Oxolinic acid (BioDeep_00000002361)

   

human metabolite blood metabolite


代谢物信息卡片


5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid

化学式: C13H11NO5 (261.0637)
中文名称: 噁喹酸, 恶喹酸
谱图信息: 最多检出来源 Homo sapiens(plant) 21.99%

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

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
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3609
CONFIDENCE standard compound; INTERNAL_ID 1034
D004791 - Enzyme Inhibitors

同义名列表

20 个代谢物同义名

5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid; 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid; 5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid; 5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylate; 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylate; 1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid; 1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylate; Oxolinate, sodium; Acidum oxolinicum; Acide oxolinique; Sodium oxolinate; Acido oxolinico; Acid, oxolinic; oxolinic acid; Oxolinate; Aqualinic; Gramurin; ossian; OA; Oxolinic acid



数据库引用编号

31 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。

亚细胞结构定位 关联基因列表
Cytoplasm 10 ACE2, CAT, CHI3L1, GADD45G, GBP4, HPRT1, KCNAB1, NEK8, RYR1, TFAP4
Peripheral membrane protein 1 KCNAB1
Endosome membrane 1 TF
Nucleus 6 GADD45G, GBP4, MPO, NEK8, TFAP4, TOP1
cytosol 6 CAT, GBP4, HPRT1, KCNAB1, LIPE, NEK8
centrosome 1 NEK8
nucleoplasm 5 ANO2, ATP2B1, MPO, TFAP4, TOP1
Cell membrane 5 ACE2, ANO2, ATP2B1, KCNAB1, LIPE
Cytoplasmic side 1 KCNAB1
Multi-pass membrane protein 5 ANO2, ATP2B1, CACNA1F, RHO, RYR1
Golgi apparatus membrane 1 GBP4
Synapse 1 ATP2B1
cell cortex 1 RYR1
cell surface 2 ACE2, TF
glutamatergic synapse 2 ANO2, ATP2B1
Golgi apparatus 2 GBP4, RHO
Golgi membrane 2 GBP4, RHO
presynaptic membrane 2 ANO2, ATP2B1
sarcolemma 1 RYR1
smooth endoplasmic reticulum 1 RYR1
Cytoplasm, cytosol 1 LIPE
Lysosome 1 MPO
plasma membrane 8 ACE2, ANO2, ATP2B1, GBP4, KCNAB1, RHO, RYR1, TF
synaptic vesicle membrane 1 ATP2B1
Membrane 9 ACE2, ANO2, ATP2B1, CACNA1F, CAT, KCNAB1, LIPE, RHO, RYR1
apical plasma membrane 2 ACE2, TF
basolateral plasma membrane 1 ATP2B1
caveola 1 LIPE
extracellular exosome 8 ACE2, ATP2B1, CAT, CHI3L1, HPRT1, MPO, RYR1, TF
endoplasmic reticulum 1 CHI3L1
extracellular space 4 ACE2, CHI3L1, MPO, TF
perinuclear region of cytoplasm 3 CHI3L1, GBP4, TF
mitochondrion 2 CAT, TFAP4
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 3 ATP2B1, CAT, MPO
Single-pass type I membrane protein 1 ACE2
Secreted 2 ACE2, TF
extracellular region 5 ACE2, CAT, CHI3L1, MPO, TF
cytoplasmic side of plasma membrane 1 KCNAB1
basal part of cell 1 TF
mitochondrial matrix 1 CAT
Cell projection, cilium 2 ACE2, NEK8
