Cefamandole (BioDeep_00000001865)

 

Secondary id: BioDeep_00001868028

human metabolite blood metabolite Chemicals and Drugs Antibiotics


代谢物信息卡片


(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-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

化学式: C18H18N6O5S2 (462.0780058)
中文名称: 头孢孟多, 头孢孟多锂
谱图信息: 最多检出来源 Homo sapiens(blood) 16.67%

分子结构信息

SMILES: CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(C4=CC=CC=C4)O)SC2)C(=O)O
InChI: InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1

描述信息

Cefamandole is only found in individuals that have used or taken this drug. It is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.Like all beta-lactam antibiotics, cefamandole 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; it is possible that cefamandole interferes with an autolysin inhibitor.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01D - Other beta-lactam antibacterials > J01DC - Second-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

18 个代谢物同义名

(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-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-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; 7-[(2-hydroxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid; (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylate; Cefamandole nafate; Compound 83405; L-Cefamandole; Cefamandolum; Cephamandole; Cefamandole; Cefamandol; Cephadole; Cefadole; CMD



数据库引用编号

19 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)

2 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

  • Qian Wang, Xuyang Liu, Ming Su, Zhihong Shi, Hanwen Sun. Study on the interaction characteristics of cefamandole with bovine serum albumin by spectroscopic technique. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2015 Feb; 136 Pt B(?):321-6. doi: 10.1016/j.saa.2014.08.145. [PMID: 25448935]
  • 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]
  • 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]
  • Dirk R de Waart, Koen van de Wetering, Cindy Kunne, Suzanne Duijst, Coen C Paulusma, Ronald P J Oude Elferink. Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug metabolism and disposition: the biological fate of chemicals. 2012 Mar; 40(3):515-21. doi: 10.1124/dmd.111.041731. [PMID: 22166395]
  • Theodoros Karaiskos, Periklis Tomos, Irene Asouhidou, Nikolaos Nikiteas, Theodoros Kontakiotis, Apostolos Papalois. Oxidative and pre-inflammatory stress in wedge resection of pulmonary parenchyma using the radiofrequency ablation technique in a swine model. Journal of cardiothoracic surgery. 2012 Jan; 7(?):7. doi: 10.1186/1749-8090-7-7. [PMID: 22260184]
  • Manthena V S Varma, Bo Feng, R Scott Obach, Matthew D Troutman, Jonathan Chupka, Howard R Miller, Ayman El-Kattan. Physicochemical determinants of human renal clearance. Journal of medicinal chemistry. 2009 Aug; 52(15):4844-52. doi: 10.1021/jm900403j. [PMID: 19445515]
  • Fernanda Crisante, Iolanda Francolini, Mariangela Bellusci, Andrea Martinelli, Lucio D'Ilario, Antonella Piozzi. Antibiotic delivery polyurethanes containing albumin and polyallylamine nanoparticles. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2009 Mar; 36(4-5):555-64. doi: 10.1016/j.ejps.2008.12.006. [PMID: 19136061]
  • Oh Yoen Kim, Antoine Monsel, Michèle Bertrand, Jean-Marc Cavaillon, Pierre Coriat, Minou Adib-Conquy. Translocation of bacterial NOD2 agonist and its link with inflammation. Critical care (London, England). 2009; 13(4):R124. doi: 10.1186/cc7980. [PMID: 19638210]
