Nalidixic acid (BioDeep_00000399063)

natural product Chemicals and Drugs

代谢物信息卡片

Nalidixic acid (NegGram)

化学式: C12H12N2O3 (232.0847882)
中文名称: 萘啶酮酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=C(C(C2=C(N1CC)N=C(C=C2)C)=O)C(O)=O
InChI: InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

描述信息

A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively.
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
C254 - Anti-Infective Agent > C255 - Urinary Anti-Infective Agent
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
D004791 - Enzyme Inhibitors
Nalidixic acid, a quinolone antibiotic, is effective against both gram-positive and gram-negative bacteria. Nalidixic acid acts in a bacteriostatic manner in lower concentrations and is bactericidal in higher concentrations. Nalidixic acid inhibits a subunit of DNA gyrase and topoisomerase IV and reversibly blocks DNA replication in susceptible bacteria[1].
Nalidixic acid, a quinolone antibiotic, is effective against both gram-positive and gram-negative bacteria. Nalidixic acid acts in a bacteriostatic manner in lower concentrations and is bactericidal in higher concentrations. Nalidixic acid inhibits a subunit of DNA gyrase and topoisomerase IV and reversibly blocks DNA replication in susceptible bacteria[1].

同义名列表

2 个代谢物同义名

Nalidixic acid; Nalidixic acid (NegGram)

数据库引用编号

18 个数据库交叉引用编号

ChEBI: CHEBI:100147
KEGG: C05079
KEGGdrug: D91720
KEGGdrug: D00183
PubChem: 4421
DrugBank: DB00779
ChEMBL: CHEMBL5
MeSH: Nalidixic Acid
CAS: 389-08-2
MoNA: CCMSLIB00003739951
MoNA: CCMSLIB00000078462
MetaboLights: MTBLC100147
PubChem: 7525
PDB-CCD: NIX
3DMET: B01807
NIKKAJI: J2.039G
RefMet: Nalidixic acid
medchemexpress: HY-B0398

