Clioquinol (BioDeep_00000177558)

   

human metabolite blood metabolite


代谢物信息卡片


5-Chloro-8-hydroxy-7-iodoquinoline

化学式: C9H5ClINO (304.91044200000005)
中文名称: 5-氯-8-羟基-7-碘喹啉
谱图信息: 最多检出来源 Homo sapiens(blood) 50%

分子结构信息

SMILES: C1=CC2=C(C(=C(C=C2Cl)I)O)N=C1
InChI: InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

描述信息

G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids > G01AC - Quinoline derivatives
P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01A - Agents against amoebiasis and other protozoal diseases > P01AA - Hydroxyquinoline derivatives
D - Dermatologicals > D08 - Antiseptics and disinfectants > D08A - Antiseptics and disinfectants > D08AH - Quinoline derivatives
D - Dermatologicals > D09 - Medicated dressings > D09A - Medicated dressings > D09AA - Medicated dressings with antiinfectives
S - Sensory organs > S02 - Otologicals > S02A - Antiinfectives > S02AA - Antiinfectives
C274 - Antineoplastic Agent > C1742 - Angiogenesis Inhibitor
C254 - Anti-Infective Agent

同义名列表

25 个代谢物同义名

5-Chloro-8-hydroxy-7-iodoquinoline; 5-Chloro-7-iodo-8-hydroxyquinoline; 7-Iodo-5-chloro-8-hydroxyquinoline; 5-Chlor-7-jod-8-hydroxy-chinolin; 5 Chloro 7 iodo 8 quinolinol; 5-Chloro-7-iodo-8-quinolinol; 5-chloro-7-iodoquinolin-8-ol; Iodochlorhydroxyquinoline; Iodochlorohydroxyquin; Iodochloroxyquinoline; Iodochlorhydroxyquin; 7-Iodo-5-chloroxine; Chloroiodoquine; Entero-vioform; Chloroiodoquin; Entero vioform; EnteroVioform; Entero-septol; Entero septol; Enteroquinol; Clioquinolum; EnteroSeptol; clioquinol; Chinoform; Vioform