ciliary membrane 1 RHO
photoreceptor inner segment 1 RHO
photoreceptor outer segment 2 CACNA1F, RHO
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 NEK8
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
perikaryon 2 CACNA1F, TOP1
Z disc 1 RYR1
cytoplasmic vesicle 2 GBP4, TF
nucleolus 1 TOP1
P-body 1 TOP1
Early endosome 1 TF
cell-cell junction 1 RHO
clathrin-coated pit 1 TF
recycling endosome 1 TF
vesicle 1 TF
Apical cell membrane 1 ACE2
Cytoplasm, perinuclear region 2 CHI3L1, GBP4
Membrane raft 1 ACE2
Cytoplasm, cytoskeleton 1 NEK8
focal adhesion 1 CAT
extracellular matrix 1 CHI3L1
Peroxisome 1 CAT
sarcoplasmic reticulum 1 RYR1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 MPO
lateral plasma membrane 1 ATP2B1
Late endosome 1 TF
neuron projection 1 ANO2
ciliary base 1 NEK8
cilium 2 ACE2, NEK8
chromatin 1 TFAP4
cell projection 1 ATP2B1
Chromosome 1 TOP1
Cell projection, cilium, photoreceptor outer segment 1 RHO
Secreted, extracellular space 1 CHI3L1
brush border membrane 1 ACE2
Nucleus, nucleolus 1 TOP1
blood microparticle 1 TF
Cytoplasm, cytoskeleton, cilium axoneme 1 NEK8
non-motile cilium 1 ANO2
sperm midpiece 1 RHO
Basolateral cell membrane 1 ATP2B1
organelle membrane 1 RYR1
fibrillar center 1 TOP1
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
chloride channel complex 1 ANO2
I band 1 RYR1
Nucleus, nucleoplasm 1 TOP1
Golgi-associated vesicle membrane 1 RHO
Presynaptic cell membrane 1 ATP2B1
basal plasma membrane 1 TF
azurophil granule 1 MPO
potassium channel complex 1 KCNAB1
voltage-gated potassium channel complex 1 KCNAB1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, TF
HFE-transferrin receptor complex 1 TF
endoplasmic reticulum lumen 2 ACE2, TF
transcription repressor complex 1 TFAP4
male germ cell nucleus 1 TOP1
voltage-gated calcium channel complex 1 CACNA1F
Photoreceptor inner segment membrane 1 RHO
specific granule lumen 1 CHI3L1
endocytic vesicle membrane 1 ACE2
endocytic vesicle 1 TF
azurophil granule lumen 1 MPO
Sarcoplasmic reticulum membrane 1 RYR1
immunological synapse 1 ATP2B1
clathrin-coated endocytic vesicle membrane 1 TF
calcium channel complex 1 RYR1
junctional sarcoplasmic reticulum membrane 1 RYR1
phagocytic vesicle lumen 1 MPO
protein-DNA complex 1 TOP1
photoreceptor outer segment membrane 1 RHO
sperm head plasma membrane 1 RHO
terminal cisterna 1 RYR1
vesicle coat 1 TF
photoreceptor disc membrane 1 RHO
catalase complex 1 CAT
rod photoreceptor outer segment 1 RHO
photoreceptor ribbon synapse 1 ATP2B1
juxtaparanode region of axon 1 KCNAB1
ryanodine receptor complex 1 RYR1
dense body 1 TF
ciliary inversin compartment 1 NEK8
[Processed angiotensin-converting enzyme 2]: Secreted 1 ACE2
[Isoform 2]: Apical cell membrane 1 ACE2


