N-acetyl-5-aminosalicylic acid (BioDeep_00000017824)

   

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


N-Acetyl-5-aminosalicylic acid, monosodium salt

化学式: C9H9NO4 (195.0531554)
中文名称: 5-乙酰氨基水杨酸
谱图信息: 最多检出来源 Homo sapiens(urine) 27.44%

分子结构信息

SMILES: CC(=O)NC1=CC(=C(C=C1)O)C(=O)O
InChI: InChI=1S/C9H9NO4/c1-5(11)10-6-2-3-8(12)7(4-6)9(13)14/h2-4,12H,1H3,(H,10,11)(H,13,14)

描述信息

N-acetyl-5-aminosalicylic acid is a metabolite of mesalazine. Mesalazine, also known as mesalamine or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammatory bowel disease, such as ulcerative colitis and mild-to-moderate Crohns disease. Mesalazine is a bowel-specific aminosalicylate drug that acts locally in the gut and has its predominant actions there, thereby having few systemic side effects. (Wikipedia)
D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates

同义名列表

6 个代谢物同义名

N-Acetyl-5-aminosalicylic acid, monosodium salt; 5-acetamido-2-hydroxybenzoic acid; N-Acetyl-5-aminosalicylic acid; N-Acetyl-5-aminosalicylate; 5-Acetylaminosalicylate; N-Acetyl Mesalazine



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

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PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

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COVID-19 Disease Map(0)

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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

