N4-Acetylsulfamethoxazole (BioDeep_00000001552)

   

human metabolite Endogenous blood metabolite Chemicals and Drugs Volatile Flavor Compounds


代谢物信息卡片


N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}ethanimidic acid

化学式: C12H13N3O4S (295.0626738)
中文名称: 醋磺胺甲噁唑
谱图信息: 最多检出来源 Homo sapiens(blood) 25.32%

分子结构信息

SMILES: c1(ccc(cc1)NC(C)=O)S(Nc1cc(C)on1)(=O)=O
InChI: InChI=1S/C12H13N3O4S/c1-8-7-12(14-19-8)15-20(17,18)11-5-3-10(4-6-11)13-9(2)16/h3-7H,1-2H3,(H,13,16)(H,14,15)

描述信息

N4-Acetylsulfamethoxazole is a metabolite of the sulfonamide bacteriostatic antibiotic sulfamethoxazole. Sulfamethoxazole is metabolized via acetylation catalyzed by liver extramitochondrial N-acetyl transferases. Acetylsulfamethoxazole is excreted in urine. Acetylsulfamethoxazole and sulfamethoxazole can be used as a probe for the molecular percentage enrichment of liver extramitochondrial acetyl-CoA. N4-Acetylsulfamethoxazole can be used as a reference for measuring sulfamethoxazole impurities and waste determination (PMID: 15307787). It is one of the critical aspects of urine and stone analysis (PMID: 3811034) and its quantitative determination in body fluids could be performed by reversed-phase high-performance liquid chromatography, a rapid, precise and simple procedure (PMID: 6668314). It is also reported the renal excretion rate of the metabolite N4-acetylsulfamethoxazole is not dependent on the urinary pH (PMID: 670346). N4-Acetylsulfamethoxazole is only found in individuals who have consumed the drug sulfamethoxazole.
D000890 - Anti-Infective Agents > D013424 - Sulfanilamides
CONFIDENCE standard compound; EAWAG_UCHEM_ID 299

同义名列表

34 个代谢物同义名

N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}ethanimidic acid; N-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]acetamide; N-{4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl}acetamide; 4-((5-Methyl-3-isoxazolyl)sulphamoyl)acetanilide; 4-((5-Methyl-3-isoxazolyl)sulfamoyl)acetanilide; Sulphisomezole-N(4)-acetic acid; N(4)-Acetylsulphulfamethoxazole; Sulfisomezole-N(sup 4)-acetate; Sulfisomezole-N(4)-acetic acid; N(4)-Acetylsulfulfamethoxazole; Sulphamethoxazole acetic acid; Sulfamethoxazole acetic acid; N4-Acetylsulfulfamethoxazole; N(4)-Acetylsulphamethoxazole; N(sup 4)-acetylsulfisomezole; N(4)-Acetylsulfamethoxazole; Sulphisomezole-N(4)-acetate; Sulfisomezole-N(4)-acetate; N4-Acetylsulphamethoxazole; N-Acetylsulphamethoxazole; N-Acetyl sulfamethoxazole; Sulphamethoxazole acetate; N4-Acetylsulfamethoxazole; N(4)-Acetylsulphisomezole; N(4)-Acetylsulfisomezole; Sulfamethoxazole acetate; Sulfisomezole-N4-acetate; Acetylsulphamethoxazole; Acetylsulfamethoxazole; N4-Acetylsulfisomezole; SMX-Acetic acid; SMX-Acetate; Gantanol; Acetylsulfamethoxazole



数据库引用编号

39 个数据库交叉引用编号

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代谢反应

0 个相关的代谢反应过程信息。

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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

