二氢吡啶类抗高血压药物的晶型应用与研究进展
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摘要
二氢吡啶类(地平类)钙通道阻滞药目前临床上常用于治疗高血压。近年来,随着地平类药物仿制药的大量出现,人们发现其药效与原研药物相比差距较大,其中原因与口服制剂晶型的差异关系密切。该文对目前国内市场上的部分地平类药物多晶型现象进行综述,介绍地平类晶型药物的临床应用与研究进展,分析同种药物不同晶型间的差异,为地平类药物的仿制药乃至新晶型地平类药物的研发提供参考和思路。
Dihydropyridine( DHP) calcium channel blockers drugs( dipine in drug names) are currently used in the treatment of hypertension clinically. In recent years,with the emergence of generic drugs,it has been found that the drug efficacy is quite different from that of the original drug,and the reason is closely related to the difference in the crystal forms of the oral preparations. This paper reviews the polymorphic phenomenon of some DHP calcium channel blockers in the domestic market,introduces the clinical application and research progress of the DHP drugs,analyzes the differences between different crystal forms of the same drugs. This work may provide references and ideas for the research and development of generic drugs or new crystalline drug of DHP drugs.
Dihydropyridine( DHP) calcium channel blockers drugs( dipine in drug names) are currently used in the treatment of hypertension clinically. In recent years,with the emergence of generic drugs,it has been found that the drug efficacy is quite different from that of the original drug,and the reason is closely related to the difference in the crystal forms of the oral preparations. This paper reviews the polymorphic phenomenon of some DHP calcium channel blockers in the domestic market,introduces the clinical application and research progress of the DHP drugs,analyzes the differences between different crystal forms of the same drugs. This work may provide references and ideas for the research and development of generic drugs or new crystalline drug of DHP drugs.
引文
[1] JARARI N,RAO N,PEELA J R,et al. A review on prescribing patterns of antihypertensive drugs[J]. Clin Hypertens,2015,22:7.
[2]郑君毅,蔡英,丛洪良.高血压药物治疗的研究进展[J].医学综述,2014,20(13):2423-2424.
[3]郭祖德,刘文彬,陈英耀.国家医保药物目录遴选的临床证据支持:以甲类抗高血压药物为例[J].中国卫生政策研究,2014,7(8):24-28.
[4] WANG A L,IADECOLA C,WANG G. New generations of dihydropyridines for treatment of hypertension[J]. J Geriatric Cardiol,2017,14(1):67-72.
[5]吕扬,杜冠华.晶型药物[M].北京:人民卫生出版社,2009.
[6]高晶,滕再进,束俭辉,等.固体制剂生产过程中的药物晶型转变[J].中国新药杂志,2018,27(9):1000-1005.
[7]刘嘉,郑明.药物多晶型的研究进展[J].西北药学杂志,2017,32(3):394-396.
[8]郝甜媛,刘欢,陈常青.晶型转化对药物稳定性的影响研究进展[J].现代药物与临床,2013,28(3):457-460.
[9]杜冠华,吕扬.固体化学药物的优势药物晶型[J].中国药学杂志,2010,45(1):5-10.
[10]金方方,尹婕,南楠.化学口服固体制剂仿制药质量和疗效一致性评价研究思考[J].药物分析杂志,2018,38(4):575-581.
[11] PABST G,LUTZ D,MOLZ K H,et al.Pharmacokinetics and bioavailability of three different galenic nifedipine preparations[J].Arzneimittel Forschung,1986,36(2):256-260.
[12] KLEINBLOESEM C H,VAN BRUMMELEN P, BREIMER D D. Nifedipine. relationship between pharmacokinetics and pharmacodynamics[J].Clin Pharm,1987,12(1):12-29.
[13] CAIRA M R,ROBBERTSE Y,BERGH J J,et al. Structural characterization,physicochemical properties,and thermal stability of three crystal forms of nifedipine[J].J Pharm Sci,2003,92(12):2519-2533.
[14] GROOFF D,LIEBENBERG W,DE VILLIERS M M.Preparation and transformation of true nifedipine polymorphs:investigated with differential scanning calorimetry and X-Ray diffraction pattern fitting methods[J].J Pharm Sci,2011,100(5):1944-1957.
