Nitroxoline (BioDeep_00000615026)
代谢物信息卡片
5-Nitroks;5-Nitrox;5-Nitroxine;5-NOK;Nitroxolina [inn-spanish];Nitroxolinum [inn-latin]
化学式: C9H6N2O3 (190.0378406)
中文名称: 5-硝基-8-羟基喹啉
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]
InChI: InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
描述信息
A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5.
C254 - Anti-Infective Agent > C258 - Antibiotic > C795 - Quinolone Antibiotic
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
同义名列表
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:67121
- KEGGdrug: D07245
- PubChem: 19910
- Metlin: METLIN85514
- DrugBank: DB01422
- ChEMBL: CHEMBL1454910
- CAS: 4008-48-4
- MetaboLights: MTBLC67121
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Yuan-Ming He, Xiu-Min Zhou, Shuo-Yi Jiang, Zu-Bin Zhang, Bi-Yin Cao, Jin-Bao Liu, Yuan-Ying Zeng, Jun Zhao, Xin-Liang Mao. TRIM25 activates AKT/mTOR by inhibiting PTEN via K63-linked polyubiquitination in non-small cell lung cancer.
Acta pharmacologica Sinica.
2022 Mar; 43(3):681-691. doi:
10.1038/s41401-021-00662-z. [PMID: 33931764] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964. [PMID: 31515284] - Timo Heinrich, Jeyaprakashnarayanan Seenisamy, Beatrix Blume, Jörg Bomke, Michel Calderini, Uwe Eckert, Manja Friese-Hamim, Rainer Kohl, Martin Lehmann, Birgitta Leuthner, Djordje Musil, Felix Rohdich, Frank T Zenke. Discovery and Structure-Based Optimization of Next-Generation Reversible Methionine Aminopeptidase-2 (MetAP-2) Inhibitors.
Journal of medicinal chemistry.
2019 05; 62(10):5025-5039. doi:
10.1021/acs.jmedchem.9b00041. [PMID: 30939017] - Youtian Hu, Lu Wang, Xu Han, Yueyang Zhou, Tonghui Zhang, Li Wang, Ting Hong, Wei Zhang, Xun-Xiang Guo, Jielin Sun, Yingxin Qi, Jing Yu, Hong Liu, Fang Wu. Discovery of a Bioactive Inhibitor with a New Scaffold for Cystathionine γ-Lyase.
Journal of medicinal chemistry.
2019 02; 62(3):1677-1683. doi:
10.1021/acs.jmedchem.8b01720. [PMID: 30562026] - Naijin Xu, Linglong Huang, Xiezhao Li, Masami Watanabe, Chaoming Li, Abai Xu, Chunxiao Liu, Qiang Li, Motoo Araki, Koichiro Wada, Yasutomo Nasu, Peng Huang. The Novel Combination of Nitroxoline and PD-1 Blockade, Exerts a Potent Antitumor Effect in a Mouse Model of Prostate Cancer.
International journal of biological sciences.
2019; 15(5):919-928. doi:
10.7150/ijbs.32259. [PMID: 31182913] - Ding Hu, Hongxia Xu, Bing Xiao, Dongdong Li, Zhuxian Zhou, Xiangrui Liu, Jianbin Tang, Youqing Shen. Albumin-Stabilized Metal-Organic Nanoparticles for Effective Delivery of Metal Complex Anticancer Drugs.
ACS applied materials & interfaces.
2018 Oct; 10(41):34974-34982. doi:
10.1021/acsami.8b12812. [PMID: 30238746] - Ivana Mareković, Zrinka Bošnjak, Karla Jurić, Mario Ćorić, Sanja Popović-Grle. Susceptibility of Escherichia coli to nitroxoline, an option for uncomplicated urinary tract infections - the first report from Croatia.
Journal of chemotherapy (Florence, Italy).