  • Ritu Aggarwal, Uma Chaudhary, Rama Sikka. Detection of Extended Spectrum β-lactamase Production Among Uropathogens. Journal of laboratory physicians. 2009 Jan; 1(1):7-10. doi: 10.4103/0974-2727.44423. [PMID: 21938241]
  • 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]
  • Yukio Kato, Seiko Takahara, Sayaka Kato, Yoshiyuki Kubo, Yoshimichi Sai, Ikumi Tamai, Hikaru Yabuuchi, Akira Tsuji. Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jun; 36(6):1088-96. doi: 10.1124/dmd.107.019125. [PMID: 18339814]
  • N Abo El-Maali, A H Osman, A A M Aly, G A A Al-Hazmi. Voltammetric analysis of Cu (II), Cd (II) and Zn (II) complexes and their cyclic voltammetry with several cephalosporin antibiotics. Bioelectrochemistry (Amsterdam, Netherlands). 2005 Feb; 65(2):95-104. doi: 10.1016/j.bioelechem.2004.09.002. [PMID: 15713559]
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  • J Berkhout, L G Visser, P J van den Broek, J A M van de Klundert, H Mattie. Clinical pharmacokinetics of cefamandole and ceftazidime administered by continuous intravenous infusion. Antimicrobial agents and chemotherapy. 2003 Jun; 47(6):1862-6. doi: 10.1128/aac.47.6.1862-1866.2003. [PMID: 12760859]
  • Suparat Khamdang, Michio Takeda, Ellappan Babu, Rie Noshiro, Maristela Lika Onozato, Akihiro Tojo, Atsushi Enomoto, Xiu-Lin Huang, Shinichi Narikawa, Naohiko Anzai, Pawinee Piyachaturawat, Hitoshi Endou. Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. European journal of pharmacology. 2003 Mar; 465(1-2):1-7. doi: 10.1016/s0014-2999(03)01381-5. [PMID: 12650826]
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  • Michio Takeda, Ellappan Babu, Shinichi Narikawa, Hitoshi Endou. Interaction of human organic anion transporters with various cephalosporin antibiotics. European journal of pharmacology. 2002 Mar; 438(3):137-42. doi: 10.1016/s0014-2999(02)01306-7. [PMID: 11909604]
  • Kyu Yong Jung, Michio Takeda, Minoru Shimoda, Shinichi Narikawa, Akihiro Tojo, Do Kyung Kim, Arthit Chairoungdua, Bong Kyu Choi, Hiroyuki Kusuhara, Yuichi Sugiyama, Takashi Sekine, Hitoshi Endou. Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life sciences. 2002 Mar; 70(16):1861-74. doi: 10.1016/s0024-3205(02)01500-x. [PMID: 12005172]
  • M G Dehne, J Mühling, A Sablotzki, H Nopens, G Hempelmann. Pharmacokinetics of antibiotic prophylaxis in major orthopedic surgery and blood-saving techniques. Orthopedics. 2001 Jul; 24(7):665-9. doi: 10.3928/0147-7447-20010701-15. [PMID: 11478553]
  • A M Lovering, T R Walsh, G C Bannister, A P MacGowan. The penetration of ceftriaxone and cefamandole into bone, fat and haematoma and relevance of serum protein binding to their penetration into bone. The Journal of antimicrobial chemotherapy. 2001 Apr; 47(4):483-6. doi: 10.1093/jac/47.4.483. [PMID: 11266427]
  • A Colau, J C Lucet, P Rufat, H Botto, G Benoit, A Jardin. Incidence and risk factors of bacteriuria after transurethral resection of the prostate. European urology. 2001 Mar; 39(3):272-6. doi: 10.1159/000052452. [PMID: 11275718]
  • K I Savitskaia, M F Trapeznikova, M V Nesterova, E V Rusanova. [Monitoring of uropathogens and their susceptibility to antibiotics]. Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic]. 2001; 46(6):12-20. doi: NULL. [PMID: 11573319]
  • J Vouillamoz, J M Entenza, C Féger, M P Glauser, P Moreillon. Quinupristin-dalfopristin combined with beta-lactams for treatment of experimental endocarditis due to Staphylococcus aureus constitutively resistant to macrolide-lincosamide-streptogramin B antibiotics. Antimicrobial agents and chemotherapy. 2000 Jul; 44(7):1789-95. doi: 10.1128/aac.44.7.1789-1795.2000. [PMID: 10858332]
