Ester Prodrugs of Flurbiprofen: Synthesis, Plasma Hydrolysis and Gastrointestinal Toxicity.

Mohan, Rhea; Ramaa, C. S.

doi:10.1002/chin.200746204

Cited by 7 publications

(8 citation statements)

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“…The nine alkyl ester prodrugs (Fig. 63 ) of flurbiprofen synthesized with an aim to reduce its gastrointestinal side-effects [ 54 ]. These were subjected to plasma hydrolysis and gastrointestinal toxicity studies.…”

Section: Resultsmentioning

confidence: 99%

Prodrugs of NSAIDs: A Review

Shah¹,

Gupta²,

Chauhan³

et al. 2017

TOMCJ

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Intoroduction:Prodrug approach deals with chemical biotransformation or enzymatic conversion or involves inactive or less active bio-reversible derivatives of active drug molecules. They have to pass through enzymatic or chemical biotransformation before eliciting their pharmacological action.Methods & Materials:The two different pharmacophores combine to give synergistic activity or may help in targeting the active drug to its target. Prodrug super seeds the problems of prodrug designing, for example solubility enhancement, bioavailability enhancement, chemical stability improvement, presystemic metabolism, site specific delivery, toxicity masking, improving patient acceptance, or eradicating undesirable adverse effects.Results:As an outcome the search for a prodrug or mutual prodrug with reduced toxicity has continued during recent years. This present review emphasizes the common help to revamp physiochemical, pharmaceutical and therapeutic effectiveness of drugs.Conclusion:This gives the researcher a common platform where they can find prodrugs of commonly used NSAIDs to overcome the gastrointestinal toxicity (irritation, ulcergenocity and bleeding).

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Section: Resultsmentioning

confidence: 99%

Prodrugs of NSAIDs: A Review

Shah¹,

Gupta²,

Chauhan³

et al. 2017

TOMCJ

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“…Alcohols form ester bonds with carboxylic groups of drug moiety. N-propyl, iso-butyl, iso-propyl, t-butyl, benzyl, cyclopentyl and cyclohexyl alcohols (Table 4) [60,61] are alcohols used as promoieties in synthesis of ester prodrugs. Iodomethyl pivalate and 2-bromo ethyl acetate are also used.…”

Section: Alcohols As Prodrug Carriersmentioning

confidence: 99%

Carriers for Prodrug Synthesis: A Review

Mehta

Chabukswar²,

Jagdale

2019

pharmaceutical-sciences

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categorized as prodrugs currently, and also that during 2008, 33 % of approved small molecular weight drugs were prodrugs [5-7]. The objective of this review is to provide the researchers with a compilation of which carriers would be suitable for prodrug synthesis and what would be their benefi ts. Classifi cation of prodrugs: According to Wermuth prodrugs can be divided into two main categories, bioprecusors and carrierlinked prodrugs [8]. Bioprecursors do not have a promoiety or carrier but yield the active compound upon biotransformation. A bioprecursor prodrug is transformed chemically through hydration (for example, lactones such as some statins), reduction (for example, sulindac, platinum (IV) complexes) or oxidation (for example, dexpanthenol, nabumetone) or metabolically to the active agent [5,9-11]. Carrier-linked prodrugs are for drugs with major drawbacks, which are linked to a nontoxic carrier or promoiety through covalent linkage to change or get

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“…Chronic use of these medications, which are used during eye surgery and for the treatment of rheumatoid arthritis, ankylosing spondylitis, and degenerative joint disease for the reduction of pain, fever and inflammation ( 13 ), has shown efficacy for treatment of gastric or duodenal ulcers in patients. Moreover, masking the free carboxylic group has been shown to improve gastrointestinal tolerability ( 14 ). It is this carboxylic acid group which lends itself to facile esterification with DMB for formation of the light-sensitive conjugates which are depicted in Fig.…”

Section: Introductionmentioning

confidence: 99%

Photochemically Controlled Drug Dosing from a Polymeric Scaffold

et al. 2017

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PurposeTo develop the first photoactive biomaterial coating capable of controlled drug dosing via inclusion of synthesised drug-3,5-dimethoxybenzoin (DMB) conjugates in a poly(2-methyoxyethyl acrylate) (pMEA) scaffold.MethodsFlurbiprofen- and naproxen-DMB conjugates were prepared via esterification and characterised via NMR spectroscopy and mass spectrometry following chromatographic purification. Conjugate photolysis was investigated in acetonitrile solution and within the pMEA matrix following exposure to low-power 365 nm irradiation. Photo-liberation of drug from pMEA into phosphate buffered saline was monitored using UV-vis spectroscopy.ResultsThe synthetic procedures yielded the desired drug conjugates with full supporting characterisation. Drug regeneration through photolysis of the synthesised conjugates was successful in both acetonitrile solution and within the pMEA scaffold upon UV irradiation. Conjugates were retained within the pMEA scaffold with exclusive drug liberation following irradiation and increased drug dose with increasing exposure. Multi-dosing capacity was demonstrated though the ability of successive irradiation periods to generate further bursts of drug.ConclusionThis study demonstrates the first application of photochemically controlled drug release from a biomaterial coating and the feasibility of using pMEA as a scaffold for housing the photoactive drug-DMB conjugates.

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Ester Prodrugs of Flurbiprofen: Synthesis, Plasma Hydrolysis and Gastrointestinal Toxicity.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 7 publications

References 0 publications

Prodrugs of NSAIDs: A Review

Prodrugs of NSAIDs: A Review

Carriers for Prodrug Synthesis: A Review

Photochemically Controlled Drug Dosing from a Polymeric Scaffold

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