Nitroaspirin (BioDeep_00000181703)
human metabolite blood metabolite
代谢物信息卡片
2-Acetoxybenzoate-2-(1-nitroxymethyl)phenyl ester
化学式: C16H13NO7 (331.0691988)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC(CO[N+]([O-])=O)=C1
InChI: InChI=1S/C16H13NO7/c1-11(18)23-15-8-3-2-7-14(15)16(19)24-13-6-4-5-12(9-13)10-22-17(20)21/h2-9H,10H2,1H3
描述信息
D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates
D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015853 - Cysteine Proteinase Inhibitors
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors
D002491 - Central Nervous System Agents > D000700 - Analgesics
D006401 - Hematologic Agents > D005343 - Fibrinolytic Agents
C471 - Enzyme Inhibitor > C1323 - Cyclooxygenase Inhibitor
D050299 - Fibrin Modulating Agents
D002317 - Cardiovascular Agents
D018501 - Antirheumatic Agents
同义名列表
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:125482
- PubChem: 119032
- HMDB: HMDB0255639
- DrugBank: DB12445
- ChEMBL: CHEMBL374385
- CAS: 175033-36-0
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
- Malgorzata Zwolinska-Wcislo, Tomasz Brzozowski, Agata Ptak-Belowska, Aneta Targosz, Katarzyna Urbanczyk, Slawomir Kwiecien, Zbigniew Sliwowski. Nitric oxide-releasing aspirin but not conventional aspirin improves healing of experimental colitis.
World journal of gastroenterology.
2011 Sep; 17(36):4076-89. doi:
10.3748/wjg.v17.i36.4076. [PMID: 22039321] - M Pawlik, R Pajdo, S Kwiecien, A Ptak-Belowska, Z Sliwowski, M Mazurkiewicz-Janik, S J Konturek, W W Pawlik, T Brzozowski. Nitric oxide (NO)-releasing aspirin exhibits a potent esophagoprotection in experimental model of acute reflux esophagitis. Role of nitric oxide and proinflammatory cytokines.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society.
2011 Feb; 62(1):75-86. doi:
. [PMID: 21451212] - Mitali Chattopadhyay, Carlos A Velazquez, April Pruski, Kamran V Nia, Khaled R Abdellatif, Larry K Keefer, Khosrow Kashfi. Comparison between 3-Nitrooxyphenyl acetylsalicylate (NO-ASA) and O2-(acetylsalicyloxymethyl)-1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (NONO-ASA) as safe anti-inflammatory, analgesic, antipyretic, antioxidant prodrugs.
The Journal of pharmacology and experimental therapeutics.
2010 Nov; 335(2):443-50. doi:
10.1124/jpet.110.171017. [PMID: 20679133] - Paolo Gresele, Stefania Marzotti, Giuseppe Guglielmini, Stefania Momi, Silvia Giannini, Pietro Minuz, Paola Lucidi, Geremia B Bolli. Hyperglycemia-induced platelet activation in type 2 diabetes is resistant to aspirin but not to a nitric oxide-donating agent.
Diabetes care.
2010 Jun; 33(6):1262-8. doi:
10.2337/dc09-2013. [PMID: 20299485] - Ulla Derhaschnig, Ingrid Schweeger-Exeli, Claudia Marsik, Francesco Cardona, Pietro Minuz, Bernd Jilma. Effects of aspirin and NO-aspirin (NCX 4016) on platelet function and coagulation in human endotoxemia.
Platelets.
2010; 21(5):320-8. doi:
10.3109/09537101003735572. [PMID: 20608787] - Priscilla Jaichander, Krithika Selvarajan, Mahdi Garelnabi, Sampath Parthasarathy. Induction of paraoxonase 1 and apolipoprotein A-I gene expression by aspirin.
Journal of lipid research.
2008 Oct; 49(10):2142-8. doi:
10.1194/jlr.m800082-jlr200. [PMID: 18519978] - S S Kwiecien, M W Pawlik, T Brzozowski, P C Konturek, Z Sliwowski, W W Pawlik, S J Konturek. Nitric oxide (NO)-releasing aspirin and (NO) donors in protection of gastric mucosa against stress.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society.