[15] BORTOLOTTI M,LONARDELLI I,PEPPONI G.Determination of the crystal structure of nifedipine form C by synchrotron powder diffraction[J]. Acta Crystallographica Section B,2011,67(Pt 4):357-364.
[16]陈睿.三种硝苯地平口服制剂一致性评价[D].济南:山东大学,2013:62-75.
[17]周星彤.硝苯地平口服制剂的仿制药质量一致性评价研究[D].青岛:青岛大学,2017:38-45.
[18]孙加琳,宋俊科,邢逞,等.临床常用尼群地平片在大鼠体内药代动力学比较研究[J].中国临床药理学与治疗学,2012,17(7):755-750.
[19]袁恒杰,陈大为,范立君.尼群地平多晶型化学稳定性影响因素考察[J].中国医院药学杂志,2004,24(11):691-693.
[20]吕扬,孙岚,杜冠华,等.尼群地平的一种优势晶型、其制法和其药物组合物与用途:ZL200810102728. X[P].2009-09-30.
[21]袁恒杰,陈大为,任耘,等.尼群地平多晶型家兔体内药动学及生物利用度的研究[J].中国医院药学杂志,2009,29(1):29-32.
[22]应剑,杜冠华.新晶型尼群地平片的生物利用度研究[C].药学发展前沿论坛及药理学博士论坛论文集,2008.
[23]孙中利.晶Ⅳ型和晶Ⅰ型尼群地平片人体药代动力学和生物等效性研究[D].济南:山东大学,2015:43-60.
[24] MORENO-CALVO E,MUNTO M,WURST K, et al.Polymorphs and solvates of nicardipine hydrochloride.Selecive stabilization of different diastereomeric racemates[J].Mol Pharm,2011,8(2):395-404.
[25]盛巍,王洪亮,杨艳芳,等.盐酸尼卡地平β晶型制备及其固体分散体研究[J].中南药学,2018,16(6):731-737.
[26]杜冠华,吕扬.固体化学药物的优势药物晶型[J].中国药学杂志,2010,45(1):5-10.
[27]郭栋,宋嘉熙,李丹,等.手性尼莫地平绝对构型的确定和关联[J].物理化学学报,2016,32(9):2241-2254.
[28]焦凌泰,张丽,杨德智,等.尼莫地平两种晶型的拉曼光谱分析和溶出度实验[J].医药导报,2017,36(10):1175-1179.
[29]杨世颖,邢逞,张丽,等.基于粉末X射线衍射技术的固体制剂晶型定性分析[J].医药导报,2015,34(7):930-934.
[30]周启蒙,宋俊科,邢逞,等.两种晶型尼莫地平片剂在恒河猴体内药代动力学研究[J].药学学报,2017,52(12):1918-1923.
[31]袁凤燕,黄希正.新型钙通道拮抗剂间-尼索地平及尼索地平[J].沈阳药科大学学报,1990,7(1):58-59.
[32] WANG H,ZHANG L,WANG Q,et al.Validated LC-MS-MS method for determination of m-nisoldipine polymorphs in rat plasma and its application to pharmacokinetic studies[J]. J Chromatogr B,2006,835(1/2):71-76.
[33]王海荣.多晶型间尼索地平的药代动力学与组织分布研究[D].石家庄:河北医科大学,2006:12-47.
[34]张永乐.间尼索地平多晶型及多无定形态的研究[D].石家庄:河北医科大学,2015:11-40.
[35] FOSSHEIM R.Crystal structure of the dihydropyridine Ca2+antagonist felodipine. dihydropyridine binding prerequisites assessed from crystallographic data[J]. J Med Chem,1986,29(2):305-307.
[36] ROLLINGER J M,BURGER A.Polymorphism of racemic felodipine and the unusual series of solid solutions in the binary system of its enantiomers[J]. J Pharm Sci,2001,90(7):949-959.
[37]张娜,张雯,庾莉菊,等.非洛地平及其制剂的晶型分析[J].中国药学杂志,2018,53(1):64-71.
