Cefoperazone (BioDeep_00000002202)

 

Secondary id: BioDeep_00000397465

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(6R,7R)-7-[(2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-(4-hydroxyphenyl)ethylidene)amino]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

化学式: C25H27N9O8S2 (645.1423942000001)
中文名称: 头孢哌酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=C(C=C2)O)C(=O)NC3C4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
InChI: InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1

描述信息

Cefoperazone is only found in individuals that have used or taken this drug. It is a semisynthetic broad-spectrum cephalosporin with a tetrazolyl moiety that is resistant to beta-lactamase. It has been proposed especially against Pseudomonas infections.Like all beta-lactam antibiotics, cefoperazone binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01D - Other beta-lactam antibacterials > J01DD - Third-generation cephalosporins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D002511 - Cephalosporins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams
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

17 个代谢物同义名

(6R,7R)-7-[(2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-(4-hydroxyphenyl)ethylidene)amino]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[(2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-(4-hydroxyphenyl)ethylidene)amino]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-[(2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)(hydroxy)methylidene]amino}-1-hydroxy-2-(4-hydroxyphenyl)ethylidene)amino]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-{2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido}-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Farmasierra brand OF cefoperazone sodium; Pfizer brand OF cefoperazone sodium; Salt, cefoperazone sodium; Sodium salt, cefoperazone; Cefoperazone sodium salt; Sodium, cefoperazone; Cefoperazone sodium; cefoperazonum; Cefoperazone; Cefoperazon; Céfobis; Cefoperazone Impurity F