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。



文献列表

  • Liping Li, Hao Wu, Jiayin Wang, Zhe Ji, Ting Fang, Hui Lu, Lan Yan, Fuming Shen, Dazhi Zhang, Yuanying Jiang, Tingjunhong Ni. Discovery of Novel 8-Hydroxyquinoline Derivatives with Potent In Vitro and In Vivo Antifungal Activity. Journal of medicinal chemistry. 2023 Dec; 66(23):16364-16376. doi: 10.1021/acs.jmedchem.3c01771. [PMID: 37975824]
  • Erin B Brazel, Aimee Tan, Stephanie L Neville, Amy R Iverson, Saumya R Udagedara, Bliss A Cunningham, Mwilye Sikanyika, David M P De Oliveira, Bernhard Keller, Lisa Bohlmann, Ibrahim M El-Deeb, Katherine Ganio, Bart A Eijkelkamp, Alastair G McEwan, Mark von Itzstein, Megan J Maher, Mark J Walker, Jason W Rosch, Christopher A McDevitt. Dysregulation of Streptococcus pneumoniae zinc homeostasis breaks ampicillin resistance in a pneumonia infection model. Cell reports. 2022 01; 38(2):110202. doi: 10.1016/j.celrep.2021.110202. [PMID: 35021083]
  • Vijaya Lakshmi Bodiga, Praveen Kumar Vemuri, Madhukar Rao Kudle, Sreedhar Bodiga. Zinc ionophores isolated from Terminalia bellirica fruit rind extract protect against cardiomyocyte hypoxia/reoxygenation injury. Bioorganic & medicinal chemistry. 2021 09; 46(?):116394. doi: 10.1016/j.bmc.2021.116394. [PMID: 34509160]
  • 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]
  • Selvarasu Maheshwaran, Muthumariappan Akilarasan, Tse-Wei Chen, Shen-Ming Chen, Elayappan Tamilalagan, Ting-Yu Jiang, Eman A Alabdullkarem, Mustafa Soylak. Electrocatalytic evaluation of graphene oxide warped tetragonal t-lanthanum vanadate (GO@LaVO4) nanocomposites for the voltammetric detection of antifungal and antiprotozoal drug (clioquinol). Mikrochimica acta. 2021 02; 188(3):102. doi: 10.1007/s00604-021-04758-5. [PMID: 33638711]
  • Satoshi Kuru. [Fifity years after the identification of the cause of SMON]. Rinsho shinkeigaku = Clinical neurology. 2021 Feb; 61(2):109-114. doi: 10.5692/clinicalneurol.cn-001500. [PMID: 33504748]
  • Ziyi Yang, Qing Song, Zhongcheng Cao, Guangjun Yu, Zhuoling Liu, Zhenghuai Tan, Yong Deng. Design, synthesis and evaluation of flurbiprofen-clioquinol hybrids as multitarget-directed ligands against Alzheimer's disease. Bioorganic & medicinal chemistry. 2020 04; 28(7):115374. doi: 10.1016/j.bmc.2020.115374. [PMID: 32089390]
  • Yuan Ke, Chaoyan Wu, Yifei Zeng, Mengge Chen, Yonghong Li, Conghua Xie, Yunfeng Zhou, Yahua Zhong, Haijun Yu. Radiosensitization of Clioquinol Combined with Zinc in the Nasopharyngeal Cancer Stem-like Cells by Inhibiting Autophagy in Vitro and in Vivo. International journal of biological sciences. 2020; 16(5):777-789. doi: 10.7150/ijbs.40305. [PMID: 32071548]
  • 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]
  • Mitchell P McInerney, Yijun Pan, Irene Volitakis, Ashley I Bush, Jennifer L Short, Joseph A Nicolazzo. The Effects of Clioquinol on P-glycoprotein Expression and Biometal Distribution in the Mouse Brain Microvasculature. Journal of pharmaceutical sciences. 2019 07; 108(7):2247-2255. doi: 10.1016/j.xphs.2019.01.030. [PMID: 30738852]
  • Tanawut Tantimongcolwat, Supaluk Prachayasittikul, Virapong Prachayasittikul. Unravelling the interaction mechanism between clioquinol and bovine serum albumin by multi-spectroscopic and molecular docking approaches. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2019 Jun; 216(?):25-34. doi: 10.1016/j.saa.2019.03.004. [PMID: 30865872]
