Cloxacillin (BioDeep_00000002184)

 

Secondary id: BioDeep_00001867639

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

化学式: C19H18ClN3O5S (435.06556480000006)
中文名称: 氯唑西林
谱图信息: 最多检出来源 Homo sapiens(blood) 84.21%

分子结构信息

SMILES: CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
InChI: InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1

描述信息

Cloxacillin is only found in individuals that have used or taken this drug. It is a semi-synthetic antibiotic that is a chlorinated derivative of oxacillin. [PubChem]By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, cloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cloxacillin interferes with an autolysin inhibitor.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01C - Beta-lactam antibacterials, penicillins > J01CF - Beta-lactamase resistant penicillins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D010406 - Penicillins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams
C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic

同义名列表

20 个代谢物同义名

(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid; 6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanate; (3-(O-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillin; Cloxacillin, Antibiotic for Culture Media Use Only; Cloxacillin, sodium; Sodium, cloxacillin; Cloxacillin Sodium; Sodium cloxacillin; Chloroxacillin; Cloxacillinum; Cloxacilline; Cloxacilina; Cloxacillin; Syntarpen; Tegopen; Orbenin; MCIPC



数据库引用编号

18 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)

3 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

  • Kasturi Devi Kondampati, Simrat Pal Singh Saini, Pritam K Sidhu, Arun Anand, Deepesh Kumar, Srinu Beesam, Jasbir Singh Bedi, Rajdeep Kaur, Rajesh Bhardwaj. Pharmacokinetic-Pharmacodynamic Study of Ampicillin-Cloxacillin Combination in Indian Thoroughbred Horses (Equus caballus) and Safety Evaluation of the Computed Dosage Regimen. Journal of equine veterinary science. 2022 08; 115(?):104020. doi: 10.1016/j.jevs.2022.104020. [PMID: 35605881]
  • Efraím A Serna-Galvis, John F Guateque-Londoño, Javier Silva-Agredo, Jazmín Porras, Yenny Ávila-Torres, Ricardo A Torres-Palma. Superior selectivity of high-frequency ultrasound toward chorine containing-pharmaceuticals elimination in urine: A comparative study with other oxidation processes through the elucidation of the degradation pathways. Ultrasonics sonochemistry. 2021 Dec; 80(?):105814. doi: 10.1016/j.ultsonch.2021.105814. [PMID: 34763213]
  • Johan Courjon, Margaux Garzaro, Pierre-Marie Roger, Raymond Ruimy, Thibaud Lavrut, Mikaël Chelli, Jean-Luc Raynier, David Chirio, Elisa Demonchy, Laura Cabane, François Jehl, Christophe Trojani, Antoine Grillon, Sylvain Goutelle. A Population Pharmacokinetic Analysis of Continuous Infusion of Cloxacillin during Staphylococcus aureus Bone and Joint Infections. Antimicrobial agents and chemotherapy. 2020 11; 64(12):. doi: 10.1128/aac.01562-20. [PMID: 32988822]
  • Murilo Henrique M Facure, Rodrigo Schneider, Danilo M Dos Santos, Daniel S Correa. Impedimetric electronic tongue based on molybdenum disulfide and graphene oxide for monitoring antibiotics in liquid media. Talanta. 2020 Sep; 217(?):121039. doi: 10.1016/j.talanta.2020.121039. [PMID: 32498857]
  • Sébastien Lalanne, Marc Le Vée, Florian Lemaitre, Pascal Le Corre, Marie-Clémence Verdier, Olivier Fardel. Differential interactions of the β-lactam cloxacillin with human renal organic anion transporters (OATs). Fundamental & clinical pharmacology. 2020 Aug; 34(4):476-483. doi: 10.1111/fcp.12541. [PMID: 32100322]
