Quinacrine (BioDeep_00000003331)

 

Secondary id: BioDeep_00000397940, BioDeep_00001867737

human metabolite blood metabolite


代谢物信息卡片


N(4)-(6-Chloro-2-methoxy-9-acridinyl)-N(1),N(1)-diethyl-1,4-pentanediamine

化学式: C23H30ClN3O (399.20772800000003)
中文名称: 疟涤平
谱图信息: 最多检出来源 Homo sapiens(blood) 11.86%

分子结构信息

SMILES: CCN(CC)CCCC(C)N=c1c2ccc(Cl)cc2[nH]c2ccc(OC)cc12
InChI: InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)

描述信息

An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2. [PubChem]
P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01A - Agents against amoebiasis and other protozoal diseases
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent
D000970 - Antineoplastic Agents
D004791 - Enzyme Inhibitors

同义名列表

30 个代谢物同义名

N(4)-(6-Chloro-2-methoxy-9-acridinyl)-N(1),N(1)-diethyl-1,4-pentanediamine; 6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine; 6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine; 3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine; 2-Methoxy-6-chloro-9-diethylaminopentylaminoacridine; Quinacrine dihyrochloride, (R)-isomer; Quinacrine dihyrochloride, (S)-isomer; Quinacrine dihydrochloride, dihydrate; Quinacrine Dihydrochloride Dihydrate; Monohydrochloride, quinacrine; Quinacrine monohydrochloride; Dihydrochloride, quinacrine; Quinacrine dihydrochloride; Hydrochloride, quinacrine; Monomesylate, quinacrine; Quinacrine hydrochloride; Quinacrine, (+-)-isomer; Monoacetate, quinacrine; Quinacrine monomesylate; Quinacrine, (R)-isomer; Quinacrine monoacetate; Quinacrine, (S)-isomer; Dimesylate, quinacrine; Quinacrine dimesylate; quinacrine; Mepacrine; Quinacrin; Acrichine; Atabrine; Atebrin