  • K A Zsirka, I Pulay, M Arr, C Williams, L Flautner. [Antibiotic prophylaxis for high risk patients undergoing cholecystectomy]. Magyar sebeszet. 2000 Jun; 53(3):104-8. doi: NULL. [PMID: 11299497]
  • S Jariyawat, T Sekine, M Takeda, N Apiwattanakul, Y Kanai, S Sophasan, H Endou. The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. The Journal of pharmacology and experimental therapeutics. 1999 Aug; 290(2):672-7. doi: . [PMID: 10411577]
  • M Bergeret, J Raymond. In-vitro bactericidal activity of cefpirome and cefamandole in combination with glycopeptides against methicillin-resistant Staphylococcus aureus. The Journal of antimicrobial chemotherapy. 1999 Feb; 43(2):291-4. doi: 10.1093/jac/43.2.291. [PMID: 11252338]
  • N Thomakos, S Maraki, T Liakakos, A Macheras, S Kanavaki, E Marinis, M Sehas, A N Margioris, G Samonis. Effect of cefamandole, cefuroxime and cefoxitin on yeast fecal flora of surgical patients. Chemotherapy. 1998 Sep; 44(5):324-7. doi: 10.1159/000007130. [PMID: 9732147]
  • Y A Que, J M Entenza, P Francioli, P Moreillon. The impact of penicillinase on cefamandole treatment and prophylaxis of experimental endocarditis due to methicillin-resistant Staphylococcus aureus. The Journal of infectious diseases. 1998 Jan; 177(1):146-54. doi: 10.1086/513805. [PMID: 9419181]
  • M G el-Sayed, M R Hassanin, M H Hafez, A A el-Komy, A Mohamed. Some pharmacodynamic and biochemical aspects of cefamandole. DTW. Deutsche tierarztliche Wochenschrift. 1997 Nov; 104(11):481-7. doi: NULL. [PMID: 9429324]
  • T Menges, A Sablotzki, I Welters, R M Wagner, B Zickmann, S Gronau, G Demirbelek, G Görlach, G Hempelmann. Concentration of cefamandole in plasma and tissues of patients undergoing cardiac surgery: the influence of different cefamandole dosage. Journal of cardiothoracic and vascular anesthesia. 1997 Aug; 11(5):565-70. doi: 10.1016/s1053-0770(97)90005-7. [PMID: 9263086]
  • Y Lin, W J Leach, W S Ammons. Synergistic effect of a recombinant N-terminal fragment of bactericidal/permeability-increasing protein and cefamandole in treatment of rabbit gram-negative sepsis. Antimicrobial agents and chemotherapy. 1996 Jan; 40(1):65-9. doi: 10.1128/aac.40.1.65. [PMID: 8787881]
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  • T Menges, J Boldt, K Scholz, R M Wagner, R Ruwoldt, I Welters, G Hempelmann. [The effect of different autotransfusion procedures on the antibiotic picture. A study on cephalosporin cefamandole]. Der Anaesthesist. 1993 Aug; 42(8):509-15. doi: NULL. [PMID: 8368471]
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  • J Field, J Webb, G C Bannister, A M Lovering, D S Reeves. Comparison of three methods of antibiotic prophylaxis in knee arthroplasty. The Journal of arthroplasty. 1992 Mar; 7(1):17-9. doi: 10.1016/0883-5403(92)90026-m. [PMID: 1564460]
  • R L Harris, J H Yuk, C Cribari, D Jernigan, J S Coselli, H J Safi, E S Crawford. Cefamandole levels during thoracoabdominal aortic aneurysm surgery. Journal of vascular surgery. 1991 Nov; 14(5):668-72. doi: 10.1067/mva.1991.30275. [PMID: 1942376]
  • J C Hall, J L Hall, K Christiansen. A comparison of the roles of cefamandole and ceftriaxone in abdominal surgery. Archives of surgery (Chicago, Ill. : 1960). 1991 Apr; 126(4):512-6. doi: 10.1001/archsurg.1991.01410280116019. [PMID: 1901204]
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