Review Article

氟喹诺酮类药物:祝福还是诅咒

卷 21, 期 13, 2020

页: [1354 - 1370] 页: 17

弟呕挨: 10.2174/1389450121666200621193355

价格: $65

摘要

氟喹诺酮类药物是世界上最有价值和最广泛使用的抗菌药物之一。本文综述了氟喹诺酮类药物从发现到黑盒预警的重大进展。在耐药性日益增加的情况下,选择抗生素药物仍然困难,但氟喹诺酮类药物的引入已在抗菌药物治疗方面开创了一个令人兴奋的新时代。这是一种合成的异质化合物,在医院和社区实践中用于治疗许多严重感染。喹诺酮类抗生素的时代始于1962年喹诺酮类抗生素原型的意外发现。氟喹诺酮的年代发展报告,纳利二酸是第一个喹诺酮获得普遍选择的治疗尿路感染。随后的药剂如左氧氟沙星、氧氟沙星、诺氟沙星、加替沙星、莫西沙星、克林弗沙星、斯帕沙星和环丙沙星是通过侧链和核操作从基本药效学基因中获得的。氟喹诺酮基序被发现是一个里程碑,对呼吸道感染、泌尿道感染、骨骼疾病、脑膜炎球菌和分枝杆菌感染、性传播疾病、皮肤感染等某些感染有效。氟喹诺酮类抗生素是最早通过抑制对染色体复制和功能至关重要的拓扑异构酶II、拓扑异构酶IV和脱氧核糖核酸旋转酶而表现出抗菌活性的完全人造抗生素。上市后的监测指出了与氟喹诺酮类药物相关的有利副作用,如光毒性、QT间期延长和过敏反应。上个世纪,氟喹诺酮类抗生素的发现、开发和临床应用降低了发病率和死亡率。

