心脑血管疾病治疗药物共晶研究进展
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摘要
药物共晶作为近年来晶型药物研究中新的方向,正在受到广泛关注。共晶研究对于改善药物的溶解度、生物利用度及物理化学稳定性具有科学意义。该文从心脑血管疾病治疗药物的角度出发,针对心力衰竭、高血压、冠心病、心律失常、脑卒中五类发病率较高的心脑血管疾病,选取近年来具有代表性的10余种药物共晶研究的最新成果进行综述,为后续相关药物的共晶研究提供参考依据。
The pharmaceutical co-crystal has attracted a lot of attention in recent years as a new direction in the research of polymorphism drugs. The research on pharmaceutical co-crystal has scientific significance for improving the solubility,bioavailability and physical or chemical stability of drugs. In this paper,from the perspective of drugs for the treatment of cardiovascular diseases( including five major types: heart failure,hypertension,coronary heart disease and arrhythmia,stroke),the latest research results of pharmaceutical co-crystal reported in recent years are reviewed,hope to provide reference for the follow-up research and promote the development of pharmaceutical co-crystal in China.
The pharmaceutical co-crystal has attracted a lot of attention in recent years as a new direction in the research of polymorphism drugs. The research on pharmaceutical co-crystal has scientific significance for improving the solubility,bioavailability and physical or chemical stability of drugs. In this paper,from the perspective of drugs for the treatment of cardiovascular diseases( including five major types: heart failure,hypertension,coronary heart disease and arrhythmia,stroke),the latest research results of pharmaceutical co-crystal reported in recent years are reviewed,hope to provide reference for the follow-up research and promote the development of pharmaceutical co-crystal in China.
引文
[1] ZAWOROTKO M J.Molecules to crystals, crystals to molecules. and back again?[J]. Crystal Growth Design,2006,7(1):4-9.
[2] DESIRAJU G R.Crystal and co-crystal,cryst[J]. Eng Commun,2003,5:466-467.
[3] DUNITZ J D.Crystal and co-crystal:a second opinion[J].Crystengcomm,2003,5(91):506.
[4]高缘,祖卉,张建军.药物共晶研究进展[J].化学进展,2010,22(5):829-836.
[5]吕扬,杜冠华.晶型药物[M].北京:人民卫生出版社,2010.
[6] SEKHON B S.Pharmaceutical co-crystals-an update[J].Int Bull Drug Res,2012,1(2):24-39
[7]陈伟伟,高润霖,刘力生,等.《中国心血管病报告2016》概要[J].中国循环杂志,2017,32(6):521-530.
[8]张娜,黄海伟,林兰,等.心血管系统治疗药物的晶型研究进展[J].现代药物与临床,2014,29(6):690-695.
[9] GORI M,SENNI M.Sacubitril/valsartan(LCZ696)for the treatment of heart failure[J]. Expert Rev Cardiovasc Ther,2016,14(2):145-153.
[10]赖鑫芬,黄耀东,宗矩.新型心力衰竭治疗药物研究进展[J].世界临床药物,2007,28(3):157-162.
[11] FENG L,KARPINSKI P H,SUTTON P,et al. LCZ696:a dual-acting sodium supramolecular complex[J].Tetrahedron Lett,2012,53(3):275-276.
[12]李凌霏,彭鹏.高血压治疗药物研究进展[J].中国药业,2011,20(13):78-80.
[13] BEG S,SWAIN S,SINGH H P,et al. Development,optimization, and characterization of solid selfnanoemulsifying drug delivery systems of valsartan using porous carriers[J]. AAPS Pharmscitech,2012,13(4):1416-1427.
[14] THOMAS J E,NAYAK U Y,JAGADISH P C,et al.Design and characterization of valsartan co-crystals to improve its aqueous solubility and dissolution behavior[J]. Res J Pharm Technol,2017,10(1):26.
[15] WANG J R,WANG X,LU L,et al.Highly crystalline forms of valsartan with superior physicochemical stability[J].Cryst Growth Des,2013,13(7):3261-3269.
