Synthesis and structure analysis of cyclodehydration product of piroxicam: A metabolite detected in dogs and monkeys

Pal, Sarbani; Bindu, P.; Dubey, P. K.; Chakraborty, Subrata; Mukherjee, Alok K.

doi:10.1016/j.ejmech.2009.03.010

Cited by 7 publications

(3 citation statements)

References 12 publications

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“…Most of the drug molecules in present use are linked with some intolerable physicochemical or biopharmaceutical factors. Nonsteroidal anti-inflammatory drugs (NSAIDs) have possibility of common adverse effects like dyspepsia or acidity and ulceration that limits their uses [1]. These NSAIDs are commonly used in the treatment of pain and inflammation in various conditions like osteo/rheumatoid arthritis (OA/RA) [2].…”

Section: Synthesis Of Piroxicam Prodrugsmentioning

confidence: 99%

Mutual Prodrugs of Piroxicam

Imran¹,

Asif²

2019

Act Scie Pharma

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Section: Synthesis Of Piroxicam Prodrugsmentioning

confidence: 99%

Mutual Prodrugs of Piroxicam

Imran¹,

Asif²

2019

Act Scie Pharma

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“…The gastrointestinal side effects such as dyspepsia and frank ulceration constitute the most frequent of every adverse reaction that are caused by nonsteroidal anti-inflammatory drugs (NSAIDs) [1]. Piroxicam, 1,2-benzothiazine-3-carboxamide-4-hydroxy-2-methyl-N-(2-pyridyl)-1,1-dioxide, is effectively employed to treat rheumatoid arthritis, osteoarthritis, and musculoskeletal inflammation [2]. It is susceptible to produce gastric ulcerations associated with gastrointestinal (GI) bleeding and hemorrhages as prominent side effects [3].…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and Gastroprotective Evaluation of Prodrugs of Piroxicam

Redasani

Shinde

Surana

2014

Ulcers

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Therapeutically potential prodrugs of piroxicam were synthesized by effective masking of enolic hydroxyl group through generation of ester congeners. The reaction facilitated using N,N′-dicyclohexylcarbodiimide coupled with acetic acid, benzoic acid, p-toluic acid, m-toluic acid, and cinnamic acid. Synthesized prodrugs were characterized for confirmation of the said structures. The modification of piroxicam showed better anti-inflammatory activity as evoked by all prodrugs. Interestingly, compound 3e, cinnamic acid ester prodrug, depicted 75 percent inhibition of rat paw edema as compared to 56 percent for parent piroxicam at 6 h of study. The present work proves the applicability not only with increased anti-inflammatory activity, but also with marked attenuation in ulcerogenicity. Novel prodrug 3e, cinnamic acid derivative, was found to be the least ulcerogenic having ulcer index of 0.67 as compared to parent drug piroxicam with 2.67.

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“…1 These NSAIDs are widely used in the treatment of pain and inflammation in many conditions, including osteoarthritis (OA) and rheumatoid arthritis (RA). 2 Succession in the side effects of gastrointestinal (GI) tract predominantly stomach ulceration, bleeding and perforation are the chief limitation in use. This is due to local action exerted by direct contact of drug with gastric mucosa.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of novel mutual prodrugs of Piroxicam

et al. 2017

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Therapeutic efficacy of piroxicam can be improved by retarding gastrointestinal side effects by means of temporarily modification of enolic hydroxyl group chemically. The NSAIDs such as aceclofenac, ibuprofen, mefenamic acid and naproxen were selected as promoities with the aim of getting synergistic effect through these well known pharmaco-counter parts. The targeted prodrugs are synthesized successfully and confirmed by characterization. Synthesis involved chlorination of NSAIDs and coupling of this acid chloride with piroxicam through enolic hydroxyl group to get ester derivatives. Mutual prodrugs were evaluated by hydrolysis study at different pH (acidic, neutral, alkaline) using phosphate buffer. Prodrug derivatives were found to be stable at acidic and neutral pH but prone to hydrolysis at alkaline pH. Thus the objective of the presented study was to overcome the undesirable side effects of NSAIDs. Thus, current studies confirms that the mutual prodrug approach can be applied effectively in order to achieve the purpose of raising effectiveness of piroxicam under two lines; firstly, masking of enolic hydroxyl group through acids and converting them to esters and secondly, utilizing the known NSAIDs for achieving the synergistic effect.

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Synthesis and structure analysis of cyclodehydration product of piroxicam: A metabolite detected in dogs and monkeys

Cited by 7 publications

References 12 publications

Mutual Prodrugs of Piroxicam

Mutual Prodrugs of Piroxicam

Anti-Inflammatory and Gastroprotective Evaluation of Prodrugs of Piroxicam

Synthesis and evaluation of novel mutual prodrugs of Piroxicam

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