2018 May; 30(3):189-191. doi:
10.1080/1120009x.2018.1452585. [PMID: 29557289] - A Sobke, O Makarewicz, M Baier, C Bär, W Pfister, S G Gatermann, M W Pletz, C Forstner. Empirical treatment of lower urinary tract infections in the face of spreading multidrug resistance: in vitro study on the effectiveness of nitroxoline.
International journal of antimicrobial agents.
2018 Feb; 51(2):213-220. doi:
10.1016/j.ijantimicag.2017.10.010. [PMID: 29111434] - H Hof. [Candiduria! What now? : Therapy of urinary tract infections with Candida].
Der Urologe. Ausg. A.
2017 Feb; 56(2):172-179. doi:
10.1007/s00120-016-0219-x. [PMID: 27590778] - Izabella J Hidi, Martin Jahn, Karina Weber, Thomas Bocklitz, Mathias W Pletz, Dana Cialla-May, Juergen Popp. Lab-on-a-Chip-Surface Enhanced Raman Scattering Combined with the Standard Addition Method: Toward the Quantification of Nitroxoline in Spiked Human Urine Samples.
Analytical chemistry.
2016 09; 88(18):9173-80. doi:
10.1021/acs.analchem.6b02316. [PMID: 27570877] - Michael Kresken, Barbara Körber-Irrgang. In vitro activity of nitroxoline against Escherichia coli urine isolates from outpatient departments in Germany.
Antimicrobial agents and chemotherapy.
2014 Nov; 58(11):7019-20. doi:
10.1128/aac.03946-14. [PMID: 25182654] - Florian M E Wagenlehner, Fabian Münch, Adrian Pilatz, Birte Bärmann, Wolfgang Weidner, Christine M Wagenlehner, Marion Straubinger, Holger Blenk, Wolfgang Pfister, Michael Kresken, Kurt G Naber. Urinary concentrations and antibacterial activities of nitroxoline at 250 milligrams versus trimethoprim at 200 milligrams against uropathogens in healthy volunteers.
Antimicrobial agents and chemotherapy.
2014; 58(2):713-21. doi:
10.1128/aac.02147-13. [PMID: 24217699] - Wei-Pin Chang, Tsu-Ming Chien, Yu-Shiuan Wang, Siou-Jin Chiu, Mei-Hui Lee, Wei-Chiao Chang, Yii-Her Chou, Ming-Feng Hou. Cox-2 gene overexpression in ureteral stump urothelial carcinoma following nephrectomy for renal cell carcinoma: a case report.
Journal of medical case reports.
2012 Jan; 6(?):44. doi:
10.1186/1752-1947-6-44. [PMID: 22289336] - Hongchao Jiang, Jori E Taggart, Xiaoxi Zhang, Doris M Benbrook, Stuart E Lind, Wei-Qun Ding. Nitroxoline (8-hydroxy-5-nitroquinoline) is more a potent anti-cancer agent than clioquinol (5-chloro-7-iodo-8-quinoline).
Cancer letters.
2011 Dec; 312(1):11-7. doi:
10.1016/j.canlet.2011.06.032. [PMID: 21899946] - Mohamed M Ghoneim, Hanaa S El-Desoky, Mohamed M Abdel-Galeil. Electrochemistry of the antibacterial and antifungal drug nitroxoline and its determination in bulk form, pharmaceutical formulation and human blood.
Bioelectrochemistry (Amsterdam, Netherlands).
2011 Feb; 80(2):162-8. doi:
10.1016/j.bioelechem.2010.08.003. [PMID: 20833114] - I V Nikolaeva, N A Shabanova, V M Bondarenko, G N Konovalova, V A Anokhin. [Species composition and antibiotic resistance of lactobacillus in infants].
Zhurnal mikrobiologii, epidemiologii i immunobiologii.
2010 Nov; ?(6):70-5. doi:
NULL. [PMID: 21384590] - A I Sow, N Diop, C T Ndour, M Soumare, M Seydi, M F Cisse, A Samb. [Urinary tract infections in Dakar: etiologies, therapeutic basis].