[38]王敏.阿折地平多晶型的研究[D].石家庄:河北医科大学,2013:56-74.
[39]林玉龙,吴海燕,郭伟,等.磺丁基醚-β-环糊精对不同晶型阿折地平的包合作用[J].中国医院药学杂志,2015,35(22):2000-2004.
[40]卜鑫珏,张涛,王驰,等.盐酸乐卡地平Ⅰ、Ⅱ晶型及无定型对制剂制备的影响[J].中国药房,2017,28(10):1346-1349.
[41] SINGHAL D,CURATOLO W.Drug polymorphism and dosage form design:a practical perspective[J]. Adv Drug Del Rev,2004,56(3):335-347.
[42] RODRIGUEZ-SPONG B,PRICE CP,JAYASANKAR A,et al.General principles of pharmaceutical solid polymorphism:a supramolecular perspective[J]. Adv Drug Del Rev,2004,56(3):241-274.
[2]郑君毅,蔡英,丛洪良.高血压药物治疗的研究进展[J].医学综述,2014,20(13):2423-2424.
[3]郭祖德,刘文彬,陈英耀.国家医保药物目录遴选的临床证据支持:以甲类抗高血压药物为例[J].中国卫生政策研究,2014,7(8):24-28.
[4] WANG A L,IADECOLA C,WANG G. New generations of dihydropyridines for treatment of hypertension[J]. J Geriatric Cardiol,2017,14(1):67-72.
[5]吕扬,杜冠华.晶型药物[M].北京:人民卫生出版社,2009.
[6]高晶,滕再进,束俭辉,等.固体制剂生产过程中的药物晶型转变[J].中国新药杂志,2018,27(9):1000-1005.
[7]刘嘉,郑明.药物多晶型的研究进展[J].西北药学杂志,2017,32(3):394-396.
[8]郝甜媛,刘欢,陈常青.晶型转化对药物稳定性的影响研究进展[J].现代药物与临床,2013,28(3):457-460.
[9]杜冠华,吕扬.固体化学药物的优势药物晶型[J].中国药学杂志,2010,45(1):5-10.
[10]金方方,尹婕,南楠.化学口服固体制剂仿制药质量和疗效一致性评价研究思考[J].药物分析杂志,2018,38(4):575-581.
[11] PABST G,LUTZ D,MOLZ K H,et al.Pharmacokinetics and bioavailability of three different galenic nifedipine preparations[J].Arzneimittel Forschung,1986,36(2):256-260.
[12] KLEINBLOESEM C H,VAN BRUMMELEN P, BREIMER D D. Nifedipine. relationship between pharmacokinetics and pharmacodynamics[J].Clin Pharm,1987,12(1):12-29.
[13] CAIRA M R,ROBBERTSE Y,BERGH J J,et al. Structural characterization,physicochemical properties,and thermal stability of three crystal forms of nifedipine[J].J Pharm Sci,2003,92(12):2519-2533.
[14] GROOFF D,LIEBENBERG W,DE VILLIERS M M.Preparation and transformation of true nifedipine polymorphs:investigated with differential scanning calorimetry and X-Ray diffraction pattern fitting methods[J].J Pharm Sci,2011,100(5):1944-1957.
[15] BORTOLOTTI M,LONARDELLI I,PEPPONI G.Determination of the crystal structure of nifedipine form C by synchrotron powder diffraction[J]. Acta Crystallographica Section B,2011,67(Pt 4):357-364.
[16]陈睿.三种硝苯地平口服制剂一致性评价[D].济南:山东大学,2013:62-75.
[17]周星彤.硝苯地平口服制剂的仿制药质量一致性评价研究[D].青岛:青岛大学,2017:38-45.
[18]孙加琳,宋俊科,邢逞,等.临床常用尼群地平片在大鼠体内药代动力学比较研究[J].中国临床药理学与治疗学,2012,17(7):755-750.
[19]袁恒杰,陈大为,范立君.尼群地平多晶型化学稳定性影响因素考察[J].中国医院药学杂志,2004,24(11):691-693.
