메뉴 건너뛰기




Volumn 88, Issue 3, 1999, Pages 337-346

Characterization of racemic species of chiral drugs using thermal analysis, thermodynamic calculation, and structural studies

Author keywords

[No Author keywords available]

Indexed keywords

ALPRENOLOL; ATENOLOL; BEVANTOLOL; DROPROPIZINE; EPHEDRINE; IBUPROFEN; IOPANOIC ACID; MANDELIC ACID; METHYLEPHEDRINE; NOREPHEDRINE; PINDOLOL; PROPRANOLOL; PSEUDOEPHEDRINE; RAZOXANE; SOBREROL; SULPIRIDE;

EID: 0033046564     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js980205u     Document Type: Article
Times cited : (113)

References (31)
  • 1
    • 0027144758 scopus 로고
    • Commonly used chiral drugs: A survey
    • Millership, J. S.; Fitzpatrick, A. Commonly used chiral drugs: a survey. Chirality 1993, 5, 573-576.
    • (1993) Chirality , vol.5 , pp. 573-576
    • Millership, J.S.1    Fitzpatrick, A.2
  • 2
    • 0347591023 scopus 로고
    • Chiral drugs
    • October 9
    • Stinson, S. C.; Chiral drugs. Chem. Eng. News 1995, October 9, 44-47. Chiral drugs. Chem. Eng. News 1997, October 20, 38-70.
    • (1995) Chem. Eng. News , pp. 44-47
    • Stinson, S.C.1
  • 3
    • 0001994187 scopus 로고    scopus 로고
    • Chiral drugs
    • October 20
    • Stinson, S. C.; Chiral drugs. Chem. Eng. News 1995, October 9, 44-47. Chiral drugs. Chem. Eng. News 1997, October 20, 38-70.
    • (1997) Chem. Eng. News , pp. 38-70
  • 4
    • 0004139080 scopus 로고
    • John Wiley and Sons: New York, (reprint edition 1991, reissued with corrections, Krieger Publishing Co.: Malabar, FL, 1994)
    • Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; John Wiley and Sons: New York, 1981 (reprint edition 1991, reissued with corrections, Krieger Publishing Co.: Malabar, FL, 1994).
    • (1981) Enantiomers, Racemates and Resolutions
    • Jacques, J.1    Collet, A.2    Wilen, S.H.3
  • 5
    • 85030354631 scopus 로고    scopus 로고
    • note
    • A homochiral crystal is composed of a single enantiomer, whereas a heterochiral crystal contains both opposite enantiomers in the crystal lattice. A racemic conglomerate is an equimolar physical mixture of homochiral crystals of both enantiomers, while a racemic compound and a pseudoracemate are heterochiral crystals. In a racemic compound, the two opposite enantiomers are paired up in the unit cell of the crystal lattice, whereas in a pseudoracemate the opposite enantiomers are arranged more or less randomly as a solid solution.
  • 6
    • 0001870117 scopus 로고
    • Chiral discrimination in crystalline enantiomer systems: Facts, interpretations, and speculations
    • Siegel, J. S., Ed.; Kluwer Academic: The Netherlands
    • Collet, A.; Ziminski, L.; Garcia, C.; Vigné-Maeder, F. Chiral discrimination in crystalline enantiomer systems: Facts, interpretations, and speculations. In NATO ASI series -Supramolecular Stereochemistry; Siegel, J. S., Ed.; Kluwer Academic: The Netherlands, 1995; pp 91-110.
    • (1995) NATO ASI Series -Supramolecular Stereochemistry , pp. 91-110
    • Collet, A.1    Ziminski, L.2    Garcia, C.3    Vigné-Maeder, F.4
  • 7
    • 0030928581 scopus 로고    scopus 로고
    • Relationship between crystal properties and physicochemical properties of chiral drugs
    • Li, Z. J.; Grant, D. J. W. Relationship between crystal properties and physicochemical properties of chiral drugs. J. Pharm. Sci. 1997, 86, 1073-1078.
    • (1997) J. Pharm. Sci. , vol.86 , pp. 1073-1078
    • Li, Z.J.1    Grant, D.J.W.2
  • 8
    • 0010044160 scopus 로고
    • Thermal analysis of chiral drug mixtures: The DSC behavior of mixtures of ephedrine-HCl and pseudoephedrine-HCL enantiomers
