Amdinocillin (BioDeep_00000003139)

 

Secondary id: BioDeep_00000399327

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(2S,5R,6R)-6-[(Azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

化学式: C15H23N3O3S (325.1460048)
中文名称: 美西林
谱图信息: 最多检出来源 Homo sapiens(blood) 25.97%

分子结构信息

SMILES: CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)O)C
InChI: InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/t10-,11+,13-/m1/s1

描述信息

Amdinocillin is only found in individuals that have used or taken this drug. It is an amidinopenicillanic acid derivative with broad spectrum antibacterial action. It is poorly absorbed if given orally and is used in urinary infections and typhus. [PubChem]Amdinocillin is a stong and specific antagonist of Penicillin Binding Protein-2 (PBP 2). It is active against gram negative bacteria, preventing cell wall synthesis by inhibiting the activity of PBP2. PBP2 is a peptidoglycan elongation initiating enzyme. Peptidoglycan is a polymer of sugars and amino acids that is the main component of bacterial cell walls.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01C - Beta-lactam antibacterials, penicillins > J01CA - Penicillins with extended spectrum
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

9 个代谢物同义名

(2S,5R,6R)-6-[(Azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-[(Azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; Penicillin HX; Mecillinamum; Amdinocillin; Mecilinamo; Mecillinam; Coactin



