Flucloxacillin (BioDeep_00000008845)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

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

化学式: C19H17ClFN3O5S (453.05614340000005)
中文名称: 氟氯西林
谱图信息: 最多检出来源 Homo sapiens(blood) 98.04%

分子结构信息

SMILES: CC1=C(C(=NO1)C2=C(C=CC=C2Cl)F)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
InChI: InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1

描述信息

Flucloxacillin is only found in individuals that have used or taken this drug. It is an antibiotic analog of cloxacillin.By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, flucloxacillin 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 flucloxacillin 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
Same as: D04196

同义名列表

14 个代谢物同义名

(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-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-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-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-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin; Flucloxacillin-sodium; Fluorochloroxacillin; Flucloxacillinum; Flucloxacilline; Flucloxacillin; Flucloxacilina; CHEMBL1622855; Floxacillin; Floxapen; MFIPC

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:5098
KEGG: C11748
PubChem: 21319
PubChem: 3364
HMDB: HMDB0014446
Metlin: METLIN2704
DrugBank: DB00301
ChEMBL: CHEMBL222645
Wikipedia: Flucloxacillin
MeSH: Floxacillin
chemspider: 20037
CAS: 5250-39-5
PMhub: MS000022547
PubChem: 13913
NIKKAJI: J8.825K
RefMet: Flucloxacillin

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)

