Olsalazine (BioDeep_00000006470)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid

化学式: C14H10N2O6 (302.05388400000004)
中文名称: 奥沙拉嗪
谱图信息: 最多检出来源 Viridiplantae(plant) 41.38%

分子结构信息

SMILES: C1=CC(=C(C=C1N=NC2=CC(=C(C=C2)O)C(=O)O)C(=O)O)O
InChI: InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)

描述信息

Olsalazine is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease and Ulcerative Colitis. Olsalazine is a derivative of salicylic acid. Inactive by itself (it is a prodrug), it is converted by the bacteria in the colon to mesalamine. Mesalamine works as an anti-inflammatory agent in treating inflammatory diseases of the intestines.
A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents > A07E - Intestinal antiinflammatory agents > A07EC - Aminosalicylic acid and similar agents
D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D005765 - Gastrointestinal Agents
D018501 - Antirheumatic Agents

同义名列表

5 个代谢物同义名

5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid; Olsalazine sodium; Olsalazine; Dipentum; Olsalazine

数据库引用编号

19 个数据库交叉引用编号

ChEBI: CHEBI:7770
KEGG: C07323
KEGGdrug: D08295
PubChem: 22419
HMDB: HMDB0015380
Metlin: METLIN1630
DrugBank: DB01250
ChEMBL: CHEMBL1208644
ChEMBL: CHEMBL425
Wikipedia: Olsalazine
chemspider: 10642377
CAS: 1004301-38-5
CAS: 15722-48-2
PMhub: MS000019517
PubChem: 9531
PDB-CCD: JBC
NIKKAJI: J227.692E
RefMet: Olsalazine
KNApSAcK: 7770

