메뉴 건너뛰기




Volumn 99, Issue 9, 2010, Pages 3676-3683

A red zwitterionic co-crystal of acetaminophen and 2,4-pyridinedicarboxylic acid

Author keywords

Co crystals; Crystal engineering; Crystal structure; Crystallization; Solid state

Indexed keywords

2,4 PYRIDINEDICARBOXYLIC ACID; AMPHOLYTE; CARBOXYLIC ACID DERIVATIVE; PARACETAMOL; UNCLASSIFIED DRUG;

EID: 77956362007     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22229     Document Type: Article
Times cited : (31)

References (49)
  • 1
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • DOI 10.1016/S0169-409X(00)00129-0, PII S0169409X00001290
    • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. 2001. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46:3-26. (Pubitemid 33653411)
    • (2000) Advanced Drug Delivery Reviews , vol.46 , Issue.1-3 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 3
    • 0034345216 scopus 로고    scopus 로고
    • Salt selection and optimisation procedures for pharmaceutical new chemical entities
    • Bastin RJ, Bowker MJ, Slater BJ. 2000. Salt selection and optimisation procedures for pharmaceutical new chemical entities. Org Proc Res Dev 4:427-435.
    • (2000) Org Proc Res Dev , vol.4 , pp. 427-435
    • Bastin, R.J.1    Bowker, M.J.2    Slater, B.J.3
  • 4
    • 0023032232 scopus 로고
    • Salt selection for basic drugs
    • Gould PL. 1986. Salt selection for basic drugs. Int J Pharm 33:201-217.
    • (1986) Int J Pharm , vol.33 , pp. 201-217
    • Gould, P.L.1
  • 5
    • 27944487022 scopus 로고    scopus 로고
    • Occurrence of pharmaceutically acceptable anions and cations in the Cambridge Structural Database
    • DOI 10.1002/jps.20441
    • Haynes DA, Jones W, Motherwell WDS. 2005. Occurrence of pharmaceutically acceptable anions and cations in the Cambridge structural database. J Pharm Sci 94:2111-2120. (Pubitemid 41665273)
    • (2005) Journal of Pharmaceutical Sciences , vol.94 , Issue.10 , pp. 2111-2120
    • Haynes, D.A.1    Jones, W.2    Motherwell, W.D.S.3
  • 6
    • 34548032742 scopus 로고    scopus 로고
    • Salt formation to improve drug solubility
    • Serajuddin ATM. 2007. Salt formation to improve drug solubility. Adv Drug Deliv Rev 59:603-616.
    • (2007) Adv Drug Deliv Rev , vol.59 , pp. 603-616
    • Serajuddin, A.T.M.1
  • 10
    • 0038481113 scopus 로고    scopus 로고
    • Pizzas, polymorphs and pills
    • Davey RJ. 2003. Pizzas, polymorphs and pills. Chem Commun 1463-1467.
    • (2003) Chem Commun , pp. 1463-1467
    • Davey, R.J.1
  • 11
    • 1042298894 scopus 로고    scopus 로고
    • A timely re-examination of drug polymorphism in pharmaceutical development and regulation
    • Grant DJW, Byrn SR. 2004. A timely re-examination of drug polymorphism in pharmaceutical development and regulation. Adv Drug Deliv Rev 56:237-239.
    • (2004) Adv Drug Deliv Rev , vol.56 , pp. 237-239
    • Grant, D.J.W.1    Byrn, S.R.2
  • 13
    • 17644407654 scopus 로고    scopus 로고
    • Crystalline polymorph selection and discovery with polymer heteronuclei
    • Price CP, Grzesiak AL, Matzger AJ. 2005. Crystalline polymorph selection and discovery with polymer heteronuclei. J Am Chem Soc 127:5512-5517.
    • (2005) J Am Chem Soc , vol.127 , pp. 5512-5517
    • Price, C.P.1    Grzesiak, A.L.2    Matzger, A.J.3
  • 14
    • 1942532087 scopus 로고    scopus 로고
    • Solvent-drop grinding: Green polymorph control of cocrystallisation
    • Trask AV, Motherwell WDS, Jones W. 2004. Solvent-drop grinding: Green polymorph control of cocrystallisation. Chem Commun 890-891. (Pubitemid 38530287)
    • (2004) Chemical Communications , Issue.7 , pp. 890-891
    • Trask, A.V.1    Motherwell, W.D.S.2    Jones, W.3
  • 15
    • 34250895007 scopus 로고    scopus 로고
    • Pharmaceutical cocrystals: An emerging approach to physical property enhancement
    • Jones W, Motherwell S, Trask AV. 2006. Pharmaceutical cocrystals: An emerging approach to physical property enhancement. MRS Bull 31:875-879.
    • (2006) MRS Bull , vol.31 , pp. 875-879
