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D6899

Sigma-Aldrich

Diclofenac sodium salt

Synonym(s):

2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid sodium salt

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About This Item

Empirical Formula (Hill Notation):
C14H10Cl2NNaO2
CAS Number:
15307-79-6
Molecular Weight:
318.13
EC Number:
239-346-4
MDL number:
MFCD00082251
UNSPSC Code:
12352200
PubChem Substance ID:
24277712
NACRES:
NA.77

biological source

synthetic

Assay

≥98% (TLC)

form

powder

mp

283-285  °C

solubility

methanol: 50 mg/mL, clear, colorless to faint yellow or tan

originator

Novartis

storage temp.

room temp

SMILES string

[Na+].[O-]C(=O)Cc1ccccc1Nc2c(Cl)cccc2Cl

InChI

1S/C14H11Cl2NO2.Na/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19;/h1-7,17H,8H2,(H,18,19);/q;+1/p-1

InChI key

KPHWPUGNDIVLNH-UHFFFAOYSA-M

Gene Information

human ... PTGS1(5742) , PTGS2(5743)

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Application

Diclofenac sodium has been used:
  • to investigate its radioprotective potential in a study
  • to determine the basic viscosity and hydrodynamic values of the solubilizers and their micellar adducts in a study
  • as a standard for potentiometric and fluorimetric determination of diclofenac in a sequential injection analysis system
  • to inhibit phase II drug metabolizing enzyme (DME) in a study to investigate the inhibitory effects of an ethanol extract of Descurainia sophia seeds on Phase I and II DMEs

Biochem/physiol Actions

Diclofenac sodium salt is a nonsteroidal anti-inflammatory drug (NSAID) that acts as a competitive and irreversible inhibitor of prostaglandin synthetase. Its analgesic and anti-inflammatory activities are based on the prevention of the synthesis of arachinodate metabolites via cyclooxygenase inhibition. It is found to hinder the conversion of arachidonic acid to prostaglandins, which mediate inflammatory process. The NSAIDs are found to inhibit both cyclooxygenase enzymes, COX-1 and COX-2, causing undesirable gastrointestinal effect. Diclofenac sodium also functions as a scavenger of free radicals and serves a radioprotective role in restoring supercoiled form of plasmid DNA damaged by radiation back to normal. Diclofenac sodium is oxidized by the donation of electron and transfer of hydrogen atom. It can be a potential radioprotective agent.
Standard NSAID and cyclooxygenase (COX) inhibitor. Major metabolites are 4´-hydroxydiclofenac and 5´-hydroxydiclofenac. Has been used as substrate selective for CYP2C9.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Acid-Sensing (Proton-gated) Ion Channels (ASICs) and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Signal Word

Danger

Hazard Statements

H301,H361d,H372,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2 - Repr. 2 - STOT RE 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Amit Alok et al.
Mutation research, 755(2), 156-162 (2013-07-06)
The potential of clinical drug diclofenac sodium which is routinely used in clinics as non-steroid anti-inflammatory drugs opens a new insight in development of radioprotector. The drug has shown its potential radioprotective efficacy in clonogenic cell survival in Chinese hamster
Simultaneous potentiometric and fluorimetric determination of diclofenac in a sequential injection analysis system
Analytica Chimica Acta, 470, 185-194 (2002)
Diclofenac sodium (GP 45840, Voltaren), a potent inhibitor of prostaglandin synthetase.
E C Ku et al.
Biochemical pharmacology, 24(5), 641-643 (1975-03-01)
Jin-Mu Yi et al.
BMC complementary and alternative medicine, 15, 441-441 (2015-12-20)
Descurainia sophia seeds have a variety of pharmacological functions and been widely used in traditional folk medicine. However, their effects on human drug metabolizing enzyme (DME) activities have not been elucidated. The present study investigated the inhibitory effects of an
Seung-Hwan Jung et al.
Redox biology, 37, 101751-101751 (2020-10-21)
Treatment with nonsteroidal anti-inflammatory drugs (NSAIDs) is associated with various side effects, including cardiovascular and hepatic disorders. Studies suggest that mitochondrial damage and oxidative stress are important mediators of toxicity, yet the underlying mechanisms are poorly understood. In this study
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