依諾沙星

**依諾沙星**
臨床資料
AHFS/Drugs.com	Multum消費者信息
MedlinePlus	a601013
給藥途徑	口服
ATC碼	J01MA04 (WHO) ;
識別資訊
	IUPAC命名法 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; ;
CAS號	74011-58-8
PubChem CID	3229;
DrugBank	DB00467 ;
ChemSpider	3116 ;
UNII	325OGW249P;
KEGG	D00310 ;
ChEBI	CHEBI:157175 ;
ChEMBL	ChEMBL826 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID5022984 ;
化學資訊
化學式	C15H17FN4O3
摩爾質量	320.32 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
熔點	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 ;

依諾沙星是一種喹諾酮類抗生素，用於治療尿路感染和淋病。^[1]^[2]

最近有研究表明它可能具有抗癌作用。^[3]

醫療用途

依諾沙星可用於治療多種感染，特別是胃腸炎，包括感染性腹瀉、呼吸道感染、淋病^[4]和尿路感染。^[5]

禁忌症和相互作用

對該物質或喹諾酮類的任何其他成員或藥物的任何成分有過敏史的受試者禁用依諾沙星。與其他氟喹諾酮類藥物一樣，依諾沙星可引起幼年動物負重關節的退行性變化。只有當預期收益大於風險時，該化合物才應用於兒童。^[6]^[7]

芬布芬與某些喹諾酮類藥物（包括依諾沙星）合用可能會增加癲癇發作的風險。因此，作為預防措施，應避免同時服用芬布芬和喹諾酮。^[8]^[9]

不良反應

與其他氟喹諾酮類藥物一樣，依諾沙星已知會引發癲癇發作或降低癲癇發作閾值。^[10]該化合物不應用於癲癇患者或有驚厥發作個人史的患者，因為這可能會促進這些疾病的發作。^[11]

藥代動力學

口服後依諾沙星從胃腸道迅速而良好地吸收。抗生素廣泛分布於全身和不同的生物組織中。組織濃度通常超過血清濃度。依諾沙星與血清蛋白的結合率為35%至40%。在腎功能正常的受試者中，血清消除半衰期約為6小時。約60%的口服給藥劑量在24小時內以原型藥物形式從尿中排出。^[12]^[13]

作用機制

依諾沙星是一種廣譜抗生素，對革蘭氏陰性和革蘭氏陽性菌均有活性。^[2]與其他氟喹諾酮類藥物一樣，依諾沙星通過抑制細菌DNA旋轉酶和拓撲異構酶IV，^[2]阻止細菌DNA複製、轉錄、修復和重組。^[14]^[15]

參考文獻

^ Enoxacin Uses, Side Effects & Warnings. Drugs.com. [2022-06-22]. （原始內容存檔於2022-06-28）（美國英語）.
^ ^2.0 ^2.1 ^2.2 Enoxacin. DrugBank Online. [2022-06-22]. （原始內容存檔於2022-06-28）（加拿大英語）.
^ 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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於2022-06-28）.

延伸閱讀

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. （原始內容存檔於2022-06-28）.

[drugs-1] Enoxacin Uses, Side Effects & Warnings. Drugs.com. [2022-06-22]. （原始內容存檔於2022-06-28）（美國英語）.

[drugbank-2] 2.0 ^2.1 ^2.2 Enoxacin. DrugBank Online. [2022-06-22]. （原始內容存檔於2022-06-28）（加拿大英語）.

[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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於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. （原始內容存檔於2022-06-28）.

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