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Details

Stereochemistry ACHIRAL
Molecular Formula C14H11Cl2NO3
Molecular Weight 312.1484
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4'-HYDROXYDICLOFENAC

SMILES

c1ccc(c(c1)CC(=O)O)Nc2c(cc(cc2Cl)O)Cl

InChI

InChIKey=KGVXVPRLBMWZLG-UHFFFAOYSA-N
InChI=1S/C14H11Cl2NO3/c15-10-6-9(18)7-11(16)14(10)17-12-4-2-1-3-8(12)5-13(19)20/h1-4,6-7,17-18H,5H2,(H,19,20)

HIDE SMILES / InChI

Molecular Formula C14H11Cl2NO3
Molecular Weight 312.1484
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

4'-Hydroxy diclofenac, a metabolite of diclofenac, suppresses prostaglandin E2 production specifically by blocking cyclooxygenase-2 activity and demonstrates anti-inflammatory properties.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
0.54 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Inhibition of cytochrome P450 2C9 activity in vitro by 5-hydroxytryptamine and adrenaline.
2001 Feb
Induction of drug metabolism enzymes and MDR1 using a novel human hepatocyte cell line.
2004 Apr
Diclofenac-induced antibodies against red blood cells are heterogeneous and recognize different epitopes.
2004 Aug
Validated assays for human cytochrome P450 activities.
2004 Jun
Effects of phenobarbital on metabolism and toxicity of diclofenac sodium in rat hepatocytes in vitro.
2004 Oct
Preparative synthesis of drug metabolites using human cytochrome P450s 3A4, 2C9 and 1A2 with NADPH-P450 reductase expressed in Escherichia coli.
2005 Feb
Development and validation of a high-throughput radiometric cyp2c9 inhibition assay using tritiated diclofenac.
2005 Mar
Efficient high performance liquid chromatograph/ultraviolet method for determination of diclofenac and 4'-hydroxydiclofenac in rat serum.
2006 Jan 18
Investigation of the immunogenicity of diclofenac and diclofenac metabolites.
2007 Jan 10
Changes in maternal liver Cyp2c and Cyp2d expression and activity during rat pregnancy.
2008 Apr 15
Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro.
2010
Hepatic clearance of reactive glucuronide metabolites of diclofenac in the mouse is dependent on multiple ATP-binding cassette efflux transporters.
2010 Apr
Identification and characterization of a bacterial cytochrome P450 for the metabolism of diclofenac.
2010 Jan
Diclofenac hypersensitivity: antibody responses to the parent drug and relevant metabolites.
2010 Oct 28
Role of drug-independent stress factors in liver injury associated with diclofenac intake.
2013 Oct 4
Histone deacetylase inhibitor valproic acid promotes the differentiation of human induced pluripotent stem cells into hepatocyte-like cells.
2014
Human NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated inactivation of reactive quinoneimine metabolites of diclofenac and mefenamic acid.
2014 Apr 21
One-electron oxidation of diclofenac by human cytochrome P450s as a potential bioactivation mechanism for formation of 2'-(glutathion-S-yl)-deschloro-diclofenac.
2014 Jan 25
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Effects of aceclofenac and its metabolite, 4′-hydroxyaceclofenac on prostaglandin E2 (PGE2) production by rheumatoid synovial cells were studies. First-passage synovial cells (106 cells/ml) from 10 patients with rheumatoid arthritis were cultured in the presence of aceclofenac and 4′-hydroxyaceclofenac in range of concentration: 0.0001 – 100 uM. After 24 h in culture, amount of PGE2 in culture medium was measured by enzyme immunoassay. It was found, that diclofenac and 4′-hydroxydiclofenac suppressed PGE2 production, with IC50 values of 1.3 ± 0.6 nM (n = 10) and 16.9 ± 8.5 nM (n= 9), respectively.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:44:54 UTC 2021
Edited
by admin
on Sat Jun 26 09:44:54 UTC 2021
Record UNII
NJF5O599EF
Record Status Validated (UNII)
Record Version
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Name Type Language
4'-HYDROXYDICLOFENAC
Common Name English
BENZENEACETIC ACID, 2-((2,6-DICHLORO-4-HYDROXYPHENYL)AMINO)-
Systematic Name English
4'-HYDROXY-DICLOFENAC
Common Name English
HYDROXYDICLOFENAC, 4'-
Common Name English
Code System Code Type Description
EPA CompTox
64118-84-9
Created by admin on Sat Jun 26 09:44:54 UTC 2021 , Edited by admin on Sat Jun 26 09:44:54 UTC 2021
PRIMARY
CAS
64118-84-9
Created by admin on Sat Jun 26 09:44:54 UTC 2021 , Edited by admin on Sat Jun 26 09:44:54 UTC 2021
PRIMARY
FDA UNII
NJF5O599EF
Created by admin on Sat Jun 26 09:44:54 UTC 2021 , Edited by admin on Sat Jun 26 09:44:54 UTC 2021
PRIMARY
PUBCHEM
116545
Created by admin on Sat Jun 26 09:44:54 UTC 2021 , Edited by admin on Sat Jun 26 09:44:54 UTC 2021
PRIMARY
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