  • Grasiele de Sousa Vieira Tavares, Débora Vasconcelos Costa Mendonça, Daniela Pagliara Lage, Juliana da Trindade Granato, Flaviano Melo Ottoni, Fernanda Ludolf, Miguel Angel Chávez-Fumagalli, Mariana Costa Duarte, Carlos Alberto Pereira Tavares, Ricardo José Alves, Elaine Soares Coimbra, Eduardo Antonio Ferraz Coelho. Antileishmanial Activity, Cytotoxicity and Mechanism of Action of Clioquinol Against Leishmania infantum and Leishmania amazonensis Species. Basic & clinical pharmacology & toxicology. 2018 Sep; 123(3):236-246. doi: 10.1111/bcpt.12990. [PMID: 29481714]
  • Shan Lu, Yuan Ke, Chaoyan Wu, Yahua Zhong, Conghua Xie, Yunfeng Zhou, Fuxiang Zhou, Haijun Yu. Radiosensitization of clioquinol and zinc in human cancer cell lines. BMC cancer. 2018 04; 18(1):448. doi: 10.1186/s12885-018-4264-2. [PMID: 29678153]
  • Mitchell P McInerney, Irene Volitakis, Ashley I Bush, William A Banks, Jennifer L Short, Joseph A Nicolazzo. Ionophore and Biometal Modulation of P-glycoprotein Expression and Function in Human Brain Microvascular Endothelial Cells. Pharmaceutical research. 2018 Mar; 35(4):83. doi: 10.1007/s11095-018-2377-6. [PMID: 29508078]
  • Akihiro Yamamoto, Maame Debrah-Pinamang, Nicholas J DiModica, Katsuhisa Kurogi, Ali A Naqvi, Ying Hui, Yoichi Sakakibara, Masahito Suiko, Ming-Cheh Liu. Identification and Characterization of the Human Cytosolic Sulfotransferases Mediating the Sulfation of Clioquinol and Iodoquinol. Drug metabolism letters. 2016; 10(3):200-205. doi: 10.2174/1872312810666160719142850. [PMID: 27449410]
  • Mohamed Wehbe, Malathi Anantha, Ian Backstrom, Ada Leung, Kent Chen, Armaan Malhotra, Katarina Edwards, Marcel B Bally. Nanoscale Reaction Vessels Designed for Synthesis of Copper-Drug Complexes Suitable for Preclinical Development. PloS one. 2016; 11(4):e0153416. doi: 10.1371/journal.pone.0153416. [PMID: 27055237]
  • Jian Wang, Yong Chang, Pu Zhang, Shao Qing Lie, Peng Fei Gao, Cheng Zhi Huang. Cu(2+)-mediated fluorescence switching of gold nanoclusters for the selective detection of clioquinol. The Analyst. 2015 Dec; 140(24):8194-200. doi: 10.1039/c5an01975c. [PMID: 26567905]
  • Rohit Mehra, Rupinder K Sodhi, Neha Aggarwal. Memory restorative ability of clioquinol in copper-cholesterol-induced experimental dementia in mice. Pharmaceutical biology. 2015; 53(9):1250-9. doi: 10.3109/13880209.2014.974061. [PMID: 25856695]
  • Marin J de Jong, Judith J Korterink, Marc A Benninga, Mirrian Hilbink, J Widdershoven, Judith M Deckers-Kocken. Dientamoeba fragilis and chronic abdominal pain in children: a case-control study. Archives of disease in childhood. 2014 Dec; 99(12):1109-13. doi: 10.1136/archdischild-2014-305942. [PMID: 25053737]
  • Husam Dabbagh-Bazarbachi, Gael Clergeaud, Isabel M Quesada, Mayreli Ortiz, Ciara K O'Sullivan, Juan B Fernández-Larrea. Zinc ionophore activity of quercetin and epigallocatechin-gallate: from Hepa 1-6 cells to a liposome model. Journal of agricultural and food chemistry. 2014 Aug; 62(32):8085-93. doi: 10.1021/jf5014633. [PMID: 25050823]
