Oxaprozin (BioDeep_00000002736)

 

Secondary id: BioDeep_00000398445

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


3-(diphenyl-1,3-oxazol-2-yl)propanoic acid

化学式: C18H15NO3 (293.105188)
中文名称: 奥沙普秦
谱图信息: 最多检出来源 Homo sapiens(blood) 50%

分子结构信息

SMILES: C1=CC=C(C=C1)C2=C(OC(=N2)CCC(=O)O)C3=CC=CC=C3
InChI: InChI=1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21)

描述信息

Oxaprozin is only found in individuals that have used or taken this drug. It is a non-narcotic, non-steroidal anti-inflammatory drug (NSAID), used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis.Anti-inflammatory effects of Oxaprozin are believed to be due to inhibition of cylooxygenase in platelets which leads to the blockage of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Oxaprozin is a non-selective NSAID, with a cell assay system showing lower COX-2 selectivity implying higher COX-1 selectivity.
M - Musculo-skeletal system > M01 - Antiinflammatory and antirheumatic products > M01A - Antiinflammatory and antirheumatic products, non-steroids > M01AE - Propionic acid derivatives
D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors
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
C471 - Enzyme Inhibitor > C1323 - Cyclooxygenase Inhibitor
D000893 - Anti-Inflammatory Agents
D004791 - Enzyme Inhibitors
Oxaprozin is an orally active and potent COX inhibitor, with IC50 values of 2.2 μM for human platelet COX-1 and and 36 μM for IL-1-stimulated human synovial cell COX-2, respectively. Oxaprozin also inhibits the activation of NF-κB. Oxaprozin induces cell apoptosis. Oxaprozin shows anti-inflammatory activity. Oxaprozin-mediated inhibition of the Akt/IKK/NF-κB pathway contributes to its anti-inflammatory properties[1][2].

同义名列表

18 个代谢物同义名

3-(diphenyl-1,3-oxazol-2-yl)propanoic acid; 4,5 Diphenyl 2 oxazolepropionic acid; 4,5-Diphenyl-2-oxazolepropionic acid; Rhoxal oxaprozin; Rhoxal-oxaprozin; Apo oxaprozin; Apo-oxaprozin; Oxaprozinum; Oxaprozine; Oxaprozina; oxaprozin; Danoprox; Duraprox; Deflam; Daypro; Dayrun; Walix; Wy21743



