메뉴 건너뛰기




Volumn 21, Issue 1, 2016, Pages

Chemical structure-related drug-like criteria of global approved drugs

Author keywords

Chemical structure related criteria; Drug design; Drug like property; Functional group; Ring system; The heavy atoms proportion

Indexed keywords

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; CARDIOVASCULAR AGENT; NEUROPROTECTIVE AGENT; NEW DRUG;

EID: 85000366430     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21010075     Document Type: Article
Times cited : (73)

References (46)
  • 1
    • 85000398095 scopus 로고    scopus 로고
    • From vision to decision
    • Price Waterhouse Coopers (PWC). PWC: London, UK, Available online:, (accessed on 16 November 2015)
    • Price Waterhouse Coopers (PWC). From Vision to Decision. Pharma 2020 Report; PWC: London, UK, 2012; Available online: http://www.pwc.com/gx/en/industries/pharmaceuticals-life-sciences/pharma-2020/vision-to-decision.html (accessed on 16 November 2015).
    • (2012) Pharma 2020 Report
  • 2
    • 29144471861 scopus 로고    scopus 로고
    • Druggability: Selecting optimized drug candidates
    • CrossRef
    • Sugiyama, Y. Druggability: Selecting optimized drug candidates. Drug Discov. Today 2005, 10, 1577-1579. [CrossRef].
    • (2005) Drug Discov. Today , vol.10 , pp. 1577-1579
    • Sugiyama, Y.1
  • 3
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • CrossRef
    • Lipinski, C.A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. 2000, 44, 235-249. [CrossRef].
    • (2000) J. Pharmacol. Toxicol. , vol.44 , pp. 235-249
    • Lipinski, C.A.1
  • 5
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • CrossRef
    • Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliver. Rev. 1997, 23, 3-25. [CrossRef].
    • (1997) Adv. Drug Deliver. Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 6
    • 0037030653 scopus 로고    scopus 로고
    • Molecular properties that influence the oral bioavailability of drug candidates
    • [CrossRef] [PubMed]
    • Veber, D.F.; Johnson, S.R.; Cheng, H.Y.; Smith, B.R.; Ward, K.W.; Kopple, K.D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 2002, 45, 2615-2623. [CrossRef] [PubMed].
    • (2002) J. Med. Chem. , vol.45 , pp. 2615-2623
    • Veber, D.F.1    Johnson, S.R.2    Cheng, H.Y.3    Smith, B.R.4    Ward, K.W.5    Kopple, K.D.6
  • 7
    • 9744232909 scopus 로고    scopus 로고
    • Time-related differences in the physical property profiles of oral drugs
    • [CrossRef] [PubMed]
    • Leeson, P.D.; Davis, A.M. Time-related differences in the physical property profiles of oral drugs. J. Med. Chem. 2004, 47, 6338-6348. [CrossRef] [PubMed].
    • (2004) J. Med. Chem. , vol.47 , pp. 6338-6348
    • Leeson, P.D.1    Davis, A.M.2
  • 8
    • 0141726877 scopus 로고    scopus 로고
    • A rule of three for fragment-based lead discovery?
    • CrossRef
    • Congreve, M.; Carr, R.; Murray, C.; Jhoti, H. A rule of three for fragment-based lead discovery? Drug Discov. Today 2003, 8, 876-877. [CrossRef].
    • (2003) Drug Discov. Today , vol.8 , pp. 876-877
    • Congreve, M.1    Carr, R.2    Murray, C.3    Jhoti, H.4
  • 9
    • 0037468884 scopus 로고    scopus 로고
    • A comparison of physiochemical property profiles of development and marketed oral drugs
    • [CrossRef] [PubMed]
    • Wenlock, M.C.; Austin, R.P.; Barton, P.; Davis, A.M.; Leeson, P.D. A comparison of physiochemical property profiles of development and marketed oral drugs. J. Med. Chem. 2003, 46, 1250-1256. [CrossRef] [PubMed].
    • (2003) J. Med. Chem. , vol.46 , pp. 1250-1256