分类词条

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

9606 - Homo sapiens: -

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

Yanfen Niu, Pingfen Yang, Hongjian Li, Qiang Li, Hua Lin, Lihui Gao, Ling Li. Olsalazine Sodium Increases Renal Urate Excretion by Modulating Urate Transporters in Hyperuricemic Animals. Biological & pharmaceutical bulletin. 2020 Nov; 43(11):1653-1659. doi: 10.1248/bpb.b20-00362. [PMID: 32863294]
Sandra Cortez-Maya, Luis Daniel Pedro-Hernández, Elena Martínez-Klimova, Teresa Ramírez-Ápan, Marcos Martínez-García. Anticancer Activity of Water-Soluble Olsalazine-PAMAM-Dendrimer-Salicylic Acid-Conjugates. Biomolecules. 2019 08; 9(8):. doi: 10.3390/biom9080360. [PMID: 31412571]
Youtian Hu, Lu Wang, Xu Han, Yueyang Zhou, Tonghui Zhang, Li Wang, Ting Hong, Wei Zhang, Xun-Xiang Guo, Jielin Sun, Yingxin Qi, Jing Yu, Hong Liu, Fang Wu. Discovery of a Bioactive Inhibitor with a New Scaffold for Cystathionine γ-Lyase. Journal of medicinal chemistry. 2019 02; 62(3):1677-1683. doi: 10.1021/acs.jmedchem.8b01720. [PMID: 30562026]
Yanfen Niu, Hongjian Li, Lihui Gao, Hua Lin, Hsiangfu Kung, Marie Chia-Mi Lin, Kwong-Sak Leung, Man-Hon Wong, Wenyong Xiong, Ling Li. Old drug, new indication: Olsalazine sodium reduced serum uric acid levels in mice via inhibiting xanthine oxidoreductase activity. Journal of pharmacological sciences. 2017 Nov; 135(3):114-120. doi: 10.1016/j.jphs.2017.10.007. [PMID: 29132796]
Eleni Karatza, Maria Vertzoni, Uwe Muenster, Christos Reppas. The Impact of Handling and Storage of Human Fecal Material on Bacterial Activity. Journal of pharmaceutical sciences. 2016 11; 105(11):3458-3461. doi: 10.1016/j.xphs.2016.07.010. [PMID: 27544433]
O A El-Kawy, I T Ibrahim, K Farah. Technetium-99 m labeling and evaluation of olsalazine: a novel agent for ulcerative colitis imaging. Journal of labelled compounds & radiopharmaceuticals. 2015 Jun; 58(8):336-41. doi: 10.1002/jlcr.3306. [PMID: 26031480]
Holger Sann, Jasmin von Erichsen, Manuela Hessmann, Andreas Pahl, Angelika Hoffmeyer. Efficacy of drugs used in the treatment of IBD and combinations thereof in acute DSS-induced colitis in mice. Life sciences. 2013 Apr; 92(12):708-18. doi: 10.1016/j.lfs.2013.01.028. [PMID: 23399699]
Yue-Meng Wan, You-Qing Zhu, Bing Xia, Jun Luo. Treating TNBS-induced colitis in rats with probiotics. The Turkish journal of gastroenterology : the official journal of Turkish Society of Gastroenterology. 2011 Oct; 22(5):486-93. doi: 10.4318/tjg.2011.0247. [PMID: 22234755]
Maria Vertzoni, Anders Carlsson, Bertil Abrahamsson, Konstantinos Goumas, Christos Reppas. Degradation kinetics of metronidazole and olsalazine by bacteria in ascending colon and in feces of healthy adults. International journal of pharmaceutics. 2011 Jul; 413(1-2):81-6. doi: 10.1016/j.ijpharm.2011.04.028. [PMID: 21540091]
Yue-meng Wan, You-qing Zhu, Bing Xia, Jun Luo. [Probiotic therapy using live combined bifidobacterium, lactobacillus and enterococcus for experimental colitis in rats model]. Zhonghua nei ke za zhi. 2010 May; 49(5):418-21. doi: . [PMID: 20646418]
Amany A Abdin, Eman M Saeid. An experimental study on ulcerative colitis as a potential target for probiotic therapy by Lactobacillus acidophilus with or without "olsalazine". Journal of Crohn's & colitis. 2008 Dec; 2(4):296-303. doi: 10.1016/j.crohns.2008.04.002. [PMID: 21172227]
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]
Lynn W Maines, Leo R Fitzpatrick, Kevin J French, Yan Zhuang, Zuping Xia, Staci N Keller, John J Upson, Charles D Smith. Suppression of ulcerative colitis in mice by orally available inhibitors of sphingosine kinase. Digestive diseases and sciences. 2008 Apr; 53(4):997-1012. doi: 10.1007/s10620-007-0133-6. [PMID: 18058233]
Lutz Buschhausen, Werner Kruis, Serhat Aymaz, Manfred Weber, Bernd Krakamp. [Characterization of proteinuria in patients with ulcerative colitis and therapy with aminosalicylates]. Medizinische Klinik (Munich, Germany : 1983). 2006 Oct; 101(10):791-5. doi: 10.1007/s00063-006-1106-9. [PMID: 17039321]
U Klotz. Colonic targeting of aminosalicylates for the treatment of ulcerative colitis. Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver. 2005 Jun; 37(6):381-8. doi: 10.1016/j.dld.2004.12.011. [PMID: 15893274]
