Oxacillin (BioDeep_00000002190)

 

Secondary id: BioDeep_00001868049

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


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

化学式: C19H19N3O5S (401.10453640000003)
中文名称: 苯唑西林
谱图信息: 最多检出来源 Homo sapiens(blood) 2.22%

分子结构信息

SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
InChI: InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1

描述信息

Oxacillin is only found in individuals that have used or taken this drug. It is an antibiotic similar to flucloxacillin used in resistant staphylococci infections. [PubChem]By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Oxacillin 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 Oxacillin interferes with an autolysin inhibitor.
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 3207

同义名列表

25 个代谢物同义名

(2S,5R,6R)-3,3-Dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-Dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acid; 6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid; 6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acid; 6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanate; 6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanate; 6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanate; (5-Methyl-3-phenyl-4-isoxazolyl)penicillin; 5-Methyl-3-phenyl-4-isoxazolyl-penicillin; Oxacillin, monosodium salt, monohydrate; Oxacillin, monosodium salt, anhydrous; Penicillin, methylphenylisoxazolyl; Methylphenylisoxazolyl penicillin; MPI-penicillin; MPi-PC; Sodium, oxacillin; Oxacillin, sodium; Sodium oxacillin; Oxacillin sodium; Oxazocilline; Oxazocillin; Prostaphlin; oxacillin; Oxacilina