    • Jones, W.1    Motherwell, S.2    Trask, A.V.3
  • 17
    • 7244241361 scopus 로고    scopus 로고
    • Variable temperature (100-360 K) single-crystal X-ray diffraction study of the orthorhombic polymorph of paracetamol (p-hydroxyacetanilide)
    • Drebushchak TN, Boldyreva EV. 2004. Variable temperature (100-360 K) single-crystal X-ray diffraction study of the orthorhombic polymorph of paracetamol (p-hydroxyacetanilide). Z Kristallogr 219:506-512.
    • (2004) Z Kristallogr , vol.219 , pp. 506-512
    • Drebushchak, T.N.1    Boldyreva, E.V.2
  • 18
    • 0033677959 scopus 로고    scopus 로고
    • Variable temperature study of the crystal structure of paracetamol (p-hydroxyacetanilide), by single crystal neutron diffraction
    • Wilson CC. 2000. Variable temperature study of the crystal structure of paracetamol (p-hydroxyacetanilide), by single crystal neutron diffraction. Z Kristallogr 215:693-701.
    • (2000) Z Kristallogr , vol.215 , pp. 693-701
    • Wilson, C.C.1
  • 20
    • 0031808764 scopus 로고    scopus 로고
    • Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution
    • Nichols G, Frampton CS. 1998. Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution. J Pharm Sci 87:684-693.
    • (1998) J Pharm Sci , vol.87 , pp. 684-693
    • Nichols, G.1    Frampton, C.S.2
  • 21
    • 0034817174 scopus 로고    scopus 로고
    • The prediction, morphology, and mechanical properties of the polymorphs of paracetamol
    • DOI 10.1021/ja0102787
    • Beyer T, Day GM, Price SL. 2001. The prediction, morphology, and mechanical properties of the polymorphs of paracetamol. J Am Chem Soc 123:5086-5094. (Pubitemid 32905664)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.21 , pp. 5086-5094
    • Beyer, T.1    Day, G.M.2    Price, S.L.3
  • 22
    • 43049105724 scopus 로고    scopus 로고
    • Effects of moisture and residual solvent on the phase stability of orthorhombic paracetamol
    • Kachrimanis K, Fucke K, Noisternig M, Siebenhaar B, Griesser UJ. 2008. Effects of moisture and residual solvent on the phase stability of orthorhombic paracetamol. Pharm Res 25:1440-1449.
    • (2008) Pharm Res , vol.25 , pp. 1440-1449
    • Kachrimanis, K.1    Fucke, K.2    Noisternig, M.3    Siebenhaar, B.4    Griesser, U.J.5
  • 24
    • 34250791543 scopus 로고    scopus 로고
    • The salt-cocrystal continuum: The influence of crystal structure on ionization state
    • Childs SL, Stahly GP, Park A. 2007. The salt-cocrystal continuum: The influence of crystal structure on ionization state. Mol Pharmaceut 4:323-338.
    • (2007) Mol Pharmaceut , vol.4 , pp. 323-338
    • Childs, S.L.1    Stahly, G.P.2    Park, A.3
  • 25
    • 70350342771 scopus 로고    scopus 로고
    • Improving mechanical properties of crystalline solids by cocrystal formation: New compressible forms of paracetamol
    • Karki S, Friscic T, Fabian L, Laity PR, Day GM, Jones W. 2009. Improving mechanical properties of crystalline solids by cocrystal formation: new compressible forms of paracetamol. Adv Mater 21:3905-3909.
    • (2009) Adv Mater , vol.21 , pp. 3905-3909
    • Karki, S.1    Friscic, T.2    Fabian, L.3    Laity, P.R.4    Day, G.M.5    Jones, W.6
  • 26
    • 37849022412 scopus 로고    scopus 로고
    • A cocrystal of pyridine-2,4-dicarboxylic acid and serine
    • Liang P. 2008. A cocrystal of pyridine-2,4-dicarboxylic acid and serine. Acta Crystallogr E 64:O43/1-O43/7.
    • (2008) Acta Crystallogr E , vol.64
    • Liang, P.1
  • 27
    • 0001752768 scopus 로고    scopus 로고
    • The Cambridge Structural Database: A quarter of a million crystal structures and rising
    • Allen FH. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Crystallogr B 58:380-388.
    • Acta Crystallogr B , vol.58 , pp. 380-388
    • Allen, F.H.1
  • 30
    • 34249106473 scopus 로고    scopus 로고
    • Efficient co-crystal screening using solution-mediated phase transformation
    • Zhang GGZ, Henry RF, Borchardt TB, Lou XC. 2007. Efficient co-crystal screening using solution-mediated phase transformation. J Pharm Sci 96:990-995.