Chang-Tai Xu, Shu-Yong Meng, Bo-Rong Pan. Drug therapy for ulcerative colitis. World journal of gastroenterology. 2004 Aug; 10(16):2311-7. doi: 10.3748/wjg.v10.i16.2311. [PMID: 15285010]
Laurie M Edmond, Mark J Hopkins, Elizabeth A Magee, John H Cummings. The effect of 5-aminosalicylic acid-containing drugs on sulfide production by sulfate-reducing and amino acid-fermenting bacteria. Inflammatory bowel diseases. 2003 Jan; 9(1):10-7. doi: 10.1097/00054725-200301000-00002. [PMID: 12656132]
W J Sandborn, S B Hanauer. Systematic review: the pharmacokinetic profiles of oral mesalazine formulations and mesalazine pro-drugs used in the management of ulcerative colitis. Alimentary pharmacology & therapeutics. 2003 Jan; 17(1):29-42. doi: 10.1046/j.1365-2036.2003.01408.x. [PMID: 12492730]
M K Chourasia, S K Jain. Pharmaceutical approaches to colon targeted drug delivery systems. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2003 Jan; 6(1):33-66. doi: . [PMID: 12753729]
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]
N Mahmud, D O'Toole, N O'Hare, P J Freyne, D G Weir, D Kelleher. Evaluation of renal function following treatment with 5-aminosalicylic acid derivatives in patients with ulcerative colitis. Alimentary pharmacology & therapeutics. 2002 Feb; 16(2):207-15. doi: 10.1046/j.1365-2036.2002.01155.x. [PMID: 11860403]
G S Birketvedt, K J Berg, O Fausa, J Florholmen. Glomerular and tubular renal functions after long-term medication of sulphasalazine, olsalazine, and mesalazine in patients with ulcerative colitis. Inflammatory bowel diseases. 2000 Nov; 6(4):275-9. doi: 10.1002/ibd.3780060404. [PMID: 11149559]
N Mahmud, D G Weir, D Kelleher. Systemic levels of free 5-aminosalicylic acid depend on the nature of the 5-aminosalicyclic acid derivative and not on disease activity or extent in patients with inflammatory bowel disease. Irish journal of medical science. 1999 Oct; 168(4):228-32. doi: 10.1007/bf02944345. [PMID: 10624358]
G Støa-Birketvedt, J Florholmen. The systemic load and efficient delivery of active 5-aminosalicylic acid in patients with ulcerative colitis on treatment with olsalazine or mesalazine. Alimentary pharmacology & therapeutics. 1999 Mar; 13(3):357-61. doi: 10.1046/j.1365-2036.1999.00483.x. [PMID: 10102969]
G Howard, K L Lynn. Renal dysfunction and the treatment of inflammatory bowel disease (IBD): a case for monitoring. Australian and New Zealand journal of medicine. 1998 Jun; 28(3):346. doi: 10.1111/j.1445-5994.1998.tb01962.x. [PMID: 9673750]
J Calviño, R Romero, E Pintos, E Losada, D Novoa, D Güimil, J Mardaras, D Sanchez-Guisande. Mesalazine-associated tubulo-interstitial nephritis in inflammatory bowel disease. Clinical nephrology. 1998 Apr; 49(4):265-7. doi: NULL. [PMID: 9582560]
G L Stretch, B J Campbell, A D Dwarakanath, M Yaqoob, A Stevenson, A I Morris, J M Rhodes. 5-amino salicylic acid absorption and metabolism in ulcerative colitis patients receiving maintenance sulphasalazine, olsalazine or mesalazine. Alimentary pharmacology & therapeutics. 1996 Dec; 10(6):941-7. doi: 10.1046/j.1365-2036.1996.85257000.x. [PMID: 8971292]
D G Karamanolis, G V Papatheodoridis, V Xourgias. Systemic absorption of 5-aminosalicylic acid in patients with inactive ulcerative colitis treated with olsalazine and mesalazine. European journal of gastroenterology & hepatology. 1996 Nov; 8(11):1083-8. doi: 10.1097/00042737-199611000-00010. [PMID: 8944370]
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]
K Ewe, K Becker, B Ueberschaer. Systemic uptake of 5-aminosalicylic acid from olsalazine and eudragit L coated mesalazine in patients with ulcerative colitis in remission. Zeitschrift fur Gastroenterologie. 1996 Apr; 34(4):225-9. doi: . [PMID: 8686349]
L A Christensen, J Fallingborg, B A Jacobsen, K Abildgaard, H H Rasmussen, S H Hansen, S N Rasmussen. Comparative bioavailability of 5-aminosalicylic acid from a controlled release preparation and an azo-bond preparation. Alimentary pharmacology & therapeutics. 1994 Jun; 8(3):289-94. doi: 10.1111/j.1365-2036.1994.tb00290.x. [PMID: 7918923]
L G Miller, J M Hopkinson, K J Motil, J E Corboy, S Andersson. Disposition of olsalazine and metabolites in breast milk. Journal of clinical pharmacology. 1993 Aug; 33(8):703-6. doi: 10.1002/j.1552-4604.1993.tb05610.x. [PMID: 8408729]