1 个相关的物种来源信息

9606 - Homo sapiens: -

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

Kristina Öbrink-Hansen, Anh Duc Pham, Mats Bue, Pelle Hanberg, Mathias Bendtsen, Josefine Slater, Lena E Friberg, Anders Thorsted, Maiken Stilling. Population Pharmacokinetics of Flucloxacillin In Bone and Soft Tissue- Standard Dosing is Not Sufficient to Achieve Therapeutic Concentrations. Pharmaceutical research. 2022 Jul; 39(7):1633-1643. doi: 10.1007/s11095-022-03197-y. [PMID: 35233728]
Mathias A F Bendtsen, Pelle Hanberg, Josefine Slater, Jakob Hansen, Kristina Öbrink-Hansen, Maiken Stilling, Mats Bue. Steady-state concentrations of flucloxacillin in porcine vertebral cancellous bone and intervertebral disc following oral and intravenous administration assessed by microdialysis. European spine journal : official publication of the European Spine Society, the European Spinal Deformity Society, and the European Section of the Cervical Spine Research Society. 2022 Jun; 31(6):1508-1514. doi: 10.1007/s00586-022-07208-9. [PMID: 35488132]
Emiel Leegwater, Annette C Westgeest, Emile F Schippers, Erik B Wilms, Cees van Nieuwkoop, Loes E Visser. Hypokalaemia in patients treated with intravenous flucloxacillin: Incidence and risk factors. British journal of clinical pharmacology. 2022 06; 88(6):2938-2945. doi: 10.1111/bcp.15236. [PMID: 35060153]
Saartje Verfaillie, Laurent Godinas, Isabel Spriet, Robin Vos, Geert M Verleden. Interaction between posaconazole and flucloxacillin in a lung transplant patient: decrease in plasma exposure of posaconazole and possible undertreatment of invasive aspergillosis: case report. BMC pulmonary medicine. 2022 Mar; 22(1):110. doi: 10.1186/s12890-022-01904-4. [PMID: 35346142]
Jonathan Save, Yok-Ai Que, José M Entenza, Camille Kolenda, Frédéric Laurent, Grégory Resch. Bacteriophages Combined With Subtherapeutic Doses of Flucloxacillin Act Synergistically Against Staphylococcus aureus Experimental Infective Endocarditis. Journal of the American Heart Association. 2022 02; 11(3):e023080. doi: 10.1161/jaha.121.023080. [PMID: 35043655]
Stephan Moser, Sophia Rehm, Nicolas Guertler, Vladimira Hinic, Sarah Dräger, Stefano Bassetti, Katharina M Rentsch, Parham Sendi, Michael Osthoff. Probability of pharmacological target attainment with flucloxacillin in Staphylococcus aureus bloodstream infection: a prospective cohort study of unbound plasma and individual MICs. The Journal of antimicrobial chemotherapy. 2021 06; 76(7):1845-1854. doi: 10.1093/jac/dkab089. [PMID: 33860325]
Selina Schießer, Florian Hitzenbichler, Martin G Kees, Alexander Kratzer, Matthias Lubnow, Bernd Salzberger, Frieder Kees, Christoph Dorn. Measurement of Free Plasma Concentrations of Beta-Lactam Antibiotics: An Applicability Study in Intensive Care Unit Patients. Therapeutic drug monitoring. 2021 04; 43(2):264-270. doi: 10.1097/ftd.0000000000000827. [PMID: 33086362]
Anis Zand Irani, Grace Borchert, Brendan Craven, Holly Gibbons. Flucloxacillin and paracetamol induced pyroglutamic acidosis. BMJ case reports. 2021 Jan; 14(1):. doi: 10.1136/bcr-2020-237536. [PMID: 33419747]
Yuhan Zhang, Yun Chun Ody, Linsey Davis. Clinical effectiveness of flucloxacillin delivery using an elastomeric device for outpatient parenteral antimicrobial therapy. British journal of community nursing. 2020 Aug; 25(8):376-380. doi: 10.12968/bjcn.2020.25.8.376. [PMID: 32772722]
Christoph Dorn, Selina Schießer, Beatrix Wulkersdorfer, Florian Hitzenbichler, Martin G Kees, Markus Zeitlinger. Determination of free clindamycin, flucloxacillin or tedizolid in plasma: Pay attention to physiological conditions when using ultrafiltration. Biomedical chromatography : BMC. 2020 Jun; 34(6):e4820. doi: 10.1002/bmc.4820. [PMID: 32115736]
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]
Mónica Teixeira, Sara Macedo, Tânia Batista, Sofia Martins, Andreia Correia, Luís Costa Matos. Flucloxacillin-Induced Hepatotoxicity - Association with HLA-B*5701. Revista da Associacao Medica Brasileira (1992). 2020; 66(1):12-17. doi: 10.1590/1806-9282.66.1.12. [PMID: 32130375]
Richard J Everts, Ronald Begg, Sharon J Gardiner, Mei Zhang, John Turnidge, Stephen T Chambers, Evan J Begg. Probenecid and food effects on flucloxacillin pharmacokinetics and pharmacodynamics in healthy volunteers. The Journal of infection. 2020 01; 80(1):42-53. doi: 10.1016/j.jinf.2019.09.004. [PMID: 31521742]