数据库引用编号

17 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

  • Parisa Khatami, Naser Mirazi, Maryam Khosravi, Maryam Bananej. Nonsteroidal Anti-inflammatory Drug Oxaprozin is Beneficial Against Seizure-induced Memory Impairment in an Experimental Model of Seizures in Rats: Impact On Oxidative Stress and Nrf2/HO-1 Signaling Pathway. Journal of molecular neuroscience : MN. 2022 Apr; 72(4):880-887. doi: 10.1007/s12031-022-01967-2. [PMID: 35084669]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Kyung Chan Park, Mahendiran Dharmasivam, Des R Richardson. The Role of Extracellular Proteases in Tumor Progression and the Development of Innovative Metal Ion Chelators that Inhibit their Activity. International journal of molecular sciences. 2020 Sep; 21(18):. doi: 10.3390/ijms21186805. [PMID: 32948029]
  • Kenichi Furihata, Katsuaki Nagasawa, Atsushi Hagino, Yuji Kumagai. A drug-drug interaction study of a novel, selective urate reabsorption inhibitor dotinurad and the non-steroidal anti-inflammatory drug oxaprozin in healthy adult males. Clinical and experimental nephrology. 2020 Mar; 24(Suppl 1):36-43. doi: 10.1007/s10157-020-01855-2. [PMID: 32076889]
  • Filitsa Dimiza, Marialena Lazou, Athanasios N Papadopoulos, Antonios G Hatzidimitriou, George Psomas. Manganese(II) coordination compounds of carboxylate non-steroidal anti-inflammatory drugs. Journal of inorganic biochemistry. 2020 02; 203(?):110906. doi: 10.1016/j.jinorgbio.2019.110906. [PMID: 31707332]
  • Shupeng Liu, Xiang Bao, Songpo Zhang, Heng Zhang, Xiaofeng Lu, Taihao Li, Zhenyi Chen, Na Chen. The study of ultrasound and iontophoresis on oxaprozin transdermal penetration using surface-enhanced Raman spectroscopy. Drug delivery and translational research. 2020 02; 10(1):83-92. doi: 10.1007/s13346-019-00664-9. [PMID: 31407271]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Marialena Lazou, Antonios G Hatzidimitriou, Athanasios N Papadopoulos, George Psomas. Zinc-oxaprozin compounds: Synthesis, structure and biological activity. Journal of inorganic biochemistry. 2019 06; 195(?):101-110. doi: 10.1016/j.jinorgbio.2019.03.016. [PMID: 30939377]
  • N Mennini, M Cirri, F Maestrelli, P Mura. Comparison of liposomal and NLC (nanostructured lipid carrier) formulations for improving the transdermal delivery of oxaprozin: Effect of cyclodextrin complexation. International journal of pharmaceutics. 2016 Dec; 515(1-2):684-691. doi: 10.1016/j.ijpharm.2016.11.013. [PMID: 27825863]
  • Franca-Maria Klingler, Markus Wolf, Sandra Wittmann, Philip Gribbon, Ewgenij Proschak. Bacterial Expression and HTS Assessment of Soluble Epoxide Hydrolase Phosphatase. Journal of biomolecular screening. 2016 Aug; 21(7):689-94. doi: 10.1177/1087057116637609. [PMID: 27009944]
  • José Lopes-de-Araújo, Ana Rute Neves, Virgínia M Gouveia, Catarina C Moura, Cláudia Nunes, Salette Reis. Oxaprozin-Loaded Lipid Nanoparticles towards Overcoming NSAIDs Side-Effects. Pharmaceutical research. 2016 Feb; 33(2):301-14. doi: 10.1007/s11095-015-1788-x. [PMID: 26350105]
  • Mian Mao, Ling Wang, Xuehua Jiang, Lin Yang. [Determination of oxaprozin in human plasma with high performance liquid chromatography (HPLC) and its application]. Sheng wu yi xue gong cheng xue za zhi = Journal of biomedical engineering = Shengwu yixue gongchengxue zazhi. 2013 Jun; 30(3):646-50. doi: NULL. [PMID: 23865335]
  • Sabina Halappanavar, Petra Jackson, Andrew Williams, Keld A Jensen, Karin S Hougaard, Ulla Vogel, Carole L Yauk, Håkan Wallin. Pulmonary response to surface-coated nanotitanium dioxide particles includes induction of acute phase response genes, inflammatory cascades, and changes in microRNAs: a toxicogenomic study. Environmental and molecular mutagenesis. 2011 Jul; 52(6):425-39. doi: 10.1002/em.20639. [PMID: 21259345]
  • Seung Yoon Lee, Jung Kook Suh, Jin Hwa Choi, Woo Jae Jeon, Mi Ae Cheong. Effect of ketorolac and diclofenac on the impairment of endothelium-dependent relaxation induced by reactive oxygen species in rabbit abdominal aorta. Korean journal of anesthesiology. 2010 Sep; 59(3):196-202. doi: 10.4097/kjae.2010.59.3.196. [PMID: 20877705]
  • Munish Ahuja, Avinash S Dhake, Surendra K Sharma, Dipak K Majumdar. Topical ocular delivery of NSAIDs. The AAPS journal. 2008 Jun; 10(2):229-41. doi: 10.1208/s12248-008-9024-9. [PMID: 18437583]
  • Shao-Fa Sun, Bo Zhou, Han-Na Hou, Yi Liu, Guang-Ya Xiang. Studies on the interaction between Oxaprozin-E and bovine serum albumin by spectroscopic methods. International journal of biological macromolecules. 2006 Nov; 39(4-5):197-200. doi: 10.1016/j.ijbiomac.2006.03.020. [PMID: 16828154]