M C Rijk, A van Schaik, J H van Tongeren. Disposition of mesalazine from mesalazine-delivering drugs in patients with inflammatory bowel disease, with and without diarrhoea. Scandinavian journal of gastroenterology. 1992 Oct; 27(10):863-8. doi: 10.3109/00365529209000155. [PMID: 1359629]
M Ryde, B Huitfeldt, R Pettersson. Relative bioavailability of olsalazine from tablets and capsules: a drug targeted for local effect in the colon. Biopharmaceutics & drug disposition. 1991 Apr; 12(3):233-46. doi: 10.1002/bdd.2510120308. [PMID: 2059673]
T Yamada, C Volkmer, M B Grisham. The effects of sulfasalazine metabolites on hemoglobin-catalyzed lipid peroxidation. Free radical biology & medicine. 1991; 10(1):41-9. doi: 10.1016/0891-5849(91)90020-4. [PMID: 1675620]
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]
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]
D Poldermans, M van Blankenstein. Pancreatitis induced by disodium azodisalicylate. The American journal of gastroenterology. 1988 May; 83(5):578-80. doi: NULL. [PMID: 2452567]
D E Campbell, T Berglindh. Pharmacology of olsalazine. Scandinavian journal of gastroenterology. Supplement. 1988; 148(?):7-12. doi: 10.3109/00365528809101539. [PMID: 3067340]
D J Hetzel, D J Shearman, J Labrooy, F Bochner, D M Imhoff, G E Gibson, R J Fitch, R Hecker, R Rowland. Olsalazine in the treatment of active ulcerative colitis: a placebo controlled clinical trial and assessment of drug disposition. Scandinavian journal of gastroenterology. Supplement. 1988; 148(?):61-9. doi: 10.3109/00365528809101552. [PMID: 3067339]
E M Ryde, N O Ahnfelt. The pharmacokinetics of olsalazine sodium in healthy volunteers after a single i.v. dose and after oral doses with and without food. European journal of clinical pharmacology. 1988; 34(5):481-8. doi: 10.1007/bf01046706. [PMID: 3203708]
R A van Hogezand. Pharmacokinetics of olsalazine and its metabolites. Scandinavian journal of gastroenterology. Supplement. 1988; 148(?):17-20. doi: 10.3109/00365528809101541. [PMID: 2906473]
M C Rijk, A van Schaik, J H van Tongeren. Disposition of 5-aminosalicylic acid by 5-aminosalicylic acid-delivering compounds. Scandinavian journal of gastroenterology. 1988 Jan; 23(1):107-12. doi: 10.3109/00365528809093858. [PMID: 2894070]
S S Rao, N W Read, C D Holdsworth. Influence of olsalazine on gastrointestinal transit in ulcerative colitis. Gut. 1987 Nov; 28(11):1474-7. doi: 10.1136/gut.28.11.1474. [PMID: 3428673]
H Sandberg-Gertzén, G Järnerot, K Bukhave, K Lauritsen, J Rask-Madsen. Effect of azodisal sodium and sulphasalazine on ileostomy output of fluid and PGE2 and PGF2 alpha in subjects with a permanent ileostomy. Gut. 1986 Nov; 27(11):1306-11. doi: 10.1136/gut.27.11.1306. [PMID: 2878859]
H Sandberg-Gertzen, J Kjellander, B Sundberg-Gillå, G Järnerot. In vitro effects of sulphasalazine, azodisal sodium, and their metabolites on Clostridium difficile and some other faecal bacteria. Scandinavian journal of gastroenterology. 1985 Jun; 20(5):607-12. doi: 10.3109/00365528509089704. [PMID: 2862692]
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K Lauritsen, J Hansen, P Bytzer, K Bukhave, J Rask-Madsen. Effects of sulphasalazine and disodium azodisalicylate on colonic PGE2 concentrations determined by equilibrium in vivo dialysis of faeces in patients with ulcerative colitis and healthy controls. Gut. 1984 Nov; 25(11):1271-8. doi: 10.1136/gut.25.11.1271. [PMID: 6149981]
K Lauritsen, J Hansen, M Ryde, J Rask-Madsen. Colonic azodisalicylate metabolism determined by in vivo dialysis in healthy volunteers and patients with ulcerative colitis. Gastroenterology. 1984 Jun; 86(6):1496-500. doi: 10.1016/s0016-5085(84)80164-x. [PMID: 6143704]
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H Sandberg-Gertzén, M Ryde, G Järnerot. Absorption and excretion of azodisal sodium and its metabolites in man after rectal administration of a single 2-g dose. Scandinavian journal of gastroenterology. 1983 May; 18(4):571-5. doi: 10.3109/00365528309181640. [PMID: 6669934]
H Sandberg-Gertzén, M Ryde, G Järnerot. Absorption and excretion of a single 1-g dose of azodisal sodium in subjects with ileostomy. Scandinavian journal of gastroenterology. 1983 Jan; 18(1):107-11. doi: 10.3109/00365528309181568. [PMID: 6675167]
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