慢性の呼吸器感染症である結核に対する新しい抗結核薬剤は、対数増殖期と分裂休止期いずれの感染菌に対しても殺菌的な活性を示す新規系統の化合物が望ましい
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- ぜんま しろみず
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1 ndoi@jata.or.jp 30 1 phase nitroimidazopyran PA-824 phase rifalazil KRM-1648 long-lasting 8-methoxy-fluoroquinolone gatifloxacin GFLX moxifloxacin MXFX ketolide ABT-773 HMR-3647 MAC MAC Caprazamycin-B CPZ-B CPZ-B CPZ-B WH The Global Alliance for TB Drug Development (GATB) GATB Aerosolized new drug in DDS
2 Current status in the development of the new anti-tuberculosis drugs orio Doi Department of Research, Research Institute of Tuberculosis, Japan Anti-Tuberculosis Association Matsuyama, Kiyose, Tokyo, Japan Tuberculosis (TB) is still the greatest single infectious cause of mortality worldwide. However, powerful new anti-tb drugs with new mechanisms of action have not been developed in the last over thirty years. It is expected that development of the new effective anti-tb drug will bring us various outcomes such as shortening the total duration treatment, improvement of the treatment completion ratio, prevention and treatment of the multiple drug resistant tuberculosis (MDR-TB) and reducing the total medical expenditure. A new anti-tb drug needs to show the well phrmacokinetic distribution and permeation into lung tissue and cells. Furthermore, it is also desired that the novel candidate exhibits the potent bactericidal activity both against exponential and stable phase of M. tuberculosis in vivo. In addition, it is ideal that the novel agent possesses narrow anti-microbial spectrum specialized only against Mycobacterial species. itroimidazopyran is the center of attention in the world today as a most potent novel drug candidate for TB. Its leading compound PA-824 is being developed at the stage of the first clinical trial phase I. PA-824 possesses two types of mechanism; inhibitions of the biosynthesis of protein and cell wall lipid of M. tuberculosis. PA-824 exhibits bactericidal activity against both replicating and static M. tuberculosis. It also shows potent bactericidal activity against MDR-M. tuberculosis. Among the new rifamycin derivatives, rifalazil (KRM-1648) is the most promising drug candidate. The development of rifalazil is in progress at the stage of the clinical trial phase II. Rifalazil demonstrates potent long-acting oral activity against M. tuberculosis both in animal models and in humans. Gatifloxacin (GFLX) and moxifloxacin (MXFX) are the 8-methoxy-fluoro- quinolone representatives. They show bactericidal activity against replicating M. tuberculosis both in vitro and in murine tuberculosis models. ABT-773 and HMR-3647 are the ketolide compound representatives; they possess a potential bactericidal activity against M. avium-intracellulare complex (MAC) in vitro, but these ketolide compounds are ineffective against macrolide resistant MAC strains. Caprazamycin-B (CPZ-B) is the promising novel antibiotic recently developed in Japan, which was isolated from Streptomyces species. In contrast to current anti-tb drugs, CPZ-B with a novel chemical structure possesses specific bactericidal activity only against Mycobacterial species especially M. tuberculosis including MDR strains and MAC isolates. CPZ-B inhibits the biosynthesis of the cell wall of Mycobacteria, and exhibits moderate therapeutic efficacy that is dose size dependent in pulmonary tuberculosis model induced in mice. Any cyto-toxicity is not observed in the preceding