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]
  • J S Giles, H Hariharan, S B Heaney. A microbiological assay for determining sarafloxacin and oxolinic acid concentrations in Atlantic salmon plasma. The new microbiologica. 1994 Apr; 17(2):155-8. doi: . [PMID: 8065273]
  • F Kondo, S Nagata, C E Tsai, K Saitanu. Determination of pyridonecarboxylic acids in plasma by reverse-phase high-performance liquid chromatography. Microbios. 1994; 77(312):181-9. doi: NULL. [PMID: 8170407]
  • H Jarboe, B R Toth, K E Shoemaker, K J Greenlees, K M Kleinow. Pharmacokinetics, bioavailability, plasma protein binding and disposition of nalidixic acid in rainbow trout (Oncorhynchus mykiss). Xenobiotica; the fate of foreign compounds in biological systems. 1993 Sep; 23(9):961-72. doi: 10.3109/00498259309057035. [PMID: 8291264]
  • A M Cárdenas, M P Cortés, E Fernández, W Peña. Lipid peroxidation and loss of potassium from red blood cells produced by phototoxic quinolones. Toxicology. 1992; 72(2):145-51. doi: 10.1016/0300-483x(92)90108-q. [PMID: 1314435]
  • H V Björklund, G Bylund. Comparative pharmacokinetics and bioavailability of oxolinic acid and oxytetracycline in rainbow trout (Oncorhynchus mykiss). Xenobiotica; the fate of foreign compounds in biological systems. 1991 Nov; 21(11):1511-20. doi: 10.3109/00498259109044401. [PMID: 1763525]
  • T Agasøster, K E Rasmussen. Automated analysis of oxolinic acid and flumequine in salmon whole blood and plasma using dialysis combined with trace enrichment as on-line sample preparation for high-performance liquid chromatography. Journal of chromatography. 1991 Mar; 564(1):171-9. doi: 10.1016/0378-4347(91)80079-r. [PMID: 1860911]
  • O B Samuelsen. Simple and rapid method for the determination of flumequine and oxolinic acid in salmon (Salmo salar) plasma by high-performance liquid chromatography and fluorescence detection. Journal of chromatography. 1990 Sep; 530(2):452-7. doi: 10.1016/s0378-4347(00)82349-x. [PMID: 2079520]
  • H V Björklund. Analysis of oxolinic acid in fish by high-performance liquid chromatography. Journal of chromatography. 1990 Aug; 530(1):75-82. doi: 10.1016/s0378-4347(00)82304-x. [PMID: 2277121]
  • K E Rasmussen, F Tønnesen, H H Thanh, A Rogstad, A Aanesrud. Solid-phase extraction and high-performance liquid chromatographic determination of flumequine and oxolinic acid in salmon plasma. Journal of chromatography. 1989 Nov; 496(2):355-64. doi: 10.1016/s0378-4347(00)82583-9. [PMID: 2613839]
  • S O Hustvedt, R Salte, T Benjaminsen. Rapid high-performance liquid chromatographic method for the determination of oxolinic acid in fish serum employing solid-phase extraction. Journal of chromatography. 1989 Sep; 494(?):335-9. doi: 10.1016/s0378-4347(00)82685-7. [PMID: 2584331]
  • A Maura, A Pino. Evaluation of the DNA-damaging and mutagenic activity of oxolinic and pipemidic acids by the granuloma pouch assay. Mutagenesis. 1988 Sep; 3(5):397-401. doi: 10.1093/mutage/3.5.397. [PMID: 3070273]
  • A A Divo, A C Sartorelli, C L Patton, F J Bia. Activity of fluoroquinolone antibiotics against Plasmodium falciparum in vitro. Antimicrobial agents and chemotherapy. 1988 Aug; 32(8):1182-6. doi: 10.1128/aac.32.8.1182. [PMID: 2847647]
  • M Portolani, P Pietrosemoli, C Cermelli, A Mannini-Palenzona, M P Grossi, L Paolini, G Barbanti-Brodano. Suppression of BK virus replication and cytopathic effect by inhibitors of prokaryotic DNA gyrase. Antiviral research. 1988 Apr; 9(3):205-18. doi: 10.1016/0166-3542(88)90004-6. [PMID: 2840850]
  • P Archimbault, G Ambroggi, S Nicolas. Oxolinic acid in the trout: bioavailability and tissue residues. Annales de recherches veterinaires. Annals of veterinary research. 1988; 19(1):39-43. doi: NULL. [PMID: 3400972]
