Riociguat (BioDeep_00000182953)
human metabolite blood metabolite
代谢物信息卡片
Methyl N-(4,6-diamino-2-{1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamic acid
化学式: C20H19FN8O2 (422.1614926)
中文名称: 利奥西呱
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CN(C1=C(N=C(N=C1N)C2=NN(C3=C2C=CC=N3)CC4=CC=CC=C4F)N)C(=O)OC
InChI: InChI=1S/C20H19FN8O2/c1-28(20(30)31-2)15-16(22)25-18(26-17(15)23)14-12-7-5-9-24-19(12)29(27-14)10-11-6-3-4-8-13(11)21/h3-9H,10H2,1-2H3,(H4,22,23,25,26)
描述信息
C - Cardiovascular system > C02 - Antihypertensives > C02K - Other antihypertensives > C02KX - Antihypertensives for pulmonary arterial hypertension
C78274 - Agent Affecting Cardiovascular System > C29707 - Vasodilating Agent
D020536 - Enzyme Activators
同义名列表
7 个代谢物同义名
Methyl N-(4,6-diamino-2-{1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamic acid; Methyl N-(4,6-diamino-2-{1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate; methyl N-(4,6-diamino-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate; Riociguatum; BAY 63-2521; Riociguat; Adempas
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:76018
- PubChem: 11304743
- HMDB: HMDB0257236
- DrugBank: DB08931
- ChEMBL: CHEMBL2107834
- Wikipedia: Riociguat
- chemspider: 9479719
- CAS: 1304478-72-5
- CAS: 625115-55-1
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
- Oskar Puk, Aleksandra Nowacka, Klaudia Smulewicz, Katarzyna Mocna, Wiktor Bursiewicz, Natalia Kęsy, Justyna Kwiecień, Michał Wiciński. Pulmonary artery targeted therapy in treatment of COVID-19 related ARDS. Literature review.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2022 Feb; 146(?):112592. doi:
10.1016/j.biopha.2021.112592. [PMID: 35062063] - Daan 't Hart, Jinhua Li, Johan van der Vlag, Tom Nijenhuis. Repurposing Riociguat to Target a Novel Paracrine Nitric Oxide-TRPC6 Pathway to Prevent Podocyte Injury.
International journal of molecular sciences.
2021 Nov; 22(22):. doi:
10.3390/ijms222212485. [PMID: 34830371] - Tomáš Hložek, Martin Štícha, Miroslava Bursová, Ivan Jelínek, Petr Tůma, Radomír Čabala. Sensitive CE-MS method for monitoring of riociguat and desmethylriociguat levels in human serum.
Electrophoresis.
2020 10; 41(18-19):1564-1567. doi:
10.1002/elps.202000135. [PMID: 32640044] - Seereddy Sravani, Mohd Aslam Saifi, Chandraiah Godugu. Riociguat ameliorates kidney injury and fibrosis in an animal model.
Biochemical and biophysical research communications.
2020 10; 530(4):706-712. doi:
10.1016/j.bbrc.2020.07.128. [PMID: 32768189] - Jeffrey A Kline, Michael A Puskarich, Jonathan W Pike, John Zagorski, Nathan J Alves. Inhaled nitric oxide to control platelet hyper-reactivity in patients with acute submassive pulmonary embolism.
Nitric oxide : biology and chemistry.
2020 03; 96(?):20-28. doi:
10.1016/j.niox.2020.01.004. [PMID: 31940502] - Pallavi Bhargava, Jaroslav Janda, Rick G Schnellmann. Elucidation of cGMP-dependent induction of mitochondrial biogenesis through PKG and p38 MAPK in the kidney.
American journal of physiology. Renal physiology.
2020 02; 318(2):F322-F328. doi:
10.1152/ajprenal.00533.2019. [PMID: 31841384] - Elodie Jacqueroux, Clément Mercier, Victor Margelidon-Cozzolino, Sophie Hodin, Laurent Bertoletti, Xavier Delavenne. In vitro assessment of P-gp and BCRP transporter-mediated drug-drug interactions of riociguat with direct oral anticoagulants.
Fundamental & clinical pharmacology.
2020 Feb; 34(1):109-119. doi:
10.1111/fcp.12504. [PMID: 31411766] - Dénes Csonka, Shirin Bruderer, Armin Schultz, Marianne Soergel, Radka Stepanova, Giancarlo Sabattini, Juan Jose Perez-Ruixo. Effect of Macitentan on the Pharmacokinetics of the Breast Cancer Resistance Protein Substrates, Rosuvastatin and Riociguat, in Healthy Male Subjects.
Clinical drug investigation.
