메뉴 건너뛰기




Volumn 37, Issue 1, 1996, Pages 7-32

Drug chirality: A consideration of the significance of the stereochemistry of antimicrobial agents

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BETA LACTAM ANTIBIOTIC; CARBENICILLIN; LATAMOXEF; OFLOXACIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT;

EID: 0029968911     PISSN: 03057453     EISSN: None     Source Type: Journal    
DOI: 10.1093/jac/37.1.7     Document Type: Review
Times cited : (109)

References (84)
  • 2
    • 0021262995 scopus 로고
    • Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology
    • Ariens, E. J. (1984). Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. European Journal of Clinical Pharmacology 26, 663-8.
    • (1984) European Journal of Clinical Pharmacology , vol.26 , pp. 663-668
    • Ariens, E.J.1
  • 3
    • 0023831145 scopus 로고
    • Stereoselectivity of bioactive xenobiotics. A pre-Pasteur attitude in medicinal chemistry, pharmacokinetics and clinical pharmacology
    • Ariens, E. J., Wuis, E. W. & Veringa, E. J. (1988). Stereoselectivity of bioactive xenobiotics. A pre-Pasteur attitude in medicinal chemistry, pharmacokinetics and clinical pharmacology. Biochemical Pharmacology 37, 9-18.
    • (1988) Biochemical Pharmacology , vol.37 , pp. 9-18
    • Ariens, E.J.1    Wuis, E.W.2    Veringa, E.J.3
  • 5
    • 0022133927 scopus 로고
    • Imipenem: First of a new class of beta-lactam antibiotics
    • Barza, M. (1985). Imipenem: first of a new class of beta-lactam antibiotics. Annals of Internal Medicine 103, 552-60.
    • (1985) Annals of Internal Medicine , vol.103 , pp. 552-560
    • Barza, M.1
  • 6
    • 0026580811 scopus 로고
    • RU 29246, the active compound of the cephalosporin prodrug-ester HR916. I. Antibacterial activity in vitro
    • Bauernfeind, A., Jungwirth, R., Eberlein, E., Kiesel, N., Adam, F., Isert, D. et al. (1992). RU 29246, the active compound of the cephalosporin prodrug-ester HR916. I. Antibacterial activity in vitro. Journal of Antibiotics 45, 505-20.
    • (1992) Journal of Antibiotics , vol.45 , pp. 505-520
    • Bauernfeind, A.1    Jungwirth, R.2    Eberlein, E.3    Kiesel, N.4    Adam, F.5    Isert, D.6
  • 7
    • 0021798830 scopus 로고
    • Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin
    • Birnbaum, J., Kahan, F. M., Kropp, H. & MacDonald, J. S. (1985). Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. American Journal of Medicine 78, Suppl. 6A. 3-21.
    • (1985) American Journal of Medicine , vol.78 , Issue.SUPPL. 6A , pp. 3-21
    • Birnbaum, J.1    Kahan, F.M.2    Kropp, H.3    MacDonald, J.S.4
  • 8
    • 0018620980 scopus 로고
    • Chromatographische racemattrennung von thalidomid und teratogene wirkung der enantiomere
    • Blaschke, G., Kraft, H. P., Fickentscher, K. & Köhler, F. (1979). Chromatographische racemattrennung von thalidomid und teratogene wirkung der enantiomere. Arzneimittel Forschung 29, 1640-2.
    • (1979) Arzneimittel Forschung , vol.29 , pp. 1640-1642
    • Blaschke, G.1    Kraft, H.P.2    Fickentscher, K.3    Köhler, F.4
  • 9
    • 9244228509 scopus 로고
    • HMSO, London
    • British Pharmacopoeia. (1993). Vol. 1, pp. 45-46, 120-121, 132-133. HMSO, London.
    • (1993) British Pharmacopoeia , vol.1 , pp. 45-46
  • 10
    • 0023846170 scopus 로고
    • The pharmacological and texicological significance of the stereochemistry of drug disposition
    • Caldwell, J., Winter, S. M. & Hutt, A. J. (1988). The pharmacological and texicological significance of the stereochemistry of drug disposition. Xenobiotica 18, Suppl. 1, 59-70.
