Synthesis and anti-inflammatory activity of a series of N-substituted naproxen glycolamides: Nitric oxide-donor naproxen prodrugs

Ranatunge, Ramani R.; Augustyniak, Michael E.; Dhawan, Vijay; Ellis, James L.; Garvey, David S.; Janero, David R.; Letts, L. Gordon; Richardson, Stewart K.; Shumway, Mathew; Trocha, A Mark; Young, Delano V.; Zemtseva, Irina S.

doi:10.1016/j.bmc.2005.11.040

Cited by 26 publications

(13 citation statements)

References 20 publications

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“…From the results, it was found that naproxen glycolamide nitrates represent a safer alternative to naproxen as anti-inflammatory medicines [14]. These compounds were evaluated for anti-inflammatory activity, drug release and gastric tolerance.…”

Section: XVImentioning

confidence: 99%

“…Selective COX-2 inhibitors are newly developed drugs and they possess the salutary analgesic and anti-inflammatory properties of NSAIDs with generally enhanced, but still not absolute, gastrointestinal (GI) tolerance [14,15]. A search for COX-2-specific inhibitors resulted in promising candidates such as valdecoxib, celecoxib, and rofecoxib.…”

Section: Introductionmentioning

confidence: 99%

“…A search for COX-2-specific inhibitors resulted in promising candidates such as valdecoxib, celecoxib, and rofecoxib. cardiovascular risk predisposes patients to heart attack and stroke with chronic use of coxibs and because of this, rofecoxib was withdrawn from the pharmaceutical market in 2004 [14]. Unfortunately, an apparent class-effect i.e.…”

Section: Introductionmentioning

confidence: 99%

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Naproxen: An Update on Physicochemical, Analytical and Pharmacological Aspects

Chander¹

2011

aiamc

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Naproxen is a propionic acid derivative related to the arylacetic acid group. This drug is one of the most popular non-steroidal anti-inflammatory agents. It is a non-selective cyclooxygenase inhibitor and is advocated for use in painful and inflammatory rheumatic and non-rheumatic conditions. In low risk patients, naproxen and ibuprofen may be the first choice agents because they are effective, well tolerated and inexpensive. Naproxen is rapidly and completely absorbed from the gastrointestinal tract with an in vivo bioavailability of 95% and elimination half-life is 12 to 17 h. It has a volume of distribution of 0.16 L/Kg and at therapeutic levels, it is more than 99% albumin-bound. Although introduced long back, several efforts have been done to develop its prodrugs and analytical procedures. The current article describes chemistry, pharmacology, pharmacokinetics, adverse effects, interactions and contraindications of naproxen. A special emphasis is laid on the review of recent literature of various prodrugs synthesized and analytical methods developed for determination of naproxen in pharmaceutical preparations.

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Section: XVImentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Naproxen: An Update on Physicochemical, Analytical and Pharmacological Aspects

Chander¹

2011

aiamc

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“…(3)) and tested their capacity of nitric oxide release in vivo and antiinflammatory, analgesic and ulcerogenic properties. Ranatunge et al [18], with a similar approach, developed an anti-inflammatory product with gastric protective effect decreasing GI injury by the COX inhibition and granting NO inhibiting COX (CINODs) as an alternative to selective COX-2 inhibitors. Some compounds were reported devoid of gastric ulcer tendency.…”

Section: Potential Therapeutical Indications and Pharmacology Of Nitrmentioning

confidence: 99%

Medicinal Chemistry and Anti-Inflammatory Activity of Nitric Oxide-Releasing NSAI Drugs

And

Küçükgüzel²

2009

MRMC

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Nitric Oxide, which acts as a non-specific cytotoxic mediator and a biological messenger on immunological competence, has been gaining significantly increasing importance. As an alternative to conventional NSAIDs having significant side effects, pharmacologically improved and therapeutically enhanced NO releasing non-steroidal anti-inflammatory drugs with less side effects are being planned to produce.

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“…(Bundgaard and Nielsen, 1988;Giammona et al, 1989;Otero Espinar et al, 1991;Chang and Tsai, 1997;Chang et al, 1998;Rautio et al, 2000;Bonina et al, 2001;Sheha et al, 2002;Khan and Khan, 2002;Chang et al, 2004;Swart et al, 2005;Ranatunge et al, 2006;Bhushan and Tanwar, 2008;Stefanko et al, 2008). Moreover, conjugation with amino acid such as L-aspartic acid has also been studied (El-Kamel et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of novel prodrugs of naproxen

et al. 2010

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A series of novel prodrugs of naproxen has been synthesized. Naproxen (1) was reacted with thionyl chloride to yield acid chloride (2) which was further reacted with glucose to form the glucosyl naproxen (3). Tetra-acetate of glucosyl naproxen was prepared and finally reacted with different amino acids to yield the title compounds. These compounds were evaluated for analgesic, anti-inflammatory activities, and for possible GI toxicity. Compound 5b depicted most potent analgesic activity with percentage inhibition of 98.15%. Compound 5a was found to be most potent anti-inflammatory agent with 76% inhibition. Compound 5n was second most active analgesic (92.26%) and anti-inflammatory (73%) agent. In vitro hydrolysis pattern of synthesized prodrugs was studied in phosphate buffer of pH 7.4 and acetate buffers of pH 3.0, 4.0, and 5.0, respectively. Selected compounds were evaluated for their ulcerogenic potential and all the tested derivatives were significantly less irritating to gastric mucosa than the parent drug.

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Synthesis and anti-inflammatory activity of a series of N-substituted naproxen glycolamides: Nitric oxide-donor naproxen prodrugs

Cited by 26 publications

References 20 publications

Naproxen: An Update on Physicochemical, Analytical and Pharmacological Aspects

Naproxen: An Update on Physicochemical, Analytical and Pharmacological Aspects

Medicinal Chemistry and Anti-Inflammatory Activity of Nitric Oxide-Releasing NSAI Drugs

Synthesis and evaluation of novel prodrugs of naproxen

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