Rolipram (BioDeep_00000183006)

   

human metabolite blood metabolite


代谢物信息卡片


3-[3-(cyclopentyloxy)-4-methoxyphenyl]-3,4-dihydro-2H-pyrrol-5-ol

化学式: C16H21NO3 (275.1521)
中文名称: 咯利普兰
谱图信息: 最多检出来源 Homo sapiens(blood) 25.73%

分子结构信息

SMILES: COC1=C(C=C(C=C1)C2CC(=O)NC2)OC3CCCC3
InChI: InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)

描述信息

D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors > D058988 - Phosphodiesterase 4 Inhibitors
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
C471 - Enzyme Inhibitor > C744 - Phosphodiesterase Inhibitor

同义名列表

6 个代谢物同义名

3-[3-(cyclopentyloxy)-4-methoxyphenyl]-3,4-dihydro-2H-pyrrol-5-ol; 4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinone; Rolipramum; rolipram; ZK 62711; Rolipram



数据库引用编号

10 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。

亚细胞结构定位 关联基因列表


文献列表

  • Leila Gobejishvili, Walter E Rodriguez, Philip Bauer, Yali Wang, Chirag Soni, Todd Lydic, Shirish Barve, Craig McClain, Claudio Maldonado. Novel Liposomal Rolipram Formulation for Clinical Application to Reduce Emesis. Drug design, development and therapy. 2022; 16(?):1301-1309. doi: 10.2147/dddt.s355796. [PMID: 35535222]
  • Divjot Virk, Amit Kumar, Amteshwar Singh Jaggi, Nirmal Singh. Ameliorative role of rolipram, PDE-4 inhibitor, against sodium arsenite-induced vascular dementia in rats. Environmental science and pollution research international. 2021 Nov; 28(44):63250-63262. doi: 10.1007/s11356-021-15189-3. [PMID: 34226994]
  • Likang Wu, Lei Xu, Yu Chen, Guohua Xu, Qunfeng Guo, Depeng Meng, Jianping Fan, Guoqiang Song, Peng Xu. Rolipram plays an anti-fibrotic effect in ligamentum flavum fibroblasts by inhibiting the activation of ERK1/2. BMC musculoskeletal disorders. 2021 Sep; 22(1):818. doi: 10.1186/s12891-021-04712-9. [PMID: 34556093]
  • 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]
  • Zafer Sahin, Sevde Nur Biltekin, Leyla Yurttas, Barkin Berk, Yağmur Özhan, Hande Sipahi, Zhan-Guo Gao, Kenneth A Jacobson, Şeref Demirayak. Novel cyanothiouracil and cyanothiocytosine derivatives as concentration-dependent selective inhibitors of U87MG glioblastomas: Adenosine receptor binding and potent PDE4 inhibition. European journal of medicinal chemistry. 2021 Feb; 212(?):113125. doi: 10.1016/j.ejmech.2020.113125. [PMID: 33422981]
  • Chia-Chih Liao, Huang-Ping Yu, Shih-Chun Yang, Ahmed Alalaiwe, You-Shan Dai, Fu-Chao Liu, Jia-You Fang. Multifunctional lipid-based nanocarriers with antibacterial and anti-inflammatory activities for treating MRSA bacteremia in mice. Journal of nanobiotechnology. 2021 Feb; 19(1):48. doi: 10.1186/s12951-021-00789-5. [PMID: 33588861]
  • Sung-Jun Park, Faiyaz Ahmad, Robert J Bahde, Andrew Philp, Jeonghan Kim, Tianjiao Huang, Myung K Kim, William C Trenkle, Jay H Chung. Potent PDE4 inhibitor activates AMPK and Sirt1 to induce mitochondrial biogenesis. PloS one. 2021; 16(6):e0253269. doi: 10.1371/journal.pone.0253269. [PMID: 34138962]
  • Lirlândia P Sousa, Vanessa Pinho, Mauro M Teixeira. Harnessing inflammation resolving-based therapeutic agents to treat pulmonary viral infections: What can the future offer to COVID-19?. British journal of pharmacology. 2020 09; 177(17):3898-3904. doi: 10.1111/bph.15164. [PMID: 32557557]