    • (1988) Xenobiotica , vol.18 , Issue.1 SUPPL. , pp. 59-70
    • Caldwell, J.1    Winter, S.M.2    Hutt, A.J.3
  • 11
    • 0023224611 scopus 로고
    • Purification and partial characterization of rat intestinal cefuroxime axetil esterase
    • Campbell, C. J., Chantrell, L. J. & Eastmond, R. (1987). Purification and partial characterization of rat intestinal cefuroxime axetil esterase. Biochemical Pharmacology 36, 2317-24.
    • (1987) Biochemical Pharmacology , vol.36 , pp. 2317-2324
    • Campbell, C.J.1    Chantrell, L.J.2    Eastmond, R.3
  • 12
    • 0025859123 scopus 로고
    • Racemic mixtures and single stereoisomers: Industrial concerns and issues in drug development
    • Cayen, M. N. (1991). Racemic mixtures and single stereoisomers: industrial concerns and issues in drug development. Chirality 3, 94-8.
    • (1991) Chirality , vol.3 , pp. 94-98
    • Cayen, M.N.1
  • 13
    • 0342390698 scopus 로고
    • Structure-activity relationships in quinolone antibacterials: Replacement of the 3-carboxylic acid group
    • Fernandes, P. B., Ed., J. R. Prous Science. Barcelona
    • Chu, D. T. W., Fernandes, P. B., Claiborne, A. K., Shen, L. & Pernet, A. G. (1989). Structure-activity relationships in quinolone antibacterials: replacement of the 3-carboxylic acid group. In Quinolones, Proceedings of an International Telesymposium (Fernandes, P. B., Ed.), pp. 37-45. J. R. Prous Science. Barcelona.
    • (1989) Quinolones, Proceedings of An International Telesymposium , pp. 37-45
    • Chu, D.T.W.1    Fernandes, P.B.2    Claiborne, A.K.3    Shen, L.4    Pernet, A.G.5
  • 14
    • 0026100364 scopus 로고
    • Synthesis, antibacterial activities and pharmacological properties of enantiomers of temafloxacin hydrochloride
    • Chu, D. T. W., Nordeen, C. W., Hardy, D- J., Swanson, R. N., Giardina, W. J., Pernet, A. G. et al. (1991). Synthesis, antibacterial activities and pharmacological properties of enantiomers of temafloxacin hydrochloride. Journal of Medicinal Chemistry 34, 168-74.
    • (1991) Journal of Medicinal Chemistry , vol.34 , pp. 168-174
    • Chu, D.T.W.1    Nordeen, C.W.2    Hardy, D.J.3    Swanson, R.N.4    Giardina, W.J.5    Pernet, A.G.6
  • 15
    • 0023099966 scopus 로고
    • Imipenem cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy
    • Clissold, S. P., Todd, P. A. & Campoli-Richards, D. M. (1987). Imipenem cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 33, 183-241.
    • (1987) Drugs , vol.33 , pp. 183-241
    • Clissold, S.P.1    Todd, P.A.2    Campoli-Richards, D.M.3
  • 17
    • 0028266514 scopus 로고
    • Levofloxacin, a review of its antibacterial activity, pharmacokinetics and therapeutic efficacy
    • Davis, R. & Bryson, H. M. (1994). Levofloxacin, a review of its antibacterial activity, pharmacokinetics and therapeutic efficacy. Drugs 47, 677-700.
    • (1994) Drugs , vol.47 , pp. 677-700
    • Davis, R.1    Bryson, H.M.2
  • 18
    • 0024312032 scopus 로고
    • The FDA perspective on the development of stereoisomers
    • De Camp, W. H. (1989). The FDA perspective on the development of stereoisomers. Chirality 1, 2-6.
    • (1989) Chirality , vol.1 , pp. 2-6
    • De Camp, W.H.1
  • 20
    • 37049049182 scopus 로고
    • Derivatives of 6-aminopenicillanic acid. Part I α-aminobenzylpenicillin and some related compounds
    • Doyle, F. P., Fosker, G. R., Naylor, J. H. C. & Smith, H. (1962). Derivatives of 6-aminopenicillanic acid. Part I α-aminobenzylpenicillin and some related compounds. Journal of the Chemical Society 1440-4.
