Nafcillin (BioDeep_00000002189)

 

Secondary id: BioDeep_00001867824

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

化学式: C21H22N2O5S (414.12493620000004)
中文名称: 萘夫西林
谱图信息: 最多检出来源 Homo sapiens(blood) 98.51%

分子结构信息

SMILES: CCOC1=C(C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)C2=CC=CC=C2C=C1
InChI: InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1

描述信息

Nafcillin is only found in individuals that have used or taken this drug. It is a semi-synthetic antibiotic related to penicillin. [PubChem]Penicillinase-resistant penicillins exert a bactericidal action against penicillin-susceptible microorganisms during the state of active multiplication. All penicillins inhibit the biosynthesis of the bacterial cell wall.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01C - Beta-lactam antibacterials, penicillins > J01CF - Beta-lactamase resistant penicillins
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
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3206

同义名列表

25 个代谢物同义名

(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-[(2-Ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,5R,6R)-6-[(2-Ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,5R,6R)-6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 6-(2-Ethoxy-1-naphthamido)penicillanic acid; 6-(2-Ethoxy-1-naphthamido)penicillanate; Nafcillin, monosodium salt, anhydrous; (2-Ethoxy-1-naphthalenyl)penicillin; (2-Ethoxy-1-naphthyl)penicillin; Nafcillin sodium salt; Naphthamidopenicillin; Sodium, nafcillin; Nafcillin, sodium; Sodium nafcillin; nafcillin sodium; SCHEMBL6462735; Nafcillinum; Nafcilline; Naphcillin; nafcillin; Nafcilina; Nafcil



