Tuberkulostatyczne chemioterapeutyki

• Autorzy: Nowak, K. , Suryło, P. , Kowalski, P.

Warianty tytułu

EN

Tuberculostatic chemotherapeutics

• Języki publikacji: PL

Abstrakty

EN

At the present time tuberculosis is completely treatable. However, it[MS1] is still a major cause of morbidity and mortality among the poorest people. Tuberculosis is the main source of death from among infectious diseases worldwide. In turn, infectious diseases remain the leading cause of death in the world today, greater than cardiovascular disease or cancer. According to the data provided by World Health Organization (WHO), one-third of the world's population is infected with Mycobacterium tuberculosis. In contrary to general expectation, the incidence of mycobacterial disease has significantly increased since 1990 worldwide. This problem has been aggravated by the human immunodeficiency virus (HIV) pandemia and the recent increase in incidences of microbial resistance to antibiotics. Another problem is the lack of the viable research program to develop the new range of the antituberculosis drugs. Since the mid 90’s no new drugs have been introduced, with the exception of a few minor modifications of existing formulas. This review presents history and current summary of the developments in the application and synthesis of tuberculostatic chemotherapeutics. One of the first type of drugs used were salts of heavy metals, which were discontinued quickly due to the high degree of their toxicity. However pirazinamide(2), introduced in 1936 is still being used today. Modern antituberculosis therapies started in 1944 with the Waksman’s discovery of the streptomycin (12). From among modern drugs the most popular are: PAS (15), INH (18), and EMB (34). Schemes 7, 8 and 14, 15 show the methods of synthesis of these compounds. Similarly, schemes 9?11 show the same for the cycloserine (22) antibiotic, and figures 2, 3 and 4 present the structures of the kanamycin 33 cyclic polipeptide 38 and ansamycin 39 antibiotics. Furthermore, detailed description of the methods of synthesis of fluorochinolones 44, 45 and 46 (introduced in 80’s) can be found in schemes 19, 20 and 22. In this article there is also information about the direction of the new research trends taking place in the field of the new antituberculosis agents.

Słowa kluczowe

PL

chemioterapia; preparaty przeciwgruźlicze; gruźlica; tuberkulostatyki

EN

tuberculosis; antituberculosis therapie

• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2003
• Tom: [Z] 57, 9-10
• Strony: 877--906
• Opis fizyczny: Bibliogr. 186 poz., schem.

Twórcy

autor

Nowak, K.

• Politechnika Krakowska, Instytut Chemii i Technologii Organicznej, ul. Warszawska 24, 31-155 Kraków

autor

Suryło, P.

• Politechnika Krakowska, Instytut Chemii i Technologii Organicznej, ul. Warszawska 24, 31-155 Kraków

autor

Kowalski, P.

• Politechnika Krakowska, Instytut Chemii i Technologii Organicznej, ul. Warszawska 24, 31-155 Kraków,