关键词: 氟喹诺酮,广谱抗生素,时间发展,药物概况,黑框警告,应用。

图形摘要

[1]
Chawan VS, Gawand KV, Badwane SV. Fluoroquinolones in India- Are we prescribing it right: A cost variation study. Natl J Physiol Pharm Pharmacol 2015; 5(4): 306-8.
[http://dx.doi.org/10.5455/njppp.2015.5.1604201547]
[2]
Emmerson AM, Jones AM. The quinolones: decades of development and use. J Antimicrob Chemother 2003; 51(Suppl. 1): 13-20.
[http://dx.doi.org/10.1093/jac/dkg208] [PMID: 12702699]
[3]
Redgrave LS, Sutton SB, Webber MA, Piddock LJ. Fluoroquinolone resistance: mechanisms, impact on bacteria, and role in evolutionary success. Trends Microbiol 2014; 22(8): 438-45.
[http://dx.doi.org/10.1016/j.tim.2014.04.007] [PMID: 24842194]
[4]
Majalekar PP, Shirote PJ, Nalawade VV, et al. Design, synthesis and comparative pharmacological assessment of novel Fluoroquinolone derivatives. Int J Pharm Sci Res 2019; 10(8): 3735-40.
[5]
Alangaden GJ, Lerner SA. The clinical use of fluoroquinolones for the treatment of mycobacterial diseases. Clin Infect Dis 1997; 25(5): 1213-21.
[http://dx.doi.org/10.1086/516116] [PMID: 9402384]
[6]
Hooper DC. Expanding uses of fluoroquinolones: opportunities and challenges. Ann Intern Med 1998; 129(11): 908-10.
[http://dx.doi.org/10.7326/0003-4819-129-11_Part_1-199812010-00015] [PMID: 9867736]
[7]
Jackson MA, Schutze GE. COMMITTEE ON INFECTIOUS DISEASES. The use of systemic & topical fluoroquinolones. Pediatrics 2016; 138(5): e1-e13.
[http://dx.doi.org/10.1542/peds.2016-2706] [PMID: 27940800]
[8]
Murray TS, Baltimore RS. Pediatric uses of fluoroquinolone antibiotics. Pediatr Ann 2007; 36(6): 336-42.
[http://dx.doi.org/10.3928/0090-4481-20070601-09] [PMID: 17727139]
[9]
Velissariou IM. The use of fluoroquinolones in children: recent advances. Expert Rev Anti Infect Ther 2006; 4(5): 853-60.
[http://dx.doi.org/10.1586/14787210.4.5.853] [PMID: 17140360]
[10]
Sarkozy G. Quinolones: a class of antimicrobial agents. Vet Med 2001; 46: 257-74.
[http://dx.doi.org/10.17221/7883-VETMED]
[11]
Richards GA, Brink AJ, Feldman C. Rational use of the fluoroquinolones. S Afr Med J 2019; 109(6): 378-81.
[http://dx.doi.org/10.7196/SAMJ.2019.v109i6.14002] [PMID: 31266554]
[12]
Sprandel KA, Rodvold KA. Safety and tolerability of fluoroquinolones. Clin Cornerstone 2003; 5(3)(Suppl. 3): S29-36.
[http://dx.doi.org/10.1016/S1098-3597(03)90027-5] [PMID: 14992418]
[13]
Mandell L, Tillotson G. Safety of fluoroquinolones: An update. Can J Infect Dis 2002; 13(1): 54-61.
[http://dx.doi.org/10.1155/2002/864789] [PMID: 18159374]
[14]
Rubinstein E. History of quinolones and their side effects. Chemotherapy 2001; 47(S3)(Suppl. 3): 3-8.
[http://dx.doi.org/10.1159/000057838] [PMID: 11549783]
[15]
Epstein AB. Fluoroquinolones: the Next Generation. Review of Optometry 2003; 140(1): 1-7.
[16]
Park-Wyllie LY, Juurlink DN, Kopp A, et al. Outpatient gatifloxacin therapy and dysglycemia in older adults Engl j med 2006; 354(13): 1352-61.
[http://dx.doi.org/10.1056/NEJMoa055191]
[17]
Bisacchi GS. Origins of the Quinolone Class of Antibacterials: An Expanded “Discovery Story”. J Med Chem 2015; 58(12): 4874-82.
[http://dx.doi.org/10.1021/jm501881c] [PMID: 25738967]
[18]
Rohlfing SR, Gerster JR, Kvam DC. Bioevaluation of the antibacterial flumequine for urinary tract use. Antimicrob Agents Chemother 1976; 10(1): 20-4.
[http://dx.doi.org/10.1128/AAC.10.1.20] [PMID: 984753]
[19]
Dalhoff A. In vitro activities of quinolones. Expert Opin Investig Drugs 1999; 8(2): 123-37.
[http://dx.doi.org/10.1517/13543784.8.2.123] [PMID: 15992068]
[20]