  • Xiaying Lu, Juan Wang, Xiaohuan Chen, Yong Jiang, Zhixing K Pan. Rolipram Protects Mice from Gram-negative Bacterium Escherichia coli-induced Inflammation and Septic Shock. Scientific reports. 2020 01; 10(1):175. doi: 10.1038/s41598-019-56899-6. [PMID: 31932743]
  • 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]
  • Maarten Ooms, Tetsuya Tsujikawa, Talakad G Lohith, Sanché N Mabins, Sami S Zoghbi, Akiko Sumitomo, Hanna Jaaro-Peled, Yasuyuki Kimura, Sanjay Telu, Victor W Pike, Toshifumi Tomoda, Robert B Innis, Akira Sawa, Masahiro Fujita. [11C](R)-Rolipram positron emission tomography detects DISC1 inhibition of phosphodiesterase type 4 in live Disc1 locus-impaired mice. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism. 2019 07; 39(7):1306-1313. doi: 10.1177/0271678x18758997. [PMID: 29430995]
  • Jasper van der Aart, Cristian Salinas, Rahul Dimber, Sabina Pampols-Maso, Ashley A Weekes, John Tonkyn, Frank A Gray, Jan Passchier, Roger N Gunn, Eugenii A Rabiner. Quantification of human brain PDE4 occupancy by GSK356278: A [11C](R)-rolipram PET study. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism. 2018 11; 38(11):2033-2040. doi: 10.1177/0271678x17720868. [PMID: 28737056]
  • Jing-Xing Yang, Te-Chih Hsiung, Fu-Chun Weng, Shiau-Li Ding, Chin-Pyng Wu, Marco Conti, Tsung-Hsien Chuang, S-L Catherine Jin. Synergistic effect of phosphodiesterase 4 inhibitor and serum on migration of endotoxin-stimulated macrophages. Innate immunity. 2018 11; 24(8):501-512. doi: 10.1177/1753425918809155. [PMID: 30409089]
  • Zhuoran Wang, Yaru Liang, Lu Zhang, Nannan Zhang, Qingfei Liu, Zhao Wang. Phosphodiesterase 4 inhibitor activates AMPK-SIRT6 pathway to prevent aging-related adipose deposition induced by metabolic disorder. Aging. 2018 09; 10(9):2394-2406. doi: 10.18632/aging.101559. [PMID: 30227388]
  • Akihiro Takano, Tolga Uz, Jesus Garcia-Segovia, Max Tsai, Gezim Lahu, Nahid Amini, Ryuji Nakao, Zhisheng Jia, Christer Halldin. A Nonhuman Primate PET Study: Measurement of Brain PDE4 Occupancy by Roflumilast Using (R)-[11C]Rolipram. Molecular imaging and biology. 2018 08; 20(4):615-622. doi: 10.1007/s11307-018-1168-0. [PMID: 29441434]
  • Yan-Qiong Guo, Gui-Hua Tang, Lan-Lan Lou, Wei Li, Bei Zhang, Bo Liu, Sheng Yin. Prenylated flavonoids as potent phosphodiesterase-4 inhibitors from Morus alba: Isolation, modification, and structure-activity relationship study. European journal of medicinal chemistry. 2018 Jan; 144(?):758-766. doi: 10.1016/j.ejmech.2017.12.057. [PMID: 29291443]
  • Sevgi Türker-Kaya, İpek Komsuoğlu Celikyurt, Umut Celikyurt, Aygül Kına. Inhibition of PDE4 by low doses of rolipram induces changes in lipid and protein components of mice heart. General physiology and biophysics. 2018 Jan; 37(1):1-12. doi: 10.4149/gpb_2017009. [PMID: 28836502]
  • Sara Ramezani, Nasim Vousooghi, Fatemeh Ramezani Kapourchali, Mahmoudreza Hadjighasem, Parisa Hayat, Naser Amini, Mohammad Taghi Joghataei. Rolipram potentiates bevacizumab-induced cell death in human glioblastoma stem-like cells. Life sciences. 2017 Mar; 173(?):11-19. doi: 10.1016/j.lfs.2017.02.005. [PMID: 28202289]