3 animal experiments. The Global Alliance for TB Drug Development (GATB), recently formed organization under WH initiative started funding pharmaceutical companies to develop the novel agents for TB. GATB has recently set up a new project called Aerosolized new drug in DDS. It has a potentially promising scope for developing new ant-tb drugs and the management of chemotherapy as well WH ) 43,000 3, HIV HIV 560 AIDS 1/3 MDR-TB MDR-TB DTS Directly bserved Treatment, Short Course WH MDR-TB MDR-TB MDR-TB 21 Mycobacterium avium-intracellulare complex MAC MDR-TB MAC MAC 28 MAC M. avium 16 M. intracellulare MAC MAC MIC new macrolide clarithromycin CAM 1944 streptomycin SM 1952 isoniazid IH 1965 rifampicin RFP 30 Table 1 2
4 Table 1. Characteristics of the current anti-tuberculosis drugs Year of introduction Antituberculosis activity Molecular target Gene(s) involved in drug resistance Mutation rate Toxicity FIRST-LIE DRUGS Isoniazid (IH) Mycolic acid synthesis inha 10-8 Low katg Rifampicin (RFP) RA polymerase (ß-subunit) rpob Low Pyrazinamide (PZA) ? pnca 10-3 Low Streptomycin (SM) Ribosomal proteins rpol, rrs, stra, 10-8 Medium s12 Ethambutol (EB) Cell wall polysaccharides emb A, B & C 10-7 Low SECD-LIE DRUGS Ethionamide (ETH) ? 10-3 High Kanamycin (KM) /Amikacin (AMK) Ribosomal proteins? 10-6 Medium Cycloserine (CS) Cell wall synthesis? High Capreomycin (CPM) ? 10-3 Medium Thioacetazone (Tbi) ? 10-3 Medium P-aminosalicylic acid (PAS) Folate biosynthesis? 10-8 Medium floxacin (FLX) DA gyrase gyra? Low
5 MAC 3 RFP IH aminoglycosides SM kanamycin KM amikacin AMK capreomycin CPM ethioamides ETH pyrazinamide (PZA) fluoroquinolones ofloxacin FLX levofloxacin LVFX ethambutol (EB) cycloserine CS para-amino-salicylic acid PAS RFP IH PZA aminoglycosides fluoroquinolones EB CS PAS DA 6 IH IH
6 itoroimidazole Fig. 1 2 * CF 3 Fig. 1. The most promising candidate nitroimidazopyran ( PA-824 ) Asterisk denotes the C3 position and AP chiral centre. itroimidazole PathoGenesis Chiron 3) nitroimidazopyran itroimidazopyran PA-824 hydroxymycolate keto-mycolate PA-824 PA- 824 IH PA-824 PA-824 WH phase
7 C H H H H H CH 2 CH Rifalazil ( KRM-1648 ) C H H H H H CH H Rifapentine ( DL-473 ) C H H H H H H H CH 2 CH Rifabutin ( Ansamycin; LM-427 ) Fig. 2. ew rifamycin derivatives
8 rifamycin Fig Ciba-Geigy Lepeti rifamycin SV RFP rifamycin RFP rifamycin P-450 MAC CAM new macrolide HIV 4) protease inhibitor Rifamycin (a) Rifalazil KRM-1648 PathoGenesis, Activbiotics 1980 rifamycin 200 MAC KRM-1648 benzoxazinorifamycin rifalazil KRM-1648 MAC ) KRM in vivo RFP rifabutin RBT in vivo RFP 3 6) Rifalazil RFP RFP rpob PathoGenesis rifalazil phase rifalazil phase 7) Rifalazil (b) Rifapentine RPT Aventis Pharma Hoechst Marion Roussel 1970 long-lasting cyclopentyl rifampicin DL-473 RPT ) FDA RPT RFP in vitro RFP RFP 10 RPT RFP RPT RFP RPT RPT DTS 9) RPT HIV (c) Rifabutin RBT Pharmacia Farmatalia Carlo Erba ( ) 10) ansamycin LM-427 RBT AIDS MAC FDA 11) MAC RBT RFP
9 RBT MAC Pharmacia RBT Caprazamycin-B Fig.3 Caprazamycin-B CPZ-B Streptomyces sp. 12) CPZ-B MAC CPZ-B CPZ-B CPZ-B H H H 2 HH HH Fig. 3. ovel antibiotic caprazamycin-b (CPZ-B) 8-methoxy-fluoroquinolones Fig.4 new fluoroquinolone FLX LVFX ciprofloxacin CPFX sparfloxacin SPFX 4 MDR-TB