    • Prankerd, R. J.; Elsabee, M. Thermal analysis of chiral drug mixtures: The DSC behavior of mixtures of ephedrine-HCl and pseudoephedrine-HCL enantiomers. Thermochim. Acta 1995, 248, 147-160.
    • (1995) Thermochim. Acta , vol.248 , pp. 147-160
    • Prankerd, R.J.1    Elsabee, M.2
  • 9
    • 0027384523 scopus 로고
    • Melting point phase diagrams of free base and hydrochloride salts of bevantolol, pindolol and propranolol
    • Neau, S. H.; Shinwari, M. K.; Hellmuth, E. W. Melting point phase diagrams of free base and hydrochloride salts of bevantolol, pindolol and propranolol. Int. J. Pharm. 1993, 99, 303-310.
    • (1993) Int. J. Pharm. , vol.99 , pp. 303-310
    • Neau, S.H.1    Shinwari, M.K.2    Hellmuth, E.W.3
  • 11
    • 0030030510 scopus 로고    scopus 로고
    • Effects of crystallization in the presence of the opposite enantiomer on the crystal properties of (SS)-(+)-pseudoephedrinium salicylate
    • Duddu, S. P.; Fung, F. K.-Y.; Grant, D. J. W. Effects of crystallization in the presence of the opposite enantiomer on the crystal properties of (SS)-(+)-pseudoephedrinium salicylate. Int. J. Pharm. 1996, 127, 53-63.
    • (1996) Int. J. Pharm. , vol.127 , pp. 53-63
    • Duddu, S.P.1    Fung, F.K.-Y.2    Grant, D.J.W.3
  • 12
    • 0030596504 scopus 로고    scopus 로고
    • Effects of excess enantiomers on the crystal properties of a racemic compound: Ephedrinium 2-naphthalenesulfonate
    • Li, Z. J.; Grant, D. J. W. Effects of excess enantiomers on the crystal properties of a racemic compound: ephedrinium 2-naphthalenesulfonate. Int. J. Pharm. 1996, 137, 21-31.
    • (1996) Int. J. Pharm. , vol.137 , pp. 21-31
    • Li, Z.J.1    Grant, D.J.W.2
  • 13
    • 0028199842 scopus 로고
    • Chiral β-blockers for transdermal delivery
    • Touitou, E.; Chow, D. D.; Lawter, J. R. Chiral β-blockers for transdermal delivery. Int. J. Pharm. 1994, 104, 19-28.
    • (1994) Int. J. Pharm. , vol.104 , pp. 19-28
    • Touitou, E.1    Chow, D.D.2    Lawter, J.R.3
  • 14
  • 15
    • 0026711093 scopus 로고
    • Further characterization of the solid forms of iopanoic acid and its enantiomers
    • Pitre, D.; De Amici, M.; Colombo, M.; Gallo, G. G.; Nebuloni, M. Further characterization of the solid forms of iopanoic acid and its enantiomers. Arch. Pharm. 1992, 32, 385-388.
    • (1992) Arch. Pharm. , vol.32 , pp. 385-388
    • Pitre, D.1    De Amici, M.2    Colombo, M.3    Gallo, G.G.4    Nebuloni, M.5
  • 16
    • 0025273280 scopus 로고
    • Racemic modification of (R,S)-3-(4-phenyl-1-piperazinyl)-1,2-propandiol and melting point diagram
    • Pitre, D.; Stradi, R. Racemic modification of (R,S)-3-(4-phenyl-1-piperazinyl)-1,2-propandiol and melting point diagram. Arch. Pharm. 1990, 323, 23-25.
    • (1990) Arch. Pharm. , vol.323 , pp. 23-25
    • Pitre, D.1    Stradi, R.2
  • 17
    • 0344145195 scopus 로고
    • Physical properties of sulpiride and its (S)-enantiomer
    • Pitre, D.; Valoti, E. Physical properties of sulpiride and its (S)-enantiomer. Arch. Pharm. 1987, 320, 859-861.
    • (1987) Arch. Pharm. , vol.320 , pp. 859-861
    • Pitre, D.1    Valoti, E.2
  • 18
    • 0026689536 scopus 로고
    • Thermal behavior and binary phase diagram of (S)-(+)-4,4′-(1-methyl-1,2-ethandiol)-bis-(2,6-piperazinedione) (dex-razoxane), a cardio-protective agent, and its (R)-(-)-enantiomer
    • Vigevani, A.; Zampieri, M.; Pellizzato, R. Thermal behavior and binary phase diagram of (S)-(+)-4,4′-(1-methyl-1,2-ethandiol)-bis-(2,6-piperazinedione) (dex-razoxane), a cardio-protective agent, and its (R)-(-)-enantiomer. J. Pharm. Biomed. Anal. 1992, 10, 31-36.
    • (1992) J. Pharm. Biomed. Anal. , vol.10 , pp. 31-36
    • Vigevani, A.1    Zampieri, M.2    Pellizzato, R.3
  • 19
    • 0027524946 scopus 로고