    • Wenlock, M.C.1    Austin, R.P.2    Barton, P.3    Davis, A.M.4    Leeson, P.D.5
  • 10
  • 12
    • 0029035114 scopus 로고
    • Transport of small molecules through the blood-brain barrier: Biology and methodology
    • CrossRef
    • Pardridge, W.M. Transport of small molecules through the blood-brain barrier: Biology and methodology. Adv. Drug Deliv. Rev. 1995, 15, 5-36. [CrossRef].
    • (1995) Adv. Drug Deliv. Rev , vol.15 , pp. 5-36
    • Pardridge, W.M.1
  • 13
    • 0035953319 scopus 로고    scopus 로고
    • Property-based design: Optimization of drug absorption and pharmacokinetics
    • [CrossRef] [PubMed]
    • Van De Waterbeemd, H.; Smith, D.A.; Beaumont, K.;Walker, D.K. Property-based design: Optimization of drug absorption and pharmacokinetics. J. Med. Chem. 2001, 44, 1313-1333. [CrossRef] [PubMed].
    • (2001) J. Med. Chem. , vol.44 , pp. 1313-1333
    • Van De Waterbeemd, H.1    Smith, D.A.2    Beaumont, K.3    Walker, D.K.4
  • 16
    • 34248593537 scopus 로고    scopus 로고
    • Simultaneous process and molecular design-A property based approach
    • Eljack, F.T.; Eden, M.R.; Kazantzi, V.; Qin, X.Y.; El-Halwagi, M.A. Simultaneous process and molecular design-A property based approach. Aiche J. 2007, 53, 1232-1239.
    • (2007) Aiche J. , vol.53 , pp. 1232-1239
    • Eljack, F.T.1    Eden, M.R.2    Kazantzi, V.3    Qin, X.Y.4    El-Halwagi, M.A.5
  • 17
    • 84896543837 scopus 로고    scopus 로고
    • Property-based design: Optimization and characterization of polyvinyl alcohol (PVA) hydrogel and PVA-matrix composite for artificial cornea
    • [CrossRef] [PubMed]
    • Jiang, H.; Zuo, Y.; Zhang, L.; Li, J.D.; Zhang, A.M.; Li, Y.B.; Yang, X.C. Property-based design: Optimization and characterization of polyvinyl alcohol (PVA) hydrogel and PVA-matrix composite for artificial cornea. J. Mater. Sci. Mater. Med. 2014, 25, 941-952. [CrossRef] [PubMed].
    • (2014) J. Mater. Sci. Mater. Med. , vol.25 , pp. 941-952
    • Jiang, H.1    Zuo, Y.2    Zhang, L.3    Li, J.D.4    Zhang, A.M.5    Li, Y.B.6    Yang, X.C.7
  • 24
    • 0029894013 scopus 로고    scopus 로고
    • The properties of known drugs. 1. Molecular frameworks
    • [CrossRef] [PubMed]
    • Bemis, G.W.; Murcko, M.A. The properties of known drugs. 1. Molecular frameworks. J. Med. Chem. 1996, 39, 2887-2893. [CrossRef] [PubMed].
    • (1996) J. Med. Chem. , vol.39 , pp. 2887-2893
    • Bemis, G.W.1    Murcko, M.A.2
  • 25
    • 0033576605 scopus 로고    scopus 로고
    • Properties of known drugs. 2. Side chains
    • [CrossRef] [PubMed]
    • Bemis, G.W.; Murcko, M.A. Properties of known drugs. 2. Side chains. J. Med. Chem. 1999, 42, 5095-5099. [CrossRef] [PubMed].
    • (1999) J. Med. Chem , vol.42 , pp. 5095-5099
    • Bemis, G.W.1    Murcko, M.A.2
  • 26
    • 0032600640 scopus 로고    scopus 로고
    • A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases
    • [CrossRef] [PubMed]
    • Ghose, A.K.; Viswanadhan, V.N.; Wendoloski, J.J. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J. Comb. Chem. 1999, 1, 55-68. [CrossRef] [PubMed].
    • (1999) J. Comb. Chem. , vol.1 , pp. 55-68
    • Ghose, A.K.1    Viswanadhan, V.N.2    Wendoloski, J.J.3
  • 27
    • 23844520095 scopus 로고    scopus 로고
    • A new rapid and effective chemistry space filter in recognizing a druglike database
    • [CrossRef] [PubMed]
    • Zheng, S.X.; Luo, X.M.; Chen, G.; Zhu, W.L.; Shen, J.H.; Chen, K.X.; Jiang, H.L. A new rapid and effective chemistry space filter in recognizing a druglike database. J. Chem. Inf. Model. 2005, 45, 856-862. [CrossRef] [PubMed].
    • (2005) J. Chem. Inf. Model , vol.45 , pp. 856-862