  • Xiang-yang Li, Yong-nian Liu, Yong-ping Li, Ming Yuan, Jun-bo Zhu. [Pharmacokinetics of sulfamethoxazole in healthy Han volunteers living at plain and in native Han and Tibetan healthy volunteers living at high altitude]. Yao xue xue bao = Acta pharmaceutica Sinica. 2011 Sep; 46(9):1117-22. doi: . [PMID: 22121785]
  • Xiang-Yang Li, Fen Gao, Zhan-Quan Li, Wei Guan, Wei-Li Feng, Ri-Li Ge. Comparison of the pharmacokinetics of sulfamethoxazole in male chinese volunteers at low altitude and acute exposure to high altitude versus subjects living chronically at high altitude: an open-label, controlled, prospective study. Clinical therapeutics. 2009 Nov; 31(11):2744-54. doi: 10.1016/j.clinthera.2009.11.019. [PMID: 20110016]
  • Insaf F Khalil, Anita M Rønn, Michael Alifrangis, Hytham A Gabar, Thomas Jelinek, Gwiria M H Satti, Ib C Bygbjerg. Response of Plasmodium falciparum to cotrimoxazole therapy: relationship with plasma drug concentrations and dihydrofolate reductase and dihydropteroate synthase genotypes. The American journal of tropical medicine and hygiene. 2005 Jul; 73(1):174-7. doi: . [PMID: 16014854]
  • Louis R Cantilena, Aspandiar G Katki, Raymond W Klecker, Jerry M Collins. Metabolism by N-acetyltransferase 1 in vitro and in healthy volunteers: a prototype for targeted inhibition. Journal of clinical pharmacology. 2004 Dec; 44(12):1405-11. doi: 10.1177/0091270004270224. [PMID: 15545312]
  • Y Zhang, K C Agarwal, M Beylot, M V Soloviev, F David, M Reider, K Y Tserng, H Brunengraber. Assay of the acetyl-CoA probe acetyl-sulfamethoxazole and of sulfamethoxazole by gas chromatography-mass spectrometry. Analytical biochemistry. 1993 Aug; 212(2):481-6. doi: 10.1006/abio.1993.1357. [PMID: 8214590]
  • J Blaser, B Joos, M Opravil, R Lüthy. Variability of serum concentrations of trimethoprim and sulfamethoxazole during high dose therapy. Infection. 1993 Jul; 21(4):206-9. doi: 10.1007/bf01728888. [PMID: 8225622]
  • R C Stevens, S C Laizure, P L Sanders, D S Stein. Multiple-dose pharmacokinetics of 12 milligrams of trimethoprim and 60 milligrams of sulfamethoxazole per kilogram of body weight per day in healthy volunteers. Antimicrobial agents and chemotherapy. 1993 Mar; 37(3):448-52. doi: 10.1128/aac.37.3.448. [PMID: 8460913]
  • M E Aguilar-Cota, F J Flores-Murrieta, J C Menéndez, E Hong, G Castañeda-Hernández. Renal and metabolic clearances of sulfamethoxazole in Mexican healthy subjects. Proceedings of the Western Pharmacology Society. 1992; 35(?):103-6. doi: NULL. [PMID: 1502208]
  • R C Stevens, S C Laizure, C L Williams, D S Stein. Pharmacokinetics and adverse effects of 20-mg/kg/day trimethoprim and 100-mg/kg/day sulfamethoxazole in healthy adult subjects. Antimicrobial agents and chemotherapy. 1991 Sep; 35(9):1884-90. doi: 10.1128/aac.35.9.1884. [PMID: 1952863]
  • D S Stein, R C Stevens, D Terry, S C Laizure, S Palte, D J Lancaster, J J Weems, C L Williams. Use of low-dose trimethoprim-sulfamethoxazole thrice weekly for primary and secondary prophylaxis of Pneumocystis carinii pneumonia in human immunodeficiency virus-infected patients. Antimicrobial agents and chemotherapy. 1991 Sep; 35(9):1705-9. doi: 10.1128/aac.35.9.1705. [PMID: 1952835]
  • M K Hellerstein, K Wu, S Kaempfer, C Kletke, C H Shackleton. Sampling the lipogenic hepatic acetyl-CoA pool in vivo in the rat. Comparison of xenobiotic probe to values predicted from isotopomeric distribution in circulating lipids and measurement of lipogenesis and acetyl-CoA dilution. The Journal of biological chemistry. 1991 Jun; 266(17):10912-9. doi: . [PMID: 2040608]
