Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H11Cl2NO3 |
Molecular Weight | 312.148 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC1=CC=CC=C1NC2=C(Cl)C=C(O)C=C2Cl
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)
Molecular Formula | C14H11Cl2NO3 |
Molecular Weight | 312.148 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/9226412
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9226412
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9226412 |
0.54 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Inhibition of cytochrome P450 2C9 activity in vitro by 5-hydroxytryptamine and adrenaline. | 2001 Feb |
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Effects of phenobarbital on metabolism and toxicity of diclofenac sodium in rat hepatocytes in vitro. | 2004 Oct |
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Preparative synthesis of drug metabolites using human cytochrome P450s 3A4, 2C9 and 1A2 with NADPH-P450 reductase expressed in Escherichia coli. | 2005 Feb |
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Development and validation of a high-throughput radiometric cyp2c9 inhibition assay using tritiated diclofenac. | 2005 Mar |
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Efficient high performance liquid chromatograph/ultraviolet method for determination of diclofenac and 4'-hydroxydiclofenac in rat serum. | 2006 Jan 18 |
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[The inhibition of CYP2C9 isoenzyme in Cunninghamella blakesleeana AS 3. 910]. | 2006 Oct |
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Effect of methamphetamine on cytochrome P450 activity. | 2007 Dec |
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Investigation of the immunogenicity of diclofenac and diclofenac metabolites. | 2007 Jan 10 |
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High-throughput cytochrome P450 inhibition assays using laser diode thermal desorption-atmospheric pressure chemical ionization-tandem mass spectrometry. | 2007 Jun 15 |
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Analytical approaches to determine cytochrome P450 inhibitory potential of new chemical entities in drug discovery. | 2007 May 1 |
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Changes in maternal liver Cyp2c and Cyp2d expression and activity during rat pregnancy. | 2008 Apr 15 |
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Simultaneous determination of aceclofenac and its three metabolites in plasma using liquid chromatography-tandem mass spectrometry. | 2008 Feb 13 |
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Isolation and characterization of a new human urinary metabolite of diclofenac applying LC-NMR-MS and high-resolution mass analyses. | 2008 Jun 9 |
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First evidence for occurrence of hydroxylated human metabolites of diclofenac and aceclofenac in wastewater using QqLIT-MS and QqTOF-MS. | 2008 Nov 1 |
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Occurrence of diclofenac and selected metabolites in sewage effluents. | 2008 Nov 1 |
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Regioselective preparation of 5-hydroxypropranolol and 4'-hydroxydiclofenac with a fungal peroxygenase. | 2009 Jun 1 |
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Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro. | 2010 |
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Hepatic clearance of reactive glucuronide metabolites of diclofenac in the mouse is dependent on multiple ATP-binding cassette efflux transporters. | 2010 Apr |
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Degradation of the drug sodium diclofenac by Trametes versicolor pellets and identification of some intermediates by NMR. | 2010 Apr 15 |
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Identification and characterization of a bacterial cytochrome P450 for the metabolism of diclofenac. | 2010 Jan |
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Diclofenac hypersensitivity: antibody responses to the parent drug and relevant metabolites. | 2010 Oct 28 |
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Role of drug-independent stress factors in liver injury associated with diclofenac intake. | 2013 Oct 4 |
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Histone deacetylase inhibitor valproic acid promotes the differentiation of human induced pluripotent stem cells into hepatocyte-like cells. | 2014 |
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Human NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated inactivation of reactive quinoneimine metabolites of diclofenac and mefenamic acid. | 2014 Apr 21 |
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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 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10215639
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
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admin
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Edited
Thu Jul 06 01:13:29 UTC 2023
by
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on
Thu Jul 06 01:13:29 UTC 2023
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Record UNII |
NJF5O599EF
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Record Status |
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