数据库引用编号

37 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

  • Lynn Chan, Noreen H Chan-Tompkins, James Como, Anthony J Guarascio. Retrospective Analysis of Adverse Drug Events Between Nafcillin Versus Cefazolin for Treatment of Methicillin-Susceptible Staphylococcus aureus Infections. The Annals of pharmacotherapy. 2020 07; 54(7):662-668. doi: 10.1177/1060028019897267. [PMID: 31888347]
  • Tristan T Timbrook, Lydia McKay, Jesse D Sutton, Emily S Spivak. Disproportionality Analysis of Safety with Nafcillin and Oxacillin with the FDA Adverse Event Reporting System (FAERS). Antimicrobial agents and chemotherapy. 2020 02; 64(3):. doi: 10.1128/aac.01818-19. [PMID: 31844017]
  • Marguerite L Monogue, Jessica K Ortwine, Wenjing Wei, Khalid Eljaaly, Kavita P Bhavan. Nafcillin versus cefazolin for the treatment of methicillin-susceptible Staphylococcus aureus bacteremia. Journal of infection and public health. 2018 Sep; 11(5):727-731. doi: 10.1016/j.jiph.2018.02.004. [PMID: 29526442]
  • Corey C Burrelli, Eleanor K Broadbent, Alice Margulis, Graham M Snyder, Howard S Gold, Christopher McCoy, Monica V Mahoney, Elizabeth B Hirsch. Does the Beta-Lactam Matter? Nafcillin versus Cefazolin for Methicillin-Susceptible Staphylococcus aureus Bloodstream Infections. Chemotherapy. 2018; 63(6):345-351. doi: 10.1159/000499033. [PMID: 30965335]
  • Brady S Moffett, Jennifer Morris, Charissa Kam, Marianne Galati, Ankhi Dutta, Ayse Akcan-Arikan. Vancomycin associated acute kidney injury in pediatric patients. PloS one. 2018; 13(10):e0202439. doi: 10.1371/journal.pone.0202439. [PMID: 30281600]
  • Russell J Benefield, Brian C Barker, Christopher M Gast, Donald P Alexander. Patient Variables Associated with Nafcillin Plasma Concentrations and Toxicity. Pharmacotherapy. 2016 09; 36(9):994-1002. doi: 10.1002/phar.1805. [PMID: 27485941]
  • J Alexander Viehman, Louise-Marie Oleksiuk, Kathleen R Sheridan, Karin E Byers, Peimei He, Bonnie A Falcione, Ryan K Shields. Adverse Events Lead to Drug Discontinuation More Commonly among Patients Who Receive Nafcillin than among Those Who Receive Oxacillin. Antimicrobial agents and chemotherapy. 2016 05; 60(5):3090-5. doi: 10.1128/aac.03122-15. [PMID: 26976858]
  • Timothy John Barreiro, Denis D Asiimwe, David Gemmel, Patrick Brine. Catastrophic chest pain: blinded by cardiopulmonary disease. BMJ case reports. 2015 Jul; 2015(?):. doi: 10.1136/bcr-2015-209928. [PMID: 26135489]
  • 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]
  • Craig B Whitman, Melissa J Wike. Possible case of nafcillin-induced acute interstitial nephritis. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists. 2012 Jun; 69(12):1049-53. doi: 10.2146/ajhp110357. [PMID: 22644982]
  • 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]
  • Mine-Ok Chang, Eun Sil Koh, Min Ju Kim, Seok Joon Shin, Cheol Whee Park, Yoon Sik Chang, Sungjin Chung. Nafcillin-induced bullous skin eruption with granulocytopenia in a patient with end-stage renal disease. Internal medicine (Tokyo, Japan). 2012; 51(3):287-9. doi: 10.2169/internalmedicine.51.6091. [PMID: 22293804]
  • Mohan Pammi, Rong Liang, John M Hicks, Jim Barrish, James Versalovic. Farnesol decreases biofilms of Staphylococcus epidermidis and exhibits synergy with nafcillin and vancomycin. Pediatric research. 2011 Dec; 70(6):578-83. doi: 10.1203/pdr.0b013e318232a984. [PMID: 21857375]
  • Hsi-Ya Huang, Wan-Ling Liu, Brenda Singco, Shih-Huan Hsieh, Yung-Han Shih. On-line concentration sample stacking coupled with water-in-oil microemulsion electrokinetic chromatography. Journal of chromatography. A. 2011 Oct; 1218(42):7663-9. doi: 10.1016/j.chroma.2011.05.091. [PMID: 21689819]
  • Volker Mai, Christopher Michael Young, Maria Ukhanova, Xiaoyu Wang, Yijun Sun, George Casella, Douglas Theriaque, Nan Li, Renu Sharma, Mark Hudak, Josef Neu. Fecal microbiota in premature infants prior to necrotizing enterocolitis. PloS one. 2011; 6(6):e20647. doi: 10.1371/journal.pone.0020647. [PMID: 21674011]
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  • M Shawn Riser, Christopher M Bland, Celeste N Rudisill, P Brandon Bookstaver. Cerebrospinal fluid penetration of high-dose daptomycin in suspected Staphylococcus aureus meningitis. The Annals of pharmacotherapy. 2010 Nov; 44(11):1832-5. doi: 10.1345/aph.1p307. [PMID: 20959502]
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  • Frédérique van Holthoon, Patrick P J Mulder, Eric O van Bennekom, Henri Heskamp, Tina Zuidema, Hans J A van Rhijn. Quantitative analysis of penicillins in porcine tissues, milk and animal feed using derivatisation with piperidine and stable isotope dilution liquid chromatography tandem mass spectrometry. Analytical and bioanalytical chemistry. 2010 Apr; 396(8):3027-40. doi: 10.1007/s00216-010-3523-0. [PMID: 20186537]
  • Shih-Huan Hsieh, Hsi-Ya Huang, Szetsen Lee. Determination of eight penicillin antibiotics in pharmaceuticals, milk and porcine tissues by nano-liquid chromatography. Journal of chromatography. A. 2009 Oct; 1216(43):7186-94. doi: 10.1016/j.chroma.2009.05.080. [PMID: 19523644]
  • 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]
  • Katerina Mastovska, Alan R Lightfield. Streamlining methodology for the multiresidue analysis of beta-lactam antibiotics in bovine kidney using liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2008 Aug; 1202(2):118-23. doi: 10.1016/j.chroma.2008.07.009. [PMID: 18656204]