  • Simony T Guerra, Henrique Orsi, Sâmea F Joaquim, Felipe F Guimarães, Bruna C Lopes, Felipe M Dalanezi, Domingos S Leite, Helio Langoni, Jose C F Pantoja, Vera L M Rall, Rodrigo T Hernandes, Simone B Lucheis, Márcio G Ribeiro. Short communication: Investigation of extra-intestinal pathogenic Escherichia coli virulence genes, bacterial motility, and multidrug resistance pattern of strains isolated from dairy cows with different severity scores of clinical mastitis. Journal of dairy science. 2020 Apr; 103(4):3606-3614. doi: 10.3168/jds.2019-17477. [PMID: 32037173]
  • Steven Y C Tong, David C Lye, Dafna Yahav, Archana Sud, J Owen Robinson, Jane Nelson, Sophia Archuleta, Matthew A Roberts, Alan Cass, David L Paterson, Hong Foo, Mical Paul, Stephen D Guy, Adrian R Tramontana, Genevieve B Walls, Stephen McBride, Narin Bak, Niladri Ghosh, Benjamin A Rogers, Anna P Ralph, Jane Davies, Patricia E Ferguson, Ravindra Dotel, Genevieve L McKew, Timothy J Gray, Natasha E Holmes, Simon Smith, Morgyn S Warner, Shirin Kalimuddin, Barnaby E Young, Naomi Runnegar, David N Andresen, Nicholas A Anagnostou, Sandra A Johnson, Mark D Chatfield, Allen C Cheng, Vance G Fowler, Benjamin P Howden, Niamh Meagher, David J Price, Sebastiaan J van Hal, Matthew V N O'Sullivan, Joshua S Davis. Effect of Vancomycin or Daptomycin With vs Without an Antistaphylococcal β-Lactam on Mortality, Bacteremia, Relapse, or Treatment Failure in Patients With MRSA Bacteremia: A Randomized Clinical Trial. JAMA. 2020 02; 323(6):527-537. doi: 10.1001/jama.2020.0103. [PMID: 32044943]
  • Wenjing Luan, Xiaolei Liu, Xuefei Wang, Yanan An, Yang Wang, Chao Wang, Keshu Shen, Hongyue Xu, Shulin Li, Mingyuan Liu, L U Yu. Inhibition of Drug Resistance of Staphylococcus aureus by Efflux Pump Inhibitor and Autolysis Inducer to Strengthen the Antibacterial Activity of β-lactam Drugs. Polish journal of microbiology. 2019 Dec; 68(4):477-491. doi: 10.33073/pjm-2019-047. [PMID: 31880892]
  • J A A S Jayaweera, W P H Abeydeera, G R Ranasinghe. Intravenously administered cloxacillin-induced neutropenia with eosinophilia in a patient with infective endocarditis: a case report. Journal of medical case reports. 2018 Dec; 12(1):384. doi: 10.1186/s13256-018-1933-3. [PMID: 30593283]
  • Aurélie Lavergne, Cécile Vigneau, Elisabeth Polard, Louise Triquet, Nathalie Rioux-Leclercq, Pierre Tattevin, Léonard Golbin. Acute kidney injury during treatment with high-dose cloxacillin: a report of 23 cases and literature review. International journal of antimicrobial agents. 2018 Sep; 52(3):344-349. doi: 10.1016/j.ijantimicag.2018.04.007. [PMID: 29665445]
  • Yothin Teethaisong, Thippawan Pimchan, Rungrudee Srisawat, Glyn Hobbs, Griangsak Eumkeb. Boesenbergia rotunda (L.) Mansf. extract potentiates the antibacterial activity of some β-lactams against β-lactam-resistant staphylococci. Journal of global antimicrobial resistance. 2018 03; 12(?):207-213. doi: 10.1016/j.jgar.2017.10.019. [PMID: 29102774]
  • Jon Ashley, Kaiyu Wu, Mikkel Fougt Hansen, Michael Stenbæk Schmidt, Anja Boisen, Yi Sun. Quantitative Detection of Trace Level Cloxacillin in Food Samples Using Magnetic Molecularly Imprinted Polymer Extraction and Surface-Enhanced Raman Spectroscopy Nanopillars. Analytical chemistry. 2017 11; 89(21):11484-11490. doi: 10.1021/acs.analchem.7b02725. [PMID: 28952718]
  • Tiphaine Legrand, Dominique Vodovar, Nicolas Tournier, Nihel Khoudour, Anne Hulin. Simultaneous Determination of Eight β-Lactam Antibiotics, Amoxicillin, Cefazolin, Cefepime, Cefotaxime, Ceftazidime, Cloxacillin, Oxacillin, and Piperacillin, in Human Plasma by Using Ultra-High-Performance Liquid Chromatography with Ultraviolet Detection. Antimicrobial agents and chemotherapy. 2016 08; 60(8):4734-42. doi: 10.1128/aac.00176-16. [PMID: 27216076]