10 2 M. kansasii M. fortuitum M. szulgai M. leprae 1 cyclopropyl 8 methoxy methoxy-fluoroquinolone 8 methoxy 8 8-methoxy-fluoroquinolone gatifloxacin GFLX moxifloxacin MXFX Bayer GFLX AM-1155 phase 13, 14) MAC LVFX MXFX Bayer CPFX Bay MXFX SPFX in vitro in vivo 15) 8-methoxy-fluoroquinolone LVFX pyridobenzaxazine 10 MXFX 7 bicyclononanyl LVFX LVFX GFLX MAC 16) ew macrolides ketolides Fig.5 MAC CAM 14 new macrolide azithromycin AZM longlasting MAC 17) ketolides ABT-773 HMR-3647 new macrolides 3 L-cladinose =C carbamate 6 ketolides 18) new macrolides MAC ketolides CAM MAC -octansulfonylacetamide Fig.6 -octanesulfonylacetamide SA in vitro slowly growing mycobacteria rapidly growing mycobacteria 19) SA SA in vivo xazolidinones xazolidinone Pharmacia
11 H H H F Me CH Me HCl H F Me CH 3/2 H 2 Moxifloxacin ( MXFX; Bay ) Gatifloxacin ( GFLX; AM-1155 ) F CH H Me 1/2 H 2 Pyridobenzoxazine derivative ( VII ) Fig methoxy-fluoroquinolones and a novel levofloxacin analogue
12 H H H H H H H Azithromycin ( AZM ) ABT-773 Me CH H 3 Me 2 Telithromycin ( TEL; HMR-3647 or RU ) Fig. 5. ew macrolide and ketolide representatives for MAC
13 50S xazolidinone linezolid LZD pnu in vitro in vivo 20) MAC LZD Pyrazinamide pyrazinamide PZA vivo pyrazinamide deamidase pyrazinoic acid ph pro-drug PZA in vitro 21) MAC in vivo Riminofenazine Fig.6 Cl S H 2 CH( ) 2 H Cl -ctanesulfonylacetamide ( SA ) Clofazimine ( B663 or Lamprene ) Fig. 6. A new candidate SA and a riminofenazine derivative 1962 M. leprae riminofenazine B663 Lamprene clofazimine CFZ Aventis MAC CFZ MAC CFZ DA CFZ 22) CFZ DDS in vivo 23, 24) 10 DDS DDS 23, 24, 25) DDS
14 DDS DDS DDS persister KM enviomycin EVM FLX LVFX SPFX new quinolone AID ational Institute of Allergy and Infectious Disease TAACF Tuberculosis Antimicrobial Acquisition and Cooperating Facility 26) WH The Global Alliance for TB Drug Development (GATB) 60 27) GATB DDS Aerosolized ew Drug in DDS M. tuberculosis H37Rv 28)
15 1) Dye C, Scheele S, Dolin P, et al.: Consensus statement. Global burden of tuberculosis: estimated incidence, prevalence, and mortality by country. WH Global Surveillance and Monitoring Project. J Am Med Ass 282: , ) The WH/IUATLD global project on anti-tuberculosis drug resistance surveillance: In Anti-tuberculosis drug resistance in the world, p.18 21, World Health rganization, Geneva, Switzerland, ) Stover CK, Warrener P, VanDevanter D R, et al. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. ature 405: , ) Richard J W, Brown BA, Griffith D E, et al.: Reduced serum levels of clarithromycin in patients treated with multidrug regimens including rifampicin or rifabutin for Mycobacterium avium M. intracellulare infection. J Infec Dis 171: 747~750, ) Saito H, Tomioka H, Sato M, et al.: In vitro antimycobacterial activity of newly synthesized benzoxazino- rifamycins. Antimicrob Agents Chemother 35: , ) benzoxazinorifamycin KRM-1648 in vivo (1). 