Trimorphs of a pharmaceutical cocrystal involving two active pharmaceutical ingredients: potential relevance to combination drugs

被引:139
作者
Aitipamula, Srinivasulu [1 ]
Chow, Pui Shan [1 ]
Tan, Reginald B. H. [1 ,2 ]
机构
[1] ASTAR, Inst Chem & Engn Sci, Singapore 627833, Singapore
[2] Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117576, Singapore
来源
CRYSTENGCOMM | 2009年 / 11卷 / 09期
关键词
CO-CRYSTAL; 2,5-DIHYDROXYBENZOIC ACID; GENTISIC ACID; SOLVENT; POLYMORPH; CARBAMAZEPINE; TRANSFORMATION; ETHENZAMIDE; DISSOLUTION; IMPROVE;
D O I
10.1039/b904616j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first example of a trimorphic cocrystal involving two active pharmaceutical ingredients (APIs), ethenzamide and gentisic acid, is reported; metastable polymorphs convert to the stable form upon solid-state grinding; pharmaceutical cocrystals involving two or more APIs have potential relevance to combination drugs.
引用
收藏
页码:1823 / 1827
页数:5
相关论文
共 51 条
[1]   L-PROLINE 2,5-DIHYDROXYBENZOIC ACID (1/1) - A ZWITTERION CO-CRYSTAL [J].
AAKEROY, CB ;
BAHRA, GS ;
BROWN, CR ;
HITCHCOCK, PB ;
PATELL, Y ;
SEDDON, KR .
ACTA CHEMICA SCANDINAVICA, 1995, 49 (10) :762-767
[2]   Do polymorphic compounds make good cocrystallizing agents?: A structural case study that demonstrates the importance of synthon flexibility [J].
Aakeröy, CB ;
Beatty, AM ;
Helfrich, BA ;
Nieuwenhuyzen, M .
CRYSTAL GROWTH & DESIGN, 2003, 3 (02) :159-165
[3]   Concomitant polymorphs of 2,2′,6,6′-tetramethyl-4,4′-terphenyldiol:: the β-quinol network reproduced in a metastable polymorph [J].
Aitipamula, S ;
Nangia, A .
CHEMICAL COMMUNICATIONS, 2005, (25) :3159-3161
[4]   Dimorphs of a 1:1 cocrystal of ethenzamide and saccharin: solid-state grinding methods result in metastable polymorph [J].
Aitipamula, Srinivasulu ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2009, 11 (05) :889-895
[5]   Crystal engineering of the composition of pharmaceutical phases.: Do pharmaceutical co-crystals represent a new path to improved medicines? [J].
Almarsson, Ö ;
Zaworotko, MJ .
CHEMICAL COMMUNICATIONS, 2004, (17) :1889-1896
[6]   Designing Co-Crystals of Pharmaceutically Relevant Compounds That Crystallize with Z′ > 1 [J].
Anderson, Kirsty M. ;
Probert, Michael R. ;
Whiteley, Christopher N. ;
Rowland, Adrian M. ;
Goeta, Andres E. ;
Steed, Jonathan W. .
CRYSTAL GROWTH & DESIGN, 2009, 9 (02) :1082-1087
[7]  
[Anonymous], 1997, SHELXL 97 SHELXS 97
[8]   The co-crystal approach to improve the exposure of a water-insoluble compound: AMG 517 sorbic acid co-crystal characterization and pharmacokinetics [J].
Bak, Annette ;
Gore, Anu ;
Yanez, Evelyn ;
Stanton, Mary ;
Tufekcic, Sunita ;
Syed, Rashid ;
Akrami, Anna ;
Rose, Mark ;
Surapaneni, Sekhar ;
Bostick, Tracy ;
King, Anthony ;
Neervannan, Sesha ;
Ostovic, Drazen ;
Koparkar, Arun .
JOURNAL OF PHARMACEUTICAL SCIENCES, 2008, 97 (09) :3942-3956
[9]   What is syncrystallization? States of the pH indicator methyl red in crystals of phthalic acid [J].
Benedict, JB ;
Cohen, DE ;
Lovell, S ;
Rohl, AL ;
Kahr, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (16) :5548-5559
[10]  
Bernstein J., 2020, Polymorphism in molecular crystals 2e, Vvol. 30