依诺沙星

**依诺沙星**
臨床資料
AHFS/Drugs.com	Multum消费者信息
MedlinePlus	a601013
给药途径	口服
ATC碼	J01MA04 (WHO) ;
识别信息
	IUPAC命名法 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; ;
CAS号	74011-58-8
PubChem CID	3229;
DrugBank	DB00467 ;
ChemSpider	3116 ;
UNII	325OGW249P;
KEGG	D00310 ;
ChEBI	CHEBI:157175 ;
ChEMBL	ChEMBL826 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID5022984 ;
化学信息
化学式	C15H17FN4O3
摩尔质量	320.32 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
熔点	220至224 °C（428至435 °F）
	SMILES Fc1c(nc2c(c1)C(=O)C(\C(=O)O)=C/N2CC)N3CCNCC3;
	InChI InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23) ; Key:IDYZIJYBMGIQMJ-UHFFFAOYSA-N ;

依诺沙星是一种喹诺酮类抗生素，用于治疗尿路感染和淋病。^[1]^[2]

最近有研究表明它可能具有抗癌作用。^[3]

医疗用途

依诺沙星可用于治疗多种感染，特别是胃肠炎，包括感染性腹泻、呼吸道感染、淋病^[4]和尿路感染。^[5]

禁忌症和相互作用

对该物质或喹诺酮类的任何其他成员或药物的任何成分有过敏史的受试者禁用依诺沙星。与其他氟喹诺酮类药物一样，依诺沙星可引起幼年动物负重关节的退行性变化。只有当预期收益大于风险时，该化合物才应用于儿童。^[6]^[7]

芬布芬与某些喹诺酮类药物（包括依诺沙星）合用可能会增加癫痫发作的风险。因此，作为预防措施，应避免同时服用芬布芬和喹诺酮。^[8]^[9]

不良反应

与其他氟喹诺酮类药物一样，依诺沙星已知会引发癫痫发作或降低癫痫发作阈值。^[10]该化合物不应用于癫痫患者或有惊厥发作个人史的患者，因为这可能会促进这些疾病的发作。^[11]

药代动力学

口服后依诺沙星从胃肠道迅速而良好地吸收。抗生素广泛分布于全身和不同的生物组织中。组织浓度通常超过血清浓度。依诺沙星与血清蛋白的结合率为35%至40%。在肾功能正常的受试者中，血清消除半衰期约为6小时。约60%的口服给药剂量在24小时内以原型药物形式从尿中排出。^[12]^[13]

作用机制

依诺沙星是一种广谱抗生素，对革兰氏阴性和革兰氏阳性菌均有活性。^[2]与其他氟喹诺酮类药物一样，依诺沙星通过抑制细菌DNA旋转酶和拓扑异构酶IV，^[2]阻止细菌DNA复制、转录、修复和重组。^[14]^[15]

