Hydrolysis kinetics of the prodrug myristyl nicotinate

水解 化学 离子强度 前药 阿伦尼乌斯图 水溶液 动力学 反应速率常数 阿累尼乌斯方程 磷酸盐 色谱法 活化能 核化学 无机化学 有机化学 生物化学 物理 量子力学
作者
Bashar Al-Taani,Razan Haddad,Aliaa Al-Tarakji,Nasr Alrabadi
出处
期刊:Pharmaceutical Development and Technology [Taylor & Francis]
卷期号:27 (10): 1083-1092
标识
DOI:10.1080/10837450.2022.2152460
摘要

Myristyl nicotinate is a prodrug of nicotinic acid. In this research, the kinetics of hydrolysis for myristyl nicotinate was studied in an aqueous phosphate buffer solution within a 5-10 pH range and constant ionic strength at a high temperature which was 80 °C to perform accelerated hydrolysis experiments. The effect of temperature, ionic strength, buffer concentrations, and buffer type was studied. The degradation was monitored using a validated HPLC method. The kinetics of hydrolysis of myristyl nicotinate was also studied in skin and liver homogenates. The hydrolysis was found to follow pseudo-first-order kinetics. The rate constant was calculated from the slope of a linear plot of Ln transformation (Ln) of the remaining parent prodrug concentration versus time. The hydrolysis was found pH- dependent, and a pH rate profile was constructed. Moreover, the hydrolysis rate of the prodrug was found to be buffer species dependent. Carbonate buffer has the most catalytic effect over borate and phosphate buffers. The effect of temperature on the kinetics of hydrolysis of myristyl nicotinate in phosphate buffer at pH 9 at 343, 348, 353, and 358°K was studied. The hydrolysis was found to follow the Arrhenius equation. From the Arrhenius plot, the half-life at 25 °C, and the activation energy were calculated and were found to be 466.5 days and 24.57 kcal mol-1, respectively. The hydrolysis of the prodrug was faster in liver and skin homogenates than those in aqueous buffer solutions. The pseudo-first-order rate constants were found to be 0.012, 0.028 min-1 for myristyl nicotinate in the liver, and skin homogenates, respectively.
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