2019 Dec; 39(12):1223-1232. doi:
10.1007/s40261-019-00857-7. [PMID: 31552642] - R Zhao, Y Jiang. Influence of riociguat treatment on pulmonary arterial hypertension : A meta-analysis of randomized controlled trials.
Herz.
2019 Nov; 44(7):637-643. doi:
10.1007/s00059-018-4697-z. [PMID: 29992431] - Stephanie Makhoul, Katharina Trabold, Stepan Gambaryan, Stefan Tenzer, Daniele Pillitteri, Ulrich Walter, Kerstin Jurk. cAMP- and cGMP-elevating agents inhibit GPIbα-mediated aggregation but not GPIbα-stimulated Syk activation in human platelets.
Cell communication and signaling : CCS.
2019 09; 17(1):122. doi:
10.1186/s12964-019-0428-1. [PMID: 31519182] - Vivek Nagaraja, Cathie Spino, Erica Bush, Pei-Suen Tsou, Robyn T Domsic, Robert Lafyatis, Tracy Frech, Jessica K Gordon, Virginia D Steen, Dinesh Khanna. A multicenter randomized, double-blind, placebo-controlled pilot study to assess the efficacy and safety of riociguat in systemic sclerosis-associated digital ulcers.
Arthritis research & therapy.
2019 09; 21(1):202. doi:
10.1186/s13075-019-1979-7. [PMID: 31481106] - Shristy S Tiwari, Balasaheb B Chavan, Bhoopendra S Kushwah, Naga Veera Yerra, Sumit Mukesh, Abhay T Sangamwar, Jagadeshwar Reddy Thaota, M V N Kumar Talluri. In vitroand in vivo investigation of metabolic fate of riociguat by HPLC-Q-TOF/MS/MS and in silico evaluation of the metabolites by ADMET predictor™.
Journal of pharmaceutical and biomedical analysis.
2019 Feb; 164(?):326-336. doi:
10.1016/j.jpba.2018.10.050. [PMID: 30412806] - Kevin P Cunningham, Robyn G Holden, Pilar M Escribano-Subias, Angel Cogolludo, Emma L Veale, Alistair Mathie. Characterization and regulation of wild-type and mutant TASK-1 two pore domain potassium channels indicated in pulmonary arterial hypertension.
The Journal of physiology.
2019 02; 597(4):1087-1101. doi:
10.1113/jp277275. [PMID: 30365877] - Rui Ma, Zhenyu Li, Xiaxia Di, Dongxiao Guo, Jianbo Ji, Shuqi Wang. Spectroscopic methodologies and molecular docking studies on the interaction of the soluble guanylate cyclase stimulator riociguat with human serum albumin.
Bioscience trends.
2018 Sep; 12(4):369-374. doi:
10.5582/bst.2018.01081. [PMID: 30101825] - Sandra Frankenreiter, Piotr Bednarczyk, Angelina Kniess, Nadja I Bork, Julia Straubinger, Piotr Koprowski, Antoni Wrzosek, Eva Mohr, Angela Logan, Michael P Murphy, Meinrad Gawaz, Thomas Krieg, Adam Szewczyk, Viacheslav O Nikolaev, Peter Ruth, Robert Lukowski. cGMP-Elevating Compounds and Ischemic Conditioning Provide Cardioprotection Against Ischemia and Reperfusion Injury via Cardiomyocyte-Specific BK Channels.
Circulation.
2017 Dec; 136(24):2337-2355. doi:
10.1161/circulationaha.117.028723. [PMID: 29051185] - Otylia Kowal-Bielecka, Jaap Fransen, Jerome Avouac, Mike Becker, Agnieszka Kulak, Yannick Allanore, Oliver Distler, Philip Clements, Maurizio Cutolo, Laszlo Czirjak, Nemanja Damjanov, Francesco Del Galdo, Christopher P Denton, Jörg H W Distler, Ivan Foeldvari, Kim Figelstone, Marc Frerix, Daniel E Furst, Serena Guiducci, Nicolas Hunzelmann, Dinesh Khanna, Marco Matucci-Cerinic, Ariane L Herrick, Frank van den Hoogen, Jacob M van Laar, Gabriela Riemekasten, Richard Silver, Vanessa Smith, Alberto Sulli, Ingo Tarner, Alan Tyndall, Joep Welling, Frederic Wigley, Gabriele Valentini, Ulrich A Walker, Francesco Zulian, Ulf Müller-Ladner. Update of EULAR recommendations for the treatment of systemic sclerosis.
Annals of the rheumatic diseases.
