School of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, and Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, P. R. China.
Medical College, Qinghai University, Qinghai 810001, P. R. China.
Mol Pharm. 2019 Dec 2;16(12):4978-4986. doi: 10.1021/acs.molpharmaceut.9b00851. Epub 2019 Oct 29.
Maximizing the pharmacological efficacy of albendazole (ABZ), an anti-echinococcosis drug, is essential in the long-term treatment of patients with echinococcosis. As a weakly alkaline drug, ABZ has a pH-dependent solubility that decreases dramatically from gastric fluid (pH 1.4) to intestinal fluid (pH 6.5), where it is absorbed. In this study, we endeavored to develop an optimized tablet formulation of ABZ to improve its dissolution and oral bioavailability from two aspects: a faster initial dissolution in the gastric pH condition (i.e., the "spring") and a more prolonged drug supersaturation in the intestinal pH condition (i.e., the "parachute"). To achieve this goal, ABZ-HCl salt was selected first, which demonstrated a higher intrinsic dissolution rate under pH 1.4 compared with the ABZ free base that is used in the commercial product Albenda. Second, by comparing the ABZ supersaturation kinetics under pH 6.5 in the presence of various polymers including poly(vinylpyrrolidone) (PVP), PVP/VA, hydroxypropyl methylcellulose (HPMC), and HPMC acetate succinate (HPMC-AS), HPMC-AS was found to be the most effective crystallization inhibitor for ABZ, likely due to the hydrophobic interaction between ABZ and HPMC-AS in an aqueous environment. The newly designed tablet formulation containing ABZ-HCl and HPMC-AS showed ∼3 times higher oral bioavailability compared with that of Albenda in Beagle dogs. More significantly, the anti-echinococcosis efficacy of the improved formulation was 2.4 times higher than that of Albenda in a secondary hepatic alveolar echinococcosis Sprague-Dawley rat model. The strategy of simultaneously improving the spring and parachute of an oral formulation of ABZ, by using a highly soluble salt and an effective polymeric crystallization inhibitor, was once again proven to be a viable and readily translatable approach to optimize the unsatisfactory oral medicines due to solubility and bioavailability limitations.
最大限度地提高抗包虫病药物阿苯达唑(ABZ)的药效对于长期治疗包虫病患者至关重要。ABZ 是一种弱碱性药物,其溶解度随 pH 值变化而显著变化,从胃液(pH1.4)到肠液(pH6.5)降低,在此条件下吸收。在这项研究中,我们努力从两个方面优化 ABZ 的片剂配方,以提高其溶解和口服生物利用度:在胃 pH 条件下(即“弹簧”)更快地初始溶解,以及在肠 pH 条件下(即“降落伞”)更持久的药物过饱和。为了实现这一目标,首先选择了 ABZ-HCl 盐,与 Albenda 商业产品中使用的 ABZ 游离碱相比,其在 pH1.4 下具有更高的内在溶解速率。其次,通过比较 pH6.5 下各种聚合物(包括聚乙烯吡咯烷酮(PVP)、PVP/VA、羟丙基甲基纤维素(HPMC)和 HPMC 醋酸琥珀酸酯(HPMC-AS))存在下的 ABZ 过饱和动力学,发现 HPMC-AS 是 ABZ 最有效的结晶抑制剂,可能是由于 ABZ 和 HPMC-AS 在水相环境中的疏水相互作用。含有 ABZ-HCl 和 HPMC-AS 的新设计片剂配方在比格犬中的口服生物利用度比 Albenda 高约 3 倍。更重要的是,在继发性肝泡状棘球蚴病斯普拉格-道利大鼠模型中,改良配方的抗包虫病疗效比 Albenda 高 2.4 倍。通过使用高溶解度盐和有效的聚合物结晶抑制剂同时改善 ABZ 口服制剂的“弹簧”和“降落伞”的策略,再次证明了这是一种可行且易于转化的方法,可以优化由于溶解度和生物利用度限制而不理想的口服药物。