    • (1962) Journal of the Chemical Society , pp. 1440-1444
    • Doyle, F.P.1    Fosker, G.R.2    Naylor, J.H.C.3    Smith, H.4
  • 21
    • 0018568810 scopus 로고
    • The penems, a new class of β-lactam antibiotics, 3. Synthesis of optically active 2-methyl-(5A)-penem-3-carboxylic acid
    • Ernest, I., Gosteli, J. & Woodward, R. B. (1979). The penems, a new class of β-lactam antibiotics, 3. Synthesis of optically active 2-methyl-(5A)-penem-3-carboxylic acid. Journal of the American Chemical Society 101, 6301-5.
    • (1979) Journal of the American Chemical Society , vol.101 , pp. 6301-6305
    • Ernest, I.1    Gosteli, J.2    Woodward, R.B.3
  • 22
    • 0028332379 scopus 로고
    • Photoisomerization kinetics of cefuroxime axetil and related compounds
    • Fabre, H., Ibork, H. & Lerner, D. A. (1994). Photoisomerization kinetics of cefuroxime axetil and related compounds. Journal of Pharmaceutical Sciences 83, 553-8.
    • (1994) Journal of Pharmaceutical Sciences , vol.83 , pp. 553-558
    • Fabre, H.1    Ibork, H.2    Lerner, D.A.3
  • 23
    • 36949061827 scopus 로고
    • Toxicity and teratogenicity of optical isomers of thalidomide
    • Fabro, S., Smith, R. L. & Williams, R. T. (1967). Toxicity and teratogenicity of optical isomers of thalidomide. Nature 215, 269.
    • (1967) Nature , vol.215 , pp. 269
    • Fabro, S.1    Smith, R.L.2    Williams, R.T.3
  • 25
    • 0023175987 scopus 로고
    • Synthesis, absolute configuration and antibacterial activity of 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid
    • Gerster, J. F., Rohlfing, S. R., Pecore, S. E., Winandy, R. M., Stern, R. M., Landmesser, J. E. et al. (1987). Synthesis, absolute configuration and antibacterial activity of 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. Journal of Medicinal Chemistry 30, 839-43.
    • (1987) Journal of Medicinal Chemistry , vol.30 , pp. 839-843
    • Gerster, J.F.1    Rohlfing, S.R.2    Pecore, S.E.3    Winandy, R.M.4    Stern, R.M.5    Landmesser, J.E.6
  • 26
  • 28
    • 0023259926 scopus 로고
    • Inhibition of the mammalian β-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids
    • Graham, D. W., Ashton, W. T., Barash, L., Brown, J. E., Brown, R. D., Canning, L. F. et al. (1987). Inhibition of the mammalian β-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids. Journal of Medicinal Chemistry 30, 1074-90.
    • (1987) Journal of Medicinal Chemistry , vol.30 , pp. 1074-1090
    • Graham, D.W.1    Ashton, W.T.2    Barash, L.3    Brown, J.E.4    Brown, R.D.5    Canning, L.F.6
  • 30
    • 9244231241 scopus 로고
    • Lateral thinking
    • 5th June
    • Hawkes, N. (1993). Lateral thinking. Times Magazine, 5th June, pp. 30-31.
    • (1993) Times Magazine , pp. 30-31
    • Hawkes, N.1
  • 33
    • 0021359208 scopus 로고
    • Enterohepatic cycling of methotrexate estimated by use of the D-isomer as a reference marker
    • Hendel, J. & Brodthagen, H. (1984). Enterohepatic cycling of methotrexate estimated by use of the D-isomer as a reference marker. European Journal of Clinical Pharmacology 26, 103-7.
    • (1984) European Journal of Clinical Pharmacology , vol.26 , pp. 103-107
    • Hendel, J.1    Brodthagen, H.2
  • 34
    • 9244257872 scopus 로고
    • The β-lactam antibiotics
    • Wolff, M. E., Ed., John Wiley, New York
    • Hoover, J. R. E. & Dunn, G. L. (1979). The β-lactam antibiotics. In Burgee's Medicinal Chemistry, 4th edn, part II (Wolff, M. E., Ed.), pp. 83-172. John Wiley, New York.
