Licofelone (BioDeep_00000180469)

   

human metabolite blood metabolite


代谢物信息卡片


2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid

化学式: C23H22ClNO2 (379.13389820000003)
中文名称: 利克飞龙
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1(C)CN2C(CC(O)=O)=C(C(=C2C1)C1=CC=CC=C1)C1=CC=C(Cl)C=C1
InChI: InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)

描述信息

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
D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors
D002491 - Central Nervous System Agents > D000700 - Analgesics
C471 - Enzyme Inhibitor > C1323 - Cyclooxygenase Inhibitor
D000893 - Anti-Inflammatory Agents
Licofelone (ML-3000) is a dual COX/5-lipoxygenase (5-LOX) inhibitor (IC50=0.21/0.18 μM, respectively) for the treatment of osteoarthritis. Licofelone exerts anti-inflammatory and anti-proliferative effects. Licofelone induces apoptosis, and decreases the production of proinflammatory leukotrienes and prostaglandins[1][2][3].

同义名列表

5 个代谢物同义名

2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid; (2,2-Dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acid; ML-3000Licofelone; Licofelone; ML-3000



数据库引用编号

6 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

  • Seyed Mehrad Razavi, Danial Khayatan, Zahra Najafi Arab, Saeideh Momtaz, Kimia Zare, Razieh Mohammad Jafari, Ahmad Reza Dehpour, Amir Hossein Abdolghaffari. Licofelone, a potent COX/5-LOX inhibitor and a novel option for treatment of neurological disorders. Prostaglandins & other lipid mediators. 2021 12; 157(?):106587. doi: 10.1016/j.prostaglandins.2021.106587. [PMID: 34517113]
  • Guangju Zhai, Jean-Pierre Pelletier, Ming Liu, Edward W Randell, Proton Rahman, Johanne Martel-Pelletier. Serum lysophosphatidylcholines to phosphatidylcholines ratio is associated with symptomatic responders to symptomatic drugs in knee osteoarthritis patients. Arthritis research & therapy. 2019 11; 21(1):224. doi: 10.1186/s13075-019-2006-8. [PMID: 31694709]
  • Catarina Pereira-Leite, Daniela Lopes-de-Campos, Philippe Fontaine, Iolanda M Cuccovia, Cláudia Nunes, Salette Reis. Licofelone-DPPC Interactions: Putting Membrane Lipids on the Radar of Drug Development. Molecules (Basel, Switzerland). 2019 Jan; 24(3):. doi: 10.3390/molecules24030516. [PMID: 30709010]
  • Zehra Tuğçe Gür, Burcu Çalışkan, Erden Banoglu. Drug discovery approaches targeting 5-lipoxygenase-activating protein (FLAP) for inhibition of cellular leukotriene biosynthesis. European journal of medicinal chemistry. 2018 Jun; 153(?):34-48. doi: 10.1016/j.ejmech.2017.07.019. [PMID: 28784429]
  • Joshi Poorvashree, Dhaneshwar Suneela. Novel drug delivery of dual acting prodrugs of hydroxychloroquine with aryl acetic acid NSAIDs: Design, kinetics and pharmacological study. Drug delivery and translational research. 2017 10; 7(5):709-730. doi: 10.1007/s13346-017-0420-5. [PMID: 28828678]
  • Roumen Balansky, Gancho Ganchev, Marietta Iltcheva, Manasi Nikolov, Sebastiano La Maestra, Rosanna T Micale, Francesco D'Agostini, Vernon E Steele, Silvio De Flora. Modulation by licofelone and celecoxib of experimentally induced cancer and preneoplastic lesions in mice exposed to cigarette smoke. Current cancer drug targets. 2015; 15(3):188-95. doi: 10.2174/1568009615666150216170008. [PMID: 25687474]
  • Nikhil R Oak, Jonathan P Gumucio, Michael D Flood, Anjali L Saripalli, Max E Davis, Julie A Harning, Evan B Lynch, Stuart M Roche, Asheesh Bedi, Christopher L Mendias. Inhibition of 5-LOX, COX-1, and COX-2 increases tendon healing and reduces muscle fibrosis and lipid accumulation after rotator cuff repair. The American journal of sports medicine. 2014 Dec; 42(12):2860-8. doi: 10.1177/0363546514549943. [PMID: 25245131]
  • Jennifer N Dulin, Edward D Karoly, Ying Wang, Henry W Strobel, Raymond J Grill. Licofelone modulates neuroinflammation and attenuates mechanical hypersensitivity in the chronic phase of spinal cord injury. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2013 Jan; 33(2):652-64. doi: 10.1523/jneurosci.6128-11.2013. [PMID: 23303944]