[16]郝玉明,韩永燕.噻嗪类利尿药在高血压患者中的应用[J].临床药物治疗杂志,2012,10(1):4-7.
[17] SANPHUI P,DEVI V K,CLARA D,et al. Cocrystals of hydrochlorothiazide:solubility and diffusion/permeability enhancements through drug–coformer interactions[J].Mol Pharm,2015,12(5):1615-1622.
[18] EL-GIZAWY S A,OSMAN M A,ARAFA M F, et al.Aerosil as a novel co-crystal co-former for improving the dissolution rate of hydrochlorothiazide[J]. Int J Pharm,2015,478(2):773-778.
[19] BHANDWALKAR O S,BHANDWALKAR M U,GHADGE D M,et al.Design and development of fast dissolving tablets of hydrochlorothiazide and atenolol co-crystals[J]. Int J Pharm Sci Res,2015,6(10):4368.
[20]张志婧.抗高血压药物的研究进展和临床应用[J].医药卫生:文摘版,2016(3):102.
[21]胡大一,孙艺红.冠心病药物治疗的最新进展和展望[J].中国实用内科杂志,2006,26(2):88-91.
[22] SHAYANFAR A,JOUYBAN A.Drug-drug coamorphous systems:characterization and physicochemical properties of coamorphous atorvastatin with carvedilol and glibenclamide[J].J Pharm Inn,2013,8(4):218-228.
[23] SHAYANFAR A,GHAVIMI H,HAMISHEKAR H,et al.Coamorphous atorvastatin calcium to improve its physicochemical and pharmacokinetic properties[J]. J Pharm Pharmaceut Sci,2013,16(4):577-587.
[24] WICAKSONO Y,WISUDYANINGSIH B,SISWOYO T A.Enhancement of solubility and dissolution rate of atorvastatin calcium by co-crystallization[J]. Trop J Pharm Res,2017,16(7):1497-1502.
[25] WICAKSONO Y,WISUDYANINGSIH B,SISWOYO T A.Cocrystal of atorvastatin calcium-malonic acid[J].Int Conf Med Health Sci,2017:75-78.
[26]李玉霞,江珊.瑞舒伐他汀的研究进展[J].心血管病学进展,2010,31(4):585-588.
[27] HAFNER A,BLATTER F,SZELAGIEWICZ M, et al.Multicomponent crystalline system of rosuvastatin calcium salt and vanillin:8.716.305[P].2014-05-06.
[28] HAFNER A,BLATTER F,SZELAGIEWICZ M, et al.Multicomponent system of rosuvastatin calcium salt and sorbitol:9.249.108[P].2016-02-02.
[29] FERRARI C,CASTELLIN A,GALVAGNI M,et al. Cocrystal intermediates of rosuvastatin and methods of using same:8.815.862[P].2014-08-26.
[30] IOELE G,GUNDUZ M G,DE L M,et al.Photodegradation studies of 1,4-dihydropyridine compounds by MCR analysis on UV spectral data[J]. Fut Med Chem,2016,8(2):107-115.
[31] YU Q,YAN Z,BAO J,et al.Taming photoinduced oxidation degradation of dihydropyridine drugs through cocrystallization[J]. Chem Commun, 2017, 53(91):12266-12269.
[32] KNAPIK-KOWALCZUK J,TU W,CHMIEL K,et al. Costabilization of amorphous pharmaceuticals-the case of nifedipine and nimodipine[J]. Mol Pharm,2018,15(6):2455-2465.
[33]张晓丹,余更生.美托洛尔治疗心律失常的现状及进展[J].儿科药学杂志,2015,21(1):59-62.
[34] BRITTAIN H G,FELICE P V.Characterization of the cocrystal products formed by metoprolol and dabigatran bases with L-theanine:9.896.411[P].2018-02-20.
[35] STEPANOVS D,JURE M,YANICHEV A,et al. Molecular salts of propranolol with dicarboxylic acids:diversity of stoichiometry, supramolecular structures and physicochemical properties[J]. Crystengcomm,2015,17(47):9023-9028.