    • (1979) Burgee's Medicinal Chemistry, 4th Edn , Issue.2 PART , pp. 83-172
    • Hoover, J.R.E.1    Dunn, G.L.2
  • 36
    • 0026065494 scopus 로고
    • Significance of the methyl group on the oxazine ring of ofloxacin derivatives in the inhibition of bacterial and mammalian type II topoisomerases
    • Hoshino, K., Sato, K., Akahane, K., Yoshida, A., Hayakawa, I., Sato, M. et al. (1991b). Significance of the methyl group on the oxazine ring of ofloxacin derivatives in the inhibition of bacterial and mammalian type II topoisomerases. Antimicrobial Agents and Chemotherapy 35, 309-12.
    • (1991) Antimicrobial Agents and Chemotherapy , vol.35 , pp. 309-312
    • Hoshino, K.1    Sato, K.2    Akahane, K.3    Yoshida, A.4    Hayakawa, I.5    Sato, M.6
  • 37
    • 0011752581 scopus 로고
    • Enantiospecific analytical methodology: Applications in drug metabolism and pharmacokinetics
    • Gibson, G. G., Ed., Taylor and Francis, London
    • Hutt, A. J. (1990). Enantiospecific analytical methodology: applications in drug metabolism and pharmacokinetics. In Progress in Drug Metabolism, Vol. 12 (Gibson, G. G., Ed.), pp. 257-361. Taylor and Francis, London.
    • (1990) Progress in Drug Metabolism , vol.12 , pp. 257-361
    • Hutt, A.J.1
  • 41
    • 0020262360 scopus 로고
    • β-Lactamase activity of renal dipeptidase against N-formimidoyl-thienamycin
    • Kim, H. S. & Campbell, B. J. (1982). β-Lactamase activity of renal dipeptidase against N-formimidoyl-thienamycin. Biochemical and Biophysical Research Communications 108, 1638-42.
    • (1982) Biochemical and Biophysical Research Communications , vol.108 , pp. 1638-1642
    • Kim, H.S.1    Campbell, B.J.2
  • 42
    • 0007179925 scopus 로고
    • CNS pharmacokinetics of quinolones. Quinolones in CNS infections
    • Fernandes, P. B., Ed.. J. R. Prous Science, Barcelona
    • Kitzes-Cohen, R. (1989). CNS pharmacokinetics of quinolones. Quinolones in CNS infections. In Quinolones, Proceedings of an International Telesymposium (Fernandes, P. B., Ed.). pp. 313-26. J. R. Prous Science, Barcelona.
    • (1989) Quinolones, Proceedings of An International Telesymposium , pp. 313-326
    • Kitzes-Cohen, R.1
  • 43
  • 44
    • 0019962519 scopus 로고
    • Metabolism of thienamycin and related carbapenem antibiotics by the renal dipeptidase, dehydropeptidase-I
    • Kropp, H., Sundelof, J. G., Hajdu, R. & Kahan, F. M. (1982). Metabolism of thienamycin and related carbapenem antibiotics by the renal dipeptidase, dehydropeptidase-I. Antimicrobial Agents and Chemotherapy 22, 62-70.
    • (1982) Antimicrobial Agents and Chemotherapy , vol.22 , pp. 62-70
    • Kropp, H.1    Sundelof, J.G.2    Hajdu, R.3    Kahan, F.M.4
  • 45
    • 0017222150 scopus 로고
    • Stereoselectivity and affinity in molecular pharmacology
    • Junker, E, Ed., Birkhäuser Verlag, Basle
    • Lehmann, P. A. F., DeMiranda, J. F. R. & Ariens, E. J. (1976). Stereoselectivity and affinity in molecular pharmacology. In Progress in Drug Research, Vol. 20 (Junker, E, Ed.), pp. 101-42. Birkhäuser Verlag, Basle.
    • (1976) Progress in Drug Research , vol.20 , pp. 101-142
    • Lehmann, P.A.F.1    DeMiranda, J.F.R.2    Ariens, E.J.3
  • 47
    • 0026519648 scopus 로고
    • RU 29 296, the active compound of the cephalosporin prodrug-ester HR 916. II Stability to β-lactamases and affinity for penicillin-binding proteins
    • Markus, A., Kiesel, N., Wollmann, T., Isert, D., Limbert, M., Schrinner, E. et al. (1992). RU 29 296, the active compound of the cephalosporin prodrug-ester HR 916. II Stability to β-lactamases and affinity for penicillin-binding proteins. Journal of Antibiotics 45, 521-6.