  • Alla V Lipeeva, Dmitry S Baev, Margarita P Dolgikh, Tatijana G Tolstikova, Elvira E Shults. Rapid Access to Oxazine Fused Furocoumarins and in vivo and in silico Studies of theirs Biological Activity. Medicinal chemistry (Shariqah (United Arab Emirates)). 2017; 13(7):625-632. doi: 10.2174/1573406413666170601114527. [PMID: 28571532]
  • Wei Wang, Yue Li, Jessica Y Zhu, Dongdong Fang, Han-Fei Ding, Zheng Dong, Qing Jing, Shi-Bing Su, Shuang Huang. Triple negative breast cancer development can be selectively suppressed by sustaining an elevated level of cellular cyclic AMP through simultaneously blocking its efflux and decomposition. Oncotarget. 2016 Dec; 7(52):87232-87245. doi: 10.18632/oncotarget.13601. [PMID: 27901486]
  • Walter Miklos, Petra Heffeter, Christine Pirker, Sonja Hager, Christian R Kowol, Sushilla van Schoonhoven, Mirjana Stojanovic, Bernhard K Keppler, Walter Berger. Loss of phosphodiesterase 4D mediates acquired triapine resistance via Epac-Rap1-Integrin signaling. Oncotarget. 2016 Dec; 7(51):84556-84574. doi: 10.18632/oncotarget.11821. [PMID: 27602951]
  • Diana V Avila, David F Barker, JingWen Zhang, Craig J McClain, Shirish Barve, Leila Gobejishvili. Dysregulation of hepatic cAMP levels via altered Pde4b expression plays a critical role in alcohol-induced steatosis. The Journal of pathology. 2016 09; 240(1):96-107. doi: 10.1002/path.4760. [PMID: 27287961]
  • Tingting Dong, Liang Zhi, Brijesh Bhayana, Mei X Wu. Cortisol-induced immune suppression by a blockade of lymphocyte egress in traumatic brain injury. Journal of neuroinflammation. 2016 08; 13(1):197. doi: 10.1186/s12974-016-0663-y. [PMID: 27561600]
  • Gary W Hoyle, Jing Chen, Connie F Schlueter, Yiqun Mo, David M Humphrey, Greg Rawson, Joe A Niño, Kenneth H Carson. Development and assessment of countermeasure formulations for treatment of lung injury induced by chlorine inhalation. Toxicology and applied pharmacology. 2016 May; 298(?):9-18. doi: 10.1016/j.taap.2016.03.001. [PMID: 26952014]
  • Kyuhee Park, Jong Suk Lee, Jung Suk Choi, Yeon-Ju Nam, Jong-Heon Han, Hoo-Dhon Byun, Myung-Jin Song, Joa-Sup Oh, Sung Gyu Kim, Yongmun Choi. Identification and Characterization of Baicalin as a Phosphodiesterase 4 Inhibitor. Phytotherapy research : PTR. 2016 Jan; 30(1):144-51. doi: 10.1002/ptr.5515. [PMID: 26549702]
  • S Sugin Lal Jabaris, Haridass Sumathy, Ramesh Girish, Shridhar Narayanan, Mani Sugumar, Chidambaram Saravana Babu, Sadagopan Thanikachalam, Mohan Thanikachalam. Phosphodiesterase-4 inhibitors ameliorates cognitive deficits in deoxycorticosterone acetate induced hypertensive rats via cAMP/CREB signaling system. Brain research. 2015 Oct; 1622(?):279-91. doi: 10.1016/j.brainres.2015.07.003. [PMID: 26168894]
  • Wenkuan Xin, Wei P Feinstein, Andrea L Britain, Cristhiaan D Ochoa, Bing Zhu, Wito Richter, Silas J Leavesley, Thomas C Rich. Estimating the magnitude of near-membrane PDE4 activity in living cells. American journal of physiology. Cell physiology. 2015 Sep; 309(6):C415-24. doi: 10.1152/ajpcell.00090.2015. [PMID: 26201952]
  • J R Bauquier, E Tudor, S R Bailey. Anti-inflammatory effects of four potential anti-endotoxaemic drugs assessed in vitro using equine whole blood assays. Journal of veterinary pharmacology and therapeutics. 2015 Jun; 38(3):290-6. doi: 10.1111/jvp.12182. [PMID: 25407884]