Bambeke FV, Michot JM, Eldere JV, et al. Quinolones in 2005 European society of clinical Microbiology and Infectious Diseases 2005; 11: 256-80.
[21]
Owens RC, Ambrose PG. Clinical use of the Fluoroquinolones Antibiotic therapy 2000; 84(60): 1447-69.https://www.ncbi.nlm.nih.gov/pubmed/12702699
[http://dx.doi.org/10.1016/S0025-7125(05)70297-2]
[22]
[https://en.wikepedia.org/wiki/Oxolinic_acid
[23]
[https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:138856
[24]
[https://pubchem.ncbi.nlm.nih.gov/compound/Oxolinic-acid
[25]
[https://www.drugbank.ca/drugs/DB00827
[26]
[https://en.wikipedia.org/wiki/Cinoxacin
[27]
Andersson MI, MacGowan AP. Development of the quinolones. J Antimicrob Chemother 2003; 51(S1)(Suppl. 1): 1-11.
[http://dx.doi.org/10.1093/jac/dkg212] [PMID: 12702698]
[28]
[https://pubchem.ncbi.nlm.nih.gov/compound/Miloxacin
[29]
[https://www.drugbank.ca/drugs/DB00817
[30]
[https://wiki2.org/en/Flumequine
[31]
[https://en.wikipedia.org/wiki/Flumequine
[32]
Appelbaum PC, Hunter PA. The fluoroquinolone antibacterials: past, present and future perspectives. Int J Antimicrob Agents 2000; 16(1): 5-15.
[http://dx.doi.org/10.1016/S0924-8579(00)00192-8] [PMID: 11185413]
[33]
[https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75250
[34]
[https://pubchem.ncbi.nlm.nih.gov/compound/Pipemidic-acid
[35]
Goldstein EJ. Norfloxacin, a fluoroquinolone antibacterial agent Alliance Academ Int Med 1987; 82(6)(2): 3-17.https://www.ncbi.nlm.nih.gov/pubmed/3111257
[http://dx.doi.org/10.1016/0002-9343(87)90612-7]
[36]
Zaffiri L, Gardner J. Toledo-Pereyra1 LH. History of antibiotics: From fuoroquinolones to Daptomycin (Part 2). J Invest Surg 2013; 26: 167-79.
[http://dx.doi.org/10.3109/08941939.2013.808461] [PMID: 23869821]
[37]
[https://www.drugbank.ca/drugs/DB01165
[38]
[https://www.drugbank.ca/drugs/DB01208
[39]
Bertino J Jr, Fish D. The safety profile of the fluoroquinolones. Clin Ther 2000; 22(7): 798-817.
[http://dx.doi.org/10.1016/S0149-2918(00)80053-3] [PMID: 10945507]
[40]
[https://www.drugbank.ca/drugs/DB00537
[41]
[https://www.drugs.com/ciprofloxacin.html
[42]
Wolfson JS, Hooper DC. Fluoroquinolone antimicrobial agents. Clin Microbiol Rev 1989; 2(4): 378-424.
[http://dx.doi.org/10.1128/CMR.2.4.378] [PMID: 2680058]
[43]
[https://www.drugbank.ca/drugs/DB01137
[44]
[https://www.drugbank.ca/drugs/DB00218
[45]
O’Donnell JA, Gelone SP. The newer fluoroquinolones. Infect Dis Clin North Am 2004; 18(3): 691-716, x..
[http://dx.doi.org/10.1016/j.idc.2004.04.011] [PMID: 15308282]
[46]
[https://www.drugbank.ca/drugs/DB01044
[47]
Sharma PC, Jain A, Jain S. Fluoroquinolone antibacterials: a review on chemistry, microbiology and therapeutic prospects. Acta Pol Pharm 2009; 66(6): 587-604.
[PMID: 20050522]
[48]
Naber KG, Adam D. Classification of fluoroquinolones. Int J Antimicrob Agents 1998; 10(4): 255-7.
[http://dx.doi.org/10.1016/S0924-8579(98)00059-4] [PMID: 9916897]
[49]
Ball P. Quinolone generations: natural history or natural selection? J Antimicrob Chemother 2000; 46(Suppl T1): 17-24.
[http://dx.doi.org/10.1093/oxfordjournals.jac.a020889] [PMID: 10997595]
[50]
Scoper SV. Review of third-and fourth-generation fluoroquinolones in ophthalmology: in-vitro and in-vivo efficacy. Adv Ther 2008; 25(10): 979-94.
[http://dx.doi.org/10.1007/s12325-008-0107-x] [PMID: 18836691]
[51]
Mather R, Karenchak LM, Romanowski EG, Kowalski RP. Fourth generation fluoroquinolones: new weapons in the arsenal of ophthalmic antibiotics. Am J Ophthalmol 2002; 133(4): 463-6.