[20]吕扬,孙岚,杜冠华,等.尼群地平的一种优势晶型、其制法和其药物组合物与用途:ZL200810102728. X[P].2009-09-30.
[21]袁恒杰,陈大为,任耘,等.尼群地平多晶型家兔体内药动学及生物利用度的研究[J].中国医院药学杂志,2009,29(1):29-32.
[22]应剑,杜冠华.新晶型尼群地平片的生物利用度研究[C].药学发展前沿论坛及药理学博士论坛论文集,2008.
[23]孙中利.晶Ⅳ型和晶Ⅰ型尼群地平片人体药代动力学和生物等效性研究[D].济南:山东大学,2015:43-60.
[24] MORENO-CALVO E,MUNTO M,WURST K, et al.Polymorphs and solvates of nicardipine hydrochloride.Selecive stabilization of different diastereomeric racemates[J].Mol Pharm,2011,8(2):395-404.
[25]盛巍,王洪亮,杨艳芳,等.盐酸尼卡地平β晶型制备及其固体分散体研究[J].中南药学,2018,16(6):731-737.
[26]杜冠华,吕扬.固体化学药物的优势药物晶型[J].中国药学杂志,2010,45(1):5-10.
[27]郭栋,宋嘉熙,李丹,等.手性尼莫地平绝对构型的确定和关联[J].物理化学学报,2016,32(9):2241-2254.
[28]焦凌泰,张丽,杨德智,等.尼莫地平两种晶型的拉曼光谱分析和溶出度实验[J].医药导报,2017,36(10):1175-1179.
[29]杨世颖,邢逞,张丽,等.基于粉末X射线衍射技术的固体制剂晶型定性分析[J].医药导报,2015,34(7):930-934.
[30]周启蒙,宋俊科,邢逞,等.两种晶型尼莫地平片剂在恒河猴体内药代动力学研究[J].药学学报,2017,52(12):1918-1923.
[31]袁凤燕,黄希正.新型钙通道拮抗剂间-尼索地平及尼索地平[J].沈阳药科大学学报,1990,7(1):58-59.
[32] WANG H,ZHANG L,WANG Q,et al.Validated LC-MS-MS method for determination of m-nisoldipine polymorphs in rat plasma and its application to pharmacokinetic studies[J]. J Chromatogr B,2006,835(1/2):71-76.
[33]王海荣.多晶型间尼索地平的药代动力学与组织分布研究[D].石家庄:河北医科大学,2006:12-47.
[34]张永乐.间尼索地平多晶型及多无定形态的研究[D].石家庄:河北医科大学,2015:11-40.
[35] FOSSHEIM R.Crystal structure of the dihydropyridine Ca2+antagonist felodipine. dihydropyridine binding prerequisites assessed from crystallographic data[J]. J Med Chem,1986,29(2):305-307.
[36] ROLLINGER J M,BURGER A.Polymorphism of racemic felodipine and the unusual series of solid solutions in the binary system of its enantiomers[J]. J Pharm Sci,2001,90(7):949-959.
[37]张娜,张雯,庾莉菊,等.非洛地平及其制剂的晶型分析[J].中国药学杂志,2018,53(1):64-71.
[38]王敏.阿折地平多晶型的研究[D].石家庄:河北医科大学,2013:56-74.
[39]林玉龙,吴海燕,郭伟,等.磺丁基醚-β-环糊精对不同晶型阿折地平的包合作用[J].中国医院药学杂志,2015,35(22):2000-2004.
[40]卜鑫珏,张涛,王驰,等.盐酸乐卡地平Ⅰ、Ⅱ晶型及无定型对制剂制备的影响[J].中国药房,2017,28(10):1346-1349.
[41] SINGHAL D,CURATOLO W.Drug polymorphism and dosage form design:a practical perspective[J]. Adv Drug Del Rev,2004,56(3):335-347.
[42] RODRIGUEZ-SPONG B,PRICE CP,JAYASANKAR A,et al.General principles of pharmaceutical solid polymorphism:a supramolecular perspective[J]. Adv Drug Del Rev,2004,56(3):241-274.