奈诺沙星

奈诺沙星
	IUPAC名; 7-[(3S,5S)-3-Amino-5-methyl-1-piperidinyl]-1-cyclopropyl-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
识别
CAS号
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
性质
化学式	C20H25N3O4
摩尔质量	371.43 g·mol−1
药理学
ATC代码	J01MB08（J01）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

奈诺沙星（Nemonoxacin）（商品名太捷信（Taigexyn））是一种非氟喹诺酮类抗菌药物^[1]。奈诺沙星的抗菌机制与其他氟喹诺酮（fluouroquinolones）相同，皆是抑制细菌的DNA旋转酶，抑制细菌DNA的合成及复制，以及细胞分裂。

奈诺沙星目前已经在台湾、中国大陆上市，在俄罗斯等地已完成三期临床试验，并完成美国第二期临床试验，正进行第三期临床试验^[2]。美国食品药品监督管理局（FDA）已授予奈诺沙星合格感染性疾病产品资格（英语：qualified infectious disease product）（QIDP）及快速审查（英语：Fast track (FDA)）资格，预期将应用于社区性肺炎（英语：community-acquired bacterial pneumonia）及急性细菌性皮肤与皮肤组织感染（英语：acute bacterial skin and skin-structure infection）^[3]。

适用范围

奈诺沙星为广谱抗生素，药效潜能较同属喹诺酮类抗细菌药的左氧氟沙星和莫西沙星为佳^[4]，可对抗多种革兰氏阳性菌、革兰氏阴性菌、非典型感染菌等。该药物的特色为能对抗多种抗药性极强的病原体，如耐甲氧西林金黄色葡萄球菌（MRSA）、抗喹诺酮之耐甲氧西林金黄色葡萄球菌（QR-MRSA）、抗万古霉素金黄色葡萄球菌（VRSA）^[5]^[6]、多重抗药性肺炎链球菌（MDRSP）、艰难梭菌（C.difficile）^[7]，以及抗盘尼西林肺炎链球菌（PRSP）等。

奈诺沙星对于部分革兰氏阴性菌的效用较弱，例如大肠杆菌、奇异变形杆菌（英语：Proteus mirabilis），及绿脓杆菌等等^[8]。

历史

奈诺沙星由宝洁（P&G）医药部门研发至Ia期临床试验。2004年10月，药物被授权给台湾太景生技公司进行后续研发，同时太景还取得了在中国大陆、台湾、韩国、印度尼西亚、马来西亚、菲律宾、新加坡和泰国的开发和商业化权利。

2009年Warner Chilcott收购了宝洁公司的全球制药业务。2010年10月，II期临床试验完成后，太景与Warner Chilcott修订了许可协议，Warner Chilcott保留了在美国和欧洲开发和商业化奈诺沙星的权利。在之后的2011年12月，Warner Chilcott将全部授权转让给太景，并退出了奈诺沙星的开发。

2012年，太景将奈诺沙星在中国大陆的生产销售权授权给浙江医药股份有限公司。2014年，太景将奈诺沙星在土耳其、俄罗斯和独联体国家的生产销售权授权给R-Pharm公司。^[9]2016年，太景将奈诺沙星在南美洲国家的生产销售权授权给Productos Científicos公司^[10]。

奈诺沙星首先于2014年在台湾上市^[11]，为全球首个上市的地区。此后，中国大陆于2016年批准了奈诺沙星的上市^[12]。

参考文献

^ 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]. （原始内容存档于2019-08-02）.
^ FDA grants QIDP and Fast Track designations to TaiGen's nemonoxacin. 23 December 2013 [2018-12-22]. （原始内容存档于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 （英语）.
^ Biotechnology, TaiGen. TaiGen Biotechnology Out-Licenses Taigexyn® (Nemonoxacin) to Productos Científicos for the Latin American Market. [2018-12-22]. （原始内容存档于2021-07-11）.
^ TaiGen releases Taigexyn (nemonoxacin) capsules in Taiwan. 16 December 2015 [2018-12-22]. （原始内容存档于2020-08-13）.
^ 苹果酸奈诺沙星 Nemonoxacin Malate. 智慧芽新药情报库. [2023-10-30]. （原始内容存档于2023-10-30）（中文（中国大陆））.

[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]. （原始内容存档于2019-08-02）.

[3] FDA grants QIDP and Fast Track designations to TaiGen's nemonoxacin. 23 December 2013 [2018-12-22]. （原始内容存档于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 （英语）.

[10] Biotechnology, TaiGen. TaiGen Biotechnology Out-Licenses Taigexyn® (Nemonoxacin) to Productos Científicos for the Latin American Market. [2018-12-22]. （原始内容存档于2021-07-11）.

[11] TaiGen releases Taigexyn (nemonoxacin) capsules in Taiwan. 16 December 2015 [2018-12-22]. （原始内容存档于2020-08-13）.

[12] 苹果酸奈诺沙星 Nemonoxacin Malate. 智慧芽新药情报库. [2023-10-30]. （原始内容存档于2023-10-30）（中文（中国大陆））.

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奈诺沙星

IUPAC名 7-[(3S,5S)-3-Amino-5-methyl-1-piperidinyl]-1-cyclopropyl-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
识别
CAS号
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
性质
化学式	C₂₀H₂₅N₃O₄
摩尔质量	371.43 g·mol⁻¹
药理学
ATC代码	J01MB08（J01）
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。