  • M Daudon, R J Reveilland, C Laurence, J Guenel. Drug-induced oxolinic acid crystalluria and nephrolithiasis. Clinical nephrology. 1987 Sep; 28(3):156. doi: NULL. [PMID: 3311504]
  • A Hammami, L Agueda, M Archambaud, N Marty, L Lapchine, G Chabanon. [In vitro study of the effects of oxolinic acid at sub-inhibitory concentrations on the activity of hemagglutinins and adhesion to uroepithelial cells by Escherichia coli isolated from urine]. Pathologie-biologie. 1987 May; 35(5):545-50. doi: . [PMID: 3302860]
  • K Hamamoto. Rapid high-performance liquid chromatographic method for the determination of oxolinic acid in chicken plasma. Journal of chromatography. 1986 Sep; 381(2):453-6. doi: 10.1016/s0378-4347(00)83614-2. [PMID: 3760102]
  • I Cifuentes, J Bellanato, A Arquillué, J Lázaro. [Presence of oxolinic acid in a renal calculus]. Archivos espanoles de urologia. 1986 Jun; 39(5):369-73. doi: NULL. [PMID: 3753049]
  • J T Smith. Frequency and expression of mutational resistance to the 4-quinolone antibacterials. Scandinavian journal of infectious diseases. Supplementum. 1986; 49(?):115-23. doi: . [PMID: 3547618]
  • S Esposito, D Galante, C Pennucci, D Barba. Occurrence of gram negative bacteria in midstream bladder urine and their sensitivity to quinoline derivatives. Microbiologica. 1985 Jul; 8(3):269-76. doi: NULL. [PMID: 3162081]
  • P F D'Arcy. Nitrofurantoin. Drug intelligence & clinical pharmacy. 1985 Jul; 19(7-8):540-7. doi: 10.1177/106002808501900706. [PMID: 3896715]
  • V Uccelli, J M Laporte, Y Michel-Briand. [Inhibition of the maintenance and transfer of antibiotic-resistance plasmids by quinolones]. Comptes rendus des seances de la Societe de biologie et de ses filiales. 1985; 179(5):696-9. doi: . [PMID: 2938699]
  • D Galante, C Pennucci, S Esposito, D Barba. Comparative in vitro activity of ciprofloxacin and five other quinoline derivatives against gram-negative isolates. Drugs under experimental and clinical research. 1985; 11(5):331-4. doi: . [PMID: 2941260]
  • E Weinberg, D L Shungu, H H Gadebusch. Effectiveness of the antimicrobial removal device, BACTEC 16B medium, and thiol broth in neutralizing antibacterial activities of imipenem, norfloxacin, and related agents. Journal of clinical microbiology. 1984 Feb; 19(2):207-9. doi: 10.1128/jcm.19.2.207-209.1984. [PMID: 6230369]
  • B François, Y Gille, N Schmuck, H Assenat, P Adeleine, P Davoine. [Variations in vitro of the efficacy of quinolones as a function of pH]. Nephrologie. 1983; 4(6):259-62. doi: NULL. [PMID: 6669186]
  • F Götz, D Frang, J Hübler, Z Nagy. Combined oral and local therapy for the dissolution of urinary calculi. International urology and nephrology. 1982; 14(3):239-46. doi: 10.1007/bf02081809. [PMID: 7161007]
  • A Yoshitake, K Kawahara, A Izawa, F Shono. [Absorption, distribution, excretion, and metabolism of 14C-miloxacin in female rats (author's transl)]. Radioisotopes. 1980 Aug; 29(8):377-81. doi: 10.3769/radioisotopes.29.8_377. [PMID: 7208993]
  • A Yoshitake, K Kawahara, F Shono, I Umeda, A Izawa, T Komatsu. Determination of miloxacin and metabolites in human serum and urine by high-pressure liquid chromatography. Antimicrobial agents and chemotherapy. 1980 Jul; 18(1):45-9. doi: 10.1128/aac.18.1.45. [PMID: 7416751]
  • A Izawa, A Yoshitake, T Komatsu. Absorption and excretion of miloxacin in mice, rats, and dogs. Antimicrobial agents and chemotherapy. 1980 Jul; 18(1):41-4. doi: 10.1128/aac.18.1.41. [PMID: 7416750]
  • A Yoshitake, K Kawahara, F Shono. [Metabolism of 14C-miloxacin in rats--metabolites in urine, bile and feces (author's transl)]. Radioisotopes. 1979 Nov; 28(11):687-91. doi: 10.3769/radioisotopes.28.11_687. [PMID: 531250]