数据库引用编号

17 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

  • Biswajit Das, Somya Ranjan Dash, Harun Patel, Saptarshi Sinha, Subhasmita Bhal, Subarno Paul, Chinmay Das, Rajalaxmi Pradhan, Iqrar Ahmed, Kunal Goutam, Chanakya Nath Kundu. Quinacrine inhibits HIF-1α/VEGF-A mediated angiogenesis by disrupting the interaction between cMET and ABCG2 in patient-derived breast cancer stem cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Aug; 117(?):154914. doi: 10.1016/j.phymed.2023.154914. [PMID: 37321076]
  • Xiangxiang Li, Jing Zhou, Zhuozhou Hu, Liang Han, Wenyang Zhao, Tongyu Wu, Chun Li, Jingjing Liu, Jia Kang, Xinping Chen. Quinacrine attenuates diet-induced obesity by inhibiting adipogenesis via activation of AMPK signaling. European journal of pharmacology. 2023 Jan; 938(?):175432. doi: 10.1016/j.ejphar.2022.175432. [PMID: 36460132]
  • Nirod Kumar Sarangi, Amrutha Prabhakaran, Tia E Keyes. Multimodal Investigation into the Interaction of Quinacrine with Microcavity-Supported Lipid Bilayers. Langmuir : the ACS journal of surfaces and colloids. 2022 05; 38(20):6411-6424. doi: 10.1021/acs.langmuir.2c00524. [PMID: 35561255]
  • Benjamin Pineda. Quinacrine, an Old Drug with Potentially usefull in the Treatment for COVID-19. Archives of medical research. 2021 11; 52(8):858-859. doi: 10.1016/j.arcmed.2021.06.002. [PMID: 34154830]
  • Nada F Abo El-Magd, Hasnaa Ali Ebrahim, Mohamed El-Sherbiny, Nada H Eisa. Quinacrine Ameliorates Cisplatin-Induced Renal Toxicity via Modulation of Sirtuin-1 Pathway. International journal of molecular sciences. 2021 Oct; 22(19):. doi: 10.3390/ijms221910660. [PMID: 34639002]
  • Lucy Martinez-Guerrero, Xiaohong Zhang, Kimberley M Zorn, Sean Ekins, Stephen H Wright. Cationic Compounds with SARS-CoV-2 Antiviral Activity and Their Interaction with Organic Cation Transporter/Multidrug and Toxin Extruder Secretory Transporters. The Journal of pharmacology and experimental therapeutics. 2021 10; 379(1):96-107. doi: 10.1124/jpet.121.000619. [PMID: 34253645]
  • M F Ara-Montojo, J Bustamante, T Sainz, S Pérez, B Jiménez-Moreno, G Ruiz-Carrascoso, P Rodríguez-Molino, J Villota, M García-López-Hortenano, M J Mellado-Peña. Intestinal giardiasis in children: Five years' experience in a reference unit. Travel medicine and infectious disease. 2021 Jul; 42(?):102082. doi: 10.1016/j.tmaid.2021.102082. [PMID: 34020030]
  • Raphael J Eberle, Danilo S Olivier, Marcos S Amaral, Ian Gering, Dieter Willbold, Raghuvir K Arni, Monika A Coronado. The Repurposed Drugs Suramin and Quinacrine Cooperatively Inhibit SARS-CoV-2 3CLpro In Vitro. Viruses. 2021 05; 13(5):. doi: 10.3390/v13050873. [PMID: 34068686]
  • 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]
  • Tomohisa Kitagawa, Atsushi Matsumoto, Ichiro Terashima, Yukifumi Uesono. Antimalarial Quinacrine and Chloroquine Lose Their Activity by Decreasing Cationic Amphiphilic Structure with a Slight Decrease in pH. Journal of medicinal chemistry. 2021 04; 64(7):3885-3896. doi: 10.1021/acs.jmedchem.0c02056. [PMID: 33775096]
  • Mónica Salas Rojas, Raúl Silva Garcia, Estela Bini, Verónica Pérez de la Cruz, Juan Carlos León Contreras, Rogelio Hernández Pando, Fernando Bastida Gonzalez, Eduardo Davila-Gonzalez, Mario Orozco Morales, Armando Gamboa Domínguez, Julio Sotelo, Benjamín Pineda. Quinacrine, an Antimalarial Drug with Strong Activity Inhibiting SARS-CoV-2 Viral Replication In Vitro. Viruses. 2021 Jan; 13(1):. doi: 10.3390/v13010121. [PMID: 33477376]
  • B Pineda, V Pérez de la Cruz, R Hernández Pando, J Sotelo. Quinacrine as a potential treatment for COVID-19 virus infection. European review for medical and pharmacological sciences. 2021 01; 25(1):556-566. doi: 10.26355/eurrev_202101_24428. [PMID: 33506949]
  • R Cañete, A L Noda, M Rodríguez, K Brito, E Herrera, P-E Kofoed, J Ursing. 5-Nitroimidazole refractory giardiasis is common in Matanzas, Cuba and effectively treated by secnidazole plus high-dose mebendazole or quinacrine: a prospective observational cohort study. Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases. 2020 Aug; 26(8):1092.e1-1092.e6. doi: 10.1016/j.cmi.2019.12.017. [PMID: 31901492]
  • Krushna Chandra Hembram, Somya Ranjan Dash, Biswajit Das, Chinmayee Sethy, Subhajit Chatterjee, Birendra Kumar Bindhani, Chanakya Nath Kundu. Quinacrine Based Gold Hybrid Nanoparticles Caused Apoptosis through Modulating Replication Fork in Oral Cancer Stem Cells. Molecular pharmaceutics. 2020 07; 17(7):2463-2472. doi: 10.1021/acs.molpharmaceut.0c00197. [PMID: 32407635]