数据库引用编号

16 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。



文献列表

  • André Birgy, Fouad Madhi, Camille Jung, Corinne Levy, Aurélie Cointe, Philippe Bidet, Claire Amaris Hobson, Stéphane Bechet, Elsa Sobral, Hoang Vuthien, Agnès Ferroni, Saïd Aberrane, Gaëlle Cuzon, Laetitia Beraud, Vincent Gajdos, Elise Launay, Didier Pinquier, Hervé Haas, Marie Desmarest, Marie-Aliette Dommergues, Robert Cohen, Stéphane Bonacorsi. Clavulanate combinations with mecillinam, cefixime or cefpodoxime against ESBL-producing Enterobacterales frequently associated with blaOXA-1 in a paediatric population with febrile urinary tract infections. The Journal of antimicrobial chemotherapy. 2021 10; 76(11):2839-2846. doi: 10.1093/jac/dkab289. [PMID: 34453533]
  • Mengyun Yin, Guoping Hu, Zhen Shen, Chengli Fang, Xuefei Zhang, Dan Li, Yohei Doi, Yu Zhang, Minggui Wang, Qinglan Guo. In Vivo Evolution of CTX-M-215, a Novel Narrow-Spectrum β-Lactamase in an Escherichia coli Clinical Isolate Conferring Resistance to Mecillinam. Antimicrobial agents and chemotherapy. 2020 10; 64(11):. doi: 10.1128/aac.00562-20. [PMID: 32868328]
  • Ilya Nikolaevich Zykov, Niels Frimodt-Møller, Lars Småbrekke, Arnfinn Sundsfjord, Ørjan Samuelsen. Efficacy of mecillinam against clinical multidrug-resistant Escherichia coli in a murine urinary tract infection model. International journal of antimicrobial agents. 2020 Feb; 55(2):105851. doi: 10.1016/j.ijantimicag.2019.11.008. [PMID: 31770624]
  • Karen Leth Nielsen, Katrine Hartung Hansen, Jesper Boye Nielsen, Jenny Dahl Knudsen, Kristian Schønning, Niels Frimodt-Møller, Frederik Boëtius Hertz, Filip Jansåker. Mutational change of CTX-M-15 to CTX-M-127 resulting in mecillinam resistant Escherichia coli during pivmecillinam treatment of a patient. MicrobiologyOpen. 2019 12; 8(12):e941. doi: 10.1002/mbo3.941. [PMID: 31573735]
  • 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]
  • Frieder Fuchs, Axel Hamprecht. Results from a Prospective In Vitro Study on the Mecillinam (Amdinocillin) Susceptibility of Enterobacterales. Antimicrobial agents and chemotherapy. 2019 04; 63(4):. doi: 10.1128/aac.02402-18. [PMID: 30917983]
  • Aurore Bousquet, Sarah Bugier, Sébastien Larréché, Christine Bigaillon, Philippe Weber, Hervé Delacour, Eric Valade, Dominique De Briel, Audrey Mérens. Clinical isolates of Escherichia coli solely resistant to mecillinam: prevalence and epidemiology. International journal of antimicrobial agents. 2018 Mar; 51(3):493-497. doi: 10.1016/j.ijantimicag.2017.11.001. [PMID: 29154843]
  • Elisabeth Thulin, Måns Thulin, Dan I Andersson. Reversion of High-level Mecillinam Resistance to Susceptibility in Escherichia coli During Growth in Urine. EBioMedicine. 2017 Sep; 23(?):111-118. doi: 10.1016/j.ebiom.2017.08.021. [PMID: 28855073]
  • Michael Kresken, Barbara Körber-Irrgang, Kurt G Naber. [In-vitro activity of mecillinam against urine isolates of Escherichia coli from outpatient departments in Germany]. Aktuelle Urologie. 2017 May; 48(3):243-247. doi: 10.1055/s-0043-102153. [PMID: 28427111]
  • C Duployez, C Loiez, C Cattoen, D Descamps, F Wallet, A Vachée. In vitro susceptibility to mecillinam of Escherichia coli strains isolated from the urine of pregnant women. Medecine et maladies infectieuses. 2016 Dec; 46(8):436-441. doi: 10.1016/j.medmal.2016.07.007. [PMID: 27609597]
  • Einar Nilsen, Marie Aasterød, Per Sandved Hustad, Anne Olaug Olsen. Mecillinam against genital Chlamydia trachomatis infection: a small-scale proof-of-concept study shows a low cure rate. The Journal of antimicrobial chemotherapy. 2016 08; 71(8):2270-2. doi: 10.1093/jac/dkw134. [PMID: 27165786]
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  • Tor J Monsen, Stig E Holm, Björn Magnus Ferry, Sven A Ferry. Mecillinam resistance and outcome of pivmecillinam treatment in uncomplicated lower urinary tract infection in women. APMIS : acta pathologica, microbiologica, et immunologica Scandinavica. 2014 Apr; 122(4):317-23. doi: 10.1111/apm.12147. [PMID: 24738161]
  • 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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  • Sławomir Chlabicz, Katarzyna Leszczynska, Witold Lukas, Laura Gualco, Giancarlo Schito, Kurt G Naber. [Uncomplicated lower urinary tract infections in females--clinical aspects, aetiology and antimicrobial resistance epidemiology. Results of the ARESC (Antimicrobial Resistance Epidemiological Survey on Cystitis) study in Poland and their implications for empiric therapy]. Przeglad epidemiologiczny. 2011; 65(2):345-51. doi: . [PMID: 21913487]
  • Eric Gomez, Martha Sanchez, Zonaira Gul, Carl Urban, Noriel Mariano, Robert H K Eng, David B Huang, Tom Chiang. Polymyxin Combination Therapy and the Use of Serum Bactericidal Titers in the Management of KPC-Producing Klebsiella pneumoniae Infections: A Report of 3 Cases. Case reports in medicine. 2011; 2011(?):659769. doi: 10.1155/2011/659769. [PMID: 22162703]
  • Lakshmiprasad Potluri, Aneta Karczmarek, Jolanda Verheul, Andre Piette, Jean-Marc Wilkin, Nadine Werth, Manuel Banzhaf, Waldemar Vollmer, Kevin D Young, Martine Nguyen-Distèche, Tanneke den Blaauwen. Septal and lateral wall localization of PBP5, the major D,D-carboxypeptidase of Escherichia coli, requires substrate recognition and membrane attachment. Molecular microbiology. 2010 Jul; 77(2):300-23. doi: 10.1111/j.1365-2958.2010.07205.x. [PMID: 20545860]
