Synthesis and evaluation of novel prodrugs of naproxen

Sharma, Prabodh Chander; Yadav, Suman; Pahwa, Rakesh; Kaushik, Dhirender; Jain, Sandeep

doi:10.1007/s00044-010-9364-8

Cited by 15 publications

(13 citation statements)

References 20 publications

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“…Free carboxylic group of S-Naproxen has severe gastrointestinal side effects on oral administration that restricts its use [2] . S-Naproxen can cause undesirable gastrointestinal toxic effects such as bleeding, dyspepsia and peptic ulcers.…”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Synthesis of S-Naproxenal oleins

Xin¹,

Jiang²

2015

Proceedings of the 2015 International Conference on Education, Management, Information and Medicine

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Abstract. S-Naproxenal oleins are compounds of S-Naproxen ((S)-2-(6-methoxy-2-naphthyl) propionic acid) and olein connected by an ester bond and can be used as potential prodrug in anti-inflammatory. In the present work, we describe for the first time the lipase-catalyzed synthesis of the S-Naproxenal oleins by transesterification between S-Naproxen and triolein in organic solvents medium. The ability of lipases to catalyze the transesterification between S-Naproxen and triolein was investigated. Only the lipase from Candida rugosa and the immobilized lipase B from Candida antarctica (Novozym 435) catalyzed the transesterification. The influences of reaction condition on the combined yield of S-Naproxenal diolein (NDO) and S-Naproxenal monoolein (NMO) were investigated. Water activity (a w ) had an obvious influence on transesterification efficacy. A maximal combined yield of 23.1 % of S-Naproxenal diolein (NDO) and S-Naproxenal monoolein (NMO) was obtained under optimum condition. These results indicated the industrial potential of the operation scheme developed in this study.

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Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Synthesis of S-Naproxenal oleins

Xin¹,

Jiang²

2015

Proceedings of the 2015 International Conference on Education, Management, Information and Medicine

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“…Naproxen [(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid] [17] was originally marketed as the prescription drug Naprosyn in 1976, and naproxen sodium was first marketed under the trade name Anaprox in 1980. It remains a prescription-only drug in much of the world.…”

Section: Introductionmentioning

confidence: 99%

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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“…Non steroidal anti-inflammatory drugs (NSAIDs) have been used for the treatment of ailments such as pain, fever and inflammation and also in chronic conditions such as arthritis, psoriasis and asthma [115][116][117][118][119][120] . NSAIDs principally act by two different mechanisms: a direct contact mechanism on the gastro intestinal (GI) mucosa through oral dose and a generalized systemic action appearing after intravenous dosing 121,122 . Their use is mainly restricted by their well known and serious adverse GI side effects such as gastroduodenal erosions, ulcerations and renal toxicities and therefore the discovery of new safer anti-inflammatory drugs represents a challenging goal for researchers 123,124 .…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%