分类词条

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。

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文献列表

Luu Quynh Huong, Thomas Chisnall, John D Rodgers, Shaun A Cawthraw, Roderick M Card. Prevalence, antibiotic resistance, and genomic characterisation of Campylobacter spp. in retail chicken in Hanoi, Vietnam. Microbial genomics. 2024 Jan; 10(1):. doi: 10.1099/mgen.0.001190. [PMID: 38294872]
Anastasia A Zhukovets, Vladimir V Chernyshov, Aidar Z Al'mukhametov, Tatiana A Seregina, Svetlana V Revtovich, Mariia A Kasatkina, Yulia E Isakova, Vitalia V Kulikova, Elena A Morozova, Anastasia I Cherkasova, Timur A Mannanov, Anastasia A Anashkina, Pavel N Solyev, Vladimir A Mitkevich, Roman A Ivanov. Novel Hydroxamic Acids Containing Aryl-Substituted 1,2,4- or 1,3,4-Oxadiazole Backbones and an Investigation of Their Antibiotic Potentiation Activity. International journal of molecular sciences. 2023 Dec; 25(1):. doi: 10.3390/ijms25010096. [PMID: 38203266]
Iñaki Deza-Cruz, María J Vilar, Martina Velasova, Manal AbuOun, Muna F Anjum, Richard P Smith. Antimicrobial resistance of Escherichia coli in the UK: comparison of single vs. pooled samples from healthy pigs. Letters in applied microbiology. 2023 Nov; ?(?):. doi: 10.1093/lambio/ovad123. [PMID: 37942558]
Łukasz Sikorski, Agnieszka Bęś, Kazimierz Warmiński. The Effect of Quinolones on Common Duckweed Lemna minor L., a Hydrophyte Bioindicator of Environmental Pollution. International journal of environmental research and public health. 2023 Mar; 20(6):. doi: 10.3390/ijerph20065089. [PMID: 36981998]
Mohamed Abdel-Monem El-Sakhawy. Combinational Effect of Selected Medicinal Plants and Antibiotics Against Pathogenic Bacteria. Pakistan journal of biological sciences : PJBS. 2023 Feb; 26(3):108-118. doi: 10.3923/pjbs.2023.108.118. [PMID: 37480267]
Fatih Donmez, Abdulahad Dogan. Investigation of the effects of three different generations of fluoroquinolone derivatives on antioxidant and immunotoxic enzyme levels in different rat tissues. Drug and chemical toxicology. 2022 Nov; 45(6):2686-2698. doi: 10.1080/01480545.2021.1982624. [PMID: 34601990]
Fernando R G Bergamini, Julia H B Nunes, Carlos Marrote Manzano, Marcos Alberto de Carvalho, Marcos Antônio Ribeiro, Ana Lucia Tasca Gois Ruiz, João Ernesto de Carvalho, Wilton Rogério Lustri, Raphael Enoque Ferraz de Paiva, Marcelo Cecconi Portes, Ana Maria da Costa Ferreira, Pedro Paulo Corbi. Investigating the antiproliferative activities of new CuII complexes with pyridine hydrazone derivatives of nalidixic acid. Journal of inorganic biochemistry. 2022 Sep; 234(?):111881. doi: 10.1016/j.jinorgbio.2022.111881. [PMID: 35691262]
Masrat Bashir, Imtiyaz Yousuf, Chandra Prakash Prasad. Mixed Ni(II) and Co(II) complexes of nalidixic acid drug: Synthesis, characterization, DNA/BSA binding profile and in vitro cytotoxic evaluation against MDA-MB-231 and HepG2 cancer cell lines. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2022 Apr; 271(?):120910. doi: 10.1016/j.saa.2022.120910. [PMID: 35077983]
Bai Wei, Ke Shang, Se-Yeoun Cha, Jun-Feng Zhang, Hyung-Kwan Jang, Min Kang. Clonal dissemination of Salmonella enterica serovar albany with concurrent resistance to ampicillin, chloramphenicol, streptomycin, sulfisoxazole, tetracycline, and nalidixic acid in broiler chicken in Korea. Poultry science. 2021 Jul; 100(7):101141. doi: 10.1016/j.psj.2021.101141. [PMID: 34089935]
Javier F Mariscotti, Eleonora García Véscovi. Serratia marcescens RamA Expression Is under PhoP-Dependent Control and Modulates Lipid A-Related Gene Transcription and Antibiotic Resistance Phenotypes. Journal of bacteriology. 2021 06; 203(13):e0052320. doi: 10.1128/jb.00523-20. [PMID: 33927048]
