奈諾沙星

奈諾沙星
	IUPAC名; 7-[(3S,5S)-3-Amino-5-methyl-1-piperidinyl]-1-cyclopropyl-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
識別
CAS號
PubChem	11993740
ChemSpider	10166207
SMILES	C[C@H]1C[C@H](N)CN(C1)c2ccc3c(c2OC)n(C4CC4)cc(c3=O)C(=O)O;
InChI	1/C20H25N3O4/c1-11-7-12(21)9-22(8-11)16-6-5-14-17(19(16)27-2)23(13-3-4-13)10-15(18(14)24)20(25)26/h5-6,10-13H,3-4,7-9,21H2,1-2H3,(H,25,26)/t11-,12-/m0/s1;
InChIKey	AVPQPGFLVZTJOR-RYUDHWBXBZ
性質
化學式	C20H25N3O4
摩爾質量	371.43 g·mol−1
藥理學
ATC代碼	J01MB08（J01）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

奈諾沙星（Nemonoxacin）（商品名太捷信（Taigexyn））是一種非氟喹諾酮類抗菌藥物^[1]。奈諾沙星的抗菌機轉與其他氟喹諾酮（fluouroquinolones）相同，皆是抑制細菌的DNA旋轉酶，抑制細菌DNA的合成及複製，以及細胞分裂。

奈諾沙星目前已經在台灣、中國大陸上市，在俄羅斯等地已完成三期臨床試驗，並完成美國第二期臨床試驗，正進行第三期臨床試驗^[2]。美國食品藥品監督管理局（FDA）已授予奈諾沙星合格感染性疾病產品資格（英語：qualified infectious disease product）（QIDP）及快速審查（英語：Fast track (FDA)）資格，預期將應用於社區性肺炎（英語：community-acquired bacterial pneumonia）及急性細菌性皮膚與皮膚組織感染（英語：acute bacterial skin and skin-structure infection）^[3]。

適用範圍

奈諾沙星為廣效性抗生素，藥效潛能較同屬喹諾酮類抗細菌藥的左氧氟沙星和莫西沙星為佳^[4]，可對抗多種革蘭氏陽性菌、革蘭氏陰性菌、非典型感染菌等。該藥物的特色為能對抗多種抗藥性極強的病原體，如耐甲氧西林金黃色葡萄球菌（MRSA）、抗喹諾酮之耐甲氧西林金黃色葡萄球菌（QR-MRSA）、抗萬古黴素金黃色葡萄球菌（VRSA）^[5]^[6]、多重抗藥性肺炎鏈球菌（MDRSP）、艱難梭菌（C.difficile）^[7]，以及抗盤尼西林肺炎鏈球菌（PRSP）等。

奈諾沙星對於部分革蘭氏陰性菌的效用較弱，例如大腸桿菌、奇異變形桿菌（英語：Proteus mirabilis），及綠膿桿菌等等^[8]。

歷史

奈諾沙星由寶僑（P&G）醫藥部門研發至Ia期臨床試驗。2004年10月，藥物被授權給台灣太景生技公司進行後續研發，同時太景還取得了在中國大陸、台灣、韓國、印度尼西亞、馬來西亞、菲律賓、新加坡和泰國的開發和商業化權利。

2009年Warner Chilcott收購了寶僑公司的全球製藥業務。2010年10月，II期臨床試驗完成後，太景與Warner Chilcott修訂了許可協議，Warner Chilcott保留了在美國和歐洲開發和商業化奈諾沙星的權利。在之後的2011年12月，Warner Chilcott將全部授權轉讓給太景，並退出了奈諾沙星的開發。

2012年，太景將奈諾沙星在中國大陸的生產銷售權授權給浙江醫藥股份有限公司。2014年，太景將奈諾沙星在土耳其、俄羅斯和獨立國協國家的生產銷售權授權給R-Pharm公司。^[9]2016年，太景將奈諾沙星在南美洲國家的生產銷售權授權給Productos Científicos公司^[10]。