  • Etheresia Pretorius, Janette Bester, Natasha Vermeulen, Boguslaw Lipinski, George S Gericke, Douglas B Kell. Profound morphological changes in the erythrocytes and fibrin networks of patients with hemochromatosis or with hyperferritinemia, and their normalization by iron chelators and other agents. PloS one. 2014; 9(1):e85271. doi: 10.1371/journal.pone.0085271. [PMID: 24416376]
  • Janna M A Ter Schure, Marrit de Vries, Jan F L Weel, Eric N van Roon, Tina E Faber. Symptoms and treatment of Dientamoeba fragilis infection in children, a retrospective study. The Pediatric infectious disease journal. 2013 Apr; 32(4):e148-50. doi: 10.1097/inf.0b013e31827f4c20. [PMID: 23190787]
  • Maksim Ionov, Nataliya V Gordiyenko, Izabela Zukowska, Elmira Tokhtaeva, Olga A Mareninova, Nina Baram, Khairulla Ziyaev, Kuralbay Rezhepov, Maria Zamaraeva. Stability and antioxidant activity of gossypol derivative immobilized on N-polyvinylpyrrolidone. International journal of biological macromolecules. 2012 Dec; 51(5):908-14. doi: 10.1016/j.ijbiomac.2012.08.005. [PMID: 22910577]
  • Aaron D Schimmer, Yulia Jitkova, Marcela Gronda, Zezhou Wang, Joseph Brandwein, Christine Chen, Vikas Gupta, Andre Schuh, Karen Yee, Jian Chen, Suzanne Ackloo, Tristan Booth, Sharon Keays, Mark D Minden. A phase I study of the metal ionophore clioquinol in patients with advanced hematologic malignancies. Clinical lymphoma, myeloma & leukemia. 2012 Oct; 12(5):330-6. doi: 10.1016/j.clml.2012.05.005. [PMID: 22683301]
  • Amy R Cameron, Katherine Wallace, Lisa Logie, Alan R Prescott, Terry G Unterman, Jean Harthill, Graham Rena. The anti-neurodegenerative agent clioquinol regulates the transcription factor FOXO1a. The Biochemical journal. 2012 Apr; 443(1):57-64. doi: 10.1042/bj20112124. [PMID: 22248233]
  • Silvio R Bareggi, Umberto Cornelli. Clioquinol: review of its mechanisms of action and clinical uses in neurodegenerative disorders. CNS neuroscience & therapeutics. 2012 Jan; 18(1):41-6. doi: 10.1111/j.1755-5949.2010.00231.x. [PMID: 21199452]
  • Hongchao Jiang, Jori E Taggart, Xiaoxi Zhang, Doris M Benbrook, Stuart E Lind, Wei-Qun Ding. Nitroxoline (8-hydroxy-5-nitroquinoline) is more a potent anti-cancer agent than clioquinol (5-chloro-7-iodo-8-quinoline). Cancer letters. 2011 Dec; 312(1):11-7. doi: 10.1016/j.canlet.2011.06.032. [PMID: 21899946]
  • Garth J S Cooper. Therapeutic potential of copper chelation with triethylenetetramine in managing diabetes mellitus and Alzheimer's disease. Drugs. 2011 Jul; 71(10):1281-320. doi: 10.2165/11591370-000000000-00000. [PMID: 21770477]
  • Omer Calka, Calka Omer, Necmettin Akdeniz, Akdeniz Necmettin, Hatice Uce Özkol, Uce Ozkol Hatice, Ayse Serap Karadag, Karadag Ayse Serap, Lütfi Behçet, Behçet Lütfi. Irritant contact dermatitis caused by Ranunculus kotschyi Boiss in 6 cases. Contact dermatitis. 2011 Mar; 64(3):174-6. doi: 10.1111/j.1600-0536.2010.01842.x. [PMID: 21272029]
  • E Kimura, T Hirano, S Yamashita, T Hirai, Y Uchida, Y Maeda, M Uchino. Cervical MRI of subacute myelo-optico-neuropathy. Spinal cord. 2011 Feb; 49(2):182-5. doi: 10.1038/sc.2010.68. [PMID: 20548321]
  • Tjaard U Hoogenraad. Paradigm shift in treatment of Alzheimer's disease: zinc therapy now a conscientious choice for care of individual patients. International journal of Alzheimer's disease. 2011; 2011(?):492686. doi: 10.4061/2011/492686. [PMID: 21949909]