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

1 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

  • Dongying Li, Yueyi Li, Jingyi Wang, Weifeng Yang, Kaiyu Cui, Renjing Su, Lu Li, Xing Ren, Xianyu Li, Yi Wang. In-depth analysis of the treatment effect and synergistic mechanism of TanReQing injection on clinical multi-drug resistant Pseudomonas aeruginosa. Microbiology spectrum. 2024 Apr; 12(4):e0272623. doi: 10.1128/spectrum.02726-23. [PMID: 38415603]
  • Xupeng Shao, Yuanyuan Ren, Na Xie, Kailiang Fan, Haiyan Sun, Jiamin Lu, Jiuxiang Wei, Xincheng Tian. Effect of Cefoperazone/Sulbactam on Blood Coagulation Function in Infected Emergency Department Patients and the Necessity of Vitamin K1 (VK1) Preventive Intervention: A Single-Center, Retrospective Analysis. Medical science monitor : international medical journal of experimental and clinical research. 2023 Jun; 29(?):e939203. doi: 10.12659/msm.939203. [PMID: 37271979]
  • Licai Mo, Jiajia Wang, Jiao Qian, Minfei Peng. Antibiotic Sensitivity of Proteus mirabilis Urinary Tract Infection in Patients with Urinary Calculi. International journal of clinical practice. 2022; 2022(?):7273627. doi: 10.1155/2022/7273627. [PMID: 36628152]
  • Nicholas A Lesniak, Alyxandria M Schubert, Hamide Sinani, Patrick D Schloss. Clearance of Clostridioides difficile Colonization Is Associated with Antibiotic-Specific Bacterial Changes. mSphere. 2021 05; 6(3):. doi: 10.1128/msphere.01238-20. [PMID: 33952668]
  • Christian Diener, Anna C H Hoge, Sean M Kearney, Ulrike Kusebauch, Sushmita Patwardhan, Robert L Moritz, Susan E Erdman, Sean M Gibbons. Non-responder phenotype reveals apparent microbiome-wide antibiotic tolerance in the murine gut. Communications biology. 2021 03; 4(1):316. doi: 10.1038/s42003-021-01841-8. [PMID: 33750910]
  • Yee-Huang Ku, Wen-Liang Yu. Cefoperazone/sulbactam: New composites against multiresistant gram negative bacteria?. Infection, genetics and evolution : journal of molecular epidemiology and evolutionary genetics in infectious diseases. 2021 03; 88(?):104707. doi: 10.1016/j.meegid.2021.104707. [PMID: 33418147]
  • Bo Zhao, Ji-Yu Chen, Ya-Bin Liao, Yan-Fang Li, Xue-Mei Jiang, Xin Bi, Mi-Feng Yang, Li Li, Jing-Jing Cui. Steroid-resistant nephrotic syndrome in infants caused by a novel compound heterozygous mutation of the NUP93: A CARE case report. Medicine. 2021 Feb; 100(6):e24627. doi: 10.1097/md.0000000000024627. [PMID: 33578576]
  • Kaihang Yu, Weiliang Zeng, Ye Xu, Wenli Liao, Wenya Xu, Tieli Zhou, Jianming Cao, Lijiang Chen. Bloodstream infections caused by ST2 Acinetobacter baumannii: risk factors, antibiotic regimens, and virulence over 6 years period in China. Antimicrobial resistance and infection control. 2021 01; 10(1):16. doi: 10.1186/s13756-020-00876-6. [PMID: 33461617]
  • Jun Miyoshi, Sonny T M Lee, Megan Kennedy, Mora Puertolas, Mary Frith, Jason C Koval, Sawako Miyoshi, Dionysios A Antonopoulos, Vanessa Leone, Eugene B Chang. Metagenomic Alterations in Gut Microbiota Precede and Predict Onset of Colitis in the IL10 Gene-Deficient Murine Model. Cellular and molecular gastroenterology and hepatology. 2021; 11(2):491-502. doi: 10.1016/j.jcmgh.2020.08.008. [PMID: 32835897]
  • Zhi Rao, Zi-Long Dang, Bin Li, Lei Zhu, Hong-Yan Qin, Xin-An Wu, Yu-Hui Wei. Determination of Total and Unbound Meropenem, Imipenem/Cilastatin, and Cefoperazone/Sulbactam in Human Plasma: Application for Therapeutic Drug Monitoring in Critically Ill Patients. Therapeutic drug monitoring. 2020 08; 42(4):578-587. doi: 10.1097/ftd.0000000000000736. [PMID: 32049891]
  • Min Kan, Yue-E Wu, Xue Li, Yi-Ning Dong, Bin Du, Zi-Xuan Guo, Hai-Yan Shi, Xin Huang, Le-Qun Su, Wen-Qi Wang, Yi Zheng, Wei Zhao. An adapted LC-MS/MS method for the determination of free plasma concentration of cefoperazone in children: Age-dependent protein binding. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 May; 1144(?):122081. doi: 10.1016/j.jchromb.2020.122081. [PMID: 32247185]
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  • Liang Meng, Lingti Kong, Chenchen Wu, Benquan Qi, Xiaofei Wu. Pharmacokinetics of cefoperazone/sulbactam in plasma and cerebrospinal fluid in patients with intraventricular hemorrhage after external ventricular drains. European journal of clinical pharmacology. 2020 Jan; 76(1):127-129. doi: 10.1007/s00228-019-02773-3. [PMID: 31642959]
  • Fikret Türkan, Zübeyir Huyut, Yıldıray Basbugan, İlhami Gülçin. Influence of some β-lactam drugs on selected antioxidant enzyme and lipid peroxidation levels in different rat tissues. Drug and chemical toxicology. 2020 Jan; 43(1):27-36. doi: 10.1080/01480545.2019.1608230. [PMID: 31060396]
  • Yan Tan, Qianhui Song, Wenfang Liu, Ming Li, Jian Xiao, Chuanpin Chen. Dual-channel Microchip Electrophoresis with Amperometric Detection System for Rapid Analysis of Cefoperazone and Sulbactam. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2019 Oct; 35(10):1103-1109. doi: 10.2116/analsci.19p088. [PMID: 31231088]
  • Yuzhu Dong, Ying Li, Ying Zhang, Tao Zhang, Li Zhu, Yaling Dong, Taotao Wang. Cefoperazone/sulbactam therapeutic drug monitoring in patients with liver cirrhosis: Potential factors affecting the pharmacokinetic/pharmacodynamic target attainment. Basic & clinical pharmacology & toxicology. 2019 Oct; 125(4):353-359. doi: 10.1111/bcpt.13245. [PMID: 31056857]
  • Jack Guinan, Shaohua Wang, Tony R Hazbun, Hariom Yadav, Shankar Thangamani. Antibiotic-induced decreases in the levels of microbial-derived short-chain fatty acids correlate with increased gastrointestinal colonization of Candida albicans. Scientific reports. 2019 06; 9(1):8872. doi: 10.1038/s41598-019-45467-7. [PMID: 31222159]
  • Ashley D Smith, Elissa D Foss, Irma Zhang, Jessica L Hastie, Nicole P Giordano, Lusine Gasparyan, Lam Phuc VinhNguyen, Alyxandria M Schubert, Deepika Prasad, Hannah L McMichael, Jinchun Sun, Richard D Beger, Vahan Simonyan, Siobhán C Cowley, Paul E Carlson. Microbiota of MR1 deficient mice confer resistance against Clostridium difficile infection. PloS one. 2019; 14(9):e0223025. doi: 10.1371/journal.pone.0223025. [PMID: 31560732]
  • Mohamed Aboubakr, Ahmed Soliman, Kamil Uney, Muammer Elmas. Plasma disposition of cefoperazone after single intravenous and intramuscular administrations in camels (Camelus dromedarius). Acta veterinaria Hungarica. 2018 Sep; 66(3):444-450. doi: 10.1556/004.2018.039. [PMID: 30264621]
  • Jack Guinan, Shankar Thangamani. Antibiotic-induced alterations in taurocholic acid levels promote gastrointestinal colonization of Candida albicans. FEMS microbiology letters. 2018 09; 365(18):. doi: 10.1093/femsle/fny196. [PMID: 30137306]
  • Yun Cai, Deqing Yang, Jin Wang, Rui Wang. Amikacin and cefoperazone/sulbactam alone or in combination against carbapenem-resistant Pseudomonas aeruginosa. Diagnostic microbiology and infectious disease. 2018 Jun; 91(2):186-190. doi: 10.1016/j.diagmicrobio.2018.01.023. [PMID: 29486972]
  • Hongbin Chen, Qi Wang, Yuyao Yin, Shuguang Li, Deng-Ke Niu, Hui Wang. Genotypic variations between wild-type and small colony variant of Staphylococcus aureus in prosthetic valve infectious endocarditis: a comparative genomic and transcriptomic analysis. International journal of antimicrobial agents. 2018 Apr; 51(4):655-658. doi: 10.1016/j.ijantimicag.2017.12.006. [PMID: 29247687]
  • Xiu-Jun Wu, Xin Huang, Hai-Yan Shi, Xing-Kai Chen, Qian Dong, Guo-Xiang Hao, Yan Li, Yi Zheng, Wei Zhao. Determination of cefoperazone and sulbactam in serum by HPLC-MS/MS: An adapted method for therapeutic drug monitoring in children. Biomedical chromatography : BMC. 2018 Apr; 32(4):. doi: 10.1002/bmc.4143. [PMID: 29148595]
  • Fikret Türkan, Zübeyir Huyut, Parham Taslimi, İlhami Gülçin. The in vivo effects of cefazolin, cefuroxime, and cefoperazon on the carbonic anhydrase in different rat tissues. Journal of biochemical and molecular toxicology. 2018 Mar; 32(3):e22041. doi: 10.1002/jbt.22041. [PMID: 29457666]
  • Bülent Şengül, Şükrü Beydemir. The interactions of cephalosporins on polyol pathway enzymes from sheep kidney. Archives of physiology and biochemistry. 2018 Feb; 124(1):35-44. doi: 10.1080/13813455.2017.1358749. [PMID: 28758816]
  • Linsheng Liu, Chenrong Huang, Yicong Bian, Liyan Miao. GC-MS based metabolomics of CSF and blood serum: Metabolic phenotype for a rat model of cefoperazone-induced disulfiram-like reaction. Biochemical and biophysical research communications. 2017 08; 490(3):1066-1073. doi: 10.1016/j.bbrc.2017.06.167. [PMID: 28668395]
  • Imran Ali, Muhammad Shabbir. Antibiotics susceptibility patterns of uropathogenic E. coli with special reference to fluoroquinolones in different age and gender groups. JPMA. The Journal of the Pakistan Medical Association. 2017 Aug; 67(8):1161-1165. doi: NULL. [PMID: 28839298]
  • Lei Yan, Chun-Rong Wu, Chen Wang, Chun-Hui Yang, Guang-Zhi Tong, Jian-Guo Tang. Effect of Candida albicans on Intestinal Ischemia-reperfusion Injury in Rats. Chinese medical journal. 2016 Jul; 129(14):1711-8. doi: 10.4103/0366-6999.185862. [PMID: 27411459]
  • Dong Hao, Zhencai Hu, Xiaoli Liu, Ting Sun, Tao Wang, Huanhuan Tian, Xiaozhi Wang. [Analysis of the distribution characteristics and drug resistance of non-fermenting bacterial infection in intensive care unit from 2009 to 2015]. Zhonghua wei zhong bing ji jiu yi xue. 2016 May; 28(5):439-44. doi: NULL. [PMID: 29920041]
  • Palak Gupta, Jharna Mandal, Sriram Krishnamurthy, Deepak Barathi, Nandini Pandit. Profile of urinary tract infections in paediatric patients. The Indian journal of medical research. 2015 Apr; 141(4):473-7. doi: 10.4103/0971-5916.159299. [PMID: 26112850]
  • Qiang Wang, Yuanxing Wu, Biyao Chen, Jianxin Zhou. Drug concentrations in the serum and cerebrospinal fluid of patients treated with cefoperazone/sulbactam after craniotomy. BMC anesthesiology. 2015; 15(?):33. doi: 10.1186/s12871-015-0012-1. [PMID: 25798070]
  • Sema Aşkin Keçeli, Ayse Willke, Gulden Sonmez Tamer, Ozden Buyukbaba Boral, Nese Sonmez, Penbe Cağatay. Interaction between caspofungin or voriconazole and cefoperazone-sulbactam or piperacillin-tazobactam by in vitro and in vivo methods. APMIS : acta pathologica, microbiologica, et immunologica Scandinavica. 2014 May; 122(5):412-7. doi: 10.1111/apm.12159. [PMID: 24033828]
  • Yun-Gi Kim, Kankanam Gamage Sanath Udayanga, Naoya Totsuka, Jason B Weinberg, Gabriel Núñez, Akira Shibuya. Gut dysbiosis promotes M2 macrophage polarization and allergic airway inflammation via fungi-induced PGE₂. Cell host & microbe. 2014 Jan; 15(1):95-102. doi: 10.1016/j.chom.2013.12.010. [PMID: 24439901]
  • 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]
  • Ken Grime, Stuart W Paine. Species differences in biliary clearance and possible relevance of hepatic uptake and efflux transporters involvement. Drug metabolism and disposition: the biological fate of chemicals. 2013 Feb; 41(2):372-8. doi: 10.1124/dmd.112.049312. [PMID: 23139379]
  • Bai-Yu Zhang, Si-Man Li, Zheng-Hua Gao, Ji-Hong Shen. [Protective effects of snake venom antimicrobial peptide OH-CATH on E. coli induced rabbit urinary tract infection models]. Dong wu xue yan jiu = Zoological research. 2013 Feb; 34(1):27-32. doi: 10.3724/sp.j.1141.2013.01027. [PMID: 23389975]
  • Manjusha Patankar, Sangita Sukumaran, Anita Chhibba, Usha Nayak, Loraine Sequeira. Comparative in-vitro activity of cefoperazone-tazobactam and cefoperazone-sulbactam combinations against ESBL pathogens in respiratory and urinary infections. The Journal of the Association of Physicians of India. 2012 Nov; 60(?):22-4. doi: . [PMID: 23767198]
  • Tuba Kayman, Seçil Abay, Harun Hizlisoy, H İbrahim Atabay, K Serdar Diker, Fuat Aydin. Emerging pathogen Arcobacter spp. in acute gastroenteritis: molecular identification, antibiotic susceptibilities and genotyping of the isolated arcobacters. Journal of medical microbiology. 2012 Oct; 61(Pt 10):1439-1444. doi: 10.1099/jmm.0.044594-0. [PMID: 22700547]
  • M Ugarte-Ruiz, S Gómez-Barrero, M C Porrero, J Alvarez, M García, M C Comerón, T M Wassenaar, L Domínguez. Evaluation of four protocols for the detection and isolation of thermophilic Campylobacter from different matrices. Journal of applied microbiology. 2012 Jul; 113(1):200-8. doi: 10.1111/j.1365-2672.2012.05323.x. [PMID: 22533742]
  • 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]
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  • Masanori Nakakariya, Midori Ono, Nobuyuki Amano, Toshiya Moriwaki, Kazuya Maeda, Yuichi Sugiyama. In vivo biliary clearance should be predicted by intrinsic biliary clearance in sandwich-cultured hepatocytes. Drug metabolism and disposition: the biological fate of chemicals. 2012 Mar; 40(3):602-9. doi: 10.1124/dmd.111.042101. [PMID: 22190695]
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