2008 Aug; 59 Suppl 2(?):103-15. doi:
". [PMID: 18812632] - V Kaddai, T Gonzalez, M Bolla, Y Le Marchand-Brustel, M Cormont. The nitric oxide-donating derivative of acetylsalicylic acid, NCX 4016, stimulates glucose transport and glucose transporters translocation in 3T3-L1 adipocytes.
American journal of physiology. Endocrinology and metabolism.
2008 Jul; 295(1):E162-9. doi:
10.1152/ajpendo.00622.2007. [PMID: 18492771] - Nalini Santanam, Sampath Parthasarathy. Aspirin is a substrate for paraoxonase-like activity: implications in atherosclerosis.
Atherosclerosis.
2007 Apr; 191(2):272-5. doi:
10.1016/j.atherosclerosis.2006.05.027. [PMID: 16793048] - Paolo Gresele, Rino Migliacci, Alessandra Procacci, Paola De Monte, Erminio Bonizzoni. Prevention by NCX 4016, a nitric oxide-donating aspirin, but not by aspirin, of the acute endothelial dysfunction induced by exercise in patients with intermittent claudication.
Thrombosis and haemostasis.
2007 Mar; 97(3):444-50. doi:
NULL. [PMID: 17334512] - Catriona M Turnbull, Clara Cena, Roberta Fruttero, Alberto Gasco, Adriano G Rossi, Ian L Megson. Mechanism of action of novel NO-releasing furoxan derivatives of aspirin in human platelets.
British journal of pharmacology.
2006 Jun; 148(4):517-26. doi:
10.1038/sj.bjp.0706743. [PMID: 16702997] - Jianjun Gao, Khosrow Kashfi, Xiaoping Liu, Basil Rigas. NO-donating aspirin induces phase II enzymes in vitro and in vivo.
Carcinogenesis.
2006 Apr; 27(4):803-10. doi:
10.1093/carcin/bgi262. [PMID: 16267095] - S G Burke, C L Wainwright, I Vojnovic, T Warner, D G Watson, B L Furman. The effect of NCX4016 [2-acetoxy-benzoate 2-(2-nitroxymethyl)-phenyl ester] on the consequences of ischemia and reperfusion in the streptozotocin diabetic rat.
The Journal of pharmacology and experimental therapeutics.
2006 Mar; 316(3):1107-14. doi:
10.1124/jpet.105.096339. [PMID: 16260580] - M V Ambrosini, G Mariucci, M G Rambotti, M Tantucci, C Covarelli, L De Angelis, P Del Soldato. Ultrastructural investigations on protective effects of NCX 4016 (nitroaspirin) on macrovascular endothelium in diabetic Wistar rats.
Journal of submicroscopic cytology and pathology.
2005 Aug; 37(2):205-13. doi:
NULL. [PMID: 16335593] - Stefano Fiorucci, Andrea Mencarelli, Alessandra Meneguzzi, Alessandro Lechi, Barbara Renga, Piero del Soldato, Antonio Morelli, Pietro Minuz. Co-administration of nitric oxide-aspirin (NCX-4016) and aspirin prevents platelet and monocyte activation and protects against gastric damage induced by aspirin in humans.
Journal of the American College of Cardiology.
2004 Aug; 44(3):635-41. doi:
10.1016/j.jacc.2004.03.079. [PMID: 15358033] - Marina Carini, Giancarlo Aldini, Marica Orioli, Angela Piccoli, Giuseppe Rossoni, Roberto Maffei Facino. Nitric oxide release and distribution following oral and intraperitoneal administration of nitroaspirin (NCX 4016) in the rat.
Life sciences.
2004 May; 74(26):3291-305. doi:
10.1016/j.lfs.2003.11.018. [PMID: 15094329] - Marina Carini, Giancarlo Aldini, Marica Orioli, Angela Piccoli, Paola Tocchetti, Roberto Maffei Facino. Chemiluminescence and LC-MS/MS analyses for the study of nitric oxide release and distribution following oral administration of nitroaspirin (NCX 4016) in healthy volunteers.