[36]蔡建华.抗血小板聚集药在缺血性脑卒中的应用[J].医学综述,2012,18(1):139-141.
[37]段云霞,陈小玉,张梓倩,等.缺血性脑卒中治疗药物研究进展[J].中央民族大学学报(自然科学版),2012,21(2):65-70.
[38] TANIGUCHI C,INOUE R,KATO M,et al.New dipyridamole salt with improved dissolution and oral bioavailability under hypochlorhydric conditions[J]. Drug Metab Pharm,2013,28(5):383-390.
[39] VEPURI S B,DEVARAJEGOWDA H C,SOLIMAN M E.Synthesis,characterization and molecular modelling of a novel dipyridamole supramolecule-X-ray structure,quantum mechanics and molecular dynamics study to comprehend the hydrogen bond structure–activity relationship[J]. J Mol Struct,2016,1105:194-204.
[40]王蔚,印卫兵,柏建岭,等.依达拉奉临床应用的安全性评价[J].中华神经科杂志,2009,42(7):486-489.
[41]张晓庆.依达拉奉药理作用和临床应用的研究进展[J].医药导报,2011,30(7):918-921.
[42] VEVERKA M,DUBAJ T,GALLOVIC J,et al. Edaravone cocrystals:synthesis, screening, and preliminary characterization[J]. Monatshefte für Chemie-Chemical Monthly,2013,144(9):1335-1349.
[43]宫平,贾薇.新型口服抗凝血药物达比加群酯[J].世界临床药物,2008,29(9):544-547.
[44]肖宜超,刘启明.新型口服抗凝药达比加群酯研究进展[J].心血管病学进展,2011,32(4):575-578.
[45]潘洋,耿立坚.复发性静脉血栓栓塞疾病的药物防治[J].医药导报,2014,33(4):473-477.
[46] SANWAL S S,VEMPALI A,MURUGESAN B, et al.Process for the preparation of crystalline form I of methanesulfonate salt of dabigatran etexilate:9. 150. 542[P].2015-10-06.
[47] ZHANG L,LIU C,XU J,et al.Crystal form of dabigatran etexilate mesylate and preparation method and use thereof:9.718.802[P].2017-08-01.
[48] LIU H Q,ZHANG W G,CAI Z Q,et al.Dabigatran etexilate tetrahydrate[J]. Acta Crystallographica Section E:Struct Reports Online,2012,68(12):3385.
[49]王磊,钟静芬,时惠麟.口服Xa因子直接抑制剂阿哌沙班的临床研究进展[J].上海医药,2012,33(17):17-20.
[50] CHEN Y,LI L,YAO J,et al.Improving the solubility and bioavailability of apixaban via apixaban-oxalic acid cocrystal[J]. Crystal Growth Design,2016,16(5):2923-2930.
[2] DESIRAJU G R.Crystal and co-crystal,cryst[J]. Eng Commun,2003,5:466-467.
[3] DUNITZ J D.Crystal and co-crystal:a second opinion[J].Crystengcomm,2003,5(91):506.
[4]高缘,祖卉,张建军.药物共晶研究进展[J].化学进展,2010,22(5):829-836.
[5]吕扬,杜冠华.晶型药物[M].北京:人民卫生出版社,2010.
[6] SEKHON B S.Pharmaceutical co-crystals-an update[J].Int Bull Drug Res,2012,1(2):24-39
[7]陈伟伟,高润霖,刘力生,等.《中国心血管病报告2016》概要[J].中国循环杂志,2017,32(6):521-530.
[8]张娜,黄海伟,林兰,等.心血管系统治疗药物的晶型研究进展[J].现代药物与临床,2014,29(6):690-695.
[9] GORI M,SENNI M.Sacubitril/valsartan(LCZ696)for the treatment of heart failure[J]. Expert Rev Cardiovasc Ther,2016,14(2):145-153.