  • Anil Kumar, Aditi Vashist, Puneet Kumar, Harikesh Kalonia, Jitendriya Mishra. Potential role of licofelone, minocycline and their combination against chronic fatigue stress induced behavioral, biochemical and mitochondrial alterations in mice. Pharmacological reports : PR. 2012; 64(5):1105-15. doi: 10.1016/s1734-1140(12)70907-6. [PMID: 23238467]
  • Altaf Mohammed, Naveena B Janakiram, Qian Li, Chang-In Choi, Yuting Zhang, Vernon E Steele, Chinthalapally V Rao. Chemoprevention of colon and small intestinal tumorigenesis in APC(Min/+) mice by licofelone, a novel dual 5-LOX/COX inhibitor: potential implications for human colon cancer prevention. Cancer prevention research (Philadelphia, Pa.). 2011 Dec; 4(12):2015-26. doi: 10.1158/1940-6207.capr-11-0233. [PMID: 21885812]
  • Puneet Kumar, Harikesh Kalonia, Anil Kumar. Role of LOX/COX pathways in 3-nitropropionic acid-induced Huntington's disease-like symptoms in rats: protective effect of licofelone. British journal of pharmacology. 2011 Sep; 164(2b):644-54. doi: 10.1111/j.1476-5381.2011.01418.x. [PMID: 21486276]
  • Harikesh Kalonia, Puneet Kumar, Anil Kumar. Licofelone attenuates quinolinic acid induced Huntington like symptoms: possible behavioral, biochemical and cellular alterations. Progress in neuro-psychopharmacology & biological psychiatry. 2011 Mar; 35(2):607-15. doi: 10.1016/j.pnpbp.2011.01.003. [PMID: 21237233]
  • J-P Pelletier, J-P Raynauld, J Caron, F Mineau, F Abram, M Dorais, B Haraoui, D Choquette, J Martel-Pelletier. Decrease in serum level of matrix metalloproteinases is predictive of the disease-modifying effect of osteoarthritis drugs assessed by quantitative MRI in patients with knee osteoarthritis. Annals of the rheumatic diseases. 2010 Dec; 69(12):2095-101. doi: 10.1136/ard.2009.122002. [PMID: 20570834]
  • Amit Gupta, Anil Kumar, S K Kulkarni. Licofelone attenuates MPTP-induced neuronal toxicity: behavioral, biochemical and cellular evidence. Inflammopharmacology. 2010 Oct; 18(5):223-32. doi: 10.1007/s10787-010-0052-6. [PMID: 20697819]
  • Jae-Hoon Choi, Hyung Jun Jeon, Jong-Gil Park, Seong Keun Sonn, Mi-Ran Lee, Mi-Ni Lee, Hye Jin You, Geun-Young Kim, Jae-Hong Kim, Mun Han Lee, Oh-Seung Kwon, Ki-Hoan Nam, Hyoung-Chin Kim, Tae-Sook Jeong, Woo Song Lee, Goo Taeg Oh. Anti-atherogenic effect of BHB-TZD having inhibitory activities on cyclooxygenase and 5-lipoxygenase in hyperlipidemic mice. Atherosclerosis. 2010 Sep; 212(1):146-52. doi: 10.1016/j.atherosclerosis.2010.05.003. [PMID: 20684827]
  • Christelle Boileau, Johanne Martel-Pelletier, Judith Caron, Philippe Msika, Georges B Guillou, Caroline Baudouin, Jean-Pierre Pelletier. Protective effects of total fraction of avocado/soybean unsaponifiables on the structural changes in experimental dog osteoarthritis: inhibition of nitric oxide synthase and matrix metalloproteinase-13. Arthritis research & therapy. 2009; 11(2):R41. doi: 10.1186/ar2649. [PMID: 19291317]
  • Wolfgang Albrecht, Anke Unger, Andreas K Nussler, Stefan Laufer. In vitro metabolism of 2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl] acetic acid (licofelone, ML3000), an inhibitor of cyclooxygenase-1 and -2 and 5-lipoxygenase. Drug metabolism and disposition: the biological fate of chemicals. 2008 May; 36(5):894-903. doi: 10.1124/dmd.108.020347. [PMID: 18268076]
  • Gabriella Coruzzi, Nicola Venturi, Silvana Spaggiari. Gastrointestinal safety of novel nonsteroidal antiinflammatory drugs: selective COX-2 inhibitors and beyond. Acta bio-medica : Atenei Parmensis. 2007 Aug; 78(2):96-110. doi: . [PMID: 17933277]
  • Cristina Vidal, Almudena Gómez-Hernández, Eva Sánchez-Galán, Alejandro González, Luis Ortega, Juan Antonio Gómez-Gerique, José Tuñón, Jesús Egido. Licofelone, a balanced inhibitor of cyclooxygenase and 5-lipoxygenase, reduces inflammation in a rabbit model of atherosclerosis. The Journal of pharmacology and experimental therapeutics. 2007 Jan; 320(1):108-16. doi: 10.1124/jpet.106.110361. [PMID: 17015640]