Emma Fox, Vesa Cheng, Matthew Rawlins, John Dyer, Bart De Keulenaer, Michael M Page, Kirsten Hoad, Jason A Roberts. Pharmacokinetics of flucloxacillin during prolonged intermittent renal replacement therapy in a 76-year-old man. Journal of chemotherapy (Florence, Italy). 2019 Nov; 31(7-8):419-423. doi: 10.1080/1120009x.2019.1681622. [PMID: 31650900]
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]
Anna V Nakauyaca, Anna P Ralph, William S Majoni, Nadarajah Kangaharan. Case Report: Concurrent Rheumatic Fever and Acute Post-Streptococcal Glomerulonephritis in a High-Burden Setting. The American journal of tropical medicine and hygiene. 2019 11; 101(5):1054-1057. doi: 10.4269/ajtmh.18-0954. [PMID: 31516109]
A C Dijkmans, D M Kweekel, C Balmforth, M J van Esdonk, J T van Dissel, J Burggraaf, I M C Kamerling. The simplified oral flucloxacillin absorption test: an accurate method to identify patients with inadequate oral flucloxacillin absorption. The Netherlands journal of medicine. 2019 09; 77(7):255-260. doi: . [PMID: 31582580]
Binbin Song, Shigeki Aoki, Cong Liu, Kousei Ito. A toll-like receptor 9 agonist sensitizes mice to mitochondrial dysfunction-induced hepatic apoptosis via the Fas/FasL pathway. Archives of toxicology. 2019 06; 93(6):1573-1584. doi: 10.1007/s00204-019-02454-1. [PMID: 30993380]
Friederike Bachmann, Thomas Adam, Frank Friedersdorff, Lutz Liefeldt, Torsten Slowinski, Klemens Budde, Johannes Waiser. Perioperative antibiotic prophylaxis in renal transplantation: a single-center comparison between two regimens and a brief survey among the Eurotransplant renal transplantation centers. World journal of urology. 2019 May; 37(5):957-967. doi: 10.1007/s00345-018-2440-2. [PMID: 30109484]
Sarah Wilkes, Inge van Berlo, Jaap Ten Oever, Frank Jansman, Rob Ter Heine. Population pharmacokinetic modelling of total and unbound flucloxacillin in non-critically ill patients to devise a rational continuous dosing regimen. International journal of antimicrobial agents. 2019 Mar; 53(3):310-317. doi: 10.1016/j.ijantimicag.2018.11.018. [PMID: 30472288]
Federica Andreoni, Masanori Toyofuku, Carmen Menzi, Ratchara Kalawong, Srikanth Mairpady Shambat, Patrice François, Annelies S Zinkernagel, Leo Eberl. Antibiotics Stimulate Formation of Vesicles in Staphylococcus aureus in both Phage-Dependent and -Independent Fashions and via Different Routes. Antimicrobial agents and chemotherapy. 2019 02; 63(2):. doi: 10.1128/aac.01439-18. [PMID: 30509943]
Mei Zhang, Grant A Moore, Paul K L Chin, Richard Everts, Evan J Begg. Simultaneous Determination of Cefalexin, Cefazolin, Flucloxacillin, and Probenecid by Liquid Chromatography-Tandem Mass Spectrometry for Total and Unbound Concentrations in Human Plasma. Therapeutic drug monitoring. 2018 12; 40(6):682-692. doi: 10.1097/ftd.0000000000000555. [PMID: 30015652]
Paul Ken Leong Chin, Philip George Drennan, Sharon Jane Gardiner, Mei Zhang, Simon Charles Dalton, Stephen Thomas Chambers, Evan James Begg. Total flucloxacillin plasma concentrations poorly reflect unbound concentrations in hospitalized patients with Staphylococcus aureus bacteraemia. British journal of clinical pharmacology. 2018 10; 84(10):2311-2316. doi: 10.1111/bcp.13673. [PMID: 29908071]
A Paolino, S Walsh, T Basu, D Creamer. Severe drug-induced kidney injury in acute generalized exanthematous pustulosis. Clinical and experimental dermatology. 2018 Apr; 43(3):323-324. doi: 10.1111/ced.13316. [PMID: 29222845]
Karin Kipper, Charlotte I S Barker, Joseph F Standing, Mike Sharland, Atholl Johnston. Development of a Novel Multipenicillin Assay and Assessment of the Impact of Analyte Degradation: Lessons for Scavenged Sampling in Antimicrobial Pharmacokinetic Study Design. Antimicrobial agents and chemotherapy. 2018 01; 62(1):. doi: 10.1128/aac.01540-17. [PMID: 29084754]
Sharon J Gardiner, Philip G Drennan, Ronald Begg, Mei Zhang, Jared K Green, Heather L Isenman, Richard J Everts, Stephen T Chambers, Evan J Begg. In healthy volunteers, taking flucloxacillin with food does not compromise effective plasma concentrations in most circumstances. PloS one. 2018; 13(7):e0199370. doi: 10.1371/journal.pone.0199370. [PMID: 30001392]
Sahand Imani, Hergen Buscher, Debbie Marriott, Sheridan Gentili, Indy Sandaradura. Too much of a good thing: a retrospective study of β-lactam concentration-toxicity relationships. The Journal of antimicrobial chemotherapy. 2017 10; 72(10):2891-2897. doi: 10.1093/jac/dkx209. [PMID: 29091190]