Bibliografia

• [1] E. Bäumiler, Wielkie leki, Iskry, Warszawa 1995.
• [2] Mała encyklopedia medycyny, praca zbiorowa, PWN, Warszawa 1982.
• [3] H. Werner, Mikrobiologia lekarska i chemioterapia, PZWL, Warszawa 1976.
• [4] S. Rolski, Chemia środków leczniczych, PZWL, Warszawa, 1964.
• [5] Patent DE 632 257 (1936).
• [6] E. Feldner, D. Pitre, Anal. Profiles Drug Subs., 1983, 12, 433.
• [7] H.P. Lambert, F.W. O’Grady, Antybiotyki i chemioterapia, Wydawnictwo Medyczne, Warszawa, 1994.
• [8] Patent DE 632 257 (1936).
• [9] Patent GB 451 304 (1936).
• [10] T. Tkaczyński, D. Tkaczyńska, Synteza i technologia chemiczna leków, PZWL, Warszawa 1984.
• [11] Patent US 2 705 714 (1955).
• [12] Patent US 2 780 624 (1957).
• [13] Patent DE 1 129 492 (1962).
• [14] Patent PL 57 038 (1969).
• [15] Patent FR 829 926 (1938).
• [16] Patent WO 01/41 772 AL
• [17] Rote Liste 1984, Editio Cantor, Aulendorf/Württ.
• [18] Patent FR 829 926 (1938).
• [19] A.R. Katritzky, Comprehensive Heterocyclic Chemistry, vol. 1, Pergamon Press 1984.
• [20] Chemia leków, A. Zejca i M. Gorczyca, PZWL, Warszawa 1998.
• [21] B. Bobrański Postępy chemii środków leczniczych, wyd. PAN, Wrocław 1980.
• [22] Antybiotyki, współczesny stan wiedzy, praca zbiorowa pod redakcją Z. Kowszyk-Gindifer, W. Sobiczewskiego, PWiWPChiL „Chemii”, Warszawa 1990.
• [23] F.E. Hahn, J. Antibiot. Therapy, 1971, 17, 29.
• [24] E. Pawelczyk, T. Hermann, Podstawy trwałości leków, PZWL, Warszawa 1982.
• [25] J. Łazowski, A. Łypka, Farmacja polska, 1983, 39 (1), 7.
• [26] F. Walter, Q. Vicens, E. Westhof, Curr. Opin. Chem. Biol., 1999,3, 694.
• [27] O. Jerrinic, S. Joseph, J. Mol. Biol., 2000, 304, 707.
• [28] S. Chodynicki, Medycyna po dyplomie, 2001,10 (7), 66.
• [29] E. Grubska-Suchanek, Służba Zdrowia, Nr 17-20 (3012-3015), 1-12 marca 2001; www.sluzbazdrowia.com.pl.
• [30] Patent US 2 472 453 (1949).
• [31] R.R. Bailey, Drugs, 1981,22,321.
• [32] Patent US 2 515 461 (1950).
• [33] Patent GB 667 108 (1952).
• [34] Patent US 3 130 131 (1964).
• [35] Patent RU 2 111 251 (1998).
• [36] A. Chmiel, S. Grudziński, Biotechnologia i chemia antybiotyków, PWN, Warszawa 1998.
• [37] A. Chmiel, Biotechnologia - podstawy mikrobiologiczne i biochemiczne, PWN, Warszawa 1994.
• [38] Patent US 2 485 106 (1949).
• [39] Patent GB 673 703 (1952).
• [40] Patent GB 698 770 (1953).
• [41] Patent GB 1 096 955 (1967).
• [42] J.K. Podlewski, A. Chwalibogowska-Podlewska, Leki współczesnej terapii, Wyd. Fundacji Büchnera, Warszawa 1998.
• [43] J. Leowski, Indian Journal of Chest Diseases and Allied Science, 1982, 24,184.
• [44] A. Das, S.L. Mukherjee, J. Am. Chem. Soc., 1953, 75, 1241.
• [45] Patent DE 50 835 (1889).
• [46] Patent US 427 564 (1890).
• [47] Patent US 2 611 732 (1952).
• [48] Patent US 2 658 073 (1953).