  • R M Hutabarat, J D Unadkat, C Sahajwalla, S McNamara, B Ramsey, A L Smith. Disposition of drugs in cystic fibrosis. I. Sulfamethoxazole and trimethoprim. Clinical pharmacology and therapeutics. 1991 Apr; 49(4):402-9. doi: 10.1038/clpt.1991.47. [PMID: 2015729]
  • A Avgerinos, G Athanasiou, S Malamataris. Rapid simultaneous determination of trimethoprim, sulphamethoxazole and acetylsulphamethoxazole in human plasma and urine by high-performance liquid chromatography. Journal of pharmaceutical and biomedical analysis. 1991; 9(6):507-10. doi: 10.1016/0731-7085(91)80254-7. [PMID: 1747405]
  • Y K Tam, J Ke, R T Coutts, D G Wyse, M R Gray. Quantification of three lidocaine metabolites and their conjugates. Pharmaceutical research. 1990 May; 7(5):504-7. doi: 10.1023/a:1015868800614. [PMID: 2367319]
  • D J Porubek, M Rundgren, P J Harvison, S D Nelson, P Moldéus. Investigation of mechanisms of acetaminophen toxicity in isolated rat hepatocytes with the acetaminophen analogues 3,5-dimethylacetaminophen and 2,6-dimethylacetaminophen. Molecular pharmacology. 1987 Jun; 31(6):647-53. doi: . [PMID: 3600610]
  • O Varoquaux, D Lajoie, C Gobert, P Cordonnier, C Ducreuzet, M Pays, C Advenier. Pharmacokinetics of the trimethoprim-sulphamethoxazole combination in the elderly. British journal of clinical pharmacology. 1985 Dec; 20(6):575-81. doi: 10.1111/j.1365-2125.1985.tb05114.x. [PMID: 3879182]
  • T B Vree, J B Vree. Excretion rates of sulfamethoxazole and N4-acetyl-sulfamethoxazole by fresh water turtles Pseudemys scripta elegans. The veterinary quarterly. 1984 Jul; 6(3):169-73. doi: 10.1080/01652176.1984.9693932. [PMID: 6485242]
  • T B Vree, J J Reekers-Ketting, J F Nouws, T H Arts. Placental transfer and renal clearance of sulphamethoxazole and its metabolite N4-acetylsulphamethoxazole in a pregnant ewe. Journal of veterinary pharmacology and therapeutics. 1983 Mar; 6(1):77-81. doi: 10.1111/j.1365-2885.1983.tb00458.x. [PMID: 6854735]
  • T B Vree, C A Hekster, E van der Kleijn. Significance of apparent half-lives of a metabolite with a higher elimination rate than its parent drug. Drug intelligence & clinical pharmacy. 1982 Feb; 16(2):126-31. doi: 10.1177/106002808201600207. [PMID: 7075463]
  • L Essers, H Korte. Comparison of the conventional methods and high-performance liquid chromatography for the determination of trimethoprim, sulfamethoxazole and its metabolite in serum. Chemotherapy. 1982; 28(4):247-52. doi: 10.1159/000238085. [PMID: 7116979]
  • R Gochin, I Kanfer, J M Haigh. Simultaneous determination of trimethoprim, sulphamethoxazole and N4-acetylsulphamethoxazole in serum and urine by high-performance liquid chromatography. Journal of chromatography. 1981 Apr; 223(1):139-45. doi: 10.1016/s0378-4347(00)80076-6. [PMID: 7251755]
  • T B Vree, Y A Hekster, J E Damsma, R van Dalen, J C Hafkenscheid, W T Friesen. Renal excretion of sulphamethoxazole and its metabolite N4-acetylsulphamethoxazole in patients with impaired kidney function. Therapeutic drug monitoring. 1981; 3(2):129-35. doi: 10.1097/00007691-198102000-00003. [PMID: 7268825]
  • C R Fernando, I C Calder, K N Ham. Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2,6-dimethyl- and N-acetyl-3,5-dimethyl-p-benzoquinone imines. Journal of medicinal chemistry. 1980 Nov; 23(11):1153-8. doi: 10.1021/jm00185a001. [PMID: 7452663]