奈諾沙星首先於2014年在台灣上市^[11]，為全球首個上市的地區。此後，中國大陸於2016年批准了奈諾沙星的上市^[12]。

參考文獻

^ Guo, B; Wu, X; Zhang, Y; Shi, Y; Yu, J; Cao, G; Zhang, J. Safety and clinical pharmacokinetics of nemonoxacin, a novel non-fluorinated quinolone, in healthy Chinese volunteers following single and multiple oral doses. Clinical Drug Investigation. 2012, 32 (7): 475–86. PMID 22650326. doi:10.2165/11632780-000000000-00000.
^ A Phase III Study to Evaluate the Efficacy and Safety of Intravenous Infusion of Nemonoxacin in Treating CAP - Full Text View - ClinicalTrials.gov. [2018-12-22]. （原始內容存檔於2019-08-02）.
^ FDA grants QIDP and Fast Track designations to TaiGen's nemonoxacin. 23 December 2013 [2018-12-22]. （原始內容存檔於2020-09-30）.
^ Liang, W; Chen, Y. C.; Cao, Y. R.; Liu, X. F.; Huang, J; Hu, J. L.; Zhao, M; Guo, Q. L.; Zhang, S. J.; Wu, X. J.; Zhu, D. M.; Zhang, Y. Y.; Zhang, J. Pharmacokinetics and Pharmacodynamics of Nemonoxacin against Streptococcus pneumoniae in an in Vitro Infection Model. Antimicrobial Agents and Chemotherapy. 2013, 57 (7): 2942–2947. PMC 3697386 . PMID 23587953. doi:10.1128/AAC.01098-12.
^ Lauderdale TL, Shiau YR, Lai JF, Chen HC, King CH. Comparative in vitro activities of nemonoxacin (TG-873870), a novel nonfluorinated quinolone, and other quinolones against clinical isolates. Antimicrob. Agents Chemother. 2010, 54: 1338–1342. PMC 2825994 . doi:10.1128/aac.01197-09.
^ Adam HJ, Laing NM, King CR, Lulashnyk B, Hoban DJ, Zhanel GG. In vitro activity of nemonoxacin, a novel nonfluorinated quinolone, against 2,440 clinical isolates. Antimicrob. Agents Chemother. 2009, 53: 4915–4920. PMC 2772340 . doi:10.1128/aac.00078-09.
^ Liao, C. H.; Ko, W. C.; Lu, J. J.; Hsueh, P. R. Characterizations of Clinical Isolates of Clostridium difficile by Toxin Genotypes and by Susceptibility to 12 Antimicrobial Agents, Including Fidaxomicin (OPT-80) and Rifaximin: A Multicenter Study in Taiwan. Antimicrobial Agents and Chemotherapy. 2012, 56 (7): 3943–3949. PMC 3393409 . PMID 22508299. doi:10.1128/AAC.00191-12.
^ van Rensburg DJ, Perng RP, Mitha IH, Bester AJ, Kasumba J, Wu RG, Ho ML, Chang LW, Chung DT, Chang YT, King CH, Hsu MC. Efficacy and safety of nemonoxacin versus levofloxacin for community-acquired pneumonia. Antimicrob. Agents Chemother. 2010, 54: 4098–4106. PMC 2944601 . doi:10.1128/aac.00295-10.
^ Poole, Raewyn M. Nemonoxacin: First Global Approval. Drugs. 2014-08, 74 (12). ISSN 0012-6667. doi:10.1007/s40265-014-0270-0 （英語）.
^ Biotechnology, TaiGen. TaiGen Biotechnology Out-Licenses Taigexyn® (Nemonoxacin) to Productos Científicos for the Latin American Market. [2018-12-22]. （原始內容存檔於2021-07-11）.
^ TaiGen releases Taigexyn (nemonoxacin) capsules in Taiwan. 16 December 2015 [2018-12-22]. （原始內容存檔於2020-08-13）.
^ 苹果酸奈诺沙星 Nemonoxacin Malate. 智慧芽新藥情報庫. [2023-10-30]. （原始內容存檔於2023-10-30）（中文（中國大陸））.