[10]赖鑫芬,黄耀东,宗矩.新型心力衰竭治疗药物研究进展[J].世界临床药物,2007,28(3):157-162.
[11] FENG L,KARPINSKI P H,SUTTON P,et al. LCZ696:a dual-acting sodium supramolecular complex[J].Tetrahedron Lett,2012,53(3):275-276.
[12]李凌霏,彭鹏.高血压治疗药物研究进展[J].中国药业,2011,20(13):78-80.
[13] BEG S,SWAIN S,SINGH H P,et al. Development,optimization, and characterization of solid selfnanoemulsifying drug delivery systems of valsartan using porous carriers[J]. AAPS Pharmscitech,2012,13(4):1416-1427.
[14] THOMAS J E,NAYAK U Y,JAGADISH P C,et al.Design and characterization of valsartan co-crystals to improve its aqueous solubility and dissolution behavior[J]. Res J Pharm Technol,2017,10(1):26.
[15] WANG J R,WANG X,LU L,et al.Highly crystalline forms of valsartan with superior physicochemical stability[J].Cryst Growth Des,2013,13(7):3261-3269.
[16]郝玉明,韩永燕.噻嗪类利尿药在高血压患者中的应用[J].临床药物治疗杂志,2012,10(1):4-7.
[17] SANPHUI P,DEVI V K,CLARA D,et al. Cocrystals of hydrochlorothiazide:solubility and diffusion/permeability enhancements through drug–coformer interactions[J].Mol Pharm,2015,12(5):1615-1622.
[18] EL-GIZAWY S A,OSMAN M A,ARAFA M F, et al.Aerosil as a novel co-crystal co-former for improving the dissolution rate of hydrochlorothiazide[J]. Int J Pharm,2015,478(2):773-778.
[19] BHANDWALKAR O S,BHANDWALKAR M U,GHADGE D M,et al.Design and development of fast dissolving tablets of hydrochlorothiazide and atenolol co-crystals[J]. Int J Pharm Sci Res,2015,6(10):4368.
[20]张志婧.抗高血压药物的研究进展和临床应用[J].医药卫生:文摘版,2016(3):102.
[21]胡大一,孙艺红.冠心病药物治疗的最新进展和展望[J].中国实用内科杂志,2006,26(2):88-91.
[22] SHAYANFAR A,JOUYBAN A.Drug-drug coamorphous systems:characterization and physicochemical properties of coamorphous atorvastatin with carvedilol and glibenclamide[J].J Pharm Inn,2013,8(4):218-228.
[23] SHAYANFAR A,GHAVIMI H,HAMISHEKAR H,et al.Coamorphous atorvastatin calcium to improve its physicochemical and pharmacokinetic properties[J]. J Pharm Pharmaceut Sci,2013,16(4):577-587.
[24] WICAKSONO Y,WISUDYANINGSIH B,SISWOYO T A.Enhancement of solubility and dissolution rate of atorvastatin calcium by co-crystallization[J]. Trop J Pharm Res,2017,16(7):1497-1502.
[25] WICAKSONO Y,WISUDYANINGSIH B,SISWOYO T A.Cocrystal of atorvastatin calcium-malonic acid[J].Int Conf Med Health Sci,2017:75-78.
[26]李玉霞,江珊.瑞舒伐他汀的研究进展[J].心血管病学进展,2010,31(4):585-588.
[27] HAFNER A,BLATTER F,SZELAGIEWICZ M, et al.Multicomponent crystalline system of rosuvastatin calcium salt and vanillin:8.716.305[P].2014-05-06.
[28] HAFNER A,BLATTER F,SZELAGIEWICZ M, et al.Multicomponent system of rosuvastatin calcium salt and sorbitol:9.249.108[P].2016-02-02.
[29] FERRARI C,CASTELLIN A,GALVAGNI M,et al. Cocrystal intermediates of rosuvastatin and methods of using same:8.815.862[P].2014-08-26.
