Diclofenac sodium (GP 45840, voltaren), a potent inhibitor of prostaglandin synthetase

Ku, Edmond C.; Wasvary, Jong M.; Cash, William D.

doi:10.1016/0006-2952(75)90186-0

Cited by 106 publications

(33 citation statements)

References 16 publications

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“…The history of diclofenac (DCL) started at early 70s when, on the basis of both experimental and clinical findings, the features of an ideal nonsteroidal anti-inflammatory drug were postulated [5][6][7][8]. They said that an effective antirheumatic agent should have an acidity constant between 4 and 5, a partition coefficient (octanol/water at pH 7.4) of c.a.…”

Section: Introductionmentioning

confidence: 99%

Structural stability of diclofenac vs. inhibition activity from ab initio molecular dynamics simulations. Comparative study with ibuprofen and ketoprofen

2017

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Diclofenac is the world known nonsteroidal antiinflammatory drug (NSAID) predicted before its syntesis on the basis of the model COX enzyme. Due to its specific structural properties the drug possesses high reactivity and outstanding tolerability. Among the key features defining the diclofenac structure is intramolecular N-H· · · O hydrogen bond confirmed during the X-ray analysis. In the present research we use static DFT calculations, the Quantum Theory of Atoms in Molecules and non-covalent interactions (NCI) index to confirm the additional intramolecular interactions, which influence the drug molecular structure. We focus on the structural stability of diclofenac as the result of the hydrogen bonds breaking/formation at finite temperature utilizing ab initio molecular dynamics simulations. The lifetime of different intramolecular hydrogen bonds is estimated. We perform also the comparative analysis of the structural stability of ibuprofen and ketoprofen molecules in the gas phase at 300 K with respect to diclofenac in terms of the NSAID inhibition activity. Due to the detailed description of diclofenac intramolecular interactions, possible drug modifications for its enhanced water solubility can be suggested.

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Section: Introductionmentioning

confidence: 99%

Structural stability of diclofenac vs. inhibition activity from ab initio molecular dynamics simulations. Comparative study with ibuprofen and ketoprofen

2017

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“…The successful effect ofdiclofenac in suppressing the inflammatory responses produced in both normal and irradiated animals might perhaps be attributed, at least in part, to its potent inhibitory effect on prostaglandin synthetase which would result in inhibition of the vasodilatation and exudation potentiating effects due to prostaglandins (Krupp et al, 1973;Ku et al, 1975); an effect common to all non-steroidal antiinflammatory drugs (Vane, 1971). Menasse et al (1978) also showed that diclofenac stabilizes lysosomal membranes and thus inhibits the release of lysosomal enzymes, which are probably responsible for the tissue destruction occurring in inflammatory rheumatic diseases.…”

Section: Discussionmentioning

confidence: 99%

Effect of exposure to radiation on the inflammatory process and its influence by diclofenac

El‐Ghazaly

Kenawy

Khayyal

et al. 1985

British J Pharmacology

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The effect of radiation exposure on the inflammatory process was studied in rats using the carrageenan‐induced paw oedema and adjuvant‐induced arthritis tests. Irradiation (0.5,1 and 2 Grays) resulted in a significant augmentation of the tissue response to carrageenan and the early phase of adjuvant‐induced arthritis, but suppressed the late phase. Diclofenac (1–5 mg kg−1) effectively reduced the exaggerated inflammatory response in irradiated animals in both the carrageenan paw oedema and adjuvant‐induced arthritis tests. The drug also had a prophylactic value in guarding against the induction of radiation damage. The inflammatory responses produced by irradiation and the benefits obtained by drug treatment may be related to changes in tissue prostaglandin levels and/or changes in the immune system.

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“…Diclofenac [2-(2,6-dichloranilino)phenylacetic acid] is the most potent member of this class of drugs. It works by reducing the production of prostaglandins [2], the chemical that causes pain, fever and inflammation. Diclofenac blocks the enzyme (cyclooxygenase) that produces prostaglandin, resulting in decrease in production of prostaglandin and hence subsequent relief from pain.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and Mechanism of Oxidation of Diclofenac Sodium by Keggin Type 12-Tungstocobalt(III) in Aqueous Medium

Sanjana¹,

Patnaik²,

Mohanty³

et al. 2017

Asian J. Chem.

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The kinetics of electron transfer reaction of diclofenac sodium with 12-tungstocobaltate (III) complex has been studied spectrophotometrically over the range 2.0 × 10 -3 ≤ [diclofenac sodium] ≤ 6.0 × 10 -3 mol/L, 6.03 ≤ pH ≤ 8.0 and at 293 ≤ T ≤ 308 K in aqueous medium at constant ionic strength I (0.5 mol/L sodium perchlorate). The electron transfer reaction showed pseudo-first order dependence in [diclofenac sodium] and [12-tungstocobaltate(III)] and less than unit order in [OH -]T. The activation parameters calculated for the electron transfer reaction favoured the formation of a precursor complex between the reactants. The product is characterized by FTIR and NMR spectra and is found to be [2-(2,6-dichloro phenylamino)phenyl]methanol.

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Diclofenac sodium (GP 45840, voltaren), a potent inhibitor of prostaglandin synthetase

Cited by 106 publications

References 16 publications

Structural stability of diclofenac vs. inhibition activity from ab initio molecular dynamics simulations. Comparative study with ibuprofen and ketoprofen

Structural stability of diclofenac vs. inhibition activity from ab initio molecular dynamics simulations. Comparative study with ibuprofen and ketoprofen

Effect of exposure to radiation on the inflammatory process and its influence by diclofenac

Kinetics and Mechanism of Oxidation of Diclofenac Sodium by Keggin Type 12-Tungstocobalt(III) in Aqueous Medium

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