9 Pharmaceutical Multicomponent Crystals: Structure, Design …
183
51. Swapna, B., Suresh, K., Nangia, A.: Color polymorphs of aldose reductase inhibitor epalrestat: configurational, conformational and synthon differences. Chem. Commun. 52, 4037–4040
(2016)
52. Igarashi, R., Nagase, H., Furuishi, T., Endo, T., Tomono, K., Ueda, H.: Crystal structure of
epalrestat non-solvate. X-Ray Struct. Anal. Online 29, 23–24 (2013)
53. Ishida, T., In, Y., Inoue, M., Ueno, Y., Tanaka, C., Hamanaka, N.: Structural elucidation of
epalrestat (ONO-2235), a potent aldose reductase inhibitor, and isomerization of its double
bonds. Tetrahedron Lett. 30, 959–962 (1989)
54. Nagase, H., Kobayashi, M., Ueda, H., Furuishi, T., Gunji, M., Endo, T., Yonemochi, E.: Crystal
structure of an epalrestat dimethanol solvate. X-Ray Struct. Anal. Online 32, 7–9 (2016)
55. Ishida, T., In, Y, Inoue, M., Tanaka, C., Hamanaka, N.: Conformation of (Z)-3-carboxymethyl[(2E)-2-methyl-3-phenylpropenylidene]rhodanine (epalrestat), a potent aldose reductase
inhibitor: X-ray crystallographic, energy calculational, and nuclear magnetic resonance Studies.
J. Chem. Soc. Perkin Trans. 2(2), 1085–1091 (1990)
56. Umeda, D., Putra, O.D., Gunji, M., Fukuzawa, K., Yonemochi, E.: Epalrestat tetrahydrofuran
monosolvate: crystal structure and phase transition. Acta Crystallogr. E Cryst. Commun. 73,
941–944 (2017)
57. Putra, O.D., Umeda, D., Fukuzawa, K., Gunji, M., Yonemochi, E.: A New solvate of epalerstat,
a drug for diabetic neuropathy. Acta Crystallogr. E Cryst. Commun. 73, 1264–1267 (2017)
58. Putra, O.D., Umeda, D., Nugraha, Y.P., Furuishi, T., Nagase, H., Fukuzawa, K., Uekusa,
H., Yonemochi, E.: Solubility improvement of epalrestat by layered structure formation via
cocrystallization. Cryst. Eng. Commun. 19, 2614–2622 (2017)
59. Umeda, Y., Fukami, T., Furuishi, T., Suzuki, T., Makimura, M., Tomono, K.: Molecular complex
consisting of two typical external medicines: intermolecular interaction between indomethacin
and lidocaine. Chem. Pharm. Bull. 55, 832–836 (2007)
60. Wang, J., Yu, Q., Dai, W., Mei, X.: Drug-drug co-crystallization presents a new opportunity
for the development of stable vitamins. Chem. Commun. 52, 3572–3575 (2016)
61. Bangalore, S., Kamalakkannan, G., Parkar, S., Messerli, F.H.: Fixed-dose combinations
improve medication compliance: a meta-analysis. Am. J. Med. 120, 713–719 (2007)
62. Vilar, L., Canadas, V., Arruda, M.J., Arahata, C., Agra, R., Pontes, L., Montenegro, L., Vilar,
C.F., Silva, L.M., Albuquerque, J.L., Gusmão, A.: Comparison of metformin, gliclazide MR
and rosiglitazone in monotherapy and in combination for type 2 diabetes. Arq. Bras. Endocrinol.
Metabol. 54, 311–318 (2010)
63. Jakobsen, D.F., Frokjaer, S., Larsen, C., Niemann, H., Buur, A.: Application of isothermal
microcalorimetry in preformulation. I. hygroscopicity of drug substances. Int. J. Pharm. 156,
67–77 (1997)
64. Childs, S.L., Chyall, L.J., Dunlap, J.T., Coates, D.A., Stahly, B.C., Stahly, G.P.: A metastable
polymorph of metformin hydrochloride: isolation and characterization using capillary crystallization and thermal microscopy techniques. Cryst. Growth Des. 4, 441–449 (2004)
65. Putra, O.D., Yonemochi, E., Uekusa, H.: Isostructural multicomponent gliclazide crystals with
improved solubility. Cryst. Growth Des. 16, 6568–6573 (2016)
66. Putra, O.D., Furuishi, T., Yonemochi, E., Terada, K., Uekusa, H.: Drug-drug multicomponent
crystals as an effective technique to overcome weaknesses in parent drugs. Cryst. Growth Des.
16, 3577–3581 (2016)
67. Tye, C.K., Sun, C.C., Amidon, G.E.: Evaluation of the effects of tableting speed on the relationships between compaction pressure, tablet tensile strength, and tablet solid fraction. J. Pharm.