    • (1992) Journal of Antibiotics , vol.45 , pp. 521-526
    • Markus, A.1    Kiesel, N.2    Wollmann, T.3    Isert, D.4    Limbert, M.5    Schrinner, E.6
  • 48
    • 0002821080 scopus 로고
    • The left hand of nature
    • Mason, S. (1984). The left hand of nature. New Scientist 101, 10-4.
    • (1984) New Scientist , vol.101 , pp. 10-14
    • Mason, S.1
  • 49
    • 0005948948 scopus 로고
    • Through the chemical looking glass
    • Matteson, D. (1991). Through the chemical looking glass. New Scientist 132, 35-9.
    • (1991) New Scientist , vol.132 , pp. 35-39
    • Matteson, D.1
  • 50
    • 0023925155 scopus 로고
    • Synthesis and in vitro activity of the penem antibiotics
    • McCombie, S. W. & Ganguly, A. K. (1988). Synthesis and in vitro activity of the penem antibiotics. Medicinal Research Reviews 8, 393-440.
    • (1988) Medicinal Research Reviews , vol.8 , pp. 393-440
    • McCombie, S.W.1    Ganguly, A.K.2
  • 52
    • 0027144758 scopus 로고
    • Commonly used chiral drugs: A survey
    • Millership, J. S. & Fitzpatrick, A. (1993). Commonly used chiral drugs: a survey. Chirality 5, 573-6.
    • (1993) Chirality , vol.5 , pp. 573-576
    • Millership, J.S.1    Fitzpatrick, A.2
  • 53
    • 0023628552 scopus 로고
    • Chiral DNA gyrase inhibitors. 2. Asymmetric synthesis and biological activity of the enantiomers of 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3- de]-1,4-benzoxazine-6-carboxylic acid (ofloxacin)
    • Mitscher, L. A., Sharma, P. N., Chu, D. T. W., Shen, L. L. & Pernet, A. G. (1987). Chiral DNA gyrase inhibitors. 2. Asymmetric synthesis and biological activity of the enantiomers of 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3- de]-1,4-benzoxazine-6-carboxylic acid (ofloxacin). Journal of Medicinal Chemistry 30, 2283-6.
    • (1987) Journal of Medicinal Chemistry , vol.30 , pp. 2283-2286
    • Mitscher, L.A.1    Sharma, P.N.2    Chu, D.T.W.3    Shen, L.L.4    Pernet, A.G.5
  • 54
    • 9244249823 scopus 로고
    • The influence of optical isomerism on the biological properties of quinolone antimicrobial agents
    • Fernandes, P. B., Ed., J. R. Prous Science, Barcelona
    • Mitscher, L. A., Sharma, P. N. & Zavod, R. M. (1989). The influence of optical isomerism on the biological properties of quinolone antimicrobial agents. In Quinolones, Proceedings of an International Telesymposium (Fernandes, P. B., Ed.), pp. 73-83. J. R. Prous Science, Barcelona.
    • (1989) Quinolones, Proceedings of An International Telesymposium , pp. 73-83
    • Mitscher, L.A.1    Sharma, P.N.2    Zavod, R.M.3
  • 56
    • 9244234354 scopus 로고
    • Drug firms sort their lefts from their rights
    • 7th November
    • Moran, N. (1993). Drug firms sort their lefts from their rights. Independent on Sunday, 7th November.
    • (1993) Independent on Sunday
    • Moran, N.1
  • 57
    • 0026597043 scopus 로고
    • Esterase activity toward the diastereomers of cefuroxime axetil in the rat and dog
    • Mosher, G. L., McBee, J. & Shaw, D. B. (1992). Esterase activity toward the diastereomers of cefuroxime axetil in the rat and dog. Pharmaceutical Research 9, 687-9.
    • (1992) Pharmaceutical Research , vol.9 , pp. 687-689
    • Mosher, G.L.1    McBee, J.2    Shaw, D.B.3
  • 58
    • 0028019730 scopus 로고
    • Chirality in new drug development. Clinical Pharmacokinetic considerations
    • Nation, R. L. (1994) Chirality in new drug development. Clinical Pharmacokinetic considerations. Clinical Pharmacokinetics 27, 249-55.
