oxolinic acid (BioDeep_00000858353)

   


代谢物信息卡片


oxolinic acid

化学式: C13H11NO5 (261.0637196)
中文名称: 噁喹酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O
InChI: InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)

描述信息

A quinolinemonocarboxylic acid having the carboxy group at position 7 as well as oxo- and ethyl groups at positions 4 and 1 respectively and a dioxolo ring fused at the 5- and 6-positions.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01M - Quinolone antibacterials
D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors
C254 - Anti-Infective Agent > C258 - Antibiotic > C795 - Quinolone Antibiotic
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
D004791 - Enzyme Inhibitors

同义名列表

1 个代谢物同义名

oxolinic acid



数据库引用编号

9 个数据库交叉引用编号

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)

2 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

  • Lawrence M Madikizela, Yannick B Nuapia, Luke Chimuka, Somandla Ncube, Anita Etale. Target and Suspect Screening of Pharmaceuticals and their Transformation Products in the Klip River, South Africa, using Ultra-High-Performance Liquid Chromatography-Mass Spectrometry. Environmental toxicology and chemistry. 2022 02; 41(2):437-447. doi: 10.1002/etc.5265. [PMID: 34888926]
  • 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]
  • Ana-Madalina Maciuca, Alexandra-Cristina Munteanu, Mirela Mihaila, Mihaela Badea, Rodica Olar, George Mihai Nitulescu, Cristian V A Munteanu, Marinela Bostan, Valentina Uivarosi. Rare-Earth Metal Complexes of the Antibacterial Drug Oxolinic Acid: Synthesis, Characterization, DNA/Protein Binding and Cytotoxicity Studies. Molecules (Basel, Switzerland). 2020 Nov; 25(22):. doi: 10.3390/molecules25225418. [PMID: 33228104]
  • 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]
  • Lilia S Ulanova, Marina Pinheiro, Carina Vibe, Claudia Nunes, Dorna Misaghian, Steven Wilson, Kaizheng Zhu, Federico Fenaroli, Hanne C Winther-Larsen, Salette Reis, Gareth Griffiths. Treatment of Francisella infections via PLGA- and lipid-based nanoparticle delivery of antibiotics in a zebrafish model. Diseases of aquatic organisms. 2017 06; 125(1):19-29. doi: 10.3354/dao03129. [PMID: 28627489]
  • Nuggehally R Srinivas. Interspecies scaling of excretory amounts using allometry - retrospective analysis with rifapentine, aztreonam, carumonam, pefloxacin, miloxacin, trovafloxacin, doripenem, imipenem, cefozopran, ceftazidime, linezolid for urinary excretion and rifapentine, cabotegravir, and dolutegravir for fecal excretion. Xenobiotica; the fate of foreign compounds in biological systems. 2016 Sep; 46(9):784-92. doi: 10.3109/00498254.2015.1121554. [PMID: 26711252]
  • Theocharis E Kydonaki, Evangelos Tsoukas, Filipa Mendes, Antonios G Hatzidimitriou, António Paulo, Lefkothea C Papadopoulou, Dionysia Papagiannopoulou, George Psomas. Synthesis, characterization and biological evaluation of (99m)Tc/Re-tricarbonyl quinolone complexes. Journal of inorganic biochemistry. 2016 07; 160(?):94-105. doi: 10.1016/j.jinorgbio.2015.12.010. [PMID: 26795497]
  • Marte Kaldestad, Gyri T Haugland, Anita Rønneseth, Heidrun I Wergeland, Ole Bent Samuelsen. Antibiotic uptake by cultured Atlantic cod leucocytes and effect on intracellular Francisella noatunensis subsp. noatunensis replication. Diseases of aquatic organisms. 2014 Feb; 108(1):11-21. doi: 10.3354/dao02696. [PMID: 24492050]
