Cilomilast (BioDeep_00000177496)

 

Secondary id: BioDeep_00000015343

human metabolite blood metabolite


代谢物信息卡片


4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid

  化学式: C20H25NO4 (343.1783)
中文名称: 西洛司特
  谱图信息: 最多检出来源 Homo sapiens(blood) 100%

分子结构信息

SMILES: COC1=C(C=C(C=C1)C2(CCC(CC2)C(=O)O)C#N)OC3CCCC3
InChI: InChI=1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)


描述信息

D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors > D058988 - Phosphodiesterase 4 Inhibitors
C471 - Enzyme Inhibitor > C744 - Phosphodiesterase Inhibitor

同义名列表

3 个代谢物同义名

4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid; Cilomilast; Ariflo



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome()

BioCyc()

PlantCyc()

代谢反应

个相关的代谢反应过程信息。

Reactome()

BioCyc()

WikiPathways()

Plant Reactome()

INOH()

PlantCyc()

COVID-19 Disease Map()

PathBank()

PharmGKB()

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。

亚细胞结构定位 关联基因列表


文献列表

  • Man Xu, Xiaowen Yu, Xia Meng, Songming Huang, Yue Zhang, Aihua Zhang, Zhanjun Jia. Inhibition of PDE4/PDE4B improves renal function and ameliorates inflammation in cisplatin-induced acute kidney injury. American journal of physiology. Renal physiology. 2020 03; 318(3):F576-F588. doi: 10.1152/ajprenal.00477.2019. [PMID: 31961716]
  • Cheng-Yu Lin, Ching-Yun Hsu, Ahmed O Elzoghby, Ahmed Alalaiwe, Tsong-Long Hwang, Jia-You Fang. Oleic acid as the active agent and lipid matrix in cilomilast-loaded nanocarriers to assist PDE4 inhibition of activated neutrophils for mitigating psoriasis-like lesions. Acta biomaterialia. 2019 05; 90(?):350-361. doi: 10.1016/j.actbio.2019.04.002. [PMID: 30951898]
  • Mario Thevis, Oliver Krug, Wilhelm Schänzer. Monitoring phosphodiesterase-4 inhibitors using liquid chromatography/(tandem) mass spectrometry in sports drug testing. Rapid communications in mass spectrometry : RCM. 2013 May; 27(9):993-1004. doi: 10.1002/rcm.6539. [PMID: 23592202]
  • Chung-Hung Shih, Ling-Hung Lin, Hsin-Te Hsu, Kuo-Hsien Wang, Chi-Yin Lai, Chien-Ming Chen, Wun-Chang Ko. Hesperetin, a Selective Phosphodiesterase 4 Inhibitor, Effectively Suppresses Ovalbumin-Induced Airway Hyperresponsiveness without Influencing Xylazine/Ketamine-Induced Anesthesia. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):472897. doi: 10.1155/2012/472897. [PMID: 22454667]
  • You-Lan Yang, Hsin-Te Hsu, Kuo-Hsien Wang, Cheng-Ying Han, Chien-Ming Chen, Chi-Ming Chen, Wun-Chang Ko. Hesperetin-7,3'-O-dimethylether selectively inhibits phosphodiesterase 4 and effectively suppresses ovalbumin-induced airway hyperresponsiveness with a high therapeutic ratio. Journal of biomedical science. 2011 Nov; 18(?):84. doi: 10.1186/1423-0127-18-84. [PMID: 22074248]
  • Wun-Chang Ko, Ling-Hung Lin, Hsin-Yi Shen, Chi-Yin Lai, Chien-Ming Chen, Chung-Hung Shih. Biochanin a, a phytoestrogenic isoflavone with selective inhibition of phosphodiesterase 4, suppresses ovalbumin-induced airway hyperresponsiveness. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):635058. doi: 10.1155/2011/635058. [PMID: 21437195]