Journal of pharmaceutical and biomedical analysis.
2004 Apr; 35(2):277-87. doi:
10.1016/s0731-7085(03)00531-4. [PMID: 15063462] - Silvia Bertuglia, Andrea Giusti, Piero Del Soldato. Antioxidant activity of nitro derivative of aspirin against ischemia-reperfusion in hamster cheek pouch microcirculation.
American journal of physiology. Gastrointestinal and liver physiology.
2004 Mar; 286(3):G437-43. doi:
10.1152/ajpgi.00339.2003. [PMID: 14563672] - Teresa Corazzi, Mario Leone, Rita Roberti, Piero Del Soldato, Paolo Gresele. Effect of nitric oxide-donating agents on human monocyte cyclooxygenase-2.
Biochemical and biophysical research communications.
2003 Nov; 311(4):897-903. doi:
10.1016/j.bbrc.2003.10.079. [PMID: 14623265] - John F Gilmer, Michael A Murphy, Jean A Shannon, Colm G Breen, Sheila A Ryder, John M Clancy. Single oral dose study of two isosorbide-based aspirin prodrugs in the dog.
The Journal of pharmacy and pharmacology.
2003 Oct; 55(10):1351-7. doi:
10.1211/0022357022007. [PMID: 14607016] - Stefano Fiorucci, Luca Santucci, John L Wallace, Marco Sardina, Mario Romano, Piero del Soldato, Antonio Morelli. Interaction of a selective cyclooxygenase-2 inhibitor with aspirin and NO-releasing aspirin in the human gastric mucosa.
Proceedings of the National Academy of Sciences of the United States of America.
2003 Sep; 100(19):10937-41. doi:
10.1073/pnas.1933204100. [PMID: 12960371] - Giuseppe Rossoni, Barbara Manfredi, Piero Del Soldato, Gianluca Polvani, Ferruccio Berti. Nitric oxide-releasing aspirin inhibits vasoconstriction in perfused tail artery of normotensive and spontaneously hypertensive rats.
European journal of pharmacology.
2003 Sep; 477(1):59-68. doi:
10.1016/j.ejphar.2003.08.004. [PMID: 14512099] - Tomasz Brzozowski, Piotr C Konturek, Stanislaw J Konturek, Slawomir Kwiecień, Zbigniew Sliwowski, Robert Pajdo, Alexandra Duda, Agata Ptak, Eckhart G Hahn. Implications of reactive oxygen species and cytokines in gastroprotection against stress-induced gastric damage by nitric oxide releasing aspirin.
International journal of colorectal disease.
2003 Jul; 18(4):320-9. doi:
10.1007/s00384-002-0451-2. [PMID: 12774247] - Stefano Fiorucci, Luca Santucci, Paolo Gresele, Roberto Maffei Faccino, Piero Del Soldato, Antonio Morelli. Gastrointestinal safety of NO-aspirin (NCX-4016) in healthy human volunteers: a proof of concept endoscopic study.
Gastroenterology.
2003 Mar; 124(3):600-7. doi:
10.1053/gast.2003.50096. [PMID: 12612897] - Stefano Fiorucci, Andrea Mencarelli, Alessandra Meneguzzi, Alessandro Lechi, Antonio Morelli, Piero del Soldato, Pietro Minuz. NCX-4016 (NO-aspirin) inhibits lipopolysaccharide-induced tissue factor expression in vivo: role of nitric oxide.
Circulation.
2002 12; 106(24):3120-5. doi:
10.1161/01.cir.0000039341.57809.1e. [PMID: 12473561] - Claudio Napoli, Eric Ackah, Filomena De Nigris, Piero Del Soldato, Francesco P D'Armiento, Ettore Crimi, Mario Condorelli, William C Sessa. Chronic treatment with nitric oxide-releasing aspirin reduces plasma low-density lipoprotein oxidation and oxidative stress, arterial oxidation-specific epitopes, and atherogenesis in hypercholesterolemic mice.