    • Zheng, S.X.1    Luo, X.M.2    Chen, G.3    Zhu, W.L.4    Shen, J.H.5    Chen, K.X.6    Jiang, H.L.7
  • 28
    • 70350409235 scopus 로고    scopus 로고
    • The impact of aromatic ring count on compound developability-are too many aromatic rings a liability in drug design?
    • [CrossRef] [PubMed]
    • Ritchie, T.J.; Macdonald, S.J.F. The impact of aromatic ring count on compound developability-Are too many aromatic rings a liability in drug design? Drug Discov. Today 2009, 14, 1011-1020. [CrossRef] [PubMed].
    • (2009) Drug Discov. Today , vol.14 , pp. 1011-1020
    • Ritchie, T.J.1    Macdonald, S.J.F.2
  • 29
    • 79851514554 scopus 로고    scopus 로고
    • The impact of aromatic ring count on compound developability: Further insights by examining carbo- and hetero-aromatic and -aliphatic ring types
    • [CrossRef] [PubMed]
    • Ritchie, T.J.; Macdonald, S.J.; Young, R.J.; Pickett, S.D. The impact of aromatic ring count on compound developability: further insights by examining carbo- and hetero-aromatic and -aliphatic ring types. Drug Discov. Today 2011, 16, 164-171. [CrossRef] [PubMed].
    • (2011) Drug Discov. Today , vol.16 , pp. 164-171
    • Ritchie, T.J.1    Macdonald, S.J.2    Young, R.J.3    Pickett, S.D.4
  • 30
    • 84865491027 scopus 로고    scopus 로고
    • The developability of heteroaromatic and heteroaliphatic rings-do some have a better pedigree as potential drug molecules than others?
    • CrossRef
    • Ritchie, T.J.; Macdonald, S.J.F.; Peace, S.; Pickett, S.D.; Luscombe, C.N. The developability of heteroaromatic and heteroaliphatic rings-Do some have a better pedigree as potential drug molecules than others? Med Chem Comm 2012, 3, 1062. [CrossRef].
    • (2012) Med Chem Comm , vol.3 , pp. 1062
    • Ritchie, T.J.1    Macdonald, S.J.F.2    Peace, S.3    Pickett, S.D.4    Luscombe, C.N.5
  • 31
    • 84906346249 scopus 로고    scopus 로고
    • What does the aromatic ring number mean for drug design?
    • [CrossRef] [PubMed]
    • Ward, S.E.; Beswick, P. What does the aromatic ring number mean for drug design? Expert Opin. Drug Dis. 2014, 9, 995-1003. [CrossRef] [PubMed].
    • (2014) Expert Opin. Drug Dis. , vol.9 , pp. 995-1003
    • Ward, S.E.1    Beswick, P.2
  • 32
    • 84898721607 scopus 로고    scopus 로고
    • Rings in drugs
    • [CrossRef] [PubMed]
    • Taylor, R.D.; MacCoss, M.; Lawson, A.D. Rings in drugs. J. Med. Chem. 2014, 57, 5845-5859. [CrossRef] [PubMed].
    • (2014) J. Med. Chem , vol.57 , pp. 5845-5859
    • Taylor, R.D.1    MacCoss, M.2    Lawson, A.D.3
  • 33
    • 84920194283 scopus 로고    scopus 로고
    • Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals
    • [CrossRef] [PubMed]
    • Vitaku, E.; Smith, D.T.; Njardarson, J.T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J. Med. Chem. 2014, 57, 10257-10274. [CrossRef] [PubMed].
    • (2014) J. Med. Chem , vol.57 , pp. 10257-10274
    • Vitaku, E.1    Smith, D.T.2    Njardarson, J.T.3
  • 34
    • 70449674250 scopus 로고    scopus 로고
    • Known drug space as a metric in exploring the boundaries of drug-like chemical space
    • [CrossRef] [PubMed]
    • Mirza, A.; Desai, R.; Reynisson, J. Known drug space as a metric in exploring the boundaries of drug-like chemical space. Eur. J. Med. Chem. 2009, 44, 5006-5011. [CrossRef] [PubMed].
    • (2009) Eur. J. Med. Chem , vol.44 , pp. 5006-5011
    • Mirza, A.1    Desai, R.2    Reynisson, J.3
  • 36
    • 22144432235 scopus 로고    scopus 로고
    • Why fluorine is an invaluable tool in medicinal chemistry