Dakar medical.
2000; 45(1):59-61. doi:
NULL. [PMID: 14666793] - V E Rodoman, V P Avdoshin, M I Andriukhin. [Disorders of kidney function in patients with benign prostatic hyperplasia].
Urologiia i nefrologiia.
1997 Nov; ?(6):24-6. doi:
NULL. [PMID: 9461783] - A Amgar, C Bonissol, B Stoiljkovic. Activity in vitro of urine samples from patients treated by nitroxoline against mycoplasmas.
Journal of chemotherapy (Florence, Italy).
1989 Jul; 1(4 Suppl):226-8. doi:
NULL. [PMID: 16312380] - P Bourlioux, H Botto, D Karam, A Amgar, M Camey. [Inhibition of bacterial adherence by nitroxoline on cellular adhesion and on urinary catheter surfaces].
Pathologie-biologie.
1989 May; 37(5):451-4. doi:
NULL. [PMID: 2674871] - D Karam, A Amgar, P Bourlioux. [Inhibition of bacterial adhesion of uropathogenic Escherichia coli strains by the urine of patients treated with nitroxoline].
Pathologie-biologie.
1988 May; 36(5):452-5. doi:
NULL. [PMID: 3043342] - E Bergogne-Berezin, G Berthelot, C Muller-Serieys. [Present status of nitroxoline].
Pathologie-biologie.
1987 Jun; 35(5 Pt 2):873-8. doi:
NULL. [PMID: 3309832] - N Lambert-Zechovsky, B Lévêque, E Bingen, G Pillion, J Chapelle, H Mathieu. [Clinical study and effect of nitroxoline on fecal flora in children].
Pathologie-biologie.
1987 May; 35(5):669-72. doi:
NULL. [PMID: 3302880] - R H Sorel, C Snelleman, A Hulshoff. High-performance liquid chromatographic analysis of nitroxoline in plasma and urine.
Journal of chromatography.
1981 Feb; 222(2):241-8. doi:
10.1016/s0378-4347(00)81056-7. [PMID: 7251741] - D Makhaĭlova, Z Tsenova, M Dzhoneĭdi, S Mikhaĭlova. [COmparative pharmacokinetic studies of 5-nitrox and 5-NOK in volunteers].
Eksperimentalna meditsina i morfologiia.
1981; 20(3):156-60. doi:
NULL. [PMID: 7030714] - D Mikhaĭlova, I Viktorov, M Dzhoneĭdi, S Mikhaĭlova, Z Tsenova. [Pharmacokinetic studies of 5-nitrox in kidney failure patients].
Eksperimentalna meditsina i morfologiia.
1981; 20(3):160-6. doi:
NULL. [PMID: 7030715] - M Korbelik. [Cytotoxicity of nitroaromatic compounds].
Arhiv za higijenu rada i toksikologiju.
1980 Sep; 31(3):227-46. doi:
NULL. [PMID: 7192543] - A Mrhar, Z Kopitar, F Kozjek, V Presl, R Karba. Clinical pharmacokinetics of nitroxoline.
International journal of clinical pharmacology and biopharmacy.
1979 Dec; 17(12):476-81. doi:
NULL. [PMID: 118941] - M R Jacobs, R G Robinson, H J Koornhof. Antibacterial activity of nitroxoline and sulphamethizole alone and in combination in urinary tract infections.
South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde.
1978 Dec; 54(23):959-62. doi:
. [PMID: 106479] - E ROESCH, A ROESCH, D HOFFTER. [POLYNEUROPATHY CAUSED BY 5-NITRO-8-HYDROXYQUINOLINE IN ANIMAL EXPERIMENTS].
Archiv fur Toxikologie.
1965 Feb; 20(?):313-22. doi:
NULL. [PMID: 14272417]