• [49] Patent WO 97 / 23 199 (1997).
• [50] Patent RU 2 155 746 (2000).
• [51] Patent CR 3 035 622 T (2.001).
• [52] Patent WO 0 177 109 (2001).
• [53] Patent US 2 558 298 (1951).
• [54] Patent GB 786 917 (1957).
• [55] Patent US 2 844 625 (1958).
• [56] The Merck Index, wyd. 12, Merck & Co., Inc. Whitehouse Station, NJ, 1996.
• [57] Patent GB 853 519 (1960).
• [58] Patent GB 877 927 (1961).
• [59] Patent US 3 012 938 (1961).
• [60] J. B. Bass, L.S. Farer, P.C. Hopwell, R. O’Brien, R.F. Jacobs, F. Ruben, D.E. Snider, G. Thornton, Am. J. Respir. Crit. Care Med., 1994,149, 1359.
• [61] D.E. Kopanoff, D.E. Snider, G.J. Caras, Am. Rev. Respir. Dis., 1978,117, 991.
• [62] Patent GB 923 848 (1963).
• [63] F.A. Kuehl, F.J. Wolf, N.R. Trenner, R.L. Peck, E. Howe, B.D. Hunnewell, G. Downing, E. Newstead, K. Folkers, R.P. Buhs, I. Putter, R. Ormond, J.E. Lyons, L. Chaiet, J. Am. Chem. Soc., 1955, 77, 2344.
• [64] Patent US 2 832 788 (1958).
• [65] Patent US 2 789 983 (1957).
• [66] Patent US 2 773 878 (1956).
• [67] Patent US 2 845 433 (1958).
• [68] Patent US 3 090 730 (1963).
• [69] P.A. Plattner, A. Boiler, H. Frick, A. Fürst, В. Hagedüs, H. Kirchensteiner, S. Majnoni, R. Schläpfer, H. Spiegelberg, Helv. Chim. Acta, 1957,40, 1531.
• [70] Patent PL 71 541 (1974).
• [71] Patent US 2 772 280 (1956).
• [72] Patent US 2 840 565 (1958).
• [73] Patent GB 799 066 (1956).
• [74] Patent GB 854 922 (1957).
• [75] Patent GB 1 031 267 (1964).
• [76] Patent US 2 815 348 (1957).
• [77] Patent US 2 794 022 (1957).
• [78] Patent US 3 117 122 (1964).
• [79] Patent GB 817 385 (1959).
• [80] Patent US 2 931 798 (1960).
• [81] Patent GB 823 516 (1959).
• [82] Patent US 2 936 307 (1960).
• [83] Patent US 2 967 177 (1961).
• [84] Patent GB 891 534 (1962).
• [85] Patent US 3 032 547 (1962).
• [86] S. Umezawa, K. Tatsuta, S. Koto, J. Antibiot. (Tokyo), 1968, 21 (5), 367.
• [87] M. Nakajima, A. Hasegawa, N. Kurihara, H. Shibata, T. Ueno, D. Nishimura, Tetrahedron Lett., 1968, 623.
• [88] S. Umezawa, K. Tatsuta, S. Koto, Bull. Chem. Soc. Jpn, 1969, 42, 533.
• [89] S. Umezawa, S. Koto, K. Tatsuta, H. Hineno, Y. Nishimura, T. Takayuki, J. Antibiot. (Tokyo), 1968, 21 (6), 424.
• [90] S. Umezawa, S. Koto, K. Tatsuta, H. Hineno, Y. Nishimura, T. Tsumura, Bull. Chem. Soc. Jpn, 1969, 42 (2), 537.
• [91] S. Umezawa, S. Koto, K. Tatsuta, T. Tsumura, Bull. Chem. Soc. Jpn, 1968, 41 (2), 533.
• [92] S. Umezawa, S. Koto, K. Tatsuta, T. Tsumura, Bull. Chem. Soc. Jpn, 1969, 42 (2), 529.
• [93] Patent US 4 208 531 (1980).
• [94] Patent US 4 337 336 (1982).
• [95] Farmakologia, A. Danysz i R. Gryglewski, PZWL, Warszawa 1982.
• [96] Farmakologia. Podstawy Farmakoterapii, red. W. Kostowski, Wydawnictwo Lekarskie PZWL, Warszawa 1998.
• [97] Patent PL 66 668 (1973).