2017 Aug; 76(8):1327-1339. doi:
10.1136/annrheumdis-2016-209909. [PMID: 27941129] - Stefanie Breitenstein, Lothar Roessig, Peter Sandner, Kelly S Lewis. Novel sGC Stimulators and sGC Activators for the Treatment of Heart Failure.
Handbook of experimental pharmacology.
2017; 243(?):225-247. doi:
10.1007/164_2016_100. [PMID: 27900610] - Xia Zhao, Zining Wang, Yukun Wang, Hong Zhang, Hartmut Blode, Kenichi Yoshikawa, Corina Becker, Sigrun Unger, Reiner Frey, Yimin Cui. Pharmacokinetics of the Soluble Guanylate Cyclase Stimulator Riociguat in Healthy Young Chinese Male Non-Smokers and Smokers: Results of a Randomized, Double-Blind, Placebo-Controlled Study.
Clinical pharmacokinetics.
2016 May; 55(5):615-24. doi:
10.1007/s40262-015-0337-4. [PMID: 26507720] - C Reiss, I Mindukshev, V Bischoff, H Subramanian, L Kehrer, A Friebe, J-P Stasch, S Gambaryan, U Walter. The sGC stimulator riociguat inhibits platelet function in washed platelets but not in whole blood.
British journal of pharmacology.
2015 Nov; 172(21):5199-210. doi:
10.1111/bph.13286. [PMID: 26282717] - Johannes-Peter Stasch, Jens Schlossmann, Berthold Hocher. Renal effects of soluble guanylate cyclase stimulators and activators: a review of the preclinical evidence.
Current opinion in pharmacology.
2015 Apr; 21(?):95-104. doi:
10.1016/j.coph.2014.12.014. [PMID: 25645316] - Mark-Jean Gnoth, Peter-Michael Hopfe, Waldemar Czembor. Determination of riociguat and its major human metabolite M-1 in human plasma by stable-isotope dilution LCMS/MS.
Bioanalysis.
2015; 7(2):193-205. doi:
10.4155/bio.14.257. [PMID: 25587836] - Jeff Sigler. Drug updates and approvals: 2014 in review.
The Nurse practitioner.
2014 Dec; 39(12):14-23; quiz 23. doi:
10.1097/01.npr.0000456393.83499.90. [PMID: 25350291] - Verena Rickert, Walter Emil Haefeli, Johanna Weiss. Pharmacokinetic interaction profile of riociguat, a new soluble guanylate cyclase stimulator, in vitro.
Pulmonary pharmacology & therapeutics.
2014 Aug; 28(2):130-7. doi:
10.1016/j.pupt.2014.02.004. [PMID: 24657506] - Nicholas Gross. The COPD pipeline XX.
COPD.
2013 Feb; 10(1):104-6. doi:
10.3109/15412555.2013.766103. [PMID: 23413896] - Ina M Ott, Markus L Alter, Karoline von Websky, Axel Kretschmer, Oleg Tsuprykov, Yuliya Sharkovska, Katharina Krause-Relle, Jens Raila, Andrea Henze, Johannes-Peter Stasch, Berthold Hocher. Effects of stimulation of soluble guanylate cyclase on diabetic nephropathy in diabetic eNOS knockout mice on top of angiotensin II receptor blockade.
PloS one.
2012; 7(8):e42623. doi:
10.1371/journal.pone.0042623. [PMID: 22900035] - Reiner Frey, Wolfgang Mück, Nina Kirschbaum, Jörn Krätzschmar, Gerrit Weimann, Georg Wensing. Riociguat (BAY 63-2521) and warfarin: a pharmacodynamic and pharmacokinetic interaction study.
Journal of clinical pharmacology.
2011 Jul; 51(7):1051-60. doi:
10.1177/0091270010378119. [PMID: 20801938] - Sandra Geschka, Axel Kretschmer, Yuliya Sharkovska, Oleg V Evgenov, Bettina Lawrenz, Andreas Hucke, Berthold Hocher, Johannes-Peter Stasch. Soluble guanylate cyclase stimulation prevents fibrotic tissue remodeling and improves survival in salt-sensitive Dahl rats.
PloS one.
2011; 6(7):e21853. doi:
10.1371/journal.pone.0021853. [PMID: 21789188] - Yuliya Sharkovska, Philipp Kalk, Bettina Lawrenz, Michael Godes, Linda Sarah Hoffmann, Kathrin Wellkisch, Sandra Geschka, Katharina Relle, Berthold Hocher, Johannes-Peter Stasch. Nitric oxide-independent stimulation of soluble guanylate cyclase reduces organ damage in experimental low-renin and high-renin models.
Journal of hypertension.
2010 Aug; 28(8):1666-75. doi:
10.1097/hjh.0b013e32833b558c. [PMID: 20613628]