数据库引用编号

35 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

  • Chuan-Yun Xiao, Jiang-Er Lan, Xiao Liu, Zhong-Lin Sun, Xiao-Jin Li, Yi-Han Yin, Simon Gibbons, Qing Mu. Acetylenic spiroketal enol ethers from Artemisia rupestris and their synergistic antibacterial effects on methicillin-resistant Staphylococcus aureus. Natural product research. 2024 Feb; 38(4):589-593. doi: 10.1080/14786419.2023.2183952. [PMID: 36855235]
  • Serim Hong, Jin-San Moon, Soon-Seek Yoon, Ha-Young Kim, Young Ju Lee. Genetic and Phenotypic Diversity of Listeria monocytogenes in Pig Slaughterhouses in Korea. Foodborne pathogens and disease. 2023 Oct; ?(?):. doi: 10.1089/fpd.2023.0053. [PMID: 37819680]
  • Evgeniy V Kondrashov, Lyudmila A Belovezhets, Nina S Shatokhina, Alexandra N Shilova, Yana A Kostyro, Yulia A Markova, Marina K Borovskaya, Gennadii B Borovskii. Design of novel water-soluble isoxazole-based antimicrobial agents and evaluation of their cytotoxicity and acute toxicity. Bioorganic chemistry. 2023 Jun; 138(?):106644. doi: 10.1016/j.bioorg.2023.106644. [PMID: 37302315]
  • Jinling Shen, Guodong Zhang, Jielin Yang, Lina Zhao, Yuan Jiang, Dehua Guo, Xuan Wang, Shuai Zhi, Xuebin Xu, Qingli Dong, Xiang Wang. Prevalence, antibiotic resistance, and molecular epidemiology of Listeria monocytogenes isolated from imported foods in China during 2018 to 2020. International journal of food microbiology. 2022 Dec; 382(?):109916. doi: 10.1016/j.ijfoodmicro.2022.109916. [PMID: 36126498]
  • Dan Deng, Zizi Mu, Xiaoyan Lv, Xincheng Jiang, Jiang Zhou, Huizhi Guo, Wenbing Zhang, Bei Wang, Yishan Lu, Jinping Wu, Hao Du, Shuhuan Zhang, Qiaoqing Xu, Qiwei Wei. Pathogenicity of Plesiomonas shigelloides and Citrobacter freundii isolated from the endangered Chinese sturgeon (Acipenser sinensis). Microbial pathogenesis. 2022 Dec; 173(Pt A):105818. doi: 10.1016/j.micpath.2022.105818. [PMID: 36216208]
  • Faiqa Arshad, Sidrah Saleem, Romeeza Tahir, Ayesha Ghazal, Aneela Khawaja, Shah Jahan. Four year trend of antimicrobial susceptibility of methicillin-resistant Staphylococcus aureus in a tertiary care hospital, Lahore. JPMA. The Journal of the Pakistan Medical Association. 2022 Feb; 72(2):296-299. doi: 10.47391/jpma.20-509. [PMID: 35320181]
  • Erzsébet Takács, Jianlong Wang, Libing Chu, Tünde Tóth, Krisztina Kovács, Anikó Bezsenyi, László Szabó, Renáta Homlok, László Wojnárovits. Elimination of oxacillin, its toxicity and antibacterial activity by using ionizing radiation. Chemosphere. 2022 Jan; 286(Pt 1):131467. doi: 10.1016/j.chemosphere.2021.131467. [PMID: 34346325]
  • Paramaporn Muangpat, Wipanee Meesil, Jatuporn Ngoenkam, Yothin Teethaisong, Rapee Thummeepak, Sutthirat Sitthisak, Sarunporn Tandhavanant, Narisara Chantratita, Helge B Bode, Apichat Vitta, Aunchalee Thanwisai. Genome analysis of secondary metabolite‑biosynthetic gene clusters of Photorhabdus akhurstii subsp. akhurstii and its antibacterial activity against antibiotic-resistant bacteria. PloS one. 2022; 17(9):e0274956. doi: 10.1371/journal.pone.0274956. [PMID: 36129957]
  • Hawa Ozien Abu, Sajjadh M J Ali, Anil Phuyal, Akil Sherif, Gregory T Williams, Iryna Chastain. DRESS syndrome in the setting of oxacillin therapy-a call for better patient preparedness: a case report. Journal of medical case reports. 2021 Dec; 15(1):613. doi: 10.1186/s13256-021-03202-9. [PMID: 34955100]
  • Carla C C R de Carvalho, Agustina Taglialegna, Adriana E Rosato. Impact of PrsA on membrane lipid composition during daptomycin-resistance-mediated β-lactam sensitization in clinical MRSA strains. The Journal of antimicrobial chemotherapy. 2021 12; 77(1):135-147. doi: 10.1093/jac/dkab356. [PMID: 34618036]