  • D Allan Butterfield, Rukhsana Sultana. Methionine-35 of aβ(1-42): importance for oxidative stress in Alzheimer disease. Journal of amino acids. 2011; 2011(?):198430. doi: 10.4061/2011/198430. [PMID: 22312456]
  • Da Hee Oh, Jun Soo Bang, Hyun Mi Choi, Hyung-In Yang, Myung Chul Yoo, Kyoung Soo Kim. Fetal bovine serum requirement for pyrrolidine dithiocarbamate-induced apoptotic cell death of MCF-7 breast tumor cells. European journal of pharmacology. 2010 Dec; 649(1-3):135-9. doi: 10.1016/j.ejphar.2010.09.048. [PMID: 20868670]
  • Chenghua Li, Juan Wang, Bing Zhou. The metal chelating and chaperoning effects of clioquinol: insights from yeast studies. Journal of Alzheimer's disease : JAD. 2010; 21(4):1249-62. doi: 10.3233/jad-2010-100024. [PMID: 21504115]
  • Akihiro Igata. Clinical studies on rising and re-rising neurological diseases in Japan--a personal contribution. Proceedings of the Japan Academy. Series B, Physical and biological sciences. 2010; 86(4):366-77. doi: 10.2183/pjab.86.366. [PMID: 20431261]
  • Nelleke Tolboom, Maqsood Yaqub, Ronald Boellaard, Gert Luurtsema, Albert D Windhorst, Philip Scheltens, Adriaan A Lammertsma, Bart N M van Berckel. Test-retest variability of quantitative [11C]PIB studies in Alzheimer's disease. European journal of nuclear medicine and molecular imaging. 2009 Oct; 36(10):1629-38. doi: 10.1007/s00259-009-1129-6. [PMID: 19384547]
  • Stuart E Lind, Jong Sung Park, John W Drexler. Pyrithione and 8-hydroxyquinolines transport lead across erythrocyte membranes. Translational research : the journal of laboratory and clinical medicine. 2009 Sep; 154(3):153-9. doi: 10.1016/j.trsl.2009.06.002. [PMID: 19665691]
  • Silvio R Bareggi, Daniela Braida, Claudia Pollera, Gianpietro Bondiolotti, Elena Formentin, Maria Puricelli, Giorgio Poli, Wilma Ponti, Mariaelvina Sala. Effects of clioquinol on memory impairment and the neurochemical modifications induced by scrapie infection in golden hamsters. Brain research. 2009 Jul; 1280(?):195-200. doi: 10.1016/j.brainres.2009.05.031. [PMID: 19463795]
  • Haruo Takahashi. [The history of adverse drug reactions, relief for these health damage and safety measures in Japan]. Yakushigaku zasshi. 2009; 44(2):64-70. doi: NULL. [PMID: 20527311]
  • Lars Lannfelt, Kaj Blennow, Henrik Zetterberg, Stellan Batsman, David Ames, John Harrison, Colin L Masters, Steve Targum, Ashley I Bush, Ross Murdoch, Janet Wilson, Craig W Ritchie. Safety, efficacy, and biomarker findings of PBT2 in targeting Abeta as a modifying therapy for Alzheimer's disease: a phase IIa, double-blind, randomised, placebo-controlled trial. The Lancet. Neurology. 2008 Sep; 7(9):779-86. doi: 10.1016/s1474-4422(08)70167-4. [PMID: 18672400]
  • Masanori Yoshioka, Toyofumi Nakanishi. [Oxidative precipitation of transthyretin--a clue to elucidate amyloidosis]. Rinsho byori. The Japanese journal of clinical pathology. 2008 May; 56(5):425-31. doi: NULL. [PMID: 18546893]
  • Robert A Colvin, Ashley I Bush, Irene Volitakis, Charles P Fontaine, Dustin Thomas, Kazuya Kikuchi, William R Holmes. Insights into Zn2+ homeostasis in neurons from experimental and modeling studies. American journal of physiology. Cell physiology. 2008 Mar; 294(3):C726-42. doi: 10.1152/ajpcell.00541.2007. [PMID: 18184873]