  • Sobhana George Sugin Lal Jabaris, Haridass Sumathy, Ramadass Satiesh Kumar, Shridhar Narayanan, Sadagopan Thanikachalam, Chidambaram Saravana Babu. Effects of rolipram and roflumilast, phosphodiesterase-4 inhibitors, on hypertension-induced defects in memory function in rats. European journal of pharmacology. 2015 Jan; 746(?):138-47. doi: 10.1016/j.ejphar.2014.10.039. [PMID: 25446433]
  • Sandro Boland, Jo Alen, Arnaud Bourin, Karolien Castermans, Nicki Boumans, Laura Panitti, Jessica Vanormelingen, Dirk Leysen, Olivier Defert. Novel Roflumilast analogs as soft PDE4 inhibitors. Bioorganic & medicinal chemistry letters. 2014 Sep; 24(18):4594-4597. doi: 10.1016/j.bmcl.2014.07.016. [PMID: 25149511]
  • S Doseyici, I Mehmetoglu, A Toker, F H Yerlikaya, E Erbay. The effects of forskolin and rolipram on cAMP, cGMP and free fatty acid levels in diet induced obesity. Biotechnic & histochemistry : official publication of the Biological Stain Commission. 2014 Jul; 89(5):388-92. doi: 10.3109/10520295.2014.883463. [PMID: 24520882]
  • Sven Flemming, Nicolas Schlegel, Christian Wunder, Michael Meir, Wolfgang Baar, Jakob Wollborn, Norbert Roewer, Christoph-Thomas Germer, Martin Alexander Schick. Phosphodiesterase 4 inhibition dose dependently stabilizes microvascular barrier functions and microcirculation in a rodent model of polymicrobial sepsis. Shock (Augusta, Ga.). 2014 Jun; 41(6):537-45. doi: 10.1097/shk.0000000000000152. [PMID: 24569506]
  • Ting-Ting Lin, Yi-You Huang, Gui-Hua Tang, Zhong-Bin Cheng, Xin Liu, Hai-Bin Luo, Sheng Yin. Prenylated coumarins: natural phosphodiesterase-4 inhibitors from Toddalia asiatica. Journal of natural products. 2014 Apr; 77(4):955-62. doi: 10.1021/np401040d. [PMID: 24597921]
  • Eric Féraille, Eva Dizin, Isabelle Roth, Jean-Paul Derouette, Ildiko Szanto, Pierre-Yves Martin, Sophie de Seigneux, Udo Hasler. NADPH oxidase 4 deficiency reduces aquaporin-2 mRNA expression in cultured renal collecting duct principal cells via increased PDE3 and PDE4 activity. PloS one. 2014; 9(1):e87239. doi: 10.1371/journal.pone.0087239. [PMID: 24466344]
  • Joseph H Holthoff, Zhen Wang, Naeem K Patil, Neriman Gokden, Philip R Mayeux. Rolipram improves renal perfusion and function during sepsis in the mouse. The Journal of pharmacology and experimental therapeutics. 2013 Nov; 347(2):357-64. doi: 10.1124/jpet.113.208520. [PMID: 24018639]
  • Elizabeth Geras-Raaka, Susanne Neumann, Marvin C Gershengorn. Persistent cAMP signaling by TSH receptors revealed by phosphodiesterase inhibition. Thyroid : official journal of the American Thyroid Association. 2013 Nov; 23(11):1484-9. doi: 10.1089/thy.2013.0089. [PMID: 23713896]
  • 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]
  • Ryuji Nakao, Christer Halldin. 'Mixed' anionic and non-ionic micellar liquid chromatography for high-speed radiometabolite analysis of positron emission tomography radioligands. Journal of chromatography. A. 2013 Mar; 1281(?):54-9. doi: 10.1016/j.chroma.2013.01.071. [PMID: 23399000]
  • Emin Mammadov, Ibrahim Atilla Aridogan, Volkan Izol, Arbil Acikalin, Deniz Abat, Abdullah Tuli, Yildirim Bayazit. Protective effects of phosphodiesterase-4-specific inhibitor rolipram on acute ischemia-reperfusion injury in rat kidney. Urology. 2012 Dec; 80(6):1390.e1-6. doi: 10.1016/j.urology.2012.07.028. [PMID: 23010343]