  • João H O S Pereira, Ana C Reis, Daniel Queirós, Olga C Nunes, Maria T Borges, Vítor J P Vilar, Rui A R Boaventura. Insights into solar TiO2-assisted photocatalytic oxidation of two antibiotics employed in aquatic animal production, oxolinic acid and oxytetracycline. The Science of the total environment. 2013 Oct; 463-464(?):274-83. doi: 10.1016/j.scitotenv.2013.05.098. [PMID: 23816421]
  • Marianthi Zampakou, Melpomeni Akrivou, Eleni G Andreadou, Catherine P Raptopoulou, Vassilis Psycharis, Anastasia A Pantazaki, George Psomas. Structure, antimicrobial activity, DNA- and albumin-binding of manganese(II) complexes with the quinolone antimicrobial agents oxolinic acid and enrofloxacin. Journal of inorganic biochemistry. 2013 Apr; 121(?):88-99. doi: 10.1016/j.jinorgbio.2012.12.013. [PMID: 23353085]
  • Alketa Tarushi, Kostas Lafazanis, Jakob Kljun, Iztok Turel, Anastasia A Pantazaki, George Psomas, Dimitris P Kessissoglou. First- and second-generation quinolone antibacterial drugs interacting with zinc(II): structure and biological perspectives. Journal of inorganic biochemistry. 2013 Apr; 121(?):53-65. doi: 10.1016/j.jinorgbio.2012.12.009. [PMID: 23353082]
  • Kalliopi C Skyrianou, Franc Perdih, Athanasios N Papadopoulos, Iztok Turel, Dimitris P Kessissoglou, George Psomas. Nickel-quinolones interaction. Part 5-Biological evaluation of nickel(II) complexes with first-, second- and third-generation quinolones. Journal of inorganic biochemistry. 2011 Oct; 105(10):1273-85. doi: 10.1016/j.jinorgbio.2011.06.005. [PMID: 21820989]
  • Hyeok Ran Kwon, Gyung Ja Choi, Yong Ho Choi, Kyoung Soo Jang, Nack-Do Sung, Mun Seong Kang, Yilseong Moon, Seung Kyu Lee, Jin-Cheol Kim. Suppression of pine wilt disease by an antibacterial agent, oxolinic acid. Pest management science. 2010 Jun; 66(6):634-9. doi: 10.1002/ps.1920. [PMID: 20151406]
  • Kalliopi C Skyrianou, Franc Perdih, Iztok Turel, Dimitris P Kessissoglou, George Psomas. Nickel-quinolones interaction. Part 2--interaction of nickel(II) with the antibacterial drug oxolinic acid. Journal of inorganic biochemistry. 2010 Feb; 104(2):161-70. doi: 10.1016/j.jinorgbio.2009.10.017. [PMID: 19939458]
  • Christopher Marlowe A Caipang, Carlo C Lazado, Monica F Brinchmann, Ingvild Berg, Viswanath Kiron. In vivo modulation of immune response and antioxidant defense in Atlantic cod, Gadus morhua following oral administration of oxolinic acid and florfenicol. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2009 Nov; 150(4):459-64. doi: 10.1016/j.cbpc.2009.07.001. [PMID: 19596082]
  • Xia Wu, Jinhua Zheng, Honghong Ding, Dehuan Ran, Wei Xu, Yuanyuan Song, Jinghe Yang. Study on the interaction between oxolinic acid aggregates and protein and its analytical application. Analytica chimica acta. 2007 Jul; 596(1):16-22. doi: 10.1016/j.aca.2007.05.051. [PMID: 17616235]
  • Yukiko Maeda, Akinori Kiba, Kouhei Ohnishi, Yasufumi Hikichi. Amino acid substitutions in GyrA of Burkholderia glumae are implicated in not only oxolinic acid resistance but also fitness on rice plants. Applied and environmental microbiology. 2007 Feb; 73(4):1114-9. doi: 10.1128/aem.02400-06. [PMID: 17194844]
  • Eric Verdon, Pierrick Couedor, Brigitte Roudaut, Pascal Sandérs. Multiresidue method for simultaneous determination of ten quinolone antibacterial residues in multimatrix/multispecies animal tissues by liquid chromatography with fluorescence detection: single laboratory validation study. Journal of AOAC International. 2005 Jul; 88(4):1179-92. doi: . [PMID: 16156083]