  • Olubunmi B Falade, Adeyinka G Falusi, Ajibola A Olaniyi, Chizoba Ezeasor, David A Kwasi, Chinedum P Babalola. Significant Pharmacokinetic Interactions Between Quinine and Ampicillin-Cloxacillin Combination. Drugs in R&D. 2016 Jun; 16(2):193-203. doi: 10.1007/s40268-016-0128-x. [PMID: 27020278]
  • Wasim El Nekidy, Nicole Dziamarski, Derrick Soong, Christine Donaldson, Muhieldean Ibrahim, Albert Kadri. Cloxacillin-induced seizure in a hemodialysis patient. Hemodialysis international. International Symposium on Home Hemodialysis. 2015 Oct; 19(4):E33-6. doi: 10.1111/hdi.12262. [PMID: 25582344]
  • T B Jonsson, T K Nilsson, L H Breimer, J Schneede, B Arfvidsson, L Norgren. Cloxacillin concentrations in serum, subcutaneous fat, and muscle in patients with chronic critical limb ischemia. European journal of clinical pharmacology. 2014 Aug; 70(8):957-63. doi: 10.1007/s00228-014-1695-9. [PMID: 24858821]
  • Karin H M Larmené-Beld, Marie-Therese L M Vries-Koenjer, Peter G J ter Horst, Wobbe Hospes. Development and validation of a liquid chromatography/tandem mass spectrometry method for the quantification of flucloxacillin and cloxacillin in microdialysis samples. Biomedical chromatography : BMC. 2014 Aug; 28(8):1096-101. doi: 10.1002/bmc.3125. [PMID: 25165789]
  • Frida Gustafsson, Alison J Foster, Sunil Sarda, Matthew H Bridgland-Taylor, J Gerry Kenna. A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. Toxicological sciences : an official journal of the Society of Toxicology. 2014 Jan; 137(1):189-211. doi: 10.1093/toxsci/kft223. [PMID: 24085192]
  • Aaron T Wolman, Michael R Gionfriddo, Gregory A Heindel, Paran Mukhija, Sarah Witkowski, Ajay Bommareddy, Adam L Vanwert. Organic anion transporter 3 interacts selectively with lipophilic β-lactam antibiotics. Drug metabolism and disposition: the biological fate of chemicals. 2013 Apr; 41(4):791-800. doi: 10.1124/dmd.112.049569. [PMID: 23344796]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Nasir Idkaidek, Tawfiq Arafat. Saliva versus plasma pharmacokinetics: theory and application of a salivary excretion classification system. Molecular pharmaceutics. 2012 Aug; 9(8):2358-63. doi: 10.1021/mp300250r. [PMID: 22784220]
  • Aurijit Sarkar, Kelcey C Anderson, Glen E Kellogg. Computational analysis of structure-based interactions and ligand properties can predict efflux effects on antibiotics. European journal of medicinal chemistry. 2012 Jun; 52(?):98-110. doi: 10.1016/j.ejmech.2012.03.008. [PMID: 22483632]
  • Frédéric Bert, Béatrice Larroque, Catherine Paugam-Burtz, Federica Dondero, François Durand, Estelle Marcon, Jacques Belghiti, Richard Moreau, Marie-Hélène Nicolas-Chanoine. Pretransplant fecal carriage of extended-spectrum β-lactamase-producing Enterobacteriaceae and infection after liver transplant, France. Emerging infectious diseases. 2012 Jun; 18(6):908-16. doi: 10.3201/eid1806.110139. [PMID: 22607885]
  • Pankaj Baral, Sanjiv Neupane, Bishnu Prasad Marasini, Kashi Ram Ghimire, Binod Lekhak, Basudha Shrestha. High prevalence of multidrug resistance in bacterial uropathogens from Kathmandu, Nepal. BMC research notes. 2012 Jan; 5(?):38. doi: 10.1186/1756-0500-5-38. [PMID: 22260454]
  • Stephen T Lacmata, Victor Kuete, Jean P Dzoyem, Simplice B Tankeo, Gerald Ngo Teke, Jules R Kuiate, Jean-Marie Pages. Antibacterial Activities of Selected Cameroonian Plants and Their Synergistic Effects with Antibiotics against Bacteria Expressing MDR Phenotypes. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):623723. doi: 10.1155/2012/623723. [PMID: 22474511]