  • A A M Stolker, P Rutgers, E Oosterink, J J P Lasaroms, R J B Peters, J A van Rhijn, M W F Nielen. Comprehensive screening and quantification of veterinary drugs in milk using UPLC-ToF-MS. Analytical and bioanalytical chemistry. 2008 Jul; 391(6):2309-22. doi: 10.1007/s00216-008-2168-8. [PMID: 18491081]
  • 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]
  • Tobin Hoppes, Marios Prikis, Alan Segal. Four cases of nafcillin-associated acute interstitial nephritis in one institution. Nature clinical practice. Nephrology. 2007 Aug; 3(8):456-61. doi: 10.1038/ncpneph0561. [PMID: 17653125]
  • Javier L Urraca, María C Moreno-Bondi, Guillermo Orellana, Börje Sellergren, Andrew J Hall. Molecularly imprinted polymers as antibody mimics in automated on-line fluorescent competitive assays. Analytical chemistry. 2007 Jul; 79(13):4915-23. doi: 10.1021/ac070277i. [PMID: 17550229]
  • Caroline Kusuma, Anna Jadanova, Tanya Chanturiya, John F Kokai-Kun. Lysostaphin-resistant variants of Staphylococcus aureus demonstrate reduced fitness in vitro and in vivo. Antimicrobial agents and chemotherapy. 2007 Feb; 51(2):475-82. doi: 10.1128/aac.00786-06. [PMID: 17101683]
  • Stephen P Fitzgerald, Nuala O'Loan, Robert I Mcconnell, El Ouard Benchikh, Nicola E Kane. Stable competitive enzyme-linked immunosorbent assay kit for rapid measurement of 11 active beta-lactams in milk, tissue, urine, and serum. Journal of AOAC International. 2007 Jan; 90(1):334-42. doi: . [PMID: 17373465]
  • Tomomi Goto, Yuko Ito, Sadaji Yamada, Hiroshi Matsumoto, Hisao Oka. High-throughput analysis of tetracycline and penicillin antibiotics in animal tissues using electrospray tandem mass spectrometry with selected reaction monitoring transition. Journal of chromatography. A. 2005 Dec; 1100(2):193-9. doi: 10.1016/j.chroma.2005.09.056. [PMID: 16214156]
  • Robin L Trotman, John C Williamson, D Matthew Shoemaker, William L Salzer. Antibiotic dosing in critically ill adult patients receiving continuous renal replacement therapy. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America. 2005 Oct; 41(8):1159-66. doi: 10.1086/444500. [PMID: 16163635]
  • Yuko Ito, Tomomi Goto, Hisao Oka, Hiroshi Matsumoto, Kazue Takeba. Application of ion-exchange cartridge clean-up in food analysis. VI. Determination of six penicillins in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry. Journal of chromatography. A. 2004 Jul; 1042(1-2):107-11. doi: 10.1016/j.chroma.2004.05.057. [PMID: 15296394]
  • A Fernández-González, R Badía Laíño, M E Diaz-García, L Guardia, A Viale. Assessment of molecularly imprinted sol-gel materials for selective room temperature phosphorescence recognition of nafcillin. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 May; 804(1):247-54. doi: 10.1016/j.jchromb.2003.12.030. [PMID: 15093178]
  • Pekka Suomalainen, Christoffer Johans, Tim Söderlund, Paavo K J Kinnunen. Surface activity profiling of drugs applied to the prediction of blood-brain barrier permeability. Journal of medicinal chemistry. 2004 Mar; 47(7):1783-8. doi: 10.1021/jm0309001. [PMID: 15027870]
  • C C Lang, S K Jamal, Z Mohamed, M R Mustafa, A M Mustafa, T C Lee. Evidence of an interaction between nifedipine and nafcillin in humans. British journal of clinical pharmacology. 2003 Jun; 55(6):588-90. doi: 10.1046/j.1365-2125.2003.01789.x. [PMID: 12814453]
  • Z Zhao, B A Baldo, K W Baumgart, D F Mallon. Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. Journal of molecular recognition : JMR. 2001 Sep; 14(5):300-7. doi: 10.1002/jmr.541. [PMID: 11746950]
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  • M E Shirtliff, J H Calhoun, J T Mader. Comparative evaluation of oral levofloxacin and parenteral nafcillin in the treatment of experimental methicillin-susceptible Staphylococcus aureus osteomyelitis in rabbits. The Journal of antimicrobial chemotherapy. 2001 Aug; 48(2):253-8. doi: 10.1093/jac/48.2.253. [PMID: 11481297]
  • Y Ito, Y Ikai, H Oka, H Matsumoto, Y Miyazaki, K Takeba, H Nagase. Application of ion-exchange cartridge clean-up in food analysis IV. Confirmatory assay of benzylpenicillin, phenoxymethylpenicillin, oxacillin, cloxacillin, nafcillin and dicloxacillin, in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry. Journal of chromatography. A. 2001 Mar; 911(2):217-23. doi: 10.1016/s0021-9673(01)00512-x. [PMID: 11293583]
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  • L K Sørensen, L K Snor, T Elkaer, H Hansen. Simultaneous determination of seven penicillins in muscle, liver and kidney tissues from cattle and pigs by a multiresidue high-performance liquid chromatographic method. Journal of chromatography. B, Biomedical sciences and applications. 1999 Nov; 734(2):307-18. doi: 10.1016/s0378-4347(99)00389-8. [PMID: 10595728]
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  • H Nikaido, M Basina, V Nguyen, E Y Rosenberg. Multidrug efflux pump AcrAB of Salmonella typhimurium excretes only those beta-lactam antibiotics containing lipophilic side chains. Journal of bacteriology. 1998 Sep; 180(17):4686-92. doi: 10.1128/jb.180.17.4686-4692.1998. [PMID: 9721312]
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