  • Martin Kunes, Jaroslav Kvetina, Dagmar Kholova, Jan Bures, Helena Tlaskalova-Hogenova, Michal Pavlik. Absorption kinetics of 5-aminosalicylic acid in rat: influence of indomethacin-induced gastrointestinal lesions and Escherichia Coli Nissle 1917 medication. Neuro endocrinology letters. 2011; 32 Suppl 1(?):46-52. doi: NULL. [PMID: 22167206]
  • Elisabetta Pastorini, Marcello Locatelli, Patrizia Simoni, Giulia Roda, Enrico Roda, Aldo Roda. Development and validation of a HPLC-ESI-MS/MS method for the determination of 5-aminosalicylic acid and its major metabolite N-acetyl-5-aminosalicylic acid in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Sep; 872(1-2):99-106. doi: 10.1016/j.jchromb.2008.07.026. [PMID: 18691952]
  • Petr Cervený, Martin Bortlík, Ales Kubena, Jirí Vlcek, Peter Laszlo Lakatos, Milan Lukás. Nonadherence in inflammatory bowel disease: results of factor analysis. Inflammatory bowel diseases. 2007 Oct; 13(10):1244-9. doi: 10.1002/ibd.20189. [PMID: 17538983]
  • W J Sandborn, S B Hanauer, A Buch. Comparative pharmacokinetics of equimolar doses of 5-aminosalicylate administered as oral mesalamine (Asacol) and balsalazide: a randomized, single-dose, crossover study in healthy volunteers. Alimentary pharmacology & therapeutics. 2004 May; 19(10):1089-98. doi: 10.1111/j.1365-2036.2004.01964.x. [PMID: 15142198]
  • I S Shaw, B A Jobson, D Silverman, J Ford, S D Hearing, D Ball, E Johnson, A Day, C S J Probert. Is your patient taking the medicine? A simple assay to measure compliance with 5-aminosalicylic acid-containing compounds. Alimentary pharmacology & therapeutics. 2002 Dec; 16(12):2053-9. doi: 10.1046/j.1365-2036.2002.01375.x. [PMID: 12452937]
  • U Knoll, P Strauhs, G Schusser, F R Ungemach. Study of the plasma pharmacokinetics and faecal excretion of the prodrug olsalazine and its metabolites after oral administration to horses. Journal of veterinary pharmacology and therapeutics. 2002 Apr; 25(2):135-43. doi: 10.1046/j.1365-2885.2002.00395.x. [PMID: 12000534]
  • E L Berryman, A C Zerouala, C Meschter, J Spenard. Intrarectal administration of 5-aminosalicylic acid to rabbits and dogs. Human & experimental toxicology. 2002 Mar; 21(3):159-63. doi: 10.1191/0960327102ht236oa. [PMID: 12102542]
  • F N Hussain, R A Ajjan, M Moustafa, J C Anderson, S A Riley. Simple method for the determination of 5-aminosalicylic and N-acetyl-5-aminosalicylic acid in rectal tissue biopsies. Journal of chromatography. B, Biomedical sciences and applications. 1998 Sep; 716(1-2):257-66. doi: 10.1016/s0378-4347(98)00323-5. [PMID: 9824239]
  • P Gionchetti, M Campieri, A Venturi, F Rizzello, M Ferretti, C Brignola, M Miglioli. Systemic availability of 5-aminosalicylic acid: comparison of delayed release and an azo-bond preparation. Alimentary pharmacology & therapeutics. 1996 Aug; 10(4):601-5. doi: 10.1046/j.1365-2036.1996.26168000.x. [PMID: 8853765]
  • R Herzog, J Leuschner. Pharmacokinetic studies of benzalazine. Arzneimittel-Forschung. 1994 Dec; 44(12):1381-3. doi: NULL. [PMID: 7848362]
  • L A Christensen, S N Rasmussen, S H Hansen. Disposition of 5-aminosalicylic acid and N-acetyl-5-aminosalicylic acid in fetal and maternal body fluids during treatment with different 5-aminosalicylic acid preparations. Acta obstetricia et gynecologica Scandinavica. 1994 May; 73(5):399-402. doi: 10.3109/00016349409006251. [PMID: 8009971]
  • H Goebell, U Klotz, B Nehlsen, P Layer. Oroileal transit of slow release 5-aminosalicylic acid. Gut. 1993 May; 34(5):669-75. doi: 10.1136/gut.34.5.669. [PMID: 8504969]
  • S M Greenfield, D J Boswell, N A Punchard, R P Thompson. The effects of 5-aminosalicylic acid and acetyl-5-aminosalicylic acid on lipid peroxidation in erythrocytes and prostaglandin production by mononuclear cells. Alimentary pharmacology & therapeutics. 1992 Dec; 6(6):671-83. doi: 10.1111/j.1365-2036.1992.tb00731.x. [PMID: 1486154]
  • M De Vos, H Verdievel, R Schoonjans, M Praet, M Bogaert, F Barbier. Concentrations of 5-ASA and Ac-5-ASA in human ileocolonic biopsy homogenates after oral 5-ASA preparations. Gut. 1992 Oct; 33(10):1338-42. doi: 10.1136/gut.33.10.1338. [PMID: 1446856]
  • G L Swift, C M Mills, J Rhodes, B K Evans, A Bennett, I A Tavares. A pharmacokinetic study of sulphasalazine and two new formulations of mesalazine. Alimentary pharmacology & therapeutics. 1992 Apr; 6(2):259-66. doi: 10.1111/j.1365-2036.1992.tb00269.x. [PMID: 1350926]
  • C De Mey, I Meineke. Prandial and diurnal effects on the absorption of orally administered enteric coated 5-aminosalicylic acid (5-ASA). British journal of clinical pharmacology. 1992 Feb; 33(2):179-82. doi: 10.1111/j.1365-2125.1992.tb04021.x. [PMID: 1550697]
  • S A Riley, I A Tavares, P M Bishai, A Bennett, V Mani. Mesalazine release from coated tablets: effect of dietary fibre. British journal of clinical pharmacology. 1991 Aug; 32(2):248-50. doi: 10.1111/j.1365-2125.1991.tb03891.x. [PMID: 1657094]
  • J Devane, S Mulligan, M Martin. Distal ileum and colon: targeted sites for 5-ASA release. European journal of drug metabolism and pharmacokinetics. 1991; Spec No 3(?):300-3. doi: NULL. [PMID: 1820897]
  • L Staerk Laursen, M Stokholm, K Bukhave, J Rask-Madsen, K Lauritsen. Disposition of 5-aminosalicylic acid by olsalazine and three mesalazine preparations in patients with ulcerative colitis: comparison of intraluminal colonic concentrations, serum values, and urinary excretion. Gut. 1990 Nov; 31(11):1271-6. doi: 10.1136/gut.31.11.1271. [PMID: 2253912]