  • Hossein Khalili, Simin Dashti-Khavidaki, Iman Karimzadeh, Sirous Jafari, Alireza Abdollahi, Mohammad Reza Shahidi, Zahra Jahangard-Rafsanjani, Taher Entezari-Maleki. Changes in 4-year antimicrobial resistance pattern of gram-positive bacteria at the main referral teaching hospital, Tehran, Iran. Acta medica Iranica. 2012; 50(7):493-504. doi: NULL. [PMID: 22930383]
  • Sarah Dawson, Simone Stahl, Nikki Paul, Jane Barber, J Gerald Kenna. In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jan; 40(1):130-8. doi: 10.1124/dmd.111.040758. [PMID: 21965623]
  • Aimé G Fankam, Victor Kuete, Igor K Voukeng, Jules R Kuiate, Jean-Marie Pages. Antibacterial activities of selected Cameroonian spices and their synergistic effects with antibiotics against multidrug-resistant phenotypes. BMC complementary and alternative medicine. 2011 Nov; 11(?):104. doi: 10.1186/1472-6882-11-104. [PMID: 22044718]
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  • Maria Hälleberg Nyman, Jan-Erik Johansson, Katarina Persson, Margareta Gustafsson. A prospective study of nosocomial urinary tract infection in hip fracture patients. Journal of clinical nursing. 2011 Sep; 20(17-18):2531-9. doi: 10.1111/j.1365-2702.2011.03769.x. [PMID: 21733026]
  • M Lenoble. [Treatment of resistant Gram-positive bacterial infections]. Medecine et maladies infectieuses. 2011 Sep; 41(9 Suppl):1-6. doi: 10.1016/s0399-077x(11)70037-3. [PMID: 22133738]
  • Mozhgan Davanipur, Maryam Pakfetrat, Jamishid Roozbeh. Cloxacillin as an antibiotic lock solution for prevention of catheter-associated infection. Iranian journal of kidney diseases. 2011 Sep; 5(5):328-31. doi: NULL. [PMID: 21876310]
  • Maria Rambla-Alegre, Rosa Martí-Centelles, Josep Esteve-Romero, Samuel Carda-Broch. Application of a liquid chromatographic procedure for the analysis of penicillin antibiotics in biological fluids and pharmaceutical formulations using sodium dodecyl sulphate/propanol mobile phases and direct injection. Journal of chromatography. A. 2011 Jul; 1218(30):4972-81. doi: 10.1016/j.chroma.2010.12.015. [PMID: 21190691]
  • Heli Simojoki, Tiina Salomäki, Suvi Taponen, Antti Iivanainen, Satu Pyörälä. Innate immune response in experimentally induced bovine intramammary infection with Staphylococcus simulans and S. epidermidis. Veterinary research. 2011 Mar; 42(?):49. doi: 10.1186/1297-9716-42-49. [PMID: 21414189]
  • Shahedur Rahman, Anowar Khasru Parvez, Rezuanul Islam, Mahboob Hossain Khan. Antibacterial activity of natural spices on multiple drug resistant Escherichia coli isolated from drinking water, Bangladesh. Annals of clinical microbiology and antimicrobials. 2011 Mar; 10(?):10. doi: 10.1186/1476-0711-10-10. [PMID: 21406097]
  • Tavitiya Sudjaritruk, Virat Sirisanthana. Successful treatment of a child with vascular pythiosis. BMC infectious diseases. 2011 Jan; 11(?):33. doi: 10.1186/1471-2334-11-33. [PMID: 21276255]
  • Ganpat J Dahe, Sachin S Kadam, Siddharth S Sabale, Dattatray P Kadam, Laxman B Sarkate, Jayesh R Bellare. In vivo evaluation of the biocompatibility of surface modified hemodialysis polysulfone hollow fibers in rat. PloS one. 2011; 6(10):e25236. doi: 10.1371/journal.pone.0025236. [PMID: 22046236]
  • Griangsak Eumkeb, Santi Sakdarat, Supatcharee Siriwong. Reversing β-lactam antibiotic resistance of Staphylococcus aureus with galangin from Alpinia officinarum Hance and synergism with ceftazidime. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Dec; 18(1):40-5. doi: 10.1016/j.phymed.2010.09.003. [PMID: 21036573]
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