Proceedings of the National Academy of Sciences of the United States of America.
2002 Sep; 99(19):12467-70. doi:
10.1073/pnas.192244499. [PMID: 12209007] - Galen M Pieper, Wolfgang Siebeneich, Cara L Olds, Christopher C Felix, Piero Del Soldato. Vascular protective actions of a nitric oxide aspirin analog in both in vitro and in vivo models of diabetes mellitus.
Free radical biology & medicine.
2002 Jun; 32(11):1143-56. doi:
10.1016/s0891-5849(02)00832-8. [PMID: 12031899] - Claudio Napoli, Giancarlo Aldini, John L Wallace, Filomena de Nigris, Roberto Maffei, Pasquale Abete, Domenico Bonaduce, Gianluigi Condorelli, Franco Rengo, Vincenzo Sica, Francesco P D'Armiento, Chiara Mignogna, Gaetano de Rosa, Mario Condorelli, Lilach O Lerman, Louis J Ignarro. Efficacy and age-related effects of nitric oxide-releasing aspirin on experimental restenosis.
Proceedings of the National Academy of Sciences of the United States of America.
2002 Feb; 99(3):1689-94. doi:
10.1073/pnas.022639399. [PMID: 11818533] - S Kato, K Suzuki, H Ukawa, Y Komoike, K Takeuchi. Low gastric toxicity of nitric oxide-releasing aspirin, NCX-4016, in rats with cirrhosis and arthritis.
Digestive diseases and sciences.
2001 Aug; 46(8):1690-9. doi:
10.1023/a:1010601520497. [PMID: 11508669] - J Keeble, O A Al-Swayeh, P K Moore. Vasorelaxant effect of nitric oxide releasing steroidal and nonsteroidal anti-inflammatory drugs.
British journal of pharmacology.
2001 Aug; 133(7):1023-8. doi:
10.1038/sj.bjp.0704161. [PMID: 11487511] - G Rossoni, B Manfredi, V D Colonna, M Bernareggi, F Berti. The nitroderivative of aspirin, NCX 4016, reduces infarct size caused by myocardial ischemia-reperfusion in the anesthetized rat.
The Journal of pharmacology and experimental therapeutics.
2001 Apr; 297(1):380-7. doi:
. [PMID: 11259566] - K Tashima, A Fujita, M Umeda, K Takeuchi. Lack of gastric toxicity of nitric oxide-releasing aspirin, NCX-4016, in the stomach of diabetic rats.
Life sciences.
2000 Aug; 67(13):1639-52. doi:
10.1016/s0024-3205(00)00746-3. [PMID: 10983857] - N Grosser, H Schröder. A common pathway for nitric oxide release from NO-aspirin and glyceryl trinitrate.
Biochemical and biophysical research communications.
2000 Jul; 274(1):255-8. doi:
10.1006/bbrc.2000.3121. [PMID: 10903927] - G Rossoni, M Berti, V D Colonna, M Bernareggi, P Del Soldato, F Berti. Myocardial protection by the nitroderivative of aspirin, NCX 4016: in vitro and in vivo experiments in the rabbit.
Italian heart journal : official journal of the Italian Federation of Cardiology.
2000 Feb; 1(2):146-55. doi:
. [PMID: 10730616] - K Takeuchi, H Ukawa, A Konaka, M Kitamura, Y Sugawa. Effect of nitric oxide-releasing aspirin derivative on gastric functional and ulcerogenic responses in rats: comparison with plain aspirin.
The Journal of pharmacology and experimental therapeutics.
1998 Jul; 286(1):115-21. doi:
NULL. [PMID: 9655849] - J L Wallace, W McKnight, T L Wilson, P Del Soldato, G Cirino. Reduction of shock-induced gastric damage by a nitric oxide-releasing aspirin derivative: role of neutrophils.
The American journal of physiology.
1997 12; 273(6):G1246-51. doi:
10.1152/ajpgi.1997.273.6.g1246. [PMID: 9435549]