  • Yukiko Maeda, Akinori Kiba, Kouhei Ohnishi, Yasufumi Hikichi. Implications of amino acid substitutions in GyrA at position 83 in terms of oxolinic acid resistance in field isolates of Burkholderia glumae, a causal agent of bacterial seedling rot and grain rot of rice. Applied and environmental microbiology. 2004 Sep; 70(9):5613-20. doi: 10.1128/aem.70.9.5613-5620.2004. [PMID: 15345450]
  • George Rigos, Ioannis Nengas, Maria Alexis, Gera M Troisi. Potential drug (oxytetracycline and oxolinic acid) pollution from Mediterranean sparid fish farms. Aquatic toxicology (Amsterdam, Netherlands). 2004 Aug; 69(3):281-8. doi: 10.1016/j.aquatox.2004.05.009. [PMID: 15276333]
  • Raphaël Delépée, Hervé Pouliquen, Hervé Le Bris. The bryophyte Fontinalis antipyretica Hedw. bioaccumulates oxytetracycline, flumequine and oxolinic acid in the freshwater environment. The Science of the total environment. 2004 Apr; 322(1-3):243-53. doi: 10.1016/j.scitotenv.2003.09.018. [PMID: 15081752]
  • O B Samuelsen, O Bergh, A Ervik. A single-dose pharmacokinetic study of oxolinic acid and vetoquinol, an oxolinic acid ester, in cod, Gadus morhua L., held in sea water at 8 degrees C and in vitro antibacterial activity of oxolinic acid against Vibrio anguillarum strains isolated from diseased cod. Journal of fish diseases. 2003 06; 26(6):339-47. doi: 10.1046/j.1365-2761.2003.00466.x. [PMID: 12899409]
  • M Yoshida, T Kitani, A Takenaka, K Kudoh, S I Katsuda, K Taya, Y Kurokawa, A Maekawa. Lack of effects of oxolinic acid on spermatogenesis in young adult and aged Wistar rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2002 Dec; 40(12):1815-25. doi: 10.1016/s0278-6915(02)00168-0. [PMID: 12419696]
  • Margarita Hernández, Francesc Borrull, Marta Calull. Using nonaqueous capillary electrophoresis to analyze several quinolones in pig kidney samples. Electrophoresis. 2002 Feb; 23(3):506-11. doi: 10.1002/1522-2683(200202)23:3<506::aid-elps506>3.0.co;2-c. [PMID: 11870754]
  • Patricia S McManus, Virginia O Stockwell, George W Sundin, Alan L Jones. Antibiotic use in plant agriculture. Annual review of phytopathology. 2002; 40(?):443-65. doi: 10.1146/annurev.phyto.40.120301.093927. [PMID: 12147767]
  • K Hamamoto, R Koike, Y Machida. The effect of soybean oil refuse powder used as vehicle on the absorption of oxolinic acid in chickens under fasting and nonfasting conditions and the correlation with in vitro dissolution. Journal of veterinary pharmacology and therapeutics. 2001 Oct; 24(5):333-41. doi: 10.1046/j.1365-2885.2001.00347.x. [PMID: 11696083]
  • O B Samuelsen, A Ervik. Absorption, tissue distribution and excretion of flumequine and oxolinic acid in corkwing wrasse (Symphodus melops) following a single intraperitoneal injection or bath treatment. Journal of veterinary pharmacology and therapeutics. 2001 Apr; 24(2):111-6. doi: 10.1046/j.1365-2885.2001.00319.x. [PMID: 11442785]
  • H Pouliquen, F Armand. Determination of oxolinic acid in faeces and urine of turbot (Scophthalmus maximus) by high-performance liquid chromatography using fluorescence detection. Journal of chromatography. B, Biomedical sciences and applications. 2000 Nov; 749(1):127-33. doi: 10.1016/s0378-4347(00)00394-7. [PMID: 11129072]