[http://dx.doi.org/10.1016/S0002-9394(02)01334-X] [PMID: 11931779]
[52]
Soni K. Fluoroquinolones: chemistry action-A review Indo glob 2012; 2(1): 42-53..http://iglobaljournal.com/wp-content/uploads/2012/05/4.-Kirti-Soni-2012.pdf
[53]
Tillotson GS. Quinolones: structure-activity relationships and future predictions. J Med Microbiol 1996; 44(5): 320-4.
[http://dx.doi.org/10.1099/00222615-44-5-320] [PMID: 8636945]
[54]
Das R, Mehta DK, Sharma V. Quinolones: Understanding the drug designing to combat drug resistance. Annals of Pharmacology and Pharmaceutics 2017; 2(9): 1-3.
[55]
Idowu T, Schweizer F. Ubiquitous nature of fluoroquinolones: The oscillation between antibacterial and anticancer activities. Antibiotics (Basel) 2017; 6(4): 1-24.
[http://dx.doi.org/10.3390/antibiotics6040026] [PMID: 29112154]
[56]
Bryskier A, Chantot JF. Classification and structure-activity relationships of fluoroquinolones. Drugs 1995; 49(Suppl. 2): 16-28.
[http://dx.doi.org/10.2165/00003495-199500492-00005] [PMID: 8549288]
[57]
Aldred KJ, Kerns RJ, Osheroff N. Mechanism of quinolone action and resistance. Biochemistry 2014; 53(10): 1565-74.
[http://dx.doi.org/10.1021/bi5000564] [PMID: 24576155]
[58]
Sood D, Kumar N, Singh A, Sakharkar MK, Tomar V, Chandra R. Antibacterial and pharmacological evaluation of fluoroquinolones: A cheoinformatics approach. Genomics Inform 2018; 16(3): 44-51.
[http://dx.doi.org/10.5808/GI.2018.16.3.44] [PMID: 30309202]
[59]
Vincent A. The quinolones: Past, present, future, Supplement article, Overview of quinolone development. Clin Infect Dis 2005; (41): (Suppl. 2): S113-9.
[60]
Schimizu M. Quinolone antibacterial agents: Their past, present, future. J Infect Chemother 1995; 1: 16-29.
[http://dx.doi.org/10.1007/BF02347726]
[61]
Oliphant CM, Green GM. Quinolones: a comprehensive review. Am Fam Physician 2002; 65(3): 455-64.
[PMID: 11858629]
[62]
Ko YH, Song PH. Current updates in and pharmacodynamics of fluoroquinolones. Korean J Urogenit Tract Infect Inflamm 2015; 10(1): 1-6.
[http://dx.doi.org/10.14777/kjutii.2015.10.1.1]
[63]
Lode H, Borner K, Koeppe P. Pharmacodynamics of fluoroquinolones. Clin Infect Dis 1998; 27(1): 33-9.
[http://dx.doi.org/10.1086/514623] [PMID: 9675446]
[64]
Norrby SR. Side-effects of quinolones: comparisons between quinolones and other antibiotics. Eur J Clin Microbiol Infect Dis 1991; 10(4): 378-83.
[http://dx.doi.org/10.1007/BF01967014] [PMID: 1864300]
[65]
Abou Heidar NF, Degheili JA, Yacoubian AA, Khauli RB. Management of urinary tract infection in women: A practical approach for everyday practice. Urol Ann 2019; 11(4): 339-46.
[http://dx.doi.org/10.4103/UA.UA_104_19] [PMID: 31649450]
[66]
Naber KG. Which fluoroquinolones are suitable for the treatment of urinary tract infections? Int J Antimicrob Agents 2001; 17(4): 331-41.
[http://dx.doi.org/10.1016/S0924-8579(00)00362-9] [PMID: 11295418]
[67]
Andriole VT. Use of quinolones in treatment of prostatitis and lower urinary tract infections. Eur J Clin Microbiol Infect Dis 1991; 10(4): 342-50.
[http://dx.doi.org/10.1007/BF01967009] [PMID: 1864295]
[68]
Naber KG. Use of Quinolones in Urinary Tract Infections and Prostatitis Inf Dis 1989; II5: S1321-37.
[http://dx.doi.org/10.1093/clinids/11.Supplement_5.S1321]
[69]
Blondeau JM. Clinical utility of the new fluoroquinolones for treating respiratory and urinary tract infections. Expert Opin Investig Drugs 2001; 10(2): 213-37.
[http://dx.doi.org/10.1517/13543784.10.2.213] [PMID: 11178338]
[70]