    • (1994) Clinical Pharmacokinetics , vol.27 , pp. 249-255
    • Nation, R.L.1
  • 59
    • 0015869555 scopus 로고
    • Advances in penicillin research
    • Harper, N. J. & Simmonds, A. B., Eds, Academic Press, London
    • Naylor, J. H. C. (1973). Advances in penicillin research. In Advances in Drug Research, Vol. 7 (Harper, N. J. & Simmonds, A. B., Eds), pp. 1-105. Academic Press, London.
    • (1973) Advances in Drug Research , vol.7 , pp. 1-105
    • Naylor, J.H.C.1
  • 62
    • 0026554353 scopus 로고
    • Species-related Stereoselective disposition of ofloxacin in the rat, dog and monkey
    • Okazaki, O., Kurata, T., Hakusui, H. & Tachizawa, H. (1992). Species-related Stereoselective disposition of ofloxacin in the rat, dog and monkey. Xenobiotica 22, 439-50.
    • (1992) Xenobiotica , vol.22 , pp. 439-450
    • Okazaki, O.1    Kurata, T.2    Hakusui, H.3    Tachizawa, H.4
  • 63
    • 0024522834 scopus 로고
    • Stereoselective metabolic disposition of enantiomers of ofloxacin in rats
    • Okazaki, O., Kurata, T. & Tachizawa, H. (1989). Stereoselective metabolic disposition of enantiomers of ofloxacin in rats. Xenobiotica 19, 419-29.
    • (1989) Xenobiotica , vol.19 , pp. 419-429
    • Okazaki, O.1    Kurata, T.2    Tachizawa, H.3
  • 65
    • 0018604650 scopus 로고
    • The penems, a new class of β-lactam antibiotics. 4. Syntheses of racemic and enantiomeric penem carboxylic acids
    • Pfaendler, H. R., Gosteli, J. & Woodward, R. B. (1979). The penems, a new class of β-lactam antibiotics. 4. Syntheses of racemic and enantiomeric penem carboxylic acids. Journal of the American Chemical Society 101, 6306-10.
    • (1979) Journal of the American Chemical Society , vol.101 , pp. 6306-6310
    • Pfaendler, H.R.1    Gosteli, J.2    Woodward, R.B.3
  • 67
    • 0028239820 scopus 로고
    • Current regulatory (draft) guidance on chiral medicinal products: Canada, EEC, Japan, United States
    • Rauws, A. G. & Groen, K. (1994). Current regulatory (draft) guidance on chiral medicinal products: Canada, EEC, Japan, United States. Chirality 6, 72-5.
    • (1994) Chirality , vol.6 , pp. 72-75
    • Rauws, A.G.1    Groen, K.2
  • 69
    • 0023688489 scopus 로고
    • Asymmetric synthesis and properties of the enantiomers of the antibacterial agent 7-(3-aminopyrrolidin-1-yl)-1 -(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride
    • Rosen, T., Chu, D. T. W., Lico, I. M., Fernandes, P. B., Shen, L., Borodkin, S. and Pernet, A. G. (1988). Asymmetric synthesis and properties of the enantiomers of the antibacterial agent 7-(3-aminopyrrolidin-1-yl)-1 -(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride. Journal of Medicinal Chemistry 31, 1586-90.
    • (1988) Journal of Medicinal Chemistry , vol.31 , pp. 1586-1590
    • Rosen, T.1    Chu, D.T.W.2    Lico, I.M.3    Fernandes, P.B.4    Shen, L.5    Borodkin, S.6    Pernet, A.G.7
  • 70
    • 0026607856 scopus 로고
    • Mode of action of new quinolones: The inhibitory activity of DNA gyrase
    • Birkhäuser Verlag, Basle
    • Sato, K., Hoshino, K. & Mitsuhashi, S. (1992a). Mode of action of new quinolones: the inhibitory activity of DNA gyrase. In Progress in Drug Research, Vol. 38, pp. 121-132. Birkhäuser Verlag, Basle.