参考文献

^ Enoxacin Uses, Side Effects & Warnings. Drugs.com. [2022-06-22]. （原始内容存档于2022-06-28）（美国英语）.
^ ^2.0 ^2.1 ^2.2 Enoxacin. DrugBank Online. [2022-06-22]. （原始内容存档于2022-06-28）（加拿大英语）.
^ Melo, Sonia; Villanueva, Alberto; Moutinho, Catia; Davalos, Veronica; Spizzo, Riccardo; Ivan, Cristina; Rossi, Simona; Setien, Fernando; Casanovas, Oriol; Simo-Riudalbas, Laia; Carmona, Javier. Small molecule enoxacin is a cancer-specific growth inhibitor that acts by enhancing TAR RNA-binding protein 2-mediated microRNA processing. Proceedings of the National Academy of Sciences of the United States of America. 2011-03-15, 108 (11) [2022-06-25]. ISSN 1091-6490. PMC 3060242 . PMID 21368194. doi:10.1073/pnas.1014720108. （原始内容存档于2022-07-12）.
^ van der Willigen, A. H.; van der Hoek, J. C.; Wagenvoort, J. H.; van Vliet, H. J.; van Klingeren, B.; Schalla, W. O.; Knapp, J. S.; van Joost, T.; Michel, M. F.; Stolz, E. Comparative double-blind study of 200- and 400-mg enoxacin given orally in the treatment of acute uncomplicated urethral gonorrhea in males. Antimicrobial Agents and Chemotherapy. 1987-04, 31 (4) [2022-06-25]. ISSN 0066-4804. PMID 3111354. doi:10.1128/AAC.31.4.535. （原始内容存档于2022-06-29）.
^ Huttunen, M.; Kunnas, K.; Saloranta, P. Enoxacin treatment of urinary tract infections in elderly patients. The Journal of Antimicrobial Chemotherapy. 1988-02,. 21 Suppl B [2022-06-25]. ISSN 0305-7453. PMID 3162900. doi:10.1093/jac/21.suppl_b.105. （原始内容存档于2022-06-25）.
^ Chalumeau, Martin; Tonnelier, Sylvie; D'Athis, Philippe; Tréluyer, Jean-Marc; Gendrel, Dominique; Bréart, Gérard; Pons, Gérard; Pediatric Fluoroquinolone Safety Study Investigators. Fluoroquinolone safety in pediatric patients: a prospective, multicenter, comparative cohort study in France. Pediatrics. 2003-06, 111 (6 Pt 1) [2022-06-25]. ISSN 1098-4275. PMID 12777590. doi:10.1542/peds.111.6.e714. （原始内容存档于2022-06-25）.
^ Committee on Infectious Diseases. The use of systemic fluoroquinolones. Pediatrics. 2006-09, 118 (3) [2022-06-25]. ISSN 1098-4275. PMID 16951028. doi:10.1542/peds.2006-1722. （原始内容存档于2022-06-17）.
^ Morita, H.; Maemura, K.; Sakai, Y.; Kaneda, Y. [A case of convulsion, loss of consciousness and subsequent acute renal failure caused by enoxacin and fenbufen]. Nihon Naika Gakkai Zasshi. The Journal of the Japanese Society of Internal Medicine. 1988-05, 77 (5) [2022-06-25]. ISSN 0021-5384. PMID 3216153. doi:10.2169/naika.77.744. （原始内容存档于2022-06-27）.
^ Masukawa, T.; Nakanishi, K.; Natsuki, R. Role of nitric oxide in the convulsions following the coadministration of enoxacin with fenbufen in mice. Japanese Journal of Pharmacology. 1998-04, 76 (4) [2022-06-25]. ISSN 0021-5198. PMID 9623721. doi:10.1254/jjp.76.425. （原始内容存档于2022-08-09）.
^ De Sarro, A.; Zappalá, M.; Chimirri, A.; Grasso, S.; De Sarro, G. B. Quinolones potentiate cefazolin-induced seizures in DBA/2 mice. Antimicrobial Agents and Chemotherapy. 1993-07, 37 (7) [2022-06-25]. ISSN 0066-4804. PMID 8395790. doi:10.1128/AAC.37.7.1497. （原始内容存档于2022-06-28）.
^ Simpson, K. J.; Brodie, M. J. Convulsions related to enoxacin. Lancet (London, England). 1985-07-20, 2 (8447). ISSN 0140-6736. PMID 2862357. doi:10.1016/s0140-6736(85)90270-3.
^ Wise, R.; Lockley, R.; Dent, J.; Webberly, M. Pharmacokinetics and tissue penetration of enoxacin. Antimicrobial Agents and Chemotherapy. 1984-07, 26 (1) [2022-06-25]. ISSN 0066-4804. PMID 6591851. doi:10.1128/AAC.26.1.17. （原始内容存档于2022-06-25）.
^ Wise, R.; Lister, D.; McNulty, C. A.; Griggs, D.; Andrews, J. M. The comparative pharmacokinetics and tissue penetration of four quinolones including intravenously administered enoxacin. Infection. 1986,. 14 Suppl 3 [2022-06-25]. ISSN 0300-8126. PMID 3463542. doi:10.1007/BF01667843. （原始内容存档于2022-06-27）.
^ Yoshida, H.; Nakamura, M.; Bogaki, M.; Ito, H.; Kojima, T.; Hattori, H.; Nakamura, S. Mechanism of action of quinolones against Escherichia coli DNA gyrase. Antimicrobial Agents and Chemotherapy. 1993-04, 37 (4) [2022-06-23]. ISSN 0066-4804. PMID 8388200. doi:10.1128/AAC.37.4.839. （原始内容存档于2022-07-06）.
^ Wolfson, J. S.; Hooper, D. C. The fluoroquinolones: structures, mechanisms of action and resistance, and spectra of activity in vitro. Antimicrobial Agents and Chemotherapy. 1985-10, 28 (4) [2022-06-23]. ISSN 0066-4804. PMID 3000292. doi:10.1128/AAC.28.4.581. （原始内容存档于2022-06-28）.

延伸阅读

Patel, S. S.; Spencer, C. M. Enoxacin: a reappraisal of its clinical efficacy in the treatment of genitourinary tract infections. Drugs. 1996-01, 51 (1) [2022-06-25]. ISSN 0012-6667. PMID 8741236. doi:10.2165/00003495-199651010-00009. （原始内容存档于2022-06-28）.

[drugs-1] Enoxacin Uses, Side Effects & Warnings. Drugs.com. [2022-06-22]. （原始内容存档于2022-06-28）（美国英语）.

[drugbank-2] 2.0 ^2.1 ^2.2 Enoxacin. DrugBank Online. [2022-06-22]. （原始内容存档于2022-06-28）（加拿大英语）.

[3] Melo, Sonia; Villanueva, Alberto; Moutinho, Catia; Davalos, Veronica; Spizzo, Riccardo; Ivan, Cristina; Rossi, Simona; Setien, Fernando; Casanovas, Oriol; Simo-Riudalbas, Laia; Carmona, Javier. Small molecule enoxacin is a cancer-specific growth inhibitor that acts by enhancing TAR RNA-binding protein 2-mediated microRNA processing. Proceedings of the National Academy of Sciences of the United States of America. 2011-03-15, 108 (11) [2022-06-25]. ISSN 1091-6490. PMC 3060242 . PMID 21368194. doi:10.1073/pnas.1014720108. （原始内容存档于2022-07-12）.