  • A E Corey, G M Rose, J D Conklin. Bioavailability of single and multiple doses of enteric-coated mesalamine and sulphasalazine. The Journal of international medical research. 1990 Nov; 18(6):441-53. doi: 10.1177/030006059001800601. [PMID: 1981363]
  • L A Christensen, J Fallingborg, K Abildgaard, B A Jacobsen, G Sanchez, S H Hansen, S Bondesen, E F Hvidberg, S N Rasmussen. Topical and systemic availability of 5-aminosalicylate: comparisons of three controlled release preparations in man. Alimentary pharmacology & therapeutics. 1990 Oct; 4(5):523-33. doi: 10.1111/j.1365-2036.1990.tb00499.x. [PMID: 2129640]
  • B Norlander, R Gotthard, M Ström. Pharmacokinetics of a 5-aminosalicylic acid enteric-coated tablet in patients with Crohn's disease or ulcerative colitis and in healthy volunteers. Alimentary pharmacology & therapeutics. 1990 Oct; 4(5):497-505. doi: 10.1111/j.1365-2036.1990.tb00496.x. [PMID: 2129637]
  • D K Yu, A T Elvin, B Morrill, L S Eichmeier, R C Lanman, M B Lanman, D H Giesing. Effect of food coadministration on 5-aminosalicylic acid oral suspension bioavailability. Clinical pharmacology and therapeutics. 1990 Jul; 48(1):26-33. doi: 10.1038/clpt.1990.113. [PMID: 2369807]
  • V S Chungi, L W Dittert, L Shargel. Pharmacokinetics of sulfasalazine metabolites in rats following concomitant oral administration of riboflavin. Pharmaceutical research. 1989 Dec; 6(12):1067-72. doi: 10.1023/a:1015938706685. [PMID: 2576130]
  • B Norlander, R Gotthard, M Ström. Pharmacokinetics of a 5-aminosalicylic acid enteric-coated tablet and suppository dosage form. Alimentary pharmacology & therapeutics. 1989 Aug; 3(4):333-42. doi: 10.1111/j.1365-2036.1989.tb00220.x. [PMID: 2518847]
  • H Allgayer, N O Ahnfelt, W Kruis, U Klotz, K Frank-Holmberg, H N Söderberg, G Paumgartner. Colonic N-acetylation of 5-aminosalicylic acid in inflammatory bowel disease. Gastroenterology. 1989 Jul; 97(1):38-41. doi: 10.1016/0016-5085(89)91412-1. [PMID: 2566551]
  • E Brendel, I Meineke, E Stüwe, H Osterwald. Stability of 5-aminosalicylic acid and 5-acetylaminosalicylic acid in plasma. Journal of chromatography. 1988 Nov; 432(?):358-62. doi: 10.1016/s0378-4347(00)80666-0. [PMID: 3220905]
  • R A van Hogezand, A van Schaik, P A van Hees, J H van Tongeren. Stability of disodium azodisalicylate (olsalazine) and metabolites in urine and faeces stored at different temperatures. European journal of drug metabolism and pharmacokinetics. 1988 Oct; 13(4):261-5. doi: 10.1007/bf03190089. [PMID: 3243321]
  • K Lauritsen, L Staerk Laursen, K Bukhave, J Rask-Madsen. Longterm olsalazine treatment: pharmacokinetics, tolerance and effects on local eicosanoid formation in ulcerative colitis and Crohn's colitis. Gut. 1988 Jul; 29(7):974-82. doi: 10.1136/gut.29.7.974. [PMID: 2840367]
  • E Nagy, I Csipo, I Degrell, G Szabo. High-performance liquid chromatographic assay of 5-aminosalicylic acid and its acetylated metabolite in biological fluids using electrochemical detection. Journal of chromatography. 1988 Mar; 425(1):214-9. doi: 10.1016/0378-4347(88)80024-0. [PMID: 3360872]
  • H Allgayer, W F Stenson. A comparison of effects of sulfasalazine and its metabolites on the metabolism of endogenous vs. exogenous arachidonic acid. Immunopharmacology. 1988 Jan; 15(1):39-46. doi: 10.1016/0162-3109(88)90041-0. [PMID: 2896181]
  • B Myers, D N Evans, J Rhodes, B K Evans, B R Hughes, M G Lee, A Richens, D Richards. Metabolism and urinary excretion of 5-amino salicylic acid in healthy volunteers when given intravenously or released for absorption at different sites in the gastrointestinal tract. Gut. 1987 Feb; 28(2):196-200. doi: 10.1136/gut.28.2.196. [PMID: 3557190]
  • E J Lee, S B Ang. Simple and sensitive high-performance liquid chromatographic assay for 5-aminosalicylic acid and acetyl-5-aminosalicylic acid in serum. Journal of chromatography. 1987 Jan; 413(?):300-4. doi: 10.1016/0378-4347(87)80243-8. [PMID: 2881937]
  • E Brendel, I Meineke, D Witsch, M Zschunke. Simultaneous determination of 5-aminosalicylic acid and 5-acetylaminosalicylic acid by high-performance liquid chromatography. Journal of chromatography. 1987 Jan; 385(?):299-304. doi: 10.1016/s0021-9673(01)94644-8. [PMID: 3558586]
  • S Bondesen, U Tage-Jensen, O Jacobsen, S H Hansen, S N Rasmussen, E F Hvidberg. 5-Aminosalicylic acid in patients with an ileo-rectal anastomosis. A comparison of the fate of sulfasalazine and Pentasa. European journal of clinical pharmacology. 1986; 31(1):23-6. doi: 10.1007/bf00870980. [PMID: 2877884]
  • H Allgayer, J Sonnenbichler, W Kruis, G Paumgartner. Determination of the pK values of 5-aminosalicylic acid and N-acetylaminosalicylic acid and comparison of the pH dependent lipid-water partition coefficients of sulphasalazine and its metabolites. Arzneimittel-Forschung. 1985; 35(9):1457-9. doi: NULL. [PMID: 2867770]
  • C O Meese, C Fischer, U Klotz. Is N-acetylation of 5-aminosalicylic acid reversible in man?. British journal of clinical pharmacology. 1984 Oct; 18(4):612-5. doi: 10.1111/j.1365-2125.1984.tb02513.x. [PMID: 6487501]
  • C Fischer, C O Meese, U Klotz. A stable isotope method for the quantification of N-acetyl-5-aminosalicylic acid in plasma and urine. Biomedical mass spectrometry. 1984 Oct; 11(10):539-44. doi: 10.1002/bms.1200111009. [PMID: 6518273]
  • A Shafii, J R Chowdhury, K M Das. Absorption, enterohepatic circulation, and excretion of 5-aminosalicylic acid in rats. The American journal of gastroenterology. 1982 May; 77(5):297-9. doi: NULL. [PMID: 6123257]