Cephapirin (BioDeep_00000002204)

 

Secondary id: BioDeep_00001867740

human metabolite Endogenous blood metabolite


代谢物信息卡片


(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

化学式: C17H17N3O6S2 (423.0558742)
中文名称: 头孢匹林
谱图信息: 最多检出来源 Homo sapiens(blood) 14.93%

分子结构信息

SMILES: CC(=O)OCC1=C(C(=O)O)N2C(=O)C(NC(=O)CSc3ccncc3)C2SC1
InChI: InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1

描述信息

Cephapirin is an injectable, first-generation cephalosporin antibiotic that has a wide spectrum of activity against gram-positive and gram-negative organisms. The bactericidal activity of cephapirin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cephapirin is more resistant to beta-lactamases than the penicillins, and therefore is effective against staphylococci, with the exception of methicillin-resistant staphylococci. Cephapirin is FDA approved for use in food-producing animals, especially dairy cattle. Cephapirin is used for the treatment of mastitis in cows. Production for use in humans has been discontinued in the United States. It is marketed under the trade name Cefadyl.
Active against gram-positive and -negative bacteria (vet. use). FDA approved for use in food producing animals, especies dairy cattle. It is used for the treatment of mastitis in cows
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01D - Other beta-lactam antibacterials > J01DB - First-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

29 个代谢物同义名

(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulphanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; Bristol-myers squibb brand OF cephapirin sodium; Bristol-myers brand OF cephapirin sodium; Apothecon brand OF cephapirin sodium; Salt, cephapirin monosodium; Monosodium salt, cephapirin; Cephapirin monosodium salt; Cephapirin, sodium; Cephapirin sodium; Sodium cephapirin; Cephapirine; Cefapirinum; Brisfirina; Cefapirine; Cefapirina; Céfaloject; Cephapirin; Metricure; BL p 1322; Cefapirin; BL-p 1322; cephaprin; Cefaprin; Cefadyl; CEPR



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)

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)

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

  • Valérie Menoud, Mirjam Holinger, Sandra Graf-Schiller, Philipp Mayer, Luc Gerber, Michael Walkenhorst, Gaby Hirsbrunner. Comparison between intrauterine application of an antibiotic and an herbal product to treat clinical endometritis in dairy cattle - A randomized multicentre field study. Research in veterinary science. 2024 Jun; 172(?):105250. doi: 10.1016/j.rvsc.2024.105250. [PMID: 38599065]
  • Meng M Li, Partha Ray, Christy Teets, Amy Pruden, Kang Xia, Katharine F Knowlton. Short communication: Increasing temperature and pH can facilitate reductions of cephapirin and antibiotic resistance genes in dairy manure slurries. Journal of dairy science. 2020 Mar; 103(3):2877-2882. doi: 10.3168/jds.2019-17453. [PMID: 31954579]
  • Ravi Kanth Bhamidipati, Ramesh Mullangi, Nuggehally R Srinivas. Interspecies scaling of urinary excretory amounts of nine drugs belonging to different therapeutic areas with diverse chemical structures - accurate prediction of the human urinary excretory amounts. Xenobiotica; the fate of foreign compounds in biological systems. 2017 Feb; 47(2):112-118. doi: 10.3109/00498254.2016.1166290. [PMID: 27093131]
  • Partha Ray, Katharine F Knowlton, Chao Shang, Kang Xia. Development and validation of a UPLC-MS/MS method to monitor cephapirin excretion in dairy cows following intramammary infusion. PloS one. 2014; 9(11):e112343. doi: 10.1371/journal.pone.0112343. [PMID: 25375097]
  • K Hausler, S M Godden, M J Schneider, A R Lightfield, M Bulthaus, D Haines. Hot topic: investigating the risk of violative meat residues in bob veal calves fed colostrum from cows treated at dry-off with cephapirin benzathine. Journal of dairy science. 2013 Apr; 96(4):2349-2355. doi: 10.3168/jds.2012-5891. [PMID: 23415519]
  • Shuyu Xie, Fenghua Wang, Yan Wang, Luyan Zhu, Zhao Dong, Xiaofang Wang, Xihe Li, Wenzhong Zhou. Acute toxicity study of tilmicosin-loaded hydrogenated castor oil-solid lipid nanoparticles. Particle and fibre toxicology. 2011 Nov; 8(?):33. doi: 10.1186/1743-8977-8-33. [PMID: 22098626]
  • Min Kyung Kim, Tae Ho Lee, Joon Hyuk Suh, Han Young Eom, Jung Won Min, Hyesun Yeom, Unyong Kim, Hyung Joon Jung, Kyung Hoi Cha, Yong Seok Choi, Jeong-Rok Youm, Sang Beom Han. Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of goserelin in rabbit plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Aug; 878(24):2235-42. doi: 10.1016/j.jchromb.2010.06.031. [PMID: 20655813]
  • Bjorn J A Berendsen, Martien L Essers, Patrick P J Mulder, Gerard D van Bruchem, Arjen Lommen, Wendy M van Overbeek, Linda A A M Stolker. Newly identified degradation products of ceftiofur and cephapirin impact the analytical approach for quantitative analysis of kidney. Journal of chromatography. A. 2009 Nov; 1216(46):8177-86. doi: 10.1016/j.chroma.2009.04.003. [PMID: 19406407]
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  • 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]
  • Petra Luckner, Matthias Brandsch. Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2005 Jan; 59(1):17-24. doi: 10.1016/j.ejpb.2004.07.008. [PMID: 15567297]
  • Eric Brouillette, Gilles Grondin, Céline Lefebvre, Brian G Talbot, François Malouin. Mouse mastitis model of infection for antimicrobial compound efficacy studies against intracellular and extracellular forms of Staphylococcus aureus. Veterinary microbiology. 2004 Aug; 101(4):253-62. doi: 10.1016/j.vetmic.2004.04.008. [PMID: 15261998]
  • Shun-Lin Li, Hua Tan, Yue-Mao Shen, Kazuyoshi Kawazoe, Xiao-Jiang Hao. A pair of new C-21 steroidal glycoside epimers from the roots of Cynanchum paniculatum. Journal of natural products. 2004 Jan; 67(1):82-4. doi: 10.1021/np034013c. [PMID: 14738392]
  • Famei Li, Dawei Zhou, Xingjie Guo. Study on the protein binding of ketoprofen using capillary electrophoresis frontal analysis compared with liquid chromatography frontal analysis. Journal of chromatographic science. 2003 Mar; 41(3):137-41. doi: 10.1093/chromsci/41.3.137. [PMID: 12725696]
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  • Clifton K Fagerquist, Alan R Lightfield. Confirmatory analysis of beta-lactam antibiotics in kidney tissue by liquid chromatography/electrospray ionization selective reaction monitoring ion trap tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2003; 17(7):660-71. doi: 10.1002/rcm.964. [PMID: 12661018]
  • James W Furbee, Omar Francone, John S Parks. In vivo contribution of LCAT to apolipoprotein B lipoprotein cholesteryl esters in LDL receptor and apolipoprotein E knockout mice. Journal of lipid research. 2002 Mar; 43(3):428-37. doi: . [PMID: 11893779]
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  • W A Moats, K L Anderson, J E Rushing, S Buckley. Conversion of cephapirin to deacetylcephapirin in milk and tissues of treated animals. Journal of agricultural and food chemistry. 2000 Feb; 48(2):498-502. doi: 10.1021/jf990638y. [PMID: 10691664]
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