  • Weiyuan Chang, Jing Chen, Connie F Schlueter, Roy J Rando, Yashwant V Pathak, Gary W Hoyle. Inhibition of chlorine-induced lung injury by the type 4 phosphodiesterase inhibitor rolipram. Toxicology and applied pharmacology. 2012 Sep; 263(2):251-8. doi: 10.1016/j.taap.2012.06.017. [PMID: 22763362]
  • Yueh-Chen Lin, Roger H Adamson, Joyce F Clark, Rolf K Reed, Fitz-Roy E Curry. Phosphodiesterase 4 inhibition attenuates plasma volume loss and transvascular exchange in volume-expanded mice. The Journal of physiology. 2012 Jan; 590(2):309-22. doi: 10.1113/jphysiol.2011.213447. [PMID: 22083598]
  • 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]
  • Huang-Ping Yu, Pei-Wen Hsieh, Yi-Ju Chang, Pei-Jen Chung, Liang-Mou Kuo, Tsong-Long Hwang. 2-(2-Fluorobenzamido)benzoate ethyl ester (EFB-1) inhibits superoxide production by human neutrophils and attenuates hemorrhagic shock-induced organ dysfunction in rats. Free radical biology & medicine. 2011 Jun; 50(12):1737-48. doi: 10.1016/j.freeradbiomed.2011.03.026. [PMID: 21457779]
  • Jiann-Jong Shen, Ming-Shan Chiang, Ming-Ling Kuo, Yann-Lii Leu, Tsong-Long Hwang, Chian-Jiun Liou, Wen-Chung Huang. Partially purified extract and viscolin from Viscum coloratum attenuate airway inflammation and eosinophil infiltration in ovalbumin-sensitized mice. Journal of ethnopharmacology. 2011 Jun; 135(3):646-53. doi: 10.1016/j.jep.2011.03.065. [PMID: 21473902]
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  • Paolo Zanotti-Fregonara, Sami S Zoghbi, Jeih-San Liow, Elise Luong, Ronald Boellaard, Robert L Gladding, Victor W Pike, Robert B Innis, Masahiro Fujita. Kinetic analysis in human brain of [11C](R)-rolipram, a positron emission tomographic radioligand to image phosphodiesterase 4: a retest study and use of an image-derived input function. NeuroImage. 2011 Feb; 54(3):1903-9. doi: 10.1016/j.neuroimage.2010.10.064. [PMID: 21034834]
  • Yueh-Chen Lin, Haris Samardzic, Roger H Adamson, Eugene M Renkin, Joyce F Clark, Rolf K Reed, Fitz-Roy E Curry. Phosphodiesterase 4 inhibition attenuates atrial natriuretic peptide-induced vascular hyperpermeability and loss of plasma volume. The Journal of physiology. 2011 Jan; 589(Pt 2):341-53. doi: 10.1113/jphysiol.2010.199588. [PMID: 21098005]
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  • Sandeep Sharma, Inshad Ali Khan, Intzar Ali, Furqan Ali, Manoj Kumar, Ashwani Kumar, Rakesh Kamal Johri, Sheikh Tasduq Abdullah, Sarang Bani, Anjali Pandey, Krishan Avtar Suri, Bishan Datt Gupta, Naresh Kumar Satti, Prabhu Dutt, Ghulam Nabi Qazi. Evaluation of the antimicrobial, antioxidant, and anti-inflammatory activities of hydroxychavicol for its potential use as an oral care agent. Antimicrobial agents and chemotherapy. 2009 Jan; 53(1):216-22. doi: 10.1128/aac.00045-08. [PMID: 18573934]
  • K Rutten, J Prickaerts, G Schaenzle, H Rosenbrock, A Blokland. Sub-chronic rolipram treatment leads to a persistent improvement in long-term object memory in rats. Neurobiology of learning and memory. 2008 Oct; 90(3):569-75. doi: 10.1016/j.nlm.2008.04.016. [PMID: 18558503]
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