73: 53 64, ) Dietze R, Teixeira L, Rocha L M C, et al.: Safety and bactericidal activity of rifalazil in patients with pulmonary tuberculosis. Antimicrob Agents Chemother 45: , ) Jarvis B, Lamb H M: Rifapentine. Drugs 56: , ) Tam C M, Chan S L, Lam C W, et al.: Rifapentine and isoniazid in the continuation phase of treating tuberculosis: initial report. Am J Respir Crit Care Med 157: , ) Brogden R, Fitton A, et al.: Rifabutin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 47: , ) ightingale S D, Cameron D W, Gordin F M, et al.: Two controlled trials of rifabutin prophylaxis against Mycobacterium avium complex infection in AIDS. ew Eng J Med 329: , ) Igarashi M, akagawa, Hattori S, et al.: Caprazamycin A-F, novel anti-tb antibiotics, from Streptomycces sp. In Abstracts Book of 42nd Interscience Conference on Antimicrobial Agents and Chemotherapy, p232, American Society for Microbiology, Washington, D. C., September, ) Fung-Tomc J, Minassian B, Kolek B, et al.: In vitro antibacterial spectrum of a new broad-spectrum 8-methoxy fluoroquinolone, gatifloxacin. J Antimicrob Chemother 45: , ) Alvirez-Freites E J, Carter J L, Cynamon M H: In vitro and in vivo activities of gatifloxacin against Mycobacterium tuberculosis. Antimicrob Agents Chemother 46:
16 , ) Miyazaki E, Miyazaki M, Chen J M, et al.: Moxifloxacin (Bay ), a new 8- methoxyquinolone, is active in a mouse model of tuberculosis. Antimicrob Agents Chemother 43: 85 89, ) Kawakami K, amba K, Tanaka M, et al.: Antimycobacterial activities of novel levofloxacin analogues. Antimicrob Agents Chemother 44: , ) Koletar S L, Berry A J, Cynamon M H, et al.: Azithromycin as treatment for disseminated Mycobacterium avium complex in AIDS patients. Antimicrob Agents Chemother 43: , ) ilius A M, Bui M H, Almer L, et al.: Comparative in vitro activity of ABT-773, a novel antibacterial ketolide. Antimicrob Agents Chemother 45: , ) Parrish M, Houston T, Jones P B, et al.: In vitro activity of a novel antimycobacterial compound, -octanesulfonylacetamide, and its effects on lipid and mycolic acid synthesis. Antimicrob Agents Chemother 45: , ) Cynamon M H, Klemens S P, Sharpe, C A, et al.: Activities of several novel oxazolidinones against Mycobacterium tuberculosis in a murine model. Antimicrob Agents Chemother 43: , ) Yamamoto S, Toida I, Watanabe, et al.: In vitro antimycobacterial activities of pyrazinamide analogs. Antimicrob Agents Chemother 39: , ) Reddy V M, adadhur G, Daneluzzi D, et al.: Antituberculosis activities of clofazimine and its new analogs B4154 and B4157. Antimicrob Agents Chemother 40: , ) Kansal R G, Gomez-Flores R, Sinha I, et al.: Therapeutic efficacy of liposomal clofazimine against Mycobacterium avium complex in mice depends on size of initial inoculum and duration of infection. Antimicrob Agents Chemother 41: 17 23, ) Adams L B, Sinha I, Frantzblau S G, et al.: Effective treatment of acute and chronic murine tuberculosis with liposome-encapusulated clofazimine. Antimicrob Agents Chemother 43: , ) Gasper M M, eves S, Portaels F, et al.: Therapeutic efficacy of liposomal rifabutin in a Mycobacterium avium model of infection. Antimicrob Agents Chemother 44: , ) rme I M: Search for new drugs for treatment of tuberculosis. Anticicrob Agents Chemother 45: , ) Brien R J: Scientific Blueprint for Tuberculosis Drug Development (Global alliance for TB Drug Development). Tuberculosis Supplement 1, 81, Churchill Livingstone: 1 52, ) Cole S T, Brosch R, Parkhill J, et al.: Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. ature 393: , 1998 Vol.50. o.11.ov.2002 [ ] P
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