  • Bhuvaneshwar Vaidya, Nishant S Kulkarni, Snehal K Shukla, Vineela Parvathaneni, Gautam Chauhan, Jenna K Damon, Apoorva Sarode, Jerome V Garcia, Nitesh Kunda, Samir Mitragotri, Vivek Gupta. Development of inhalable quinacrine loaded bovine serum albumin modified cationic nanoparticles: Repurposing quinacrine for lung cancer therapeutics. International journal of pharmaceutics. 2020 Mar; 577(?):118995. doi: 10.1016/j.ijpharm.2019.118995. [PMID: 31935471]
  • Silvia Biggi, Michael Pancher, Claudia Stincardini, Silvia Luotti, Tania Massignan, Andrea Dalle Vedove, Andrea Astolfi, Pamela Gatto, Graziano Lolli, Maria Letizia Barreca, Valentina Bonetto, Valentina Adami, Emiliano Biasini. Identification of compounds inhibiting prion replication and toxicity by removing PrPC from the cell surface. Journal of neurochemistry. 2020 01; 152(1):136-150. doi: 10.1111/jnc.14805. [PMID: 31264722]
  • 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]
  • Sabrina Forveille, Juliette Humeau, Allan Sauvat, Lucillia Bezu, Guido Kroemer, Oliver Kepp. Quinacrine-mediated detection of intracellular ATP. Methods in enzymology. 2019; 629(?):103-113. doi: 10.1016/bs.mie.2019.05.050. [PMID: 31727236]
  • Mariachiara Buccarelli, Matteo Marconi, Simone Pacioni, Ivana De Pascalis, Quintino Giorgio D'Alessandris, Maurizio Martini, Barbara Ascione, Walter Malorni, Luigi Maria Larocca, Roberto Pallini, Lucia Ricci-Vitiani, Paola Matarrese. Inhibition of autophagy increases susceptibility of glioblastoma stem cells to temozolomide by igniting ferroptosis. Cell death & disease. 2018 08; 9(8):841. doi: 10.1038/s41419-018-0864-7. [PMID: 30082680]
  • Ana Requena-Méndez, Pilar Goñi, Encarnación Rubio, Diana Pou, Victoria Fumadó, Silvia Lóbez, Edelweiss Aldasoro, Juan Cabezos, Maria Eugenia Valls, Begoña Treviño, Antonio Federico Martínez Montseny, Antonio Clavel, Joaquim Gascon, José Muñoz. The Use of Quinacrine in Nitroimidazole-resistant Giardia Duodenalis: An Old Drug for an Emerging Problem. The Journal of infectious diseases. 2017 03; 215(6):946-953. doi: 10.1093/infdis/jix066. [PMID: 28453841]
  • Anna-Maria Kreidler, Roland Benz, Holger Barth. Chloroquine derivatives block the translocation pores and inhibit cellular entry of Clostridium botulinum C2 toxin and Bacillus anthracis lethal toxin. Archives of toxicology. 2017 Mar; 91(3):1431-1445. doi: 10.1007/s00204-016-1716-9. [PMID: 27106023]
  • Abdulrahman K Al Asmari, Khalid Tariq Al Sadoon, Ali Ahmed Obaid, Deivakadatcham Yesunayagam, Mohammad Tariq. Protective effect of quinacrine against glycerol-induced acute kidney injury in rats. BMC nephrology. 2017 01; 18(1):41. doi: 10.1186/s12882-017-0450-8. [PMID: 28129740]
  • Wenlin Huang, Zhongsheng Zhang, Ximena Barros-Álvarez, Cho Yeow Koh, Ranae M Ranade, J Robert Gillespie, Sharon A Creason, Sayaka Shibata, Christophe L M J Verlinde, Wim G J Hol, Frederick S Buckner, Erkang Fan. Structure-guided design of novel Trypanosoma brucei Methionyl-tRNA synthetase inhibitors. European journal of medicinal chemistry. 2016 Nov; 124(?):1081-1092. doi: 10.1016/j.ejmech.2016.10.024. [PMID: 27788467]
  • Natalia S Voynova, Carole Roubaty, Hector M Vazquez, Shamroop K Mallela, Christer S Ejsing, Andreas Conzelmann. Saccharomyces cerevisiae Is Dependent on Vesicular Traffic between the Golgi Apparatus and the Vacuole When Inositolphosphorylceramide Synthase Aur1 Is Inactivated. Eukaryotic cell. 2015 Dec; 14(12):1203-16. doi: 10.1128/ec.00117-15. [PMID: 26432633]
  • Xue-Tao Li, Zhi-Yan Zhou, Ying Jiang, Mei-Li He, Lian-Qun Jia, Lin Zhao, Lan Cheng, Tian-Zhu Jia. PEGylated VRB plus quinacrine cationic liposomes for treating non-small cell lung cancer. Journal of drug targeting. 2015 Apr; 23(3):232-43. doi: 10.3109/1061186x.2014.979829. [PMID: 25417934]
  • Xue-Tao Li, Rui-Jun Ju, Xiu-Ying Li, Fan Zeng, Ji-Feng Shi, Lei Liu, Cheng-Xiang Zhang, Meng-Ge Sun, Jin-Ning Lou, Wan-Liang Lu. Multifunctional targeting daunorubicin plus quinacrine liposomes, modified by wheat germ agglutinin and tamoxifen, for treating brain glioma and glioma stem cells. Oncotarget. 2014 Aug; 5(15):6497-511. doi: 10.18632/oncotarget.2267. [PMID: 25153726]