  • Katherine A Price, Gulay Filiz, Aphrodite Caragounis, Tai Du, Katrina M Laughton, Colin L Masters, Robyn A Sharples, Andrew F Hill, Qiao-Xin Li, Paul S Donnelly, Kevin J Barnham, Peter J Crouch, Anthony R White. Activation of epidermal growth factor receptor by metal-ligand complexes decreases levels of extracellular amyloid beta peptide. The international journal of biochemistry & cell biology. 2008; 40(9):1901-17. doi: 10.1016/j.biocel.2008.01.033. [PMID: 18346929]
  • Tong-Lay Lau, John D Gehman, John D Wade, Colin L Masters, Kevin J Barnham, Frances Separovic. Cholesterol and Clioquinol modulation of A beta(1-42) interaction with phospholipid bilayers and metals. Biochimica et biophysica acta. 2007 Dec; 1768(12):3135-44. doi: 10.1016/j.bbamem.2007.08.027. [PMID: 17920561]
  • Aphrodite Caragounis, Tai Du, Gulay Filiz, Katrina M Laughton, Irene Volitakis, Robyn A Sharples, Robert A Cherny, Colin L Masters, Simon C Drew, Andrew F Hill, Qiao-Xin Li, Peter J Crouch, Kevin J Barnham, Anthony R White. Differential modulation of Alzheimer's disease amyloid beta-peptide accumulation by diverse classes of metal ligands. The Biochemical journal. 2007 Nov; 407(3):435-50. doi: 10.1042/bj20070579. [PMID: 17680773]
  • Katherine A Price, Peter J Crouch, Anthony R White. Therapeutic treatment of Alzheimer's disease using metal complexing agents. Recent patents on CNS drug discovery. 2007 Nov; 2(3):180-7. doi: 10.2174/157488907782411774. [PMID: 18221229]
  • Danielle G Smith, Roberto Cappai, Kevin J Barnham. The redox chemistry of the Alzheimer's disease amyloid beta peptide. Biochimica et biophysica acta. 2007 Aug; 1768(8):1976-90. doi: 10.1016/j.bbamem.2007.02.002. [PMID: 17433250]
  • W-H Chen, M Wang, S-S Yu, L Su, D-M Zhu, J-Q She, X-J Cao, D-Y Ruan. Clioquinol and vitamin B12 (cobalamin) synergistically rescue the lead-induced impairments of synaptic plasticity in hippocampal dentate gyrus area of the anesthetized rats in vivo. Neuroscience. 2007 Jul; 147(3):853-64. doi: 10.1016/j.neuroscience.2007.04.042. [PMID: 17555879]
  • Stephanie Schäfer, Frank-Gerald Pajonk, Gerd Multhaup, Thomas A Bayer. Copper and clioquinol treatment in young APP transgenic and wild-type mice: effects on life expectancy, body weight, and metal-ion levels. Journal of molecular medicine (Berlin, Germany). 2007 Apr; 85(4):405-13. doi: 10.1007/s00109-006-0140-7. [PMID: 17211610]
  • Jonathan H Fox, Jibrin A Kama, Gregory Lieberman, Raman Chopra, Kate Dorsey, Vanita Chopra, Irene Volitakis, Robert A Cherny, Ashley I Bush, Steven Hersch. Mechanisms of copper ion mediated Huntington's disease progression. PloS one. 2007 Mar; 2(3):e334. doi: 10.1371/journal.pone.0000334. [PMID: 17396163]
  • Gianpietro Bondiolotti, Mariaelvina Sala, Claudia Pollera, Marco Gervasoni, Maria Puricelli, Wilma Ponti, Silvio R Bareggi. Pharmacokinetics and distribution of clioquinol in golden hamsters. The Journal of pharmacy and pharmacology. 2007 Mar; 59(3):387-93. doi: 10.1211/jpp.59.3.0008. [PMID: 17331342]
  • Rosanna Squitti, Carlo C Quattrocchi, Gloria Dal Forno, Piero Antuono, David R Wekstein, Concetta R Capo, Carlo Salustri, Paolo M Rossini. Ceruloplasmin (2-D PAGE) Pattern and Copper Content in Serum and Brain of Alzheimer Disease Patients. Biomarker insights. 2007 Feb; 1(?):205-13. doi: 10.1177/117727190600100019. [PMID: 19690651]