I Hansson, L-M Tamminen, S Frosth, L-L Fernström, U Emanuelson, S Boqvist. Occurrence of Campylobacter spp. in Swedish calves, common sequence types and antibiotic resistance patterns. Journal of applied microbiology. 2021 Jun; 130(6):2111-2122. doi: 10.1111/jam.14914. [PMID: 33119192]
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]
David A Baltrus, Caitlin Smith, MacKenzie Derrick, Courtney Leligdon, Zoe Rosenthal, Madison Mollico, Andrew Moore, Meara Clark. Genomic Background Governs Opposing Responses to Nalidixic Acid upon Megaplasmid Acquisition in Pseudomonas. mSphere. 2021 02; 6(1):. doi: 10.1128/msphere.00008-21. [PMID: 33597171]
Sharmin Siddiqui, Anam Mujeeb, Faisal Ameen, Hassan Mubarak Ishqi, Sayeed Ur Rehman, Mohammad Tabish. Investigating the mechanism of binding of nalidixic acid with deoxyribonucleic acid and serum albumin: a biophysical and molecular docking approaches. Journal of biomolecular structure & dynamics. 2021 Feb; 39(2):570-585. doi: 10.1080/07391102.2020.1711808. [PMID: 31910794]
Bárbara Bueloni, Daniele Sanna, Eugenio Garribba, Guillermo R Castro, Ignacio E León, Germán A Islan. Design of nalidixic acid‑vanadium complex loaded into chitosan hybrid nanoparticles as smart strategy to inhibit bacterial growth and quorum sensing. International journal of biological macromolecules. 2020 Oct; 161(?):1568-1580. doi: 10.1016/j.ijbiomac.2020.07.304. [PMID: 32777416]
S Kumar, M Singh, D E Cosby, N A Cox, H Thippareddi. Efficacy of peroxy acetic acid in reducing Salmonella and Campylobacter spp. populations on chicken breast fillets. Poultry science. 2020 May; 99(5):2655-2661. doi: 10.1016/j.psj.2019.12.045. [PMID: 32359602]
Ali Hozzari, Payam Behzadi, Parisa Kerishchi Khiabani, Mohammad Sholeh, Niloofar Sabokroo. Clinical cases, drug resistance, and virulence genes profiling in Uropathogenic Escherichia coli. Journal of applied genetics. 2020 May; 61(2):265-273. doi: 10.1007/s13353-020-00542-y. [PMID: 31950434]
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]
Joseline Barbosa Aboim, Deborah Terra de Oliveira, Vanessa Albuquerque de Mescouto, André Silva Dos Reis, Geraldo Narciso da Rocha Filho, Agenor Valadares Santos, Luciana Pereira Xavier, Alberdan Silva Santos, Evonnildo Costa Gonçalves, Luis Adriano Santos do Nascimento. Optimization of Light Intensity and NaNO3 Concentration in Amazon Cyanobacteria Cultivation to Produce Biodiesel. Molecules (Basel, Switzerland). 2019 Jun; 24(12):. doi: 10.3390/molecules24122326. [PMID: 31238580]
Manish Kumar, Gyanendra Kumar, Navin Kumar Mogha, Ritu Jain, Firasat Hussain, Dhanraj T Masram. Structure, DNA/proteins binding, docking and cytotoxicity studies of copper(II) complexes with the first quinolone drug nalidixic acid and 2,2'‑dipyridylamine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2019 Apr; 212(?):94-104. doi: 10.1016/j.saa.2018.12.045. [PMID: 30616168]
Shih-Chun Yang, Tse-Hung Huang, Chun-Hui Chiu, Wei-Ling Chou, Ahmed Alalaiwe, Yuan-Chieh Yeh, Kuan-Wen Su, Jia-You Fang. The atopic dermatitis-like lesion and the associated MRSA infection and barrier dysfunction can be alleviated by 2,4-dimethoxy-6-methylbenzene-1,3-diol from Antrodia camphorata. Journal of dermatological science. 2018 Nov; 92(2):188-196. doi: 10.1016/j.jdermsci.2018.09.002. [PMID: 30219520]
Erika Elizabeth Morales-Irigoyen, Yolanda de Las Mercedes Gómez-Y-Gómez, Jorge Luis Flores-Moreno, Marina Olivia Franco-Hernández. A bionanohybrid ZnAl-NADS ecological pesticide as a treatment for soft rot disease in potato (Solanum tuberosum L.). Environmental science and pollution research international. 2018 Aug; 25(22):21430-21439. doi: 10.1007/s11356-017-9875-7. [PMID: 28921162]
José Luis Guzmán-Martín, José María Navarro-Marí, Manuela Expósito-Ruiz, José Gutiérrez-Fernández. Nalidixic acid surrogate test for susceptibility to ciprofloxacin in Salmonella. Revisiting the question. Journal of medical microbiology. 2018 Jul; 67(7):965-967. doi: 10.1099/jmm.0.000755. [PMID: 29767616]
