Intra-Articular Injection of Tenoxicam in the Treatment of Osteoarthritis of the Knee

Ünlü, Zeliha; Ay, Kamuran

doi:10.1300/j094v14n04_05

Journal of Musculoskeletal Pain

2006

DOI: 10.1300/j094v14n04_05

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Intra-Articular Injection of Tenoxicam in the Treatment of Osteoarthritis of the Knee

Zeliha Ünlü

Kamuran Ay

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Cited by 3 publications

(1 citation statement)

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“…It has a longer half-life and one-a-day advantage over 2. Thus, it has achieved a significant role in the treatment of rheumatic diseases over the last decades [17] [18].…”

mentioning

confidence: 99%

Site‐Specific Acid–Base Properties of Tenoxicam

Kóczián

Völgyi

Kökösi

et al. 2007

Helvetica Chimica Acta

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The Hammett approach, as a new deductive tool, was introduced to characterize the otherwise inaccessible minor protonation pathway of tenoxicam (1), the non-steroidal anti-inflammatory drug. A total of eight compounds, constituting a systematic series of side chain-substituted analogues of tenoxicam and piroxicam (2), were synthesized and studied in terms of acidÀbase properties and Hammett constants to identify the ideal replacement of the unprotonated pyridin-2-yl group, a key moiety in both molecules. Hammett constants of the phenyl substituents have been found to be in a linear correlation with the experimental log K values of the enolate sites, the basic moiety of the extended conjugated system in this family of piroxicam derivatives. Then, a similar correlation was observed for the analogous tenoxicam derivatives. After identifying the 2-aza Hammett constant of the pyridin-2-yl group and the corresponding log K value, the site-specific acid -base properties of tenoxicam could be quantitated. This novel method is assessed to be a fine-tuning tool to find the ideal substituent by using analogue-based deductive method to obtain site-specific constants of the minor protonation/deprotonation pathway in drugs and biomolecules. The tenoxicam microconstant values indicate that the enolate moiety is of extremely low basicity (reflected by the log k O ¼ 3.70 and log k O N ¼ 1.09 values), which can, however, be interpreted in terms of the peculiar ring system and the overwhelming electron-withdrawing effects of the adjacent heteroatoms. A diagram depicting the pH-dependent distribution of 1 microspecies is also presented.

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“…It has a longer half-life and one-a-day advantage over 2. Thus, it has achieved a significant role in the treatment of rheumatic diseases over the last decades [17] [18].…”

mentioning

confidence: 99%

Site‐Specific Acid–Base Properties of Tenoxicam

Kóczián

Völgyi

Kökösi

et al. 2007

Helvetica Chimica Acta

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show abstract

Reduction of systemic exposure and side effects by intra-articular injection of anti-inflammatory agents for osteoarthritis: what is the safer strategy?

Xie

Wang

Chen

et al. 2023

Journal of Drug Targeting

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Thanks to Reviewers and Moving on

Russell¹

2006

Journal of Musculoskeletal Pain

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Intra-Articular Injection of Tenoxicam in the Treatment of Osteoarthritis of the Knee

Cited by 3 publications

References 27 publications

Site‐Specific Acid–Base Properties of Tenoxicam

Site‐Specific Acid–Base Properties of Tenoxicam

Reduction of systemic exposure and side effects by intra-articular injection of anti-inflammatory agents for osteoarthritis: what is the safer strategy?

Thanks to Reviewers and Moving on

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