  • Wei-Qun Ding, Bolin Liu, Joshua L Vaught, Richard D Palmiter, Stuart E Lind. Clioquinol and docosahexaenoic acid act synergistically to kill tumor cells. Molecular cancer therapeutics. 2006 Jul; 5(7):1864-72. doi: 10.1158/1535-7163.mct-06-0067. [PMID: 16891473]
  • G P Bondiolotti, C Pollera, R Pirola, S R Bareggi. Determination of 5-chloro-7-iodo-8-quinolinol (clioquinol) in plasma and tissues of hamsters by high-performance liquid chromatography and electrochemical detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jun; 837(1-2):87-91. doi: 10.1016/j.jchromb.2006.04.014. [PMID: 16714152]
  • Luna Benvenisti-Zarom, Jing Chen, Raymond F Regan. The oxidative neurotoxicity of clioquinol. Neuropharmacology. 2005 Oct; 49(5):687-94. doi: 10.1016/j.neuropharm.2005.04.023. [PMID: 15992834]
  • P Jassar, J Jose, J J Homer. Otic drops used to clear a blocked grommet: an in vitro prospective randomized controlled study with blinded assessment. Clinical otolaryngology and allied sciences. 2004 Dec; 29(6):602-5. doi: 10.1111/j.1365-2273.2004.00880.x. [PMID: 15533145]
  • Vinod K Sharma, Gomathy Sethuraman, Taru Garg, Kaushal K Verma, M Ramam. Patch testing with the Indian standard series in New Delhi. Contact dermatitis. 2004 Nov; 51(5-6):319-21. doi: 10.1111/j.0105-1873.2004.0459k.x. [PMID: 15606668]
  • P Murali Doraiswamy, Anne E Finefrock. Metals in our minds: therapeutic implications for neurodegenerative disorders. The Lancet. Neurology. 2004 Jul; 3(7):431-4. doi: 10.1016/s1474-4422(04)00809-9. [PMID: 15207800]
  • D K Bosman, M A Benninga, P van de Berg, G C Kooijman, T van Gool. [Dientamoeba fragilis: possibly an important cause of persistent abdominal pain in children]. Nederlands tijdschrift voor geneeskunde. 2004 Mar; 148(12):575-9. doi: NULL. [PMID: 15074181]
  • Craig W Ritchie, Ashley I Bush, Andrew Mackinnon, Steve Macfarlane, Maree Mastwyk, Lachlan MacGregor, Lyn Kiers, Robert Cherny, Qiao-Xin Li, Amanda Tammer, Darryl Carrington, Christine Mavros, Irene Volitakis, Michel Xilinas, David Ames, Stephen Davis, Konrad Beyreuther, Rudolph E Tanzi, Colin L Masters. Metal-protein attenuation with iodochlorhydroxyquin (clioquinol) targeting Abeta amyloid deposition and toxicity in Alzheimer disease: a pilot phase 2 clinical trial. Archives of neurology. 2003 Dec; 60(12):1685-91. doi: 10.1001/archneur.60.12.1685. [PMID: 14676042]
  • Toshiaki Takasu. [SMON--a model of the iatrogenic disease]. Rinsho shinkeigaku = Clinical neurology. 2003 Nov; 43(11):866-9. doi: NULL. [PMID: 15152488]
  • Kevin J Barnham, Giuseppe D Ciccotosto, Anna K Tickler, Feda E Ali, Danielle G Smith, Nicholas A Williamson, Yuen-Han Lam, Darryl Carrington, Deborah Tew, Gulcan Kocak, Irene Volitakis, Frances Separovic, Colin J Barrow, John D Wade, Colin L Masters, Robert A Cherny, Cyril C Curtain, Ashley I Bush, Roberto Cappai. Neurotoxic, redox-competent Alzheimer's beta-amyloid is released from lipid membrane by methionine oxidation. The Journal of biological chemistry. 2003 Oct; 278(44):42959-65. doi: 10.1074/jbc.m305494200. [PMID: 12925530]
  • P Murali Doraiswamy. Non-cholinergic strategies for treating and preventing Alzheimer's disease. CNS drugs. 2002; 16(12):811-24. doi: 10.2165/00023210-200216120-00003. [PMID: 12421115]