[1] Guo, B; Wu, X; Zhang, Y; Shi, Y; Yu, J; Cao, G; Zhang, J. Safety and clinical pharmacokinetics of nemonoxacin, a novel non-fluorinated quinolone, in healthy Chinese volunteers following single and multiple oral doses. Clinical Drug Investigation. 2012, 32 (7): 475–86. PMID 22650326. doi:10.2165/11632780-000000000-00000.

[2] A Phase III Study to Evaluate the Efficacy and Safety of Intravenous Infusion of Nemonoxacin in Treating CAP - Full Text View - ClinicalTrials.gov. [2018-12-22]. （原始內容存檔於2019-08-02）.

[3] FDA grants QIDP and Fast Track designations to TaiGen's nemonoxacin. 23 December 2013 [2018-12-22]. （原始內容存檔於2020-09-30）.

[4] Liang, W; Chen, Y. C.; Cao, Y. R.; Liu, X. F.; Huang, J; Hu, J. L.; Zhao, M; Guo, Q. L.; Zhang, S. J.; Wu, X. J.; Zhu, D. M.; Zhang, Y. Y.; Zhang, J. Pharmacokinetics and Pharmacodynamics of Nemonoxacin against Streptococcus pneumoniae in an in Vitro Infection Model. Antimicrobial Agents and Chemotherapy. 2013, 57 (7): 2942–2947. PMC 3697386 . PMID 23587953. doi:10.1128/AAC.01098-12.

[5] Lauderdale TL, Shiau YR, Lai JF, Chen HC, King CH. Comparative in vitro activities of nemonoxacin (TG-873870), a novel nonfluorinated quinolone, and other quinolones against clinical isolates. Antimicrob. Agents Chemother. 2010, 54: 1338–1342. PMC 2825994 . doi:10.1128/aac.01197-09.

[6] Adam HJ, Laing NM, King CR, Lulashnyk B, Hoban DJ, Zhanel GG. In vitro activity of nemonoxacin, a novel nonfluorinated quinolone, against 2,440 clinical isolates. Antimicrob. Agents Chemother. 2009, 53: 4915–4920. PMC 2772340 . doi:10.1128/aac.00078-09.

[7] Liao, C. H.; Ko, W. C.; Lu, J. J.; Hsueh, P. R. Characterizations of Clinical Isolates of Clostridium difficile by Toxin Genotypes and by Susceptibility to 12 Antimicrobial Agents, Including Fidaxomicin (OPT-80) and Rifaximin: A Multicenter Study in Taiwan. Antimicrobial Agents and Chemotherapy. 2012, 56 (7): 3943–3949. PMC 3393409 . PMID 22508299. doi:10.1128/AAC.00191-12.

[8] van Rensburg DJ, Perng RP, Mitha IH, Bester AJ, Kasumba J, Wu RG, Ho ML, Chang LW, Chung DT, Chang YT, King CH, Hsu MC. Efficacy and safety of nemonoxacin versus levofloxacin for community-acquired pneumonia. Antimicrob. Agents Chemother. 2010, 54: 4098–4106. PMC 2944601 . doi:10.1128/aac.00295-10.

[9] Poole, Raewyn M. Nemonoxacin: First Global Approval. Drugs. 2014-08, 74 (12). ISSN 0012-6667. doi:10.1007/s40265-014-0270-0 （英語）.

[10] Biotechnology, TaiGen. TaiGen Biotechnology Out-Licenses Taigexyn® (Nemonoxacin) to Productos Científicos for the Latin American Market. [2018-12-22]. （原始內容存檔於2021-07-11）.

[11] TaiGen releases Taigexyn (nemonoxacin) capsules in Taiwan. 16 December 2015 [2018-12-22]. （原始內容存檔於2020-08-13）.

[12] 苹果酸奈诺沙星 Nemonoxacin Malate. 智慧芽新藥情報庫. [2023-10-30]. （原始內容存檔於2023-10-30）（中文（中國大陸））.

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