  • Pradip Datta, Deven Scurlock, Amitava Dasgupta. Analytic performance evaluation of a new turbidimetric immunoassay for phenytoin on the ADVIA 1650 analyzer: effect of phenytoin metabolite and analogue. Therapeutic drug monitoring. 2005 Jun; 27(3):305-8. doi: 10.1097/01.ftd.0000164315.13825.dd. [PMID: 15905800]
  • Walter F Kean. Oxaprozin: kinetic and dynamic profile in the treatment of pain. Current medical research and opinion. 2004 Aug; 20(8):1275-7. doi: 10.1185/030079904125004420. [PMID: 15324530]
  • Jeffrey R LaDuca, Peter H Bouman, Anthony A Gaspari. Nonsteroidal antiinflammatory drug-induced pseudoporphyria: a case series. Journal of cutaneous medicine and surgery. 2002 Jul; 6(4):320-6. doi: 10.1007/s10227-001-0051-8. [PMID: 12118363]
  • Y Hu, S Tu, P Liu. A randomized, controlled, single-blind trial of leflunomide in the treatment of rheumatoid arthritis. Journal of Tongji Medical University = Tong ji yi ke da xue xue bao. 2001; 21(1):72-4. doi: 10.1007/bf02888043. [PMID: 11523255]
  • A Marland, P Sarkar, R Leavitt, E Lee-Ruff, J Ramnauth. The elimination profiles of oxaprozin in equine urine and serum after a 4.8-g dose. Journal of analytical toxicology. 1999 Jul; 23(4):242-6. doi: 10.1093/jat/23.4.242. [PMID: 10445486]
  • T Nishikawa, Y Kamijo, H Ohtani, A D Fraser. Oxaprozin interference with urinary benzodiazepine immunoassays and noninterference with receptor assay. Journal of analytical toxicology. 1999 Mar; 23(2):125-6. doi: 10.1093/jat/23.2.125. [PMID: 10192417]
  • S Al-Khenaizan, J F Schechter, D Sasseville. Pseudoporphyria induced by propionic acid derivatives. Journal of cutaneous medicine and surgery. 1999 Jan; 3(3):162-6. doi: 10.1177/120347549900300314. [PMID: 10082597]
  • N M Davies. Clinical pharmacokinetics of oxaprozin. Clinical pharmacokinetics. 1998 Dec; 35(6):425-36. doi: 10.2165/00003088-199835060-00002. [PMID: 9884815]
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  • A D Fraser, P Howell. Oxaprozin cross-reactivity in three commercial immunoassays for benzodiazepines in urine. Journal of analytical toxicology. 1998 Jan; 22(1):50-4. doi: 10.1093/jat/22.1.50. [PMID: 9491969]
  • A Karim, R Noveck, F G McMahon, M Smith, S Crosby, M Adams, J Wilton. Oxaprozin and piroxicam, nonsteroidal antiinflammatory drugs with long half-lives: effect of protein-binding differences on steady-state pharmacokinetics. Journal of clinical pharmacology. 1997 Apr; 37(4):267-78. doi: 10.1002/j.1552-4604.1997.tb04302.x. [PMID: 9115051]
  • G Ingrish, R L Rietschel. Oxaprozin-induced pseudoporphyria. Archives of dermatology. 1996 Dec; 132(12):1519-20. doi: NULL. [PMID: 8961891]
  • A Karim. Inverse nonlinear pharmacokinetics of total and protein unbound drug (oxaprozin): clinical and pharmacokinetic implications. Journal of clinical pharmacology. 1996 Nov; 36(11):985-97. doi: 10.1177/009127009603601102. [PMID: 8973987]
  • M Ogawa, S Ueda, Y Hamano, K Ito, H Saisho, B Akikusa. Membranous nephropathy associated with oxaprozin treatment. Nephron. 1996; 74(2):439-40. doi: 10.1159/000189356. [PMID: 8893177]
  • A F Aubry, N Markoglou, M H Adams, J Longstreth, I W Wainer. The effect of co-administered drugs on oxaprozin binding to human serum albumin. The Journal of pharmacy and pharmacology. 1995 Nov; 47(11):937-44. doi: 10.1111/j.2042-7158.1995.tb03274.x. [PMID: 8708989]
  • M Pulini. False-positive benzodiazepine urine test due to oxaprozin. JAMA. 1995 Jun; 273(24):1905-6. doi: NULL. [PMID: 7783293]
  • T Matuch-Hite, P Jones, J Moriarity. Interference of oxaprozin with benzodiazepines via enzyme immunoassay technique. Journal of analytical toxicology. 1995 Mar; 19(2):130. doi: 10.1093/jat/19.2.130. [PMID: 7769785]
  • P D Camara, L Audette, K Velletri, P Breitenbecher, M Rosner, W C Griffiths. False-positive immunoassay results for urine benzodiazepine in patients receiving oxaprozin (Daypro). Clinical chemistry. 1995 Jan; 41(1):115-6. doi: . [PMID: 7813058]
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  • U A Knuth, J Kühne, J Crosby, M Bals-Pratsch, R W Kelly, E Nieschlag. Indomethacin and oxaprozin lower seminal prostaglandin levels but do not influence sperm motion characteristics and serum hormones of young healthy men in a placebo-controlled double-blind trial. Journal of andrology. 1989 Mar; 10(2):108-19. doi: 10.1002/j.1939-4640.1989.tb00071.x. [PMID: 2497096]
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  • S Higuchi, Y Osada, Y Shioiri, S Nakaike, M Muramatsu, M Tanaka, I Arai, F Amanuma, S Otomo, H Aihara. [Anti-inflammatory activity of a non-steroidal anti-inflammatory agent, oxaprozin, in experimental models]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica. 1984 May; 83(5):383-94. doi: . [PMID: 6432656]
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