Shams WE, Evans ME. Guide to selection of fluoroquinolones in patients with lower respiratory tract infections. Drugs 2005; 65(7): 949-91.
[http://dx.doi.org/10.2165/00003495-200565070-00004] [PMID: 15892589]
[71]
Zimmerli W, Widmer AF, Blatter M, et al. Role of rifampin for treatment of orthopedic implantrelated staphylococcal infections: A randomized controlled trial J Am Med Ass 1537; 279(19): 1537-41.
[72]
Li HK, Rombach I, Zambellas R, et al. OVIVA Trial Collaborators. Oral versus intravenous antibiotics for bone and joint infection. N Engl J Med 2019; 380(5): 425-36.
[http://dx.doi.org/10.1056/NEJMoa1710926] [PMID: 30699315]
[73]
Sarathy J, Blanc L, Alvarez-Cabrera N, et al. Fluoroquinolones efficacy against tuberculosis is driven by penetration into lesions and activity against resident bacterial populations. Antimicrob Agents Chemother 2019; 63(5): 1-16.
[http://dx.doi.org/10.1128/AAC.02516-18] [PMID: 30803965]
[74]
Edlund C, Nord CE. Ecological effect of gatifloxacin on the normal human intestinal microflora. J Chemother 1999; 11(1): 50-3.
[http://dx.doi.org/10.1179/joc.1999.11.1.50] [PMID: 10078781]
[75]
Chen M, Guo Q, Wang Y, et al. Shifts in the antibiotic Susceptibility, Serogroups, and clonal complexes of Neisseria meningitidis in shanghai, china: A time trend analysis of the pre-quinolone and quinolone eras. PLoS Med 2015; 12(6)e1001838.
[http://dx.doi.org/10.1371/journal.pmed.1001838] [PMID: 26057853]
[76]
Cottagnoud P, Taube MG. Fluoroquinolones in the treatment of meningitis Cur infect Dis 2003; 5(329): 6.
[http://dx.doi.org/10.1007/s11908-003-0011-0]
[77]
Sendzik J, Lode H, Stahlmann R. Quinolone-induced arthropathy: an update focusing on new mechanistic and clinical data. Int J Antimicrob Agents 2009; 33(3): 194-200.
[http://dx.doi.org/10.1016/j.ijantimicag.2008.08.004] [PMID: 18835137]
[78]
Ball P. Efficacy and safety of levofloxacin in the context of other contemporary fluoroquinolones: a review. Curr Ther Res Clin Exp 2003; 64(9): 646-61.
[http://dx.doi.org/10.1016/j.curtheres.2003.11.003] [PMID: 24944413]
[79]
Ball P. Adverse drug reactions: implications for the development of fluoroquinolones. J Antimicrob Chemother 2003; 51(Suppl. 1): 21-7.
[http://dx.doi.org/10.1093/jac/dkg209] [PMID: 12702700]
[80]
Lewis T, Cook J. Fluoroquinolones and tendinopathy: a guide for athletes and sports clinicians and a systematic review of the literature. J Athl Train 2014; 49(3): 422-7.
[http://dx.doi.org/10.4085/1062-6050-49.2.09] [PMID: 24762232]
[81]
Golomb BA, Koslik HJ, Redd AJ. Fluoroquinolone-induced serious, persistent, multisymptom adverse effects. BMJ Case Rep 2015; 2015: 1-10.
[PMID: 26438672]
[82]
Daneman N, Lu H, Redelmeier DA. Fluoroquinolones and collagen associated severe adverse events: a longitudinal cohort study. BMJ Open 2015; 5(11)e010077.
[http://dx.doi.org/10.1136/bmjopen-2015-010077] [PMID: 26582407]
[83]
Choi SH, Kim EY, Kim YJ. Systemic use of fluoroquinolone in children. Korean J Pediatr 2013; 56(5): 196-201.
[http://dx.doi.org/10.3345/kjp.2013.56.5.196] [PMID: 23741232]
[84]
Mathews B, Thalody AA, Miraj SS, Kunhikatta V, Rao M, Saravu K. Adverse Effects of Fluoroquinolones: A retrospective cohort study in a south indian tertiary healthcare facility. Antibiotics (Basel) 2019; 8(3): 1-17.
[http://dx.doi.org/10.3390/antibiotics8030104] [PMID: 31357640]
[85]
Michalak K, Sobolewska-Włodarczyk A, Włodarczyk M, Sobolewska J, Woźniak P, Sobolewski B. Treatment of the fluoroquinolone - associated disability: The pathobiochemical implications. Oxid Med Cell Longev 2017.20178023935