  • Chung-Hung Shih, Tzu-Jung Huang, Chien-Ming Chen, Yun-Lian Lin, Wun-Chang Ko. S-Petasin, the Main Sesquiterpene of Petasites formosanus, Inhibits Phosphodiesterase Activity and Suppresses Ovalbumin-Induced Airway Hyperresponsiveness. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):132374. doi: 10.1093/ecam/nep088. [PMID: 19641087]
  • Thomas M Ehrman, David J Barlow, Peter J Hylands. In silico search for multi-target anti-inflammatories in Chinese herbs and formulas. Bioorganic & medicinal chemistry. 2010 Mar; 18(6):2204-2218. doi: 10.1016/j.bmc.2010.01.070. [PMID: 20188577]
  • Marie-Pierre Pruniaux, Vincent Lagente, Malika Ouaged, Bernadette Bertin, François Moreau, Christine Julien-Larose, Marie-Noelle Rocher, Christelle Leportier, Brigitte Martin, Anita Bouget, Jean-Pierre Dubuit, Catherine Burnouf, Annette M Doherty, Claude P Bertrand. Relationship between phosphodiesterase type 4 inhibition and anti-inflammatory activity of CI-1044 in rat airways. Fundamental & clinical pharmacology. 2010 Feb; 24(1):73-82. doi: 10.1111/j.1472-8206.2009.00725.x. [PMID: 19650853]
  • Manthena V S Varma, Bo Feng, R Scott Obach, Matthew D Troutman, Jonathan Chupka, Howard R Miller, Ayman El-Kattan. Physicochemical determinants of human renal clearance. Journal of medicinal chemistry. 2009 Aug; 52(15):4844-52. doi: 10.1021/jm900403j. [PMID: 19445515]
  • 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]
  • Allen J Duplantier, Elizabeth L Bachert, John B Cheng, Victoria L Cohan, Teresa H Jenkinson, Kenneth G Kraus, Michael W McKechney, Joann D Pillar, John W Watson. SAR of a series of 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines as potent inhibitors of human eosinophil phosphodiesterase. Journal of medicinal chemistry. 2007 Jan; 50(2):344-9. doi: 10.1021/jm060904g. [PMID: 17228876]
  • Leonid M Berezhkovskiy. Determination of drug binding to plasma proteins using competitive equilibrium binding to dextran-coated charcoal. Journal of pharmacokinetics and pharmacodynamics. 2006 Oct; 33(5):595-608. doi: 10.1007/s10928-006-9024-2. [PMID: 16841186]
  • E Neil Schachter. Cilomilast. Drugs of today (Barcelona, Spain : 1998). 2006 Apr; 42(4):237-47. doi: 10.1358/dot.2006.42.4.973582. [PMID: 16703120]
  • Ellena J Growcott, Karen G Spink, Xiaohui Ren, Saliha Afzal, Kathy H Banner, John Wharton. Phosphodiesterase type 4 expression and anti-proliferative effects in human pulmonary artery smooth muscle cells. Respiratory research. 2006 Jan; 7(?):9. doi: 10.1186/1465-9921-7-9. [PMID: 16423283]
  • Geoff Down, Sarah Siederer, Sam Lim, Peter Daley-Yates. Clinical pharmacology of Cilomilast. Clinical pharmacokinetics. 2006; 45(3):217-33. doi: 10.2165/00003088-200645030-00001. [PMID: 16509757]
  • Zheng Huang, Joseph A Mancini. Phosphodiesterase 4 inhibitors for the treatment of asthma and COPD. Current medicinal chemistry. 2006; 13(27):3253-62. doi: 10.2174/092986706778773040. [PMID: 17168849]
  • Antonio Maurizio Vignola. PDE4 inhibitors in COPD--a more selective approach to treatment. Respiratory medicine. 2004 Jun; 98(6):495-503. doi: 10.1016/j.rmed.2003.12.012. [PMID: 15191033]
  • Regina Draheim, Ute Egerland, Chris Rundfeldt. Anti-inflammatory potential of the selective phosphodiesterase 4 inhibitor N-(3,5-dichloro-pyrid-4-yl)-[1-(4-fluorobenzyl)-5-hydroxy-indole-3-yl]-glyoxylic acid amide (AWD 12-281), in human cell preparations. The Journal of pharmacology and experimental therapeutics. 2004 Feb; 308(2):555-63. doi: 10.1124/jpet.103.059097. [PMID: 14610230]