Sci. 94, 465–472 (2005)
68. Patel, S., Kaushal, A.M., Bansal, A.K.: Compression physics in the formulation development
of tablets. Crit. Rev. Ther. Drug Carrier Syst. 23, 1–65 (2006)
69. Bag, P.P., Chen, M., Sun, C.C., Reddy, C.M.: Direct correlation among crystal structure,
mechanical behaviour and tabletability in a trimorphic molecular compound. CrystEngComm
14, 3865–3867 (2012)
70. Canonica, G.W., Blaiss, M.: Antihistaminic, anti-inflammatory, and antiallergic properties of
the nonsedating second-generation antihistamine desloratadine: a review of the evidence. World
Allergy Organ. J. 4, 47–53 (2011)
183
51. Swapna, B., Suresh, K., Nangia, A.: Color polymorphs of aldose reductase inhibitor epalrestat: configurational, conformational and synthon differences. Chem. Commun. 52, 4037–4040
(2016)
52. Igarashi, R., Nagase, H., Furuishi, T., Endo, T., Tomono, K., Ueda, H.: Crystal structure of
epalrestat non-solvate. X-Ray Struct. Anal. Online 29, 23–24 (2013)
53. Ishida, T., In, Y., Inoue, M., Ueno, Y., Tanaka, C., Hamanaka, N.: Structural elucidation of
epalrestat (ONO-2235), a potent aldose reductase inhibitor, and isomerization of its double
bonds. Tetrahedron Lett. 30, 959–962 (1989)
54. Nagase, H., Kobayashi, M., Ueda, H., Furuishi, T., Gunji, M., Endo, T., Yonemochi, E.: Crystal
structure of an epalrestat dimethanol solvate. X-Ray Struct. Anal. Online 32, 7–9 (2016)
55. Ishida, T., In, Y, Inoue, M., Tanaka, C., Hamanaka, N.: Conformation of (Z)-3-carboxymethyl[(2E)-2-methyl-3-phenylpropenylidene]rhodanine (epalrestat), a potent aldose reductase
inhibitor: X-ray crystallographic, energy calculational, and nuclear magnetic resonance Studies.
J. Chem. Soc. Perkin Trans. 2(2), 1085–1091 (1990)
56. Umeda, D., Putra, O.D., Gunji, M., Fukuzawa, K., Yonemochi, E.: Epalrestat tetrahydrofuran
monosolvate: crystal structure and phase transition. Acta Crystallogr. E Cryst. Commun. 73,
941–944 (2017)
57. Putra, O.D., Umeda, D., Fukuzawa, K., Gunji, M., Yonemochi, E.: A New solvate of epalerstat,
a drug for diabetic neuropathy. Acta Crystallogr. E Cryst. Commun. 73, 1264–1267 (2017)
58. Putra, O.D., Umeda, D., Nugraha, Y.P., Furuishi, T., Nagase, H., Fukuzawa, K., Uekusa,
H., Yonemochi, E.: Solubility improvement of epalrestat by layered structure formation via
cocrystallization. Cryst. Eng. Commun. 19, 2614–2622 (2017)
59. Umeda, Y., Fukami, T., Furuishi, T., Suzuki, T., Makimura, M., Tomono, K.: Molecular complex
consisting of two typical external medicines: intermolecular interaction between indomethacin
and lidocaine. Chem. Pharm. Bull. 55, 832–836 (2007)
60. Wang, J., Yu, Q., Dai, W., Mei, X.: Drug-drug co-crystallization presents a new opportunity
for the development of stable vitamins. Chem. Commun. 52, 3572–3575 (2016)
61. Bangalore, S., Kamalakkannan, G., Parkar, S., Messerli, F.H.: Fixed-dose combinations
improve medication compliance: a meta-analysis. Am. J. Med. 120, 713–719 (2007)
62. Vilar, L., Canadas, V., Arruda, M.J., Arahata, C., Agra, R., Pontes, L., Montenegro, L., Vilar,
C.F., Silva, L.M., Albuquerque, J.L., Gusmão, A.: Comparison of metformin, gliclazide MR
and rosiglitazone in monotherapy and in combination for type 2 diabetes. Arq. Bras. Endocrinol.
Metabol. 54, 311–318 (2010)
63. Jakobsen, D.F., Frokjaer, S., Larsen, C., Niemann, H., Buur, A.: Application of isothermal
microcalorimetry in preformulation. I. hygroscopicity of drug substances. Int. J. Pharm. 156,
67–77 (1997)
64. Childs, S.L., Chyall, L.J., Dunlap, J.T., Coates, D.A., Stahly, B.C., Stahly, G.P.: A metastable
polymorph of metformin hydrochloride: isolation and characterization using capillary crystallization and thermal microscopy techniques. Cryst. Growth Des. 4, 441–449 (2004)
65. Putra, O.D., Yonemochi, E., Uekusa, H.: Isostructural multicomponent gliclazide crystals with
improved solubility. Cryst. Growth Des. 16, 6568–6573 (2016)
66. Putra, O.D., Furuishi, T., Yonemochi, E., Terada, K., Uekusa, H.: Drug-drug multicomponent
crystals as an effective technique to overcome weaknesses in parent drugs. Cryst. Growth Des.
16, 3577–3581 (2016)
67. Tye, C.K., Sun, C.C., Amidon, G.E.: Evaluation of the effects of tableting speed on the relationships between compaction pressure, tablet tensile strength, and tablet solid fraction. J. Pharm.
Sci. 94, 465–472 (2005)
68. Patel, S., Kaushal, A.M., Bansal, A.K.: Compression physics in the formulation development
of tablets. Crit. Rev. Ther. Drug Carrier Syst. 23, 1–65 (2006)
69. Bag, P.P., Chen, M., Sun, C.C., Reddy, C.M.: Direct correlation among crystal structure,
mechanical behaviour and tabletability in a trimorphic molecular compound. CrystEngComm
14, 3865–3867 (2012)
70. Canonica, G.W., Blaiss, M.: Antihistaminic, anti-inflammatory, and antiallergic properties of
the nonsedating second-generation antihistamine desloratadine: a review of the evidence. World
Allergy Organ. J. 4, 47–53 (2011)