  • O B Samuelsen, B Hjeltnes, L Torkildsen. Efficacy of orally administered oxolinic acid and Vetoquinol, an oxolinic acid ester, for the treatment of furunculosis in Atlantic salmon Salmo salar held in seawater. Diseases of aquatic organisms. 1999 Jun; 37(1):53-9. doi: 10.3354/dao037053. [PMID: 10439903]
  • I Poher, G Blanc. Pharmacokinetics of a discontinuous absorption process of oxolinic acid in turbot, Scophthalmus maximus, after a single oral administration. Xenobiotica; the fate of foreign compounds in biological systems. 1998 Nov; 28(11):1061-73. doi: 10.1080/004982598238958. [PMID: 9879638]
  • M J Figueras, I Inza, F Polo, J Guarro. Evaluation of the oxolinic acid--esculin--azide medium for the isolation and enumeration of faecal streptococci in a routine monitoring programme for bathing waters. Canadian journal of microbiology. 1998 Oct; 44(10):998-1002. doi: 10.1139/cjm-44-10-998. [PMID: 9933917]
  • B Roudaut. Elimination of oxolinic acid in eggs after oral treatment of laying hens. British poultry science. 1998 Mar; 39(1):47-52. doi: 10.1080/00071669889385. [PMID: 9568298]
  • I Durán Merás, T Galeano Díaz, M I Rodriguez Cáceres, F Salinas López. Determination of the chemotherapeutic quinolonic and cinolonic derivatives in urine by high-performance liquid chromatography with ultraviolet and fluorescence detection in series. Journal of chromatography. A. 1997 Nov; 787(1-2):119-27. doi: 10.1016/s0021-9673(97)00630-4. [PMID: 9445649]
  • S Loussouarn, H Pouliquen, F Armand. High-performance liquid chromatographic determination of oxolinic acid in the plasma of seabass (Dicentrarchus labrax) anaesthetized with 2-phenoxyethanol. Journal of chromatography. B, Biomedical sciences and applications. 1997 Sep; 698(1-2):251-9. doi: 10.1016/s0378-4347(97)00283-1. [PMID: 9367215]
  • I Poher, G Blanc, S Loussouarn. Pharmacokinetics of oxolinic acid in sea-bass, Dicentrarchus labrax (L., 1758), after a single rapid intravascular injection. Journal of veterinary pharmacology and therapeutics. 1997 Aug; 20(4):267-75. doi: 10.1046/j.1365-2885.1997.00062.x. [PMID: 9280366]
  • R Ueno, T Aoki. High-performance liquid chromatographic method for the rapid and simultaneous determination of sulfamonomethoxine, miloxacin and oxolinic acid in serum and muscle of cultured fish. Journal of chromatography. B, Biomedical applications. 1996 Jun; 682(1):179-81. doi: 10.1016/0378-4347(96)00078-3. [PMID: 8832440]
  • T Yamada, J Nakamura, Y Okuno, S Hosokawa, M Matsuo, H Yamada, M Ohta. A possible mechanism for the increase in serum luteinizing hormone levels in male rats by oxolinic acid. Toxicology and applied pharmacology. 1995 Sep; 134(1):35-42. doi: 10.1006/taap.1995.1166. [PMID: 7676456]
  • B Martinsen, T E Horsberg. Comparative single-dose pharmacokinetics of four quinolones, oxolinic acid, flumequine, sarafloxacin, and enrofloxacin, in Atlantic salmon (Salmo salar) held in seawater at 10 degrees C. Antimicrobial agents and chemotherapy. 1995 May; 39(5):1059-64. doi: 10.1128/aac.39.5.1059. [PMID: 7625789]
  • T Yamada, J Nakamura, M Murakami, Y Okuno, S Hosokawa, M Matsuo, H Yamada. The correlation of serum luteinizing hormone levels with the induction of Leydig cell tumors in rats by oxolinic acid. Toxicology and applied pharmacology. 1994 Nov; 129(1):146-54. doi: 10.1006/taap.1994.1238. [PMID: 7974488]
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