    • Begue, J.P.; Bonnet-Delpon, D. Why fluorine is an invaluable tool in medicinal chemistry. Chim. Oggi. 2005, 23, 3-5.
    • (2005) Chim. Oggi. , vol.23 , pp. 3-5
    • Begue, J.P.1    Bonnet-Delpon, D.2
  • 37
    • 35348938545 scopus 로고    scopus 로고
    • The role of fluorine in medicinal chemistry
    • [CrossRef] [PubMed]
    • Shah, P.; Westwell, A.D. The role of fluorine in medicinal chemistry. J. Enzym. Inhib. Med. Chem. 2007, 22, 527-540. [CrossRef] [PubMed].
    • (2007) J. Enzym. Inhib. Med. Chem , vol.22 , pp. 527-540
    • Shah, P.1    Westwell, A.D.2
  • 38
    • 33746372978 scopus 로고    scopus 로고
    • Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules
    • CrossRef
    • Kirk, K.L. Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules. J. Fluorine Chem. 2006, 127, 1013-1029. [CrossRef].
    • (2006) J. Fluorine Chem. , vol.127 , pp. 1013-1029
    • Kirk, K.L.1
  • 39
    • 84918563509 scopus 로고    scopus 로고
    • Beyond C, H, O, and N! analysis of the elemental composition of U.S. FDA approved drug architectures
    • [CrossRef] [PubMed]
    • Smith, B.R.; Eastman, C.M.; Njardarson, J.T. Beyond C, H, O, and N! analysis of the elemental composition of U.S. FDA approved drug architectures. J. Med. Chem. 2014, 57, 9764-9773. [CrossRef] [PubMed].
    • (2014) J. Med. Chem , vol.57 , pp. 9764-9773
    • Smith, B.R.1    Eastman, C.M.2    Njardarson, J.T.3
  • 40
    • 84894601276 scopus 로고    scopus 로고
    • Data-mining for sulfur and fluorine: An evaluation of pharmaceuticals to reveal opportunities for drug design and discovery
    • [CrossRef] [PubMed]
    • Ilardi, E.A.; Vitaku, E.; Njardarson, J.T. Data-mining for sulfur and fluorine: An evaluation of pharmaceuticals to reveal opportunities for drug design and discovery. J. Med. Chem. 2014, 57, 2832-2842. [CrossRef] [PubMed].
    • (2014) J. Med. Chem , vol.57 , pp. 2832-2842
    • Ilardi, E.A.1    Vitaku, E.2    Njardarson, J.T.3
  • 41
    • 34547770279 scopus 로고    scopus 로고
    • New uses for old drugs
    • [CrossRef] [PubMed]
    • Chong, C.R.; Sullivan, D.J. New uses for old drugs. Nature 2007, 448, 645-646. [CrossRef] [PubMed].
    • (2007) Nature , vol.448 , pp. 645-646
    • Chong, C.R.1    Sullivan, D.J.2
  • 42
    • 84960953605 scopus 로고    scopus 로고
    • Available online:, (accessed on 17 November)
    • Sci Finder. Available online: https://scifinder.cas.org (accessed on 17 November 2015).
    • (2015) Sci Finder
  • 43
    • 84925340940 scopus 로고    scopus 로고
    • Available online:, (accessed on 17 November)
    • DrugBank Database. Available online: http://Www.Drugbank.Ca (accessed on 17 November 2015).
    • (2015) DrugBank Database
  • 44
    • 84987832133 scopus 로고    scopus 로고
    • Available online:, (accessed on 17 November)
    • Thomson Reuters Integrity. Available online: https://integrity.thomson-pharma.com (accessed on 17 November 2015).
    • (2015) Thomson Reuters Integrity
  • 45
    • 85000724114 scopus 로고    scopus 로고
    • Available online:, (accessed on 17 November)
    • Thomson Reuters Cortellis. Available online: https://cortellis.thomsonreuterslifesciences.com (accessed on 17 November 2015).
    • (2015) Thomson Reuters Cortellis
  • 46
    • 33644900716 scopus 로고    scopus 로고
    • The role of blood-brain barrier studies in the pharmaceutical industry
    • [CrossRef] [PubMed]
    • Reichel, A. The role of blood-brain barrier studies in the pharmaceutical industry. Curr. Drug Metab. 2006, 7, 183-203. [CrossRef] [PubMed].
    • (2006) Curr. Drug Metab. , vol.7 , pp. 183-203
    • Reichel, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.