  • Jun-Lan Liu, Tian-Ming Li, Ni Zhong, Xing Wang, Jie Jiang, Wen-Xia Zhang, Rong Tang, Yin-Juan Guo, Yun Liu, Jiang Hu, Li-Hua He, Jin Tang, Wen-Juan Wu, Min Li. Current status of oxacillin-susceptible mecA-positive Staphylococcus aureus infection in Shanghai, China: A multicenter study. Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi. 2021 Dec; 54(6):1070-1077. doi: 10.1016/j.jmii.2020.07.021. [PMID: 32819837]
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  • Micah Dettweiler, Roberta J Melander, Gina Porras, Caitlin Risener, Lewis Marquez, Tharanga Samarakoon, Christian Melander, Cassandra L Quave. A Clerodane Diterpene from Callicarpa americana Resensitizes Methicillin-Resistant Staphylococcus aureus to β-Lactam Antibiotics. ACS infectious diseases. 2020 07; 6(7):1667-1673. doi: 10.1021/acsinfecdis.0c00307. [PMID: 32579326]
  • Angela Bisio, Anna M Schito, Francesca Pedrelli, Ombeline Danton, Jakob K Reinhardt, Giulio Poli, Tiziano Tuccinardi, Thomas Bürgi, Francesco De Riccardis, Mauro Giacomini, Daniela Calzia, Isabella Panfoli, Gian Carlo Schito, Matthias Hamburger, Nunziatina De Tommasi. Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana. Journal of natural products. 2020 04; 83(4):1027-1042. doi: 10.1021/acs.jnatprod.9b01024. [PMID: 32182064]
  • Fernanda Cristina Bergamo Alves, Mariana Albano, Bruna Fernanda Murbach Teles Andrade, Jéssica Luana Chechi, Ana Flávia Marques Pereira, Alessandra Furlanetto, Vera Lúcia Mores Rall, Ana Angélica Henrique Fernandes, Lucilene Delazari Dos Santos, Lidiane Nunes Barbosa, Ary Fernandes Junior. Comparative Proteomics of Methicillin-Resistant Staphylococcus aureus Subjected to Synergistic Effects of the Lantibiotic Nisin and Oxacillin. Microbial drug resistance (Larchmont, N.Y.). 2020 Mar; 26(3):179-189. doi: 10.1089/mdr.2019.0038. [PMID: 31237481]
  • 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]
  • Su-Jeong Kim, Dong Chan Moon, Seung-Chun Park, Hee Young Kang, Seok Hyeon Na, Suk-Kyung Lim. Antimicrobial resistance and genetic characterization of coagulase-negative staphylococci from bovine mastitis milk samples in Korea. Journal of dairy science. 2019 Dec; 102(12):11439-11448. doi: 10.3168/jds.2019-17028. [PMID: 31548061]
  • Luigi Ronga, Angela Abbasciano, Carla Calia, Adriana Mosca, Michelina Battista, Eleonora Sparapano, Carmela De Carlo, Giuseppe Miragliotta, Raffaele Del Prete. Trends in the antibiotic resistance of S. aureus clinical isolates: a 4 years retrospective study in a teaching hospital in South Italy. Le infezioni in medicina. 2019 Sep; 27(3):266-273. doi: . [PMID: 31545770]
  • Amirthasingam Manoraj, Vasanthi Thevanesam, B M R Bandara, Asela Ekanayake, Veranja Liyanapathirana. Synergistic activity between Triphala and selected antibiotics against drug resistant clinical isolates. BMC complementary and alternative medicine. 2019 Aug; 19(1):199. doi: 10.1186/s12906-019-2618-1. [PMID: 31375093]
  • Feng Yang, Shidong Zhang, Xiaofei Shang, Xurong Wang, Ling Wang, Yan Sun. Short communication: N-Acetylcysteine-mediated augmentation of β-lactam antibacterial activity against methicillin-resistant Staphylococcus aureus isolated from bovine mastitis cases. Journal of dairy science. 2019 Aug; 102(8):6920-6922. doi: 10.3168/jds.2019-16389. [PMID: 31178194]
  • Lana Taha, Marc Stegger, Bo Söderquist. Staphylococcus lugdunensis: antimicrobial susceptibility and optimal treatment options. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology. 2019 Aug; 38(8):1449-1455. doi: 10.1007/s10096-019-03571-6. [PMID: 31144243]
  • Mingxia Song, Shiben Wang, Zengtao Wang, Zhiyang Fu, Shengchao Zhou, Huabin Cheng, Zhuo Liang, Xianqing Deng. Synthesis, antimicrobial and cytotoxic activities, and molecular docking studies of N-arylsulfonylindoles containing an aminoguanidine, a semicarbazide, and a thiosemicarbazide moiety. European journal of medicinal chemistry. 2019 Mar; 166(?):108-118. doi: 10.1016/j.ejmech.2019.01.038. [PMID: 30685534]