    • Phase diagram of (R)- and (S)-hydroxy-2-pyrrolidone mixtures: A new case of a conglomerate forming system
    • Di Silvestro, G.; Palmisano, G.; Pellegata, R. Phase diagram of (R)- and (S)-hydroxy-2-pyrrolidone mixtures: A new case of a conglomerate forming system. J. Pharm. Sci. 1993, 82, 758-760.
    • (1993) J. Pharm. Sci. , vol.82 , pp. 758-760
    • Di Silvestro, G.1    Palmisano, G.2    Pellegata, R.3
  • 21
    • 0344145189 scopus 로고    scopus 로고
    • A molecular modeling study of chiral drug crystals: Structural analysis and lattice energy calculations
    • (b) Li, Z. J.; Grant, D. J. W. A molecular modeling study of chiral drug crystals: structural analysis and lattice energy calculations. Pharm. Res. 1996, 13 Suppl., S-340, PDD-7430.
    • (1996) Pharm. Res. , vol.13 , Issue.SUPPL.
    • Li, Z.J.1    Grant, D.J.W.2
  • 22
    • 85030354700 scopus 로고    scopus 로고
    • note
    • -1 (see ref 3).
  • 23
    • 85030358004 scopus 로고    scopus 로고
    • note
    • 8 but no structural analysis was given. Because the material is not commercially available, further testing could not be performed.
  • 24
    • 0000602940 scopus 로고
    • On the validity of Wallach's rule: On the density and stability of racemic crystals compared with their chiral counterparts
    • Brock, C. P.; Schweizer, W. B.; Dunitz, J. D. On the validity of Wallach's rule: On the density and stability of racemic crystals compared with their chiral counterparts. J. Am. Chem. Soc. 1991, 113, 9811-9820.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9811-9820
    • Brock, C.P.1    Schweizer, W.B.2    Dunitz, J.D.3
  • 25
    • 0027513775 scopus 로고
    • Solid-state nuclear magnetic resonance spectroscopy: Theory and pharmaceutical applications
    • Bugay, D. E. Solid-state nuclear magnetic resonance spectroscopy: theory and pharmaceutical applications. Pharm. Res. 1993, 10, 317-327.
    • (1993) Pharm. Res. , vol.10 , pp. 317-327
    • Bugay, D.E.1
  • 27
    • 0000672426 scopus 로고
    • Solid-state NMR and X-ray crystallography: Complementary tools for structure determination
    • Etter, M. C.; Hoye, R. C.; Vojta, G. A. Solid-state NMR and X-ray crystallography: complementary tools for structure determination. Cryst. Rev. 1988, 1, 281-338.
    • (1988) Cryst. Rev. , vol.1 , pp. 281-338
    • Etter, M.C.1    Hoye, R.C.2    Vojta, G.A.3
  • 28
    • 0024145042 scopus 로고
    • Solid-state NMR: Opportunities and challenges
    • In NMR and X-ray Crystallography: Interfaces and Challenges; Etter, M. C., Ed.
    • Maciel, G. E.; Jagannathan, N. R.; Frye, J. S. Solid-state NMR: opportunities and challenges. In NMR and X-ray Crystallography: Interfaces and Challenges; Etter, M. C., Ed.; Trans. Am. Crystallogr. Assoc. 1988, 24, 1-23.
    • (1988) Trans. Am. Crystallogr. Assoc. , vol.24 , pp. 1-23
    • Maciel, G.E.1    Jagannathan, N.R.2    Frye, J.S.3
  • 30
    • 0041966120 scopus 로고
    • Croissance d'un énantiomère en milieu quasi-racémique: Cas du dichloroacétate de norfenfluramine
    • Coquerel, G.; Perez, G.; Hartman, P. Croissance d'un énantiomère en milieu quasi-racémique: cas du dichloroacétate de norfenfluramine. J. Cryst. Growth 1988, 88, 511-521.
    • (1988) J. Cryst. Growth , vol.88 , pp. 511-521
    • Coquerel, G.1    Perez, G.2    Hartman, P.3
  • 31
    • 0344145189 scopus 로고    scopus 로고
    • Thermal analysis as a method for characterizing racemic species
    • Li, Z. J.; Grant, D. J. W. Thermal analysis as a method for characterizing racemic species. Pharm. Res. 1996, 13 Suppl., S-340, PDD-7429.
    • (1996) Pharm. Res. , vol.13 , Issue.SUPPL.
    • Li, Z.J.1    Grant, D.J.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.