[4] van der Willigen, A. H.; van der Hoek, J. C.; Wagenvoort, J. H.; van Vliet, H. J.; van Klingeren, B.; Schalla, W. O.; Knapp, J. S.; van Joost, T.; Michel, M. F.; Stolz, E. Comparative double-blind study of 200- and 400-mg enoxacin given orally in the treatment of acute uncomplicated urethral gonorrhea in males. Antimicrobial Agents and Chemotherapy. 1987-04, 31 (4) [2022-06-25]. ISSN 0066-4804. PMID 3111354. doi:10.1128/AAC.31.4.535. （原始内容存档于2022-06-29）.

[5] Huttunen, M.; Kunnas, K.; Saloranta, P. Enoxacin treatment of urinary tract infections in elderly patients. The Journal of Antimicrobial Chemotherapy. 1988-02,. 21 Suppl B [2022-06-25]. ISSN 0305-7453. PMID 3162900. doi:10.1093/jac/21.suppl_b.105. （原始内容存档于2022-06-25）.

[6] Chalumeau, Martin; Tonnelier, Sylvie; D'Athis, Philippe; Tréluyer, Jean-Marc; Gendrel, Dominique; Bréart, Gérard; Pons, Gérard; Pediatric Fluoroquinolone Safety Study Investigators. Fluoroquinolone safety in pediatric patients: a prospective, multicenter, comparative cohort study in France. Pediatrics. 2003-06, 111 (6 Pt 1) [2022-06-25]. ISSN 1098-4275. PMID 12777590. doi:10.1542/peds.111.6.e714. （原始内容存档于2022-06-25）.

[7] Committee on Infectious Diseases. The use of systemic fluoroquinolones. Pediatrics. 2006-09, 118 (3) [2022-06-25]. ISSN 1098-4275. PMID 16951028. doi:10.1542/peds.2006-1722. （原始内容存档于2022-06-17）.

[8] Morita, H.; Maemura, K.; Sakai, Y.; Kaneda, Y. [A case of convulsion, loss of consciousness and subsequent acute renal failure caused by enoxacin and fenbufen]. Nihon Naika Gakkai Zasshi. The Journal of the Japanese Society of Internal Medicine. 1988-05, 77 (5) [2022-06-25]. ISSN 0021-5384. PMID 3216153. doi:10.2169/naika.77.744. （原始内容存档于2022-06-27）.

[9] Masukawa, T.; Nakanishi, K.; Natsuki, R. Role of nitric oxide in the convulsions following the coadministration of enoxacin with fenbufen in mice. Japanese Journal of Pharmacology. 1998-04, 76 (4) [2022-06-25]. ISSN 0021-5198. PMID 9623721. doi:10.1254/jjp.76.425. （原始内容存档于2022-08-09）.

[10] De Sarro, A.; Zappalá, M.; Chimirri, A.; Grasso, S.; De Sarro, G. B. Quinolones potentiate cefazolin-induced seizures in DBA/2 mice. Antimicrobial Agents and Chemotherapy. 1993-07, 37 (7) [2022-06-25]. ISSN 0066-4804. PMID 8395790. doi:10.1128/AAC.37.7.1497. （原始内容存档于2022-06-28）.

[11] Simpson, K. J.; Brodie, M. J. Convulsions related to enoxacin. Lancet (London, England). 1985-07-20, 2 (8447). ISSN 0140-6736. PMID 2862357. doi:10.1016/s0140-6736(85)90270-3.

[12] Wise, R.; Lockley, R.; Dent, J.; Webberly, M. Pharmacokinetics and tissue penetration of enoxacin. Antimicrobial Agents and Chemotherapy. 1984-07, 26 (1) [2022-06-25]. ISSN 0066-4804. PMID 6591851. doi:10.1128/AAC.26.1.17. （原始内容存档于2022-06-25）.

[13] Wise, R.; Lister, D.; McNulty, C. A.; Griggs, D.; Andrews, J. M. The comparative pharmacokinetics and tissue penetration of four quinolones including intravenously administered enoxacin. Infection. 1986,. 14 Suppl 3 [2022-06-25]. ISSN 0300-8126. PMID 3463542. doi:10.1007/BF01667843. （原始内容存档于2022-06-27）.

[14] Yoshida, H.; Nakamura, M.; Bogaki, M.; Ito, H.; Kojima, T.; Hattori, H.; Nakamura, S. Mechanism of action of quinolones against Escherichia coli DNA gyrase. Antimicrobial Agents and Chemotherapy. 1993-04, 37 (4) [2022-06-23]. ISSN 0066-4804. PMID 8388200. doi:10.1128/AAC.37.4.839. （原始内容存档于2022-07-06）.

[15] Wolfson, J. S.; Hooper, D. C. The fluoroquinolones: structures, mechanisms of action and resistance, and spectra of activity in vitro. Antimicrobial Agents and Chemotherapy. 1985-10, 28 (4) [2022-06-23]. ISSN 0066-4804. PMID 3000292. doi:10.1128/AAC.28.4.581. （原始内容存档于2022-06-28）.

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