• [98] R.G. Wikinson, R.G. Shephard, C. Baukhan, J. Am. Chem. Soc., 1961, 83, 2212.
• [99] Patent US 3 579 586 (1971).
• [100] Patent CH 574 389 (1796).
• [101] Patent US 3 847 991 (1974).
• [102] T. Shiba, S. Nomoto, T. Wakamiya, Experientia, 1976, 32, 1109.
• [103] T. Shiba, S. Nomoto, T. Teshima, T. Wakamiya, Tetrahedron Lett., 1976, 3907.
• [104] S. Nomoto, T. Teshima, T. Wakamiya, T. Shiba, J. Antibiot., 1977, 30, 955.
• [105] S. Nomoto, T. Teshima, T. Wakamiya, T. Shiba, Peptide Chemistry, 1976, 109.
• [106] S. Nomoto, T. Teshima, T. Wakamiya, T. Shiba, Tetrahedron, 1978, 34, 921.
• [107] S. Nomoto, T. Shiba, Buli. Chem. Soc. Jpn, 1979, 52(6), 1709.
• [108] Patent GB 920 563 (1963).
• [109] Patent US 3 143 468 (1964).
• [110] Patent US 4 026 766 (1977).
• [111] Patent GB 687 500 (1953).
• [112] Patent US 2 828 245 (1958).
• [113] Patent US 2 920 998 (1960).
• [114] Patent US 3 639 580 (1972).
• [115] Patent US 3 892 732 (1975).
• [116] P. Sensi, P. Margalith, M.T. Timbal, II Farmaco Ed. Sci., 1959, 14, 146.
• [117] Patent US 3 150 046 (1964).
• [118] Patent PL 99 292 (1978).
• [119] Patent PL 102 110 (1980).
• [120] Patent PL 115 340 (1982).
• [121] H. Bojarska-Dahling, K. Bujnowski, Wiad. Chem., 1988,42, 221.
• [122] K. Bujnowski, Wiad. Chem., 1995, 49, 39.
• [123] Patent US 3 313 804 (1967).
• [124] Z. Lachowicz-Szynalik, Terapia-Pneumonologia, listopad 1999, www.terapia.com.pl.
• [125] C. Grassi, V. Peona, Eur. Respir. J., 1995, 8 (supp. 20), 714.
• [126] C.M. Tam, S.L. Chan, C.W. Lam, C.C. Leung, K.M. Kam, J.S. Morris, D.A. Mitchison, Am. J. Respir. Crit. Care Med., 1998, 157, 1726.
• [127] www.fda.gov/cder/consumerinfo/druginfo/priftin.htm.
• [128] M.D. Yates, C.H. Collins, J. Antbacterial Chemotherapy, 1983, 10, 147.
• [129] Patent US 4 086 225 (1978).
• [130] Patent US 4 164 499 (1979).
• [131] Patent US 4 219 478 (1980).
• [132] Patent GB 1 603 127 (1981).
• [133] M.M. Mc Gregor, P. Olliaro, L. Wolmarans, B. Mabuza, B. Bredell, N.K. Felten, P.B. Fourie, Am. J. Respir. Crit. Care Med., 1996, 154, 1462.
• [134] Patent US 3 342 810 (1967).
• [135] Patent US 4 002 752 (1977).
• [136] H. Lüllmann, K. Mohr, A. Ziegler, D. Bieger, Kieszonkowy atlas farmakologii, Wydawnictwo Lekarskie, PZWL, Warszawa 1995.
• [137] Indeks leków medycyny praktycznej 2000, wyd. II, Wydawnictwo Medycyna Praktyczna, Kraków 2000.
• [138] H. Kawaguchi, T. Naito, S. Nakagawa, K.J. Fujisawa, J. Antibiot., 1972, 25, 695.
• [139] Patent US 3 781 268 (1973).
• [140] Patent GB 1 401 221 (1975).
• [141] Patent US 4 902 790 (1990).
• [142] Patent US 5 763 587 (1998).
• [143] К. Nowak, P. Suryło, P. Kowalski, Farmacja Polska, 2002, 58 (7), 336.
• [144] A. Watanabe, T. Kikuchi, A.B. Lutfor, Y. Tokue, H. Takahashi, S. Fujimura, S. Shoji, Y. Honda, Y. Nakai, T. Nukiwa, Journal of Infection and Chemotherapy, 1999, 5 (3), 149.