  • Hari Babu Tatipaka, J Robert Gillespie, Arnab K Chatterjee, Neil R Norcross, Matthew A Hulverson, Ranae M Ranade, Pendem Nagendar, Sharon A Creason, Joshua McQueen, Nicole A Duster, Advait Nagle, Frantisek Supek, Valentina Molteni, Tanja Wenzler, Reto Brun, Richard Glynne, Frederick S Buckner, Michael H Gelb. Substituted 2-phenylimidazopyridines: a new class of drug leads for human African trypanosomiasis. Journal of medicinal chemistry. 2014 Feb; 57(3):828-35. doi: 10.1021/jm401178t. [PMID: 24354316]
  • Muhammad Usman, Mohammad Siddiq. Probing the micellar properties of Quinacrine 2HCl and its binding with surfactants and human serum albumin. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2013 Sep; 113(?):182-90. doi: 10.1016/j.saa.2013.04.089. [PMID: 23727671]
  • Caroline Roy, Valérie Gagné, Maria J G Fernandes, François Marceau. High affinity capture and concentration of quinacrine in polymorphonuclear neutrophils via vacuolar ATPase-mediated ion trapping: comparison with other peripheral blood leukocytes and implications for the distribution of cationic drugs. Toxicology and applied pharmacology. 2013 Jul; 270(2):77-86. doi: 10.1016/j.taap.2013.04.004. [PMID: 23603060]
  • Annaliese K Franz, Megan A Danielewicz, Diana M Wong, Lisa A Anderson, Jordan R Boothe. Phenotypic screening with oleaginous microalgae reveals modulators of lipid productivity. ACS chemical biology. 2013 May; 8(5):1053-62. doi: 10.1021/cb300573r. [PMID: 23521767]
  • Ceren Kencebay, Narin Derin, Ozlem Ozsoy, Dijle Kipmen-Korgun, Gamze Tanriover, Nihal Ozturk, Goksun Basaranlar, Piraye Yargicoglu-Akkiraz, Berna Sozen, Aysel Agar. Merit of quinacrine in the decrease of ingested sulfite-induced toxic action in rat brain. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Feb; 52(?):129-36. doi: 10.1016/j.fct.2012.11.015. [PMID: 23168241]
  • Ranjan Preet, Purusottam Mohapatra, Dipon Das, Shakti R Satapathy, Tathagata Choudhuri, Michael D Wyatt, Chanakya N Kundu. Lycopene synergistically enhances quinacrine action to inhibit Wnt-TCF signaling in breast cancer cells through APC. Carcinogenesis. 2013 Feb; 34(2):277-86. doi: 10.1093/carcin/bgs351. [PMID: 23129580]
  • Andrzej Woznica, Agnieszka Nowak, Przemyslaw Ziemski, Mirosław Kwasniewski, Tytus Bernas. Stimulatory effect of xenobiotics on oxidative electron transport of chemolithotrophic nitrifying bacteria used as biosensing element. PloS one. 2013; 8(1):e53484. doi: 10.1371/journal.pone.0053484. [PMID: 23326438]
  • Tyler Spata, Daniel Bobek, Bryan A Whitson, Sampath Parthasarathy, Peter J Mohler, Robert S D Higgins, Ahmet Kilic. A nonthoracotomy myocardial infarction model in an ovine using autologous platelets. BioMed research international. 2013; 2013(?):938047. doi: 10.1155/2013/938047. [PMID: 24367790]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Takahiro Shimizu, Kenjiro Tanaka, Kumiko Nakamura, Keisuke Taniuchi, Kunihiko Yokotani. Brain phospholipase C, diacylglycerol lipase and monoacylglycerol lipase are involved in (±)-epibatidine-induced activation of central adrenomedullary outflow in rats. European journal of pharmacology. 2012 Sep; 691(1-3):93-102. doi: 10.1016/j.ejphar.2012.07.017. [PMID: 22796670]
  • Chim W Chan, Rita Spathis, Dana M Reiff, Stacy E McGrath, Ralph M Garruto, J Koji Lum. Diversity of Plasmodium falciparum chloroquine resistance transporter (pfcrt) exon 2 haplotypes in the Pacific from 1959 to 1979. PloS one. 2012; 7(1):e30213. doi: 10.1371/journal.pone.0030213. [PMID: 22272308]
  • Hanna Appelqvist, Linnea Sandin, Karin Björnström, Paul Saftig, Brett Garner, Karin Ollinger, Katarina Kågedal. Sensitivity to lysosome-dependent cell death is directly regulated by lysosomal cholesterol content. PloS one. 2012; 7(11):e50262. doi: 10.1371/journal.pone.0050262. [PMID: 23166840]
  • Thuy Nguyen, Yuji Sakasegawa, Katsumi Doh-Ura, Mei-Lin Go. Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position. European journal of medicinal chemistry. 2011 Jul; 46(7):2917-29. doi: 10.1016/j.ejmech.2011.04.016. [PMID: 21531054]
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  • Alenka Kuznik, Mojca Bencina, Urban Svajger, Matjaz Jeras, Blaz Rozman, Roman Jerala. Mechanism of endosomal TLR inhibition by antimalarial drugs and imidazoquinolines. Journal of immunology (Baltimore, Md. : 1950). 2011 Apr; 186(8):4794-804. doi: 10.4049/jimmunol.1000702. [PMID: 21398612]
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  • Jie Wang, David A Richards. Spatial regulation of exocytic site and vesicle mobilization by the actin cytoskeleton. PloS one. 2011; 6(12):e29162. doi: 10.1371/journal.pone.0029162. [PMID: 22195014]
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