  • S K Kulkarni, Vijay Pal Singh. Licofelone--a novel analgesic and anti-inflammatory agent. Current topics in medicinal chemistry. 2007; 7(3):251-63. doi: 10.2174/156802607779941305. [PMID: 17305568]
  • Vijay Pal Singh, Chandrashekhar S Patil, Shrinivas K Kulkarni. Effect of licofelone against NSAIDs-induced gastrointestinal ulceration and inflammation. Indian journal of experimental biology. 2005 Mar; 43(3):247-53. doi: ". [PMID: 15816411]
  • Serenella Rotondo, Katarzyna Krauze-Brzósko, Stefano Manarini, Virgilio Evangelista, Chiara Cerletti. Licofelone, an inhibitor of cyclooxygenase and 5-lipoxygenase, specifically inhibits cyclooxygenase-1-dependent platelet activation. European journal of pharmacology. 2004 Mar; 488(1-3):79-83. doi: 10.1016/j.ejphar.2004.02.006. [PMID: 15044038]
  • Bernard Bannwarth. Is licofelone, a dual inhibitor of cyclo-oxygenase and 5-lipoxygenase, a promising alternative in anti-inflammatory therapy?. Fundamental & clinical pharmacology. 2004 Feb; 18(1):125-30. doi: 10.1046/j.1472-8206.2003.00217.x. [PMID: 14748764]
  • S Laufer. Osteoarthritis therapy--are there still unmet needs?. Rheumatology (Oxford, England). 2004 Feb; 43 Suppl 1(?):i9-15. doi: 10.1093/rheumatology/keh103. [PMID: 14752170]
  • Fabio Celotti, Thierry Durand. The metabolic effects of inhibitors of 5-lipoxygenase and of cyclooxygenase 1 and 2 are an advancement in the efficacy and safety of anti-inflammatory therapy. Prostaglandins & other lipid mediators. 2003 Jul; 71(3-4):147-62. doi: 10.1016/s1098-8823(03)00039-x. [PMID: 14518558]
  • Stefano Fiorucci, Eleonora Distrutti, Octavio Menezes de Lima, Mario Romano, Andrea Mencarelli, Miriam Barbanti, Ernesto Palazzini, Antonio Morelli, John L Wallace. Relative contribution of acetylated cyclo-oxygenase (COX)-2 and 5-lipooxygenase (LOX) in regulating gastric mucosal integrity and adaptation to aspirin. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2003 Jun; 17(9):1171-3. doi: 10.1096/fj.02-0777fje. [PMID: 12709408]
  • S Tries, S Laufer, P Radziwon, H K Breddin. Antithrombotic and platelet function inhibiting effects of ML3000, a new antiinflammatory drug with Cox/5-LOX inhibitory activity. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2002 Mar; 51(3):129-34. doi: 10.1007/pl00000284. [PMID: 12005203]
  • D V Jovanovic, J C Fernandes, J Martel-Pelletier, F C Jolicoeur, P Reboul, S Laufer, S Tries, J P Pelletier. In vivo dual inhibition of cyclooxygenase and lipoxygenase by ML-3000 reduces the progression of experimental osteoarthritis: suppression of collagenase 1 and interleukin-1beta synthesis. Arthritis and rheumatism. 2001 Oct; 44(10):2320-30. doi: 10.1002/1529-0131(200110)44:10<2320::aid-art394>3.0.co;2-p. [PMID: 11665972]
  • B Fyrnys, R Claus, G Wolf, H P Deigner. Oxidized low density lipoprotein stimulates protein kinase C (PKC) activity and expression of PKC-isotypes via prostaglandin-H-synthase in P388D1 cells. Advances in experimental medicine and biology. 1997; 407(?):93-8. doi: 10.1007/978-1-4899-1813-0_14. [PMID: 9321937]
  • H P Deigner, C E Freyberg, S Laufer. Distribution and excretion of [14C]-labelled [2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5- yl]- [2'-14C]-acetic acid in rats. Arzneimittel-Forschung. 1995 Mar; 45(3):272-6. doi: NULL. [PMID: 7741783]
  • D R Algate, J Augustin, P R Atterson, D J Beard, C M Jobling, S Laufer, P L Munt, S Tries. General pharmacology of [2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3- dihydro-1H-pyrrolizine-5-yl]-acetic acid in experimental animals. Arzneimittel-Forschung. 1995 Feb; 45(2):159-65. doi: NULL. [PMID: 7710439]
  • S Laufer, S Tries, J Augustin, R Elsässer, W Albrecht, R Guserle, D R Algate, P R Atterson, P L Munt. Acute and chronic anti-inflammatory properties of [2,2-dimethyl-6-(4- chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl]-acetic acid. Arzneimittel-Forschung. 1995 Jan; 45(1):27-32. doi: NULL. [PMID: 7893265]