied. Supersomes from baculovirus-expressing single isoforms were used as the enzyme source. Phenacetin O-deethylation (CYP1A2), diclofenac 4-hydroxylation (CYP2C9), mephenytoin 4-hydroxylation (CYP2C19), dextromethorphan O-demethylation (CYP2D6), chlorzoxazone 6-hydroxylation (CYP2E1) and midazolam 1-hydroxylation (CYP3A4) were used as the probes. Results show that all the five examined PUFAs competitively inhibited CYP2C9- and CYP2C19-catalyzed metabolic reactions, with Ki values ranging from 1.7 to 4.7 microM and 2.3 to 7.4 microM, respectively. Among these, AA, EPA and DHA tended to have greater inhibitory potencies (lower IC(50) and Ki values) than LA and LN. In addition, these five PUFAs also competitively inhibited the metabolic reactions catalyzed by CYP1A2, 2E1 and 3A4 to a lesser extent (Ki values>10 microM). On the other hand, palmitic and stearic acids, the saturated fatty acids, had no inhibitory effect on the activities of six human CYP isozymes at concentrations up to 200 microM. Incubation of PUFAs with CYP2C9 or CYP2C19 in the presence of NADPH resulted in the decrease of PUFA concentrations in the incubation mixtures. These results indicate that the PUFAs are potent inhibitors as well as the substrates of CYP2C9 and CYP2C19.