  • M Bayés, X Rabasseda, J R Prous. Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology. 2003 Jul; 25(6):483-506. doi: . [PMID: 12949633]
  • M Motasim Billah, Nicola Cooper, Michael Minnicozzi, Julie Warneck, Peng Wang, John A Hey, William Kreutner, Charles A Rizzo, Sidney R Smith, Simon Young, Richard W Chapman, Hazel Dyke, Nang-Yang Shih, John J Piwinski, Francis M Cuss, John Montana, Ashit K Ganguly, Robert W Egan. Pharmacology of N-(3,5-dichloro-1-oxido-4-pyridinyl)-8-methoxy-2-(trifluoromethyl)-5-quinoline carboxamide (SCH 351591), a novel, orally active phosphodiesterase 4 inhibitor. The Journal of pharmacology and experimental therapeutics. 2002 Jul; 302(1):127-37. doi: 10.1124/jpet.302.1.127. [PMID: 12065709]
  • Guorong Lin, Karin E Bornfeldt. Cyclic AMP-specific phosphodiesterase 4 inhibitors promote ABCA1 expression and cholesterol efflux. Biochemical and biophysical research communications. 2002 Jan; 290(2):663-9. doi: 10.1006/bbrc.2001.6259. [PMID: 11785950]
  • D G Souza, G D Cassali, S Poole, M M Teixeira. Effects of inhibition of PDE4 and TNF-alpha on local and remote injuries following ischaemia and reperfusion injury. British journal of pharmacology. 2001 Nov; 134(5):985-94. doi: 10.1038/sj.bjp.0704336. [PMID: 11682446]
  • M A Giembycz. Cilomilast: a second generation phosphodiesterase 4 inhibitor for asthma and chronic obstructive pulmonary disease. Expert opinion on investigational drugs. 2001 Jul; 10(7):1361-79. doi: 10.1517/13543784.10.7.1361. [PMID: 11772257]
  • B D Zussman, C C Davie, J Kelly, R D Murdoch, D J Clark, J P Schofield, C Walls, C Birrell, D Webber, J Quinlan, S Y Ritchie, A Carr. Bioavailability of the oral selective phosphodiesterase 4 inhibitor cilomilast. Pharmacotherapy. 2001 Jun; 21(6):653-60. doi: 10.1592/phco.21.7.653.34569. [PMID: 11401178]
  • B D Zussman, J Kelly, R D Murdoch, D J Clark, Mbchb, C Schubert, H Collie. Cilomilast: pharmacokinetic and pharmacodynamic interactions with digoxin. Clinical therapeutics. 2001 Jun; 23(6):921-31. doi: 10.1016/s0149-2918(01)80079-5. [PMID: 11440291]
  • D C Underwood, S Bochnowicz, R R Osborn, C J Kotzer, M A Luttmann, D W Hay, P D Gorycki, S B Christensen, T J Torphy. Antiasthmatic activity of the second-generation phosphodiesterase 4 (PDE4) inhibitor SB 207499 (Ariflo) in the guinea pig. The Journal of pharmacology and experimental therapeutics. 1998 Dec; 287(3):988-95. doi: NULL. [PMID: 9864284]
  • D E Griswold, E F Webb, A M Badger, P D Gorycki, P A Levandoski, M A Barnette, M Grous, S Christensen, T J Torphy. SB 207499 (Ariflo), a second generation phosphodiesterase 4 inhibitor, reduces tumor necrosis factor alpha and interleukin-4 production in vivo. The Journal of pharmacology and experimental therapeutics. 1998 Nov; 287(2):705-11. doi: NULL. [PMID: 9808700]
  • H J Hilderson, M J De Wolf, A R Lagrou, W S Dierick. Subcellular structure of bovine thyroid gland. A study on bovine thyroid membranes by buoyant-density-gradient centrifugation in a B-XIV zonal rotor. The Biochemical journal. 1975 Dec; 152(3):601-7. doi: 10.1042/bj1520601. [PMID: 5997]