  • S Kalowski, P Kincaid-Smith, R Pavillard. Oxolinic acid in the treatment of urinary tract infections. The Medical journal of Australia. 1979 Apr; 1(8):345-7. doi: 10.5694/j.1326-5377.1979.tb112154.x. [PMID: 449828]
  • M Biagini, G Curatola, G Gabbrielli, Q Maggiore. [Oxolinic acid treatment of urinary sepsis in patients with renal insufficiency]. Minerva medica. 1979 Feb; 70(9):675-8. doi: . [PMID: 440624]
  • J Montagut, J C Cazard. [Treatment of severe urinary infection in the elderly. Clinical and bacteriological study of 130 cases (author's transl)]. La semaine des hopitaux : organe fonde par l'Association d'enseignement medical des hopitaux de Paris. 1979 Jan; 55(3-4):189-91. doi: . [PMID: 219527]
  • B A Peddie, P J Little, A R Sincock. Urinary tract infection in general practice. The New Zealand medical journal. 1978 Oct; 88(622):317-20. doi: NULL. [PMID: 366474]
  • H F Eichenwald, G H McCracken. Antimicrobial therapy in infants and children. Part I. Review of antimicrobial agents. The Journal of pediatrics. 1978 Sep; 93(3):337-56. doi: 10.1016/s0022-3476(78)81139-1. [PMID: 211213]
  • J Croize, P Le Noc. [Present frequency of the different Serratia species isolated in Grenoble University Hospital Center (author's transl)]. Pathologie-biologie. 1977 Nov; 25(9):617-21. doi: NULL. [PMID: 341050]
  • C J Soussy, M Thibault, M D Kitzis, J F Acar, J Duval, Y A Chabbert. [Comparative study of six quinolone antibacterials (author's transl)]. Annales de microbiologie. 1977 Jul; 128B(1):19-33. doi: NULL. [PMID: 907268]
  • H Agui, T Mitani, A Izawa, T Komatsu, T Nakagome. Studies on quinoline derivatives and related compounds. 5. Synthesis and antimicrobial activity of novel 1-alkoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids. Journal of medicinal chemistry. 1977 Jun; 20(6):791-6. doi: 10.1021/jm00216a010. [PMID: 406396]
  • R M Shapera, J M Matsen. Oxolinic acid therapy for urinary tract infections in children. American journal of diseases of children (1960). 1977 Jan; 131(1):34-7. doi: 10.1001/archpedi.1977.02120140036004. [PMID: 319651]
  • S Turi, K Streitman, L Murányi. The effect of Gramurin treatment in urinary tract infections proved by bladder punction. Therapia Hungarica (English edition). 1977; 25(4):169-72. doi: NULL. [PMID: 605416]
  • G Ziv. Clinical pharmacology of oxolinic acid in young dairy calves. American journal of veterinary research. 1976 May; 37(5):513-6. doi: . [PMID: 776048]
  • J P Sanford, N N Linh, E Kutscher, K Arnold, K Gould. Oxolinic acid in the treatment of typhoid fever due to chloramphenicol-resistant strains of Salmonella typhi. Antimicrobial agents and chemotherapy. 1976 Mar; 9(3):387-92. doi: 10.1128/aac.9.3.387. [PMID: 1259398]
  • P T Männistö. Pharmacokinetics of nalidixinic acid and oxolinic acid in healthy women. Clinical pharmacology and therapeutics. 1976 Jan; 19(1):37-46. doi: 10.1002/cpt197619137. [PMID: 1245092]
  • M Drummond. Proceedings: a bacteriological and clinical assessment of a new drug-oxolinic acid. British journal of urology. 1975 Apr; 47(2):233-4. doi: NULL. [PMID: 1097025]
  • F E Pittman. Letter: Adverse effects of Lomotil. Gastroenterology. 1974 Aug; 67(2):408-10. doi: 10.1016/s0016-5085(19)32910-5. [PMID: 4546571]
  • H L DuPont, R B Hornick. Adverse effect of lomotil therapy in shigellosis. JAMA. 1973 Dec; 226(13):1525-8. doi: NULL. [PMID: 4587313]
  • H L DuPont, R B Hornick. Clinical approach to infectious diarrheas. Medicine. 1973 Jul; 52(4):265-70. doi: NULL. [PMID: 4578991]
  • M C Crew, M D Melgar, L J Haynes, R L Gala, F J Di Carlo. Comparative metabolism of oxolinic acid by the rat, rabbit and dog. Xenobiotica; the fate of foreign compounds in biological systems. 1971 Mar; 1(2):193-201. doi: 10.3109/00498257109044390. [PMID: 5173021]