• [145] Informacja o leku - Levaquin: www.ortho-mcneiI.com/products/pi/pdfs/levatab.pdf.
• [146] R. Davis, H.M. Bryson, Drugs, 1994, 48 (I), 132.
• [147] D.N. Fish, A.T. Chow, Clin. Pharmacokinet., 1997, 32 (2), 101.
• [148] S.E. Berning, T.A. Cherry, M.D. Iseman, Clin. Infect. Dis., 2001, 32 (4), 643.
• [149] L. Richeldi, M. Covi, G. Ferrara, F. Franco, P. Vailati, E. Meschiari, L.M. Fabbri, G. Velluti, Monaldi Arch. Chest. Dis., 2002, 57, 39.
• [150] Patent US 4 382 892 (1983).
• [151] Patent US 5 521 310 (1996).
• [152] Patent US 4 670 444 (1987).
• [153] Patent DE 3 142 854 (1983).
• [154] Patent ES 2009072 (1989).
• [155] Patent US 5 639 886 (1997).
• [156] K. Grohe, Chem. in Britan, 1992, 28 (1), 34.
• [157] Patent US 4 795 751 (1989).
• [158] C.M. Passarotti, M.V. Valenti, D. Passarelle, M. Martinelli, Bol. Chim. Farmacéutico, 1999,138 (7), 311.
• [159] A.G. Brown, D. Butterworth, H. Cole, G. Hanscob, J.D. Hood, C. Reading, G.N. Rolinson, J. Antibiot., 1976, 29, 668.
• [160] Patent US 4 427 690 (1984).
• [161] Patent CZ 279 076 (1994).
• [162] Patent BG 52 134 (1997).
• [163] Patent US 4 562 073 (1985).
• [164] Patent EP 97 446 (1983).
• [165] World Health Organization.: WHO tuberculosis; programme framework for effective tuberculosis control, WHO/TB/94, Geneva, World Health Organization p. 179.
• [166] Patent US 5 104 875 (1992).
• [167] Patent WO 02 087 547 (2002).
• [168] Patent US 3 718 655 (1973).
• [169] Patent US 4 450 274 (1984).
• [170] Patent CN 1 337 231 (2002).
• [171] Patent CN 1 337 232 (2002).
• [172] T. Rutter, BMJ, 1997, 315, 445.
• [173] www.tech-db.ru/istc/db/projects.nsf7pijn/G-865.
• [174] Patent US 5 441 955 (1995).
• [175] Patent WO 1995 13 807 (1995).
• [176] V. Klimesova, J. Koci, K. Waisser, J. Kaustova, Farmaco, 2002, 57 (4), 259.
• [177] E. Osińska, Naturalne substancje czynne-występujące w roślinach, http://kjlidke.home.pl/rosliny.htm.
• [178] Patent US 5 399 558 (1995).
• [179] Y.-M. Lin, M.T. Flavin, C.S. Cassidy, A. Mar, F-Ch. Chen, Bioorg. Med. Chem. Lett., 2001,11, 2101.
• [180] R.B. Goldschmidt, Current Orthopaedics, 2000, 14, 18.
• [181] C.J.L. Murray, K. Styblo, A. Rouillon, Disease Control Priorities in Developing Countries, D.T. Jamison i W.H. Mosley Eds., Oxford University Press, New York, 1993.
• [182] K. Styblo, Bull. Int. Union Tuberc., 1990, 65, 24.
• [183] A. Lopez, Disease Control Priorities in Developing Countries, D.T. Jamison i W.H. Mosley Eds., Oxford University Press, New York, 1993.
• [184] P. Kościelniak, „Choroba biednych”, Rzeczpospolita 27 marca 2003
• [185] В. Blessington, J. O’Sullivan, Chem. in Britain, 1994, 30 (7), 566.
• [186] A.M. Rouhi, Chem. Eng. News, 1999, 77 (20), 52.

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