[30] IOELE G,GUNDUZ M G,DE L M,et al.Photodegradation studies of 1,4-dihydropyridine compounds by MCR analysis on UV spectral data[J]. Fut Med Chem,2016,8(2):107-115.
[31] YU Q,YAN Z,BAO J,et al.Taming photoinduced oxidation degradation of dihydropyridine drugs through cocrystallization[J]. Chem Commun, 2017, 53(91):12266-12269.
[32] KNAPIK-KOWALCZUK J,TU W,CHMIEL K,et al. Costabilization of amorphous pharmaceuticals-the case of nifedipine and nimodipine[J]. Mol Pharm,2018,15(6):2455-2465.
[33]张晓丹,余更生.美托洛尔治疗心律失常的现状及进展[J].儿科药学杂志,2015,21(1):59-62.
[34] BRITTAIN H G,FELICE P V.Characterization of the cocrystal products formed by metoprolol and dabigatran bases with L-theanine:9.896.411[P].2018-02-20.
[35] STEPANOVS D,JURE M,YANICHEV A,et al. Molecular salts of propranolol with dicarboxylic acids:diversity of stoichiometry, supramolecular structures and physicochemical properties[J]. Crystengcomm,2015,17(47):9023-9028.
[36]蔡建华.抗血小板聚集药在缺血性脑卒中的应用[J].医学综述,2012,18(1):139-141.
[37]段云霞,陈小玉,张梓倩,等.缺血性脑卒中治疗药物研究进展[J].中央民族大学学报(自然科学版),2012,21(2):65-70.
[38] TANIGUCHI C,INOUE R,KATO M,et al.New dipyridamole salt with improved dissolution and oral bioavailability under hypochlorhydric conditions[J]. Drug Metab Pharm,2013,28(5):383-390.
[39] VEPURI S B,DEVARAJEGOWDA H C,SOLIMAN M E.Synthesis,characterization and molecular modelling of a novel dipyridamole supramolecule-X-ray structure,quantum mechanics and molecular dynamics study to comprehend the hydrogen bond structure–activity relationship[J]. J Mol Struct,2016,1105:194-204.
[40]王蔚,印卫兵,柏建岭,等.依达拉奉临床应用的安全性评价[J].中华神经科杂志,2009,42(7):486-489.
[41]张晓庆.依达拉奉药理作用和临床应用的研究进展[J].医药导报,2011,30(7):918-921.
[42] VEVERKA M,DUBAJ T,GALLOVIC J,et al. Edaravone cocrystals:synthesis, screening, and preliminary characterization[J]. Monatshefte für Chemie-Chemical Monthly,2013,144(9):1335-1349.
[43]宫平,贾薇.新型口服抗凝血药物达比加群酯[J].世界临床药物,2008,29(9):544-547.
[44]肖宜超,刘启明.新型口服抗凝药达比加群酯研究进展[J].心血管病学进展,2011,32(4):575-578.
[45]潘洋,耿立坚.复发性静脉血栓栓塞疾病的药物防治[J].医药导报,2014,33(4):473-477.
[46] SANWAL S S,VEMPALI A,MURUGESAN B, et al.Process for the preparation of crystalline form I of methanesulfonate salt of dabigatran etexilate:9. 150. 542[P].2015-10-06.
[47] ZHANG L,LIU C,XU J,et al.Crystal form of dabigatran etexilate mesylate and preparation method and use thereof:9.718.802[P].2017-08-01.
[48] LIU H Q,ZHANG W G,CAI Z Q,et al.Dabigatran etexilate tetrahydrate[J]. Acta Crystallographica Section E:Struct Reports Online,2012,68(12):3385.
[49]王磊,钟静芬,时惠麟.口服Xa因子直接抑制剂阿哌沙班的临床研究进展[J].上海医药,2012,33(17):17-20.
[50] CHEN Y,LI L,YAO J,et al.Improving the solubility and bioavailability of apixaban via apixaban-oxalic acid cocrystal[J]. Crystal Growth Design,2016,16(5):2923-2930.