[http://dx.doi.org/10.1155/2017/8023935] [PMID: 29147464]
[86]
Liu X, Ma J, Huang L, et al. Fluoroquinolones increase the risk of serious arrhythmias: A systematic review and meta-analysis. Medicine (Baltimore) 2017; 96(44)e8273
[http://dx.doi.org/10.1097/MD.0000000000008273] [PMID: 29095256]
[87]
Gorelik E, Masarwa R, Perlman A, et al. Fluoroquinolones and cardiovascular risk: A systematic review, meta-analysis and network meta-analysis. Drug Saf 2019; 42(4): 529-38.
[http://dx.doi.org/10.1007/s40264-018-0751-2] [PMID: 30368737]
[88]
Bolon MK. The newer fluoroquinolones Med clin N Am 2011; 95: 793-817.https://www.ncbi.nlm.nih.gov/pubmed/19909896
[http://dx.doi.org/10.1016/j.mcna.2011.03.006]
[89]
Sarro A, Sarro G. Adverse reactions to fluoroquinolones An overview on mechanistic aspects Cur med chem 2001; 8: 371-84.https://www.ncbi.nlm.nih.gov/pubmed/11172695
[90]
Molnar DM, Kremzner ME. Fluoroquinolones: A hot topic for pharmacists and the food and drug administration’s division of drug information. J Am Pharm Assoc 2019; 59(1): 13-6.
[PMID: 30348510]
[91]
Fernandez TD, Ariza A. Palomares. Hypersensitivity to fluoroquinolones. Med (Baltimore) 2016; 95(23)e3679
[92]
Khurana G, Arora S, Pawar PK. Ocular insert for sustained delivery of gatifloxacin sesquihydrate: Preparation and evaluations. Int J Pharm Investig 2012; 2(2): 70-7.
[http://dx.doi.org/10.4103/2230-973X.100040] [PMID: 23119235]
[93]
Rajalakshmi R, Padmaja C. Formulation and assessment of gemifloxacin mesylate ocular in situ gelling system. Int Res J Pharm 2013; 4(10): 33-8.
[http://dx.doi.org/10.7897/2230-8407.041009]
[94]
Gaikwad VD, Yadav VD, Gaikwad MD. Novel sustained release and swellable gastroretentive dosage form for ciprofloxacin hydrochloride. Int J Pharm Investig 2014; 4(2): 88-92.
[http://dx.doi.org/10.4103/2230-973X.133057] [PMID: 25006553]
[95]
Guguloth M, Bomma R, Veerabrahma K. Development of sustained release floating drug delivery system for norfloxacin: in vitro and in vivo evaluation. PDA J Pharm Sci Technol 2011; 65(3): 198-206.
[http://dx.doi.org/10.5731/pdajpst.2011.00685] [PMID: 22293231]
[96]
Chavanpatil MD, Jain P, Chaudhari S, Shear R, Vavia PR. Novel sustained release, swellable and bioadhesive gastroretentive drug delivery system for ofloxacin. Int J Pharm 2006; 316(1-2): 86-92.
[http://dx.doi.org/10.1016/j.ijpharm.2006.02.038] [PMID: 16567072]
[97]
Gupta H, Malik A, Khar RK, Ali A, Bhatnagar A, Mittal G. Physiologically active hydrogel (in situ gel) of sparfloxacin and its evaluation for ocular retention using gamma scintigraphy. J Pharm Bioallied Sci 2015; 7(3): 195-200.
[http://dx.doi.org/10.4103/0975-7406.160015] [PMID: 26229353]
[98]
El-Zahaby SA, Kassem AA, El-Kamel AH. Design and evaluation of gastroretentive levofloxacin floating mini-tablets-in-capsule system for eradication of Helicobacter pylori. Saudi Pharm J 2014; 22(6): 570-9.
[http://dx.doi.org/10.1016/j.jsps.2014.02.009] [PMID: 25561871]
[99]
Satyanandam S, Murala S. PH-Induced in situ gelling system of lomefloxacin for sustained ocular delivery. Int J Pharm Sci Drug Res 2015; 7(5): 1-4.
[100]
[https://www.hse.ie/eng/services/list/2/gp/antibioticprescribing/drug-interactions/fluoroquinolone-warning-2019.html
[101]
Tanne JH. FDA adds “black box” warning label to fluoroquinolone antibiotics. BMJ 2008; 337(7662): a816.
[http://dx.doi.org/10.1136/bmj.a816] [PMID: 18632714]
[102]
[https://www.medpagetoday.com/infectiousdisease/generalinfectiousdisease/73954

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy