Aztreonam (BioDeep_00000006355)

 

Secondary id: BioDeep_00001870263

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


2-{[(Z)-[(2-amino-1,3-thiazol-4-yl)({[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene]amino]oxy}-2-methylpropanoic acid

化学式: C13H17N5O8S2 (435.0519)
中文名称: 氨曲南
谱图信息: 最多检出来源 not specific(not specific) 0%

分子结构信息

SMILES: CC1C(C(=O)N1S(=O)(=O)O)NC(=O)C(=NOC(C)(C)C(=O)O)C2=CSC(=N2)N
InChI: InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1

描述信息

Aztreonam is only found in individuals that have used or taken this drug. It is a monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms. [PubChem]The bactericidal action of aztreonam results from the inhibition of bacterial cell wall synthesis due to a high affinity of aztreonam for penicillin binding protein 3 (PBP3). By binding to PBP3, aztreonam 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 aztreonam interferes with an autolysin inhibitor.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01D - Other beta-lactam antibacterials > J01DF - Monobactams
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

23 个代谢物同义名

2-{[(Z)-[(2-amino-1,3-thiazol-4-yl)({[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene]amino]oxy}-2-methylpropanoic acid; (Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulphO-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid; (Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfO-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid; (Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulphO-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionate; (Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfO-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionate; Bristol myers squibb brand OF aztreonam; Bristol-myers squibb brand OF aztreonam; Sanofi winthrop brand OF aztreonam; Squibb brand OF aztreonam; Esteve brand OF aztreonam; Aztreonam esteve brand; Aztreonam squibb brand; Aztreonamum; Az-threonam; Az threonam; Azthreonam; Primbactam; Monobactam; Urobactam; aztreonam; Azactam; AZT; Aztreonam



数据库引用编号

22 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)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 4 ALB, CAT, DHFR, ELANE
Peripheral membrane protein 1 CYP27A1
Endoplasmic reticulum membrane 2 MOXD1, OSTC
Mitochondrion membrane 1 CYP27A1
Nucleus 2 ALB, OMP
cytosol 7 ALB, CAT, DHFR, ELANE, GPT, OMP, STX1A
phagocytic vesicle 1 ELANE
centrosome 1 ALB
Cell membrane 2 STX1A, TNF
lamellipodium 1 STX2
Multi-pass membrane protein 1 OSTC
Synapse 1 OMP
cell surface 3 ELANE, TNF, TNR
glutamatergic synapse 1 TNR
Golgi apparatus 1 ALB
mitochondrial inner membrane 2 CYP27A1, FECH
neuronal cell body 2 OMP, TNF
synaptic vesicle 2 STX1A, STX2
plasma membrane 6 IGHE, INSRR, ST14, STX1A, STX2, TNF
synaptic vesicle membrane 1 STX1A
Membrane 5 CAT, INSRR, OSTC, ST14, STX2
axon 3 INSRR, OMP, STX1A
basolateral plasma membrane 2 ST14, STX2
extracellular exosome 5 ALB, CAT, ELANE, GPT, SPINK1
endoplasmic reticulum 2 ALB, OSTC
extracellular space 10 ALB, CPZ, CRP, ELANE, IGHE, MOXD1, ST14, STX2, TNF, TNR
Schaffer collateral - CA1 synapse 1 TNR
mitochondrion 4 CAT, CYP27A1, DHFR, FECH
protein-containing complex 3 ALB, CAT, STX2
intracellular membrane-bounded organelle 2 CAT, STX2
Single-pass type I membrane protein 3 IGHE, INSRR, MOXD1
Secreted 3 ALB, CRP, SPINK1
extracellular region 8 ALB, CAT, CRP, ELANE, IGHE, STX1A, TNF, TNR
[Isoform 2]: Secreted 1 STX1A
mitochondrial matrix 3 CAT, CYP27A1, FECH
anchoring junction 1 ALB
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 STX1A
nuclear membrane 1 STX1A
external side of plasma membrane 2 ST14, TNF
Secreted, extracellular space, extracellular matrix 2 CPZ, TNR
recycling endosome 1 TNF
Single-pass type II membrane protein 2 ST14, TNF
presynaptic active zone membrane 2 STX1A, STX2
Mitochondrion inner membrane 2 CYP27A1, FECH
Membrane raft 2 TNF, TNR
focal adhesion 1 CAT
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 ELANE, TNR
secretory granule 1 ELANE
receptor complex 1 INSRR
neuron projection 1 STX1A
ciliary basal body 1 ALB
IgE immunoglobulin complex 1 IGHE
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
[Isoform 2]: Cell membrane 1 IGHE
Endomembrane system 2 STX1A, STX2
SNARE complex 2 STX1A, STX2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
secretory granule membrane 1 MOXD1
endoplasmic reticulum lumen 1 ALB
transcription repressor complex 1 ELANE
platelet alpha granule lumen 1 ALB
specific granule lumen 1 ELANE
azurophil granule lumen 1 ELANE
perineuronal net 1 TNR
Single-pass type IV membrane protein 1 STX1A
Synapse, synaptosome 1 STX1A
Cytoplasmic vesicle, phagosome 1 ELANE
[Isoform 3]: Cell membrane 1 IGHE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
catalase complex 1 CAT
oligosaccharyltransferase complex 1 OSTC
insulin receptor complex 1 INSRR
tenascin complex 1 TNR
ciliary transition fiber 1 ALB
synaptobrevin 2-SNAP-25-syntaxin-1a complex 1 STX1A
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Gabriela Kroneislová, Jan Závora, Vanda Gabriela Adámková, Anna Rýdlová, Václava Adámková. In vitro activity of antibiotics potentially effective against difficult-to-treat strains of Gram-negative rods: retrospective study. Scientific reports. 2024 04; 14(1):8310. doi: 10.1038/s41598-024-59036-0. [PMID: 38594467]
  • Sun Miao, Yanyan Zhang, Cong Men, Yiou Mao, Jiane Zuo. A combined evaluation of the characteristics and antibiotic resistance induction potential of antibiotic wastewater during the treatment process. Journal of environmental sciences (China). 2024 Apr; 138(?):626-636. doi: 10.1016/j.jes.2023.04.002. [PMID: 38135426]
  • Ruixian Guo, Xinyan Ma, Huibo Xu, Yuanyuan Ma, Rui Zhang, Xinyan Liu, Binan Lu, Jingpu Zhang, Ying Han. In silico prediction and a systematic toxicology-based in vivo investigation uncovering the mechanism of aquatic toxicity caused by beta-lactam antibiotics. Chemosphere. 2024 Feb; 349(?):140884. doi: 10.1016/j.chemosphere.2023.140884. [PMID: 38065262]
  • Jiankang Zhao, Danni Pu, Ziyao Li, Xinmeng Liu, Yulin Zhang, Yongli Wu, Feilong Zhang, Chen Li, Xianxia Zhuo, Binghuai Lu, Bin Cao. In vitro activity of cefiderocol, a siderophore cephalosporin, against carbapenem-resistant hypervirulent Klebsiella pneumoniae in China. Antimicrobial agents and chemotherapy. 2023 12; 67(12):e0073523. doi: 10.1128/aac.00735-23. [PMID: 38014944]
  • Jian-Guo Li, Xiao-Feng Chen, Ting-Yin Lu, Jing Zhang, Shu-He Dai, Jian Sun, Ya-Hong Liu, Xiao-Ping Liao, Yu-Feng Zhou. Increased Activity of β-Lactam Antibiotics in Combination with Carvacrol against MRSA Bacteremia and Catheter-Associated Biofilm Infections. ACS infectious diseases. 2023 Dec; 9(12):2482-2493. doi: 10.1021/acsinfecdis.3c00338. [PMID: 38019707]
  • Hye-Ri Jung, Yu Jin Lee, Serim Hong, Sunghyun Yoon, Suk-Kyung Lim, Young Ju Lee. Current status of β-lactam antibiotic use and characterization of β-lactam-resistant Escherichia coli from commercial farms by integrated broiler chicken operations in Korea. Poultry science. 2023 Dec; 102(12):103091. doi: 10.1016/j.psj.2023.103091. [PMID: 37839166]
  • Lujie Liang, Lan-Lan Zhong, Lin Wang, Dianrong Zhou, Yaxin Li, Jiachen Li, Yong Chen, Wanfei Liang, Wenjing Wei, Chenchen Zhang, Hui Zhao, Lingxuan Lyu, Nicole Stoesser, Yohei Doi, Fang Bai, Siyuan Feng, Guo-Bao Tian. A new variant of the colistin resistance gene MCR-1 with co-resistance to β-lactam antibiotics reveals a potential novel antimicrobial peptide. PLoS biology. 2023 Dec; 21(12):e3002433. doi: 10.1371/journal.pbio.3002433. [PMID: 38091366]
  • Sayani Bhattacharyya. In vitro/In vivo Evaluation of Elastic Nano-lipid Carriers of Aztreonam for Pneumonic Lungs. Pharmaceutical nanotechnology. 2023 Jun; 11(3):294-302. doi: 10.2174/2211738511666230223141759. [PMID: 36815648]
  • Yu-Hang Yan, Hao-Sheng Ding, Kai-Rong Zhu, Bin-Song Mu, Yang Zheng, Meng-Yi Huang, Cong Zhou, Wen-Fang Li, Zhenling Wang, Yong Wu, Guo-Bo Li. Metal binding pharmacophore click-derived discovery of new broad-spectrum metallo-β-lactamase inhibitors. European journal of medicinal chemistry. 2023 May; 257(?):115473. doi: 10.1016/j.ejmech.2023.115473. [PMID: 37209449]
  • Qiang Ma, Guilai Wang, Na Li, Xin Wang, Xinyun Kang, Yanni Mao, Guiqin Wang. Insights into the Effects and Mechanism of Andrographolide-Mediated Recovery of Susceptibility of Methicillin-Resistant Staphylococcus aureus to β-Lactam Antibiotics. Microbiology spectrum. 2023 Feb; 11(1):e0297822. doi: 10.1128/spectrum.02978-22. [PMID: 36602386]
  • 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]
  • Yixin Kang, Lu Xie, Jiyong Yang, Junchang Cui. Optimal treatment of ceftazidime-avibactam and aztreonam-avibactam against bloodstream infections or lower respiratory tract infections caused by extensively drug-resistant or pan drug-resistant (XDR/PDR) Pseudomonas aeruginosa. Frontiers in cellular and infection microbiology. 2023; 13(?):1023948. doi: 10.3389/fcimb.2023.1023948. [PMID: 37457958]
  • Muriel Masi, Julia Vergalli, Ishan Ghai, Andrea Barba-Bon, Thérèse Schembri, Werner M Nau, Daniel Lafitte, Mathias Winterhalter, Jean-Marie Pagès. Cephalosporin translocation across enterobacterial OmpF and OmpC channels, a filter across the outer membrane. Communications biology. 2022 10; 5(1):1059. doi: 10.1038/s42003-022-04035-y. [PMID: 36198902]
  • Keith A Rodvold, Mark H Gotfried, Vipul Gupta, Amanda Ek, Praveen Srivastava, Angela Talley, Jon Bruss. Plasma and Intrapulmonary Concentrations of Tebipenem following Oral Administration of Tebipenem Pivoxil Hydrobromide to Healthy Adult Subjects. Antimicrobial agents and chemotherapy. 2022 Jul; 66(7):e0059022. doi: 10.1128/aac.00590-22. [PMID: 35762796]
  • Gina Patel, Keith A Rodvold, Vipul K Gupta, Jon Bruss, Leanne Gasink, Floni Bajraktari, Yang Lei, Akash Jain, Praveen Srivastava, Angela K Talley. Pharmacokinetics of Oral Tebipenem Pivoxil Hydrobromide in Subjects with Various Degrees of Renal Impairment. Antimicrobial agents and chemotherapy. 2022 05; 66(5):e0240721. doi: 10.1128/aac.02407-21. [PMID: 35420493]
  • Gabriele Bianco, Matteo Boattini, Sara Comini, Roberto Casale, Marco Iannaccone, Rossana Cavallo, Cristina Costa. Occurrence of multi-carbapenemases producers among carbapenemase-producing Enterobacterales and in vitro activity of combinations including cefiderocol, ceftazidime-avibactam, meropenem-vaborbactam, and aztreonam in the COVID-19 era. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology. 2022 Apr; 41(4):573-580. doi: 10.1007/s10096-022-04408-5. [PMID: 35061145]
  • Yahui Li, Minghua Yuan, Dong Ding, Xiong Jiang, Qing Ye, Fujiang Guo. Isolation and structural characterization of eight impurities in aztreonam. Journal of pharmaceutical and biomedical analysis. 2022 Feb; 210(?):114587. doi: 10.1016/j.jpba.2022.114587. [PMID: 35026590]
  • Anna Olsson, Marcus Hong, Hissa Al-Farsi, Christian G Giske, Pernilla Lagerbäck, Thomas Tängdén. Interactions of Polymyxin B in Combination with Aztreonam, Minocycline, Meropenem, and Rifampin against Escherichia coli Producing NDM and OXA-48-Group Carbapenemases. Antimicrobial agents and chemotherapy. 2021 11; 65(12):e0106521. doi: 10.1128/aac.01065-21. [PMID: 34516251]
  • Freddy Frost, Gregory R Young, Laura Wright, Nahida Miah, Darren L Smith, Craig Winstanley, Martin J Walshaw, Joanne L Fothergill, Dilip Nazareth. The clinical and microbiological utility of inhaled aztreonam lysine for the treatment of acute pulmonary exacerbations of cystic fibrosis: An open-label randomised crossover study (AZTEC-CF). Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society. 2021 11; 20(6):994-1002. doi: 10.1016/j.jcf.2020.12.012. [PMID: 33358119]
  • Kun Feng, Nan Jia, Peijuan Zhu, Serubbabel Sy, Yanfei Liu, Dandan Dong, Shixing Zhu, Jiayuan Zhang, Yuwei Liu, Frederico S Martins, Hugh Gong, Zhihua Lv, Mingming Yu, Sherwin K B Sy, Yuanqi Zhu. Aztreonam/avibactam effect on pharmacodynamic indices for mutant selection of Escherichia coli and Klebsiella pneumoniae harbouring serine- and New Delhi metallo-β-lactamases. The Journal of antimicrobial chemotherapy. 2021 10; 76(11):2875-2883. doi: 10.1093/jac/dkab292. [PMID: 34383928]
  • Wen-Jung Lu, Pang-Hung Hsu, Hong-Ting Victor Lin. A Novel Cooperative Metallo-β-Lactamase Fold Metallohydrolase from Pathogen Vibrio vulnificus Exhibits β-Lactam Antibiotic-Degrading Activities. Antimicrobial agents and chemotherapy. 2021 08; 65(9):e0032621. doi: 10.1128/aac.00326-21. [PMID: 34228542]
  • Punit J Shah, Thuytram Tran, Francis Emelogu, Farheen Tariq. Aztreonam, Ceftazidime/Avibactam, and Colistin Combination for the Management of Carbapenemase-Producing Klebsiella Pneumoniae Bacteremia: A Case Report. Journal of pharmacy practice. 2021 Aug; 34(4):653-657. doi: 10.1177/0897190019882262. [PMID: 31698984]
  • Francesco Perrotta, Marco Paolo Perrini. Successful Treatment of Klebsiella pneumoniae NDM Sepsis and Intestinal Decolonization with Ceftazidime/Avibactam Plus Aztreonam Combination in a Patient with TTP Complicated by SARSCoV-2 Nosocomial Infection. Medicina (Kaunas, Lithuania). 2021 Apr; 57(5):. doi: 10.3390/medicina57050424. [PMID: 33924769]
  • Andrew Billnitzer, Peter W Kaplan. Generalized Periodic Discharges With Triphasic Morphology in the Setting of Aztreonam Neurotoxicity. Clinical EEG and neuroscience. 2021 Jan; 52(1):66-68. doi: 10.1177/1550059420917842. [PMID: 32401538]
  • Eleonora Camilleri, Niccolò Maggini, Matteo Piccica, Annarita Botta, Daniela Poli. A rare case of prothrombin time prolongation. Internal and emergency medicine. 2021 01; 16(1):237-239. doi: 10.1007/s11739-020-02408-x. [PMID: 32557092]
  • Edurne Peña-Mendizabal, Sergi Morais, Ángel Maquieira. Boosting the sensitivity of in vitroβ-lactam allergy diagnostic tests. Chemical communications (Cambridge, England). 2020 Oct; 56(80):11973-11976. doi: 10.1039/d0cc04903d. [PMID: 33033809]
  • Edurne Peña-Mendizabal, Sergi Morais, Ángel Maquieira. Neo-antigens for the serological diagnosis of IgE-mediated drug allergic reactions to antibiotics cephalosporin, carbapenem and monobactam. Scientific reports. 2020 09; 10(1):16037. doi: 10.1038/s41598-020-73109-w. [PMID: 32994501]
  • Ying Sun, Xueyuan Liao, Zhigang Huang, Yaliu Xie, Yanbin Liu, Cuicui Ma, Boguang Jiang, Li Zhang, Yuhang Yan, Guobo Li, Xingjun Cheng, Qi Yin, Charles Z Ding, Liang Shen, Jian Li, Shuhui Chen, Yuquan Wei, Zhenling Wang, Xiawei Wei. Therapeutic Effect and Mechanisms of the Novel Monosulfactam 0073. Antimicrobial agents and chemotherapy. 2020 09; 64(10):. doi: 10.1128/aac.00529-20. [PMID: 32718961]
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  • Edyta Konecka, Joanna Mokracka, Sylwia Krzymińska, Adam Kaznowski. Evaluation of The Pathogenic Potential of Insecticidal Serratia marcescens Strains to Humans. Polish journal of microbiology. 2019; 68(2):185-191. doi: 10.21307/pjm-2019-018. [PMID: 31257791]
  • Alan E Gross, Hongmei Xu, Diansong Zhou, Nidal Al-Huniti. Simplified Aztreonam Dosing in Patients with End-Stage Renal Disease: Results of a Monte Carlo Simulation. Antimicrobial agents and chemotherapy. 2018 11; 62(11):. doi: 10.1128/aac.01066-18. [PMID: 30150467]
  • Wenxia Zhang, Yan Guo, Jiayin Li, Yiyuan Zhang, Yang Yang, Dong Dong, Demei Zhu, Ping He, Fupin Hu. In vitro and in vivo bactericidal activity of ceftazidime-avibactam against Carbapenemase-producing Klebsiella pneumoniae. Antimicrobial resistance and infection control. 2018; 7(?):142. doi: 10.1186/s13756-018-0435-9. [PMID: 30479755]
  • Barry J Plant, Damian G Downey, Joe A Eustace, Cedric Gunaratnam, Charles S Haworth, Andrew M Jones, Edward F McKone, Daniel G Peckham, R Ian Ketchell, Diana Bilton. A treatment evaluator tool to monitor the real-world effectiveness of inhaled aztreonam lysine in cystic fibrosis. Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society. 2017 Nov; 16(6):695-701. doi: 10.1016/j.jcf.2017.02.006. [PMID: 28392014]
  • Yusuke Yamanaka, Akira Shimabukuro. Septic abortion presenting as a right lower trapezius abscess secondary to Bacteroides fragilis bacteraemia. BMJ case reports. 2017 Aug; 2017(?):. doi: 10.1136/bcr-2016-219135. [PMID: 28827296]
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