Nadine Pinder, Thorsten Brenner, Stefanie Swoboda, Markus A Weigand, Torsten Hoppe-Tichy. Therapeutic drug monitoring of beta-lactam antibiotics - Influence of sample stability on the analysis of piperacillin, meropenem, ceftazidime and flucloxacillin by HPLC-UV. Journal of pharmaceutical and biomedical analysis. 2017 Sep; 143(?):86-93. doi: 10.1016/j.jpba.2017.05.037. [PMID: 28578254]
Alexandra Maier-Salamon, Salwa Ahmed Elgendy, Brigitte Meyer, Matthias Vossen, Theresia Thalhammer, Florian Thalhammer, Walter Jäger. Pharmacokinetics of flucloxacillin and its metabolites in patients with renal failure: Impact on liver toxicity . International journal of clinical pharmacology and therapeutics. 2017 Sep; 55(9):701-711. doi: 10.5414/cp202796. [PMID: 28737131]
Eline W Muilwijk, Bart G J Dekkers, Stefanie S V Henriet, Paul E Verweij, Bregje Witjes, Astrid M L Oude Lashof, Geert H Groeneveld, Johannes van der Hoeven, Jan Willem C Alffenaar, Frans G M Russel, Frank van de Veerdonk, Roger J M Brüggemann. Flucloxacillin Results in Suboptimal Plasma Voriconazole Concentrations. Antimicrobial agents and chemotherapy. 2017 09; 61(9):. doi: 10.1128/aac.00915-17. [PMID: 28717040]
Heather Walker, Andrea Patton, Gwen Bayne, Charis Marwick, Jacqueline Sneddon, Peter Davey, Dilip Nathwani, Samira Bell. Reduction in post-operative acute kidney injury following a change in antibiotic prophylaxis policy for orthopaedic surgery: an observational study. The Journal of antimicrobial chemotherapy. 2016 09; 71(9):2598-605. doi: 10.1093/jac/dkw166. [PMID: 27231276]
Rusheng Chew, Marion L Woods. Flucloxacillin does not achieve therapeutic cerebrospinal fluid levels against meticillin-sensitive Staphylococcus aureus in adults: A case report and review of the literature. International journal of antimicrobial agents. 2016 Mar; 47(3):229-31. doi: 10.1016/j.ijantimicag.2015.12.009. [PMID: 26915477]
Gregor Jatzlauk, Karina Althaus, Ulrike Strobel, Volker Kiefel, Jan Wesche, Klaus Muehlenberg, Andreas Greinacher, Tamam Bakchoul. Flucloxacillin-induced immune thrombocytopenia. Transfusion. 2016 Jan; 56(1):67-72. doi: 10.1111/trf.13284. [PMID: 26331798]
Ryan Nattrass, Lee Faulkner, Marc Vocanson, Daniel J Antoine, Anja Kipar, Gerry Kenna, Jean-Francois Nicolas, B Kevin Park, Dean J Naisbitt. Activation of Flucloxacillin-Specific CD8+ T-Cells With the Potential to Promote Hepatocyte Cytotoxicity in a Mouse Model. Toxicological sciences : an official journal of the Society of Toxicology. 2015 Jul; 146(1):146-56. doi: 10.1093/toxsci/kfv077. [PMID: 25877613]
Laurence Weinberg, Faizan Zia, Stan Tay, Nicholas Roubos. Haemodialysis catheter-related giant right atrial and superior cava thrombi. BMJ case reports. 2015 Feb; 2015(?):. doi: 10.1136/bcr-2015-209350. [PMID: 25721842]
Shohei Takai, Satonori Higuchi, Azusa Yano, Koichi Tsuneyama, Tatsuki Fukami, Miki Nakajima, Tsuyoshi Yokoi. Involvement of immune- and inflammatory-related factors in flucloxacillin-induced liver injury in mice. Journal of applied toxicology : JAT. 2015 Feb; 35(2):142-51. doi: 10.1002/jat.3002. [PMID: 24652713]
Mohd H Abdul-Aziz, Craig McDonald, Brett McWhinney, Jacobus P J Ungerer, Jeffrey Lipman, Jason A Roberts. Low flucloxacillin concentrations in a patient with central nervous system infection: the need for plasma and cerebrospinal fluid drug monitoring in the ICU. The Annals of pharmacotherapy. 2014 Oct; 48(10):1380-4. doi: 10.1177/1060028014540610. [PMID: 24951308]
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]
S Craxford, E Bayley, M Needoff. Antibiotic-associated complications following lower limb arthroplasty: a comparison of two prophylactic regimes. European journal of orthopaedic surgery & traumatology : orthopedie traumatologie. 2014 May; 24(4):539-43. doi: 10.1007/s00590-013-1348-1. [PMID: 24178085]
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Sudhakar Rao Challagundla, David Knox, Amanda Hawkins, David Hamilton, Robert W V Flynn, Sue Robertson, Chris Isles. Renal impairment after high-dose flucloxacillin and single-dose gentamicin prophylaxis in patients undergoing elective hip and knee replacement. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2013 Mar; 28(3):612-9. doi: 10.1093/ndt/gfs458. [PMID: 23197677]
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