  • P Aelenei, C M Rimbu, E Guguianu, G Dimitriu, A C Aprotosoaie, M Brebu, C E Horhogea, A Miron. Coriander essential oil and linalool - interactions with antibiotics against Gram-positive and Gram-negative bacteria. Letters in applied microbiology. 2019 Feb; 68(2):156-164. doi: 10.1111/lam.13100. [PMID: 30471142]
  • Kirby R Lattwein, Himanshu Shekhar, Willem J B van Wamel, Tammy Gonzalez, Andrew B Herr, Christy K Holland, Klazina Kooiman. An in vitro proof-of-principle study of sonobactericide. Scientific reports. 2018 02; 8(1):3411. doi: 10.1038/s41598-018-21648-8. [PMID: 29467474]
  • María Yolanda Rios, Víctor Navarro, M Ángeles Ramírez-Cisneros, Enrique Salazar-Rios. Sulfur-Containing Aristoloxazines and Other Constituents of the Roots of Aristolochia orbicularis. Journal of natural products. 2017 12; 80(12):3112-3119. doi: 10.1021/acs.jnatprod.7b00226. [PMID: 29210585]
  • Mayra Fernanda Echeverría Medina, Peter Adeniyi Alaba, María Elena Estrada-Zuñiga, Valente Velázquez-Ordoñez, Alberto Barbabosa-Pliego, Mohmaed Z M Salem, María Uxúa Alonso-Fresán, Luis Miguel Camacho-Díaz, Abdelfattah Z M Salem. Anti-staphylococcal properties of four plant extracts against sensitive and multi-resistant bacterial strains isolated from cattle and rabbits. Microbial pathogenesis. 2017 Dec; 113(?):286-294. doi: 10.1016/j.micpath.2017.10.053. [PMID: 29101063]
  • Yuuki Shimozu, Teruo Kuroda, Tomofusa Tsuchiya, Tsutomu Hatano. Structures and Antibacterial Properties of Isorugosins H-J, Oligomeric Ellagitannins from Liquidambar formosana with Characteristic Bridging Groups between Sugar Moieties. Journal of natural products. 2017 10; 80(10):2723-2733. doi: 10.1021/acs.jnatprod.7b00496. [PMID: 29019685]
  • Tian Zhou, Zhi Li, Ok-Hwa Kang, Su-Hyun Mun, Yun-Soo Seo, Ryong Kong, Dong-Won Shin, Xiang-Qian Liu, Dong-Yeul Kwon. Antimicrobial activity and synergism of ursolic acid 3-O-α-L-arabinopyranoside with oxacillin against methicillin-resistant Staphylococcus aureus. International journal of molecular medicine. 2017 Oct; 40(4):1285-1293. doi: 10.3892/ijmm.2017.3099. [PMID: 28848992]
  • Hong-Bing Liu, Gianluigi Lauro, Robert D O'Connor, Katheryn Lohith, Michelle Kelly, Patrick Colin, Giuseppe Bifulco, Carole A Bewley. Tulongicin, an Antibacterial Tri-Indole Alkaloid from a Deep-Water Topsentia sp. Sponge. Journal of natural products. 2017 09; 80(9):2556-2560. doi: 10.1021/acs.jnatprod.7b00452. [PMID: 28837335]
  • Sara Edwirgens Costa Benício Vasconcelos, Hider Machado Melo, Theodora Thays Arruda Cavalcante, Francisco Eduardo Aragão Catunda Júnior, Mário Geraldo de Carvalho, Francisca Gleire Rodrigues Menezes, Oscarina Viana de Sousa, Renata Albuquerque Costa. Plectranthus amboinicus essential oil and carvacrol bioactive against planktonic and biofilm of oxacillin- and vancomycin-resistant Staphylococcus aureus. BMC complementary and alternative medicine. 2017 Sep; 17(1):462. doi: 10.1186/s12906-017-1968-9. [PMID: 28915875]
  • Aida Lahmar, Ahmed Bedoui, Imen Mokdad-Bzeouich, Zaineb Dhaouifi, Zahar Kalboussi, Imed Cheraif, Kamel Ghedira, Leila Chekir-Ghedira. Reversal of resistance in bacteria underlies synergistic effect of essential oils with conventional antibiotics. Microbial pathogenesis. 2017 May; 106(?):50-59. doi: 10.1016/j.micpath.2016.10.018. [PMID: 27815129]
  • Chiu-Fai Kuok, Sai-On Hoi, Chi-Fai Hoi, Chi-Hong Chan, Io-Hong Fong, Cheong-Kei Ngok, Li-Rong Meng, Pedro Fong. Synergistic antibacterial effects of herbal extracts and antibiotics on methicillin-resistant Staphylococcus aureus: A computational and experimental study. Experimental biology and medicine (Maywood, N.J.). 2017 04; 242(7):731-743. doi: 10.1177/1535370216689828. [PMID: 28118725]
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