N Arora, S Kumar, N K Satti, A Ali, P Gupta, M Katoch. A strain of Streptomyces sp. isolated from rhizospheric soil of Crataegus oxycantha producing nalidixic acid, a synthetic antibiotic. Journal of applied microbiology. 2018 Jun; 124(6):1393-1400. doi: 10.1111/jam.13736. [PMID: 29457331]
Manal Mohamed Elhassan Taha, Hisham Elraih Homeida, Omer Mohammed Elhassan Dafalla, Siddig Ibrahim Abdelwahab. Multidrug resistance, prevalence and phylogenetic analysis of genes encoding class II and III integrons in clinically isolated Escherichia coli. Cellular and molecular biology (Noisy-le-Grand, France). 2018 Apr; 64(5):122-126. doi: 10.14715/cmb/2018.64.5.21. [PMID: 29729705]
Fatemeh Fardsanei, Mohammad Mehdi Soltan Dallal, Masoumeh Douraghi, Hamed Memariani, Bita Bakhshi, Taghi Zahraei Salehi, Farhad Nikkhahi. Antimicrobial resistance, virulence genes and genetic relatedness of Salmonella enterica serotype Enteritidis isolates recovered from human gastroenteritis in Tehran, Iran. Journal of global antimicrobial resistance. 2018 03; 12(?):220-226. doi: 10.1016/j.jgar.2017.10.005. [PMID: 29045813]
Yeon Soo Chung, Yoon Sung Hu, Sook Shin, Suk Kyung Lim, Soo Jin Yang, Yong Ho Park, Kun Taek Park. Mechanisms of quinolone resistance in Escherichia coli isolated from companion animals, pet-owners, and non-pet-owners. Journal of veterinary science. 2017 Dec; 18(4):449-456. doi: 10.4142/jvs.2017.18.4.449. [PMID: 28385014]
Elina Karhu, Janne Isojärvi, Pia Vuorela, Leena Hanski, Adyary Fallarero. Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy. Journal of natural products. 2017 10; 80(10):2602-2608. doi: 10.1021/acs.jnatprod.6b01052. [PMID: 29043803]
Birgitta C Burckhardt, Maja Henjakovic, Yohannes Hagos, Gerhard Burckhardt. Differential Interaction of Dantrolene, Glafenine, Nalidixic Acid, and Prazosin with Human Organic Anion Transporters 1 and 3. The Journal of pharmacology and experimental therapeutics. 2017 09; 362(3):450-458. doi: 10.1124/jpet.117.241406. [PMID: 28630284]
Shima Mahmoudi, Babak Pourakbari, Mina Moradzadeh, Hamid Eshaghi, Amitis Ramezani, Mohammad Taghi Haghi Ashtiani, Sepideh Keshavarz Valian, Setareh Mamishi. Prevalence and antimicrobial susceptibility of Salmonella and Shigella spp. among children with gastroenteritis in an Iranian referral hospital. Microbial pathogenesis. 2017 Aug; 109(?):45-48. doi: 10.1016/j.micpath.2017.05.023. [PMID: 28526638]
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Jana Ščerbová, Andrea Lauková. Sensitivity to Enterocins of Thermophilic Campylobacter spp. from Different Poultry Species. Foodborne pathogens and disease. 2016 12; 13(12):668-673. doi: 10.1089/fpd.2016.2158. [PMID: 27602434]
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Behrooz Zargar, Hooshang Parham, Amir Hatamie. Hollow Fiber Liquid Based Microextraction of Nalidixic Acid in Urine Samples Using Aliquat 336 as a Carrier Combined with High-Performance Liquid Chromatography. Journal of chromatographic science. 2016 Feb; 54(2):257-63. doi: 10.1093/chromsci/bmv117. [PMID: 26270081]
Robert Skov, Erika Matuschek, Maria Sjölund-Karlsson, Jenny Åhman, Andreas Petersen, Marc Stegger, Mia Torpdahl, Gunnar Kahlmeter. Development of a Pefloxacin Disk Diffusion Method for Detection of Fluoroquinolone-Resistant Salmonella enterica. Journal of clinical microbiology. 2015 Nov; 53(11):3411-7. doi: 10.1128/jcm.01287-15. [PMID: 26292292]
Beata Korchowiec, Jacek Korchowiec, Marcelina Gorczyca, Jean-Bernard Regnouf de Vains, Ewa Rogalska. Molecular organization of nalidixate conjugated calixarenes in bacterial model membranes probed by molecular dynamics simulation and Langmuir monolayer studies. The journal of physical chemistry. B. 2015 Feb; 119(7):2990-3000. doi: 10.1021/jp507151r. [PMID: 25602178]
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