  • Heidi Lindbäck, Johan Lindbäck, Staffan Sylvan, Asa Melhus. Low frequency of antibiotic resistance among urine isolates of Escherichia coli in the community, despite a major hospital outbreak with Klebsiella pneumoniae producing CTX-M-15 in Uppsala County. Scandinavian journal of infectious diseases. 2010 Apr; 42(4):243-8. doi: 10.3109/00365540903470655. [PMID: 20085420]
  • F M E Wagenlehner, C Wagenlehner, O Savov, L Gualco, G Schito, K G Naber. [Clinical aspects and epidemiology of uncomplicated cystitis in women. German results of the ARESC Study]. Der Urologe. Ausg. A. 2010 Feb; 49(2):253-61. doi: 10.1007/s00120-009-2145-7. [PMID: 19943031]
  • Ioannis Katsarolis, Garyphallia Poulakou, Sofia Athanasia, Jenny Kourea-Kremastinou, Niki Lambri, Elias Karaiskos, Periklis Panagopoulos, Flora V Kontopidou, Dionysios Voutsinas, Georgios Koratzanis, Maria Kanellopoulou, Georgios Adamis, Helen Vagiakou, Pigi Perdikaki, Helen Giamarellou, Kyriaki Kanellakopoulou. Acute uncomplicated cystitis: from surveillance data to a rationale for empirical treatment. International journal of antimicrobial agents. 2010 Jan; 35(1):62-7. doi: 10.1016/j.ijantimicag.2009.08.018. [PMID: 19906513]
  • Cenk Aypak, Adalet Altunsoy, Nurşen Düzgün. Empiric antibiotic therapy in acute uncomplicated urinary tract infections and fluoroquinolone resistance: a prospective observational study. Annals of clinical microbiology and antimicrobials. 2009 Oct; 8(?):27. doi: 10.1186/1476-0711-8-27. [PMID: 19852849]
  • J M Hansen, H Fjeldsøe-Nielsen, S Sulim, M Kemp, J J Christensen. Actinomyces species: A danish survey on human infections and microbiological characteristics. The open microbiology journal. 2009 Jul; 3(?):113-20. doi: 10.2174/1874285800903010113. [PMID: 19657460]
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  • Kurt G Naber, Giancarlo Schito, Henry Botto, Juan Palou, Teresita Mazzei. Surveillance study in Europe and Brazil on clinical aspects and Antimicrobial Resistance Epidemiology in Females with Cystitis (ARESC): implications for empiric therapy. European urology. 2008 Nov; 54(5):1164-75. doi: 10.1016/j.eururo.2008.05.010. [PMID: 18511178]
  • Amee R Manges, Helen Tabor, Patricia Tellis, Caroline Vincent, Pierre-Paul Tellier. Endemic and epidemic lineages of Escherichia coli that cause urinary tract infections. Emerging infectious diseases. 2008 Oct; 14(10):1575-83. doi: 10.3201/eid1410.080102. [PMID: 18826822]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Tamimount Mohammadi, Aneta Karczmarek, Muriel Crouvoisier, Ahmed Bouhss, Dominique Mengin-Lecreulx, Tanneke den Blaauwen. The essential peptidoglycan glycosyltransferase MurG forms a complex with proteins involved in lateral envelope growth as well as with proteins involved in cell division in Escherichia coli. Molecular microbiology. 2007 Aug; 65(4):1106-21. doi: 10.1111/j.1365-2958.2007.05851.x. [PMID: 17640276]
  • M I Issack, H Y Yee Kin Tet, P Morlat. Antimicrobial resistance among enterobacteriaceae causing uncomplicated urinary tract infections in Mauritius: consequences of past misuse of antibiotics. Journal of chemotherapy (Florence, Italy). 2007 Apr; 19(2):222-5. doi: 10.1179/joc.2007.19.2.222. [PMID: 17434833]
  • Hilde K Skudal, Nils Grude, Bjørn-Erik Kristiansen. [Increasing antibiotic resistance in urinary tract infections]. Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke. 2006 Apr; 126(8):1058-60. doi: NULL. [PMID: 16619066]
  • Nils Grude, Yngvar Tveten, Andrew Jenkins, Bjørn-Erik Kristiansen. Uncomplicated urinary tract infections. Bacterial findings and efficacy of empirical antibacterial treatment. Scandinavian journal of primary health care. 2005 Jun; 23(2):115-9. doi: 10.1080/02813430510015287. [PMID: 16036551]
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  • M B Kerrn, C Struve, J Blom, N Frimodt-Møller, K A Krogfelt. Intracellular persistence of Escherichia coli in urinary bladders from mecillinam-treated mice. The Journal of antimicrobial chemotherapy. 2005 Mar; 55(3):383-6. doi: 10.1093/jac/dki002. [PMID: 15681580]
  • Robert Skov, Niels Frimodt-Moller, Paul Menday, Frank Espersen. Susceptibility testing of urinary isolates of Escherichia coli to mecillinam using NCCLS methodology. International journal of antimicrobial agents. 2005 Mar; 25(3):198-204. doi: 10.1016/j.ijantimicag.2004.08.014. [PMID: 15737512]
  • Bjørn Blomberg, Bjørg Evjen Olsen, Sven Gudmund Hinderaker, Nina Langeland, Petro Gasheka, Roland Jureen, Gunnar Kvåle, Tore Midtvedt. Antimicrobial resistance in urinary bacterial isolates from pregnant women in rural Tanzania: implications for public health. Scandinavian journal of infectious diseases. 2005; 37(4):262-8. doi: 10.1080/00365540410021045. [PMID: 15871165]
  • M B Kerrn, N Frimodt-Møller, F Espersen. Urinary concentrations and urine ex-vivo effect of mecillinam and sulphamethizole. Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases. 2004 Jan; 10(1):54-61. doi: 10.1111/j.1469-0691.2004.00737.x. [PMID: 14706087]
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