    • (1992) Progress in Drug Research , vol.38 , pp. 121-132
    • Sato, K.1    Hoshino, K.2    Mitsuhashi, S.3
  • 71
  • 73
    • 0002498426 scopus 로고
    • Quinolone-DNA interaction
    • Hooper, D. C. & Wolfson, J. S., Eds, American Society for Microbiology, Washington, DC
    • Shen, L. L. (1993). Quinolone-DNA interaction. In Quinolone Antimicrobial Agents, 2nd edn (Hooper, D. C. & Wolfson, J. S., Eds), pp. 77-95. American Society for Microbiology, Washington, DC.
    • (1993) Quinolone Antimicrobial Agents, 2nd Edn , pp. 77-95
    • Shen, L.L.1
  • 74
    • 0028693339 scopus 로고
    • Molecular mechanisms of DNA Gyrase inhibition by quinolone antibacterials
    • (Liu, L. F., Ed.) Advances in Pharmacology, Academic Press, London
    • Shen, L. L. (1994). Molecular mechanisms of DNA Gyrase inhibition by quinolone antibacterials. In DNA Topoisomerases: Biochemistry and Molecular Biology (Liu, L. F., Ed.) Advances in Pharmacology, Vol. 29A, pp. 285-304. Academic Press, London.
    • (1994) DNA Topoisomerases: Biochemistry and Molecular Biology , vol.29 A , pp. 285-304
    • Shen, L.L.1
  • 75
    • 2642696757 scopus 로고
    • Quinolone-DNA interaction: How a small drug molecule acquires high DNA binding affinity and specificity
    • Pullman. B. & Jortner, J., Eds, Kluwer Academic, Dordrecht
    • Shen, L. L., Bures, M. G., Chu, D. T. W. & Plattner, J. J. (1990). Quinolone-DNA interaction: how a small drug molecule acquires high DNA binding affinity and specificity. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions (Pullman. B. & Jortner, J., Eds), pp. 495-512. Kluwer Academic, Dordrecht.
    • (1990) Molecular Basis of Specificity in Nucleic Acid-Drug Interactions , pp. 495-512
    • Shen, L.L.1    Bures, M.G.2    Chu, D.T.W.3    Plattner, J.J.4
  • 76
    • 0024546107 scopus 로고
    • Mechanism of inhibition of DNA gyrase by quinolone antibacterials: A cooperative drug-DNA binding model
    • Shen, L. L., Mitscher, L. A., Sharma, P. N., O'Donnell, T. J., Chu, D. W. T., Cooper, C. S. et al. (1989). Mechanism of inhibition of DNA gyrase by quinolone antibacterials: a cooperative drug-DNA binding model. Biochemistry 28, 3886-94.
    • (1989) Biochemistry , vol.28 , pp. 3886-3894
    • Shen, L.L.1    Mitscher, L.A.2    Sharma, P.N.3    O'Donnell, T.J.4    Chu, D.W.T.5    Cooper, C.S.6
  • 78
    • 0027167457 scopus 로고
    • The so-called "interconversion" of stereoisomeric drugs: An attempt at clarification
    • Testa, B., Carrupt, P.-A. & Gal, J. (1993). The so-called "interconversion" of stereoisomeric drugs: an attempt at clarification. Chirality 5, 105-11.
    • (1993) Chirality , vol.5 , pp. 105-111
    • Testa, B.1    Carrupt, P.-A.2    Gal, J.3
  • 81
    • 0021961394 scopus 로고
    • Importance of drug enantiomers in clinical pharmacology
    • Williams, K. & Lee, E. (1985). Importance of drug enantiomers in clinical pharmacology. Drugs 30, 333-54.
    • (1985) Drugs , vol.30 , pp. 333-354
    • Williams, K.1    Lee, E.2
  • 83
    • 0019349474 scopus 로고
    • Plasma protein binding and urinary excretion of R- And 5-epimers of an arylmalonylamino-1-oxacephem I: In humans
    • Yamada, H., Ichihashi, T., Hirano, K. & Kinoshita, H. (1981). Plasma protein binding and urinary excretion of R- and 5-epimers of an arylmalonylamino-1-oxacephem I: in humans. Journal of Pharmaceutical Sciences 70, 112-3.
    • (1981) Journal of Pharmaceutical Sciences , vol.70 , pp. 112-113
    • Yamada, H.1    Ichihashi, T.2    Hirano, K.3    Kinoshita, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.