    • (2007) J Pharm Sci , vol.96 , pp. 990-995
    • Zhang, G.G.Z.1    Henry, R.F.2    Borchardt, T.B.3    Lou, X.C.4
  • 32
    • 65249100590 scopus 로고    scopus 로고
    • Inel Corp.: Artenay, France
    • Symphonix; Inel Corp.: Artenay, France.
    • Symphonix
  • 33
    • 65249134247 scopus 로고    scopus 로고
    • Materials Data, Inc.: Livermore, CA
    • Jade 6.5; Materials Data, Inc.: Livermore, CA, 2002.
    • (2002) Jade 6.5
  • 34
    • 33645166398 scopus 로고    scopus 로고
    • 6.45 ed., Madison, WI, USA Bruker AXS Inc.
    • 1997-2003. SAINT-Plus. 6.45 ed., Madison, WI, USA Bruker AXS Inc.
    • (1997) SAINT-Plus
  • 35
    • 77956365565 scopus 로고    scopus 로고
    • v6.3.1ed., Madison, WI, USA: Bruker AXS Inc.
    • 2004. XSHELL. v6.3.1ed., Madison, WI, USA: Bruker AXS Inc.
    • (2004) XSHELL
  • 37
    • 4243943295 scopus 로고    scopus 로고
    • Generalized gradient approximation made simple
    • Perdew JP, Burke K, Ernzerhof M. 1996. Generalized gradient approximation made simple. Phys Rev Lett 77:3865. (Pubitemid 126631804)
    • (1996) Physical Review Letters , vol.77 , Issue.18 , pp. 3865-3868
    • Perdew, J.P.1    Burke, K.2    Ernzerhof, M.3
  • 39
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke AD. 1993. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648-5652.
    • (1993) J Chem Phys , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 40
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee C, Yang W, Parr RG. 1988. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785.
    • (1988) Phys Rev B , vol.37 , pp. 785
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 42
    • 85031337103 scopus 로고    scopus 로고
    • Calculated values were obtained from the Sci-Finder Scholar database (version 2007) calculated using Advanced Chemistry Development (ACD/Labs) Software (version 8.14) for Solaris (copyright 1994-2010 ACD/Labs)
    • Calculated values were obtained from the Sci-Finder Scholar database (version 2007) calculated using Advanced Chemistry Development (ACD/Labs) Software (version 8.14) for Solaris (copyright 1994-2010 ACD/Labs).
  • 46
    • 0001697672 scopus 로고    scopus 로고
    • Designing linear hydrogen-bonded arrays by using substituted charge-transfer complexes. The crystal structure of the 1: 1 adduct of indole-2-carboxylic acid with 3,5-dinitrobenzoic acid
    • Lynch DE, Smith G, Byriel KA, Kennard CHL. 1998. Designing linear hydrogen-bonded arrays by using substituted charge-transfer complexes. The crystal structure of the 1: 1 adduct of indole-2-carboxylic acid with 3,5-dinitrobenzoic acid. Aust J Chem 51:1019-1024.
    • (1998) Aust J Chem , vol.51 , pp. 1019-1024
    • Lynch, D.E.1    Smith, G.2    Byriel, K.A.3    Kennard, C.H.L.4
  • 47
    • 37049084077 scopus 로고
    • Molecular recognition involving an interplay of O- H···O, C-H···O, and π···π-interactions. The anomalous crystal-structure of the 1:1 complex 3,5-dinitrobenzoic acid-4-(N,N-dimethylamino) benzoic acid
    • Sharma CVK, Panneerselvam K, Pilati T, Desiraju GR. 1993. Molecular recognition involving an interplay of O-H···O, C-H···O, and π···π-interactions. The anomalous crystal-structure of the 1:1 complex 3,5-dinitrobenzoic acid-4-(N,N-dimethylamino) benzoic acid. J Chem Soc Perk T 2:2209-2216.
    • (1993) J Chem Soc Perk T , vol.2 , pp. 2209-2216
    • Sharma, C.V.K.1    Panneerselvam, K.2    Pilati, T.3    Desiraju, G.R.4
  • 48
    • 0035801532 scopus 로고    scopus 로고
    • "Total synthesis" supramolecular style: Design and hydrogen-bond-directed assembly of ternary supermolecules
    • Aakeröy CB, Beatty AM, Helfrich BA. 2001. "Total synthesis" supramolecular style: Design and hydrogen-bond-directed assembly of ternary supermolecules. Angew Chem Int Ed 40:3240-3242.
    • (2001) Angew Chem Int Ed , vol.40 , pp. 3240-3242
    • Aakeröy, C.B.1    Beatty, A.M.2    Helfrich, B.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.