  • B Regland, W Lehmann, I Abedini, K Blennow, M Jonsson, I Karlsson, M Sjögren, A Wallin, M Xilinas, C G Gottfries. Treatment of Alzheimer's disease with clioquinol. Dementia and geriatric cognitive disorders. 2001 Nov; 12(6):408-14. doi: 10.1159/000051288. [PMID: 11598313]
  • M S Yassin, J Ekblom, C Löfberg, L Oreland. Transmethylation reactions and autoradiographic distribution of vitamin B12: effects of clioquinol treatment in mice. Japanese journal of pharmacology. 1998 Sep; 78(1):55-61. doi: 10.1254/jjp.78.55. [PMID: 9804062]
  • Y Matsuki, S Yoshimura, M Abe. [SMON and pharmacokinetics of chinoform with special reference to animal species difference]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1997 Nov; 117(10-11):936-56. doi: 10.1248/yakushi1947.117.10-11_936. [PMID: 9414602]
  • N Ohshima, H Kotaki, Y Saitoh, F Nakagawa, Z Tamura. Sex difference of the metabolic disposition of clioquinol in rats. Journal of pharmacobio-dynamics. 1989 Jul; 12(7):371-7. doi: 10.1248/bpb1978.12.371. [PMID: 2531797]
  • S Hori, K Kayanuma, S Ohtani, H Sugiura, H Kotaki, T Tsubaki. Effects of 5-chloro-7-iodo-8-hydroxyquinoline (clioquinol) and nerve growth factor on DNA, RNA and protein syntheses in neonatal rat superior cervical ganglia. Pharmacology & toxicology. 1988 Oct; 63(4):225-32. doi: 10.1111/j.1600-0773.1988.tb00945.x. [PMID: 2461553]
  • N Ohshima, H Kotaki, S Hori, Y Saitoh, F Nakagawa, Z Tamura. Changes in lipid peroxide concentrations in plasma and tissues by repeated administration of clioquinol to neonatal rats. Journal of pharmacobio-dynamics. 1988 Jun; 11(6):424-9. doi: 10.1248/bpb1978.11.424. [PMID: 2971795]
  • Y Matsuki, T Ito, K Fukuhara, M Abe, T Othaki, T Nambara. Determination of chinoform in biological fluids and nervous tissues of the dog by gas chromatography-mass spectrometry. Archives of toxicology. 1987 Feb; 59(5):374-8. doi: 10.1007/bf00295093. [PMID: 2953322]
  • H Kotaki, S Hori, Y Saitoh, F Nakagawa, Z Tamura. Absorption, distribution and metabolism of clioquinol in clioquinol-sensitive and -resistant neonatal rats. Journal of pharmacobio-dynamics. 1986 Dec; 9(12):970-4. doi: NULL. [PMID: 2952786]
  • H Tanaka, Z Tamura. Analysis of chinoform binding to human serum albumin by an improved partition equilibrium method. Journal of pharmacobio-dynamics. 1986 Dec; 9(12):1015-22. doi: 10.1248/bpb1978.9.1015. [PMID: 2952785]
  • G K Paliĭ, S A Ivanova. [Sensitivity of fungi in the genus Candida to antimicrobial preparations]. Antibiotiki i meditsinskaia biotekhnologiia = Antibiotics and medical biotechnology. 1986 Mar; 31(3):218-20. doi: NULL. [PMID: 2940962]
  • K Yagi, K Ohtsuka, N Ohishi. Lipid peroxidation caused by chinoform-ferric chelate in cultured neural retinal cells. Experientia. 1985 Dec; 41(12):1561-3. doi: 10.1007/bf01964807. [PMID: 2934270]
  • Y Ishibashi, Y Nakabayashi, A Kukita, Y Benno, T Mitsuoka. Abnormalities of fecal flora in patients with acrodermatitis enteropathica. The Journal of dermatology. 1985 Jun; 12(3):219-25. doi: 10.1111/j.1346-8138.1985.tb01565.x. [PMID: 2934452]
  • F W Ezzedeen, S J Stohs, K L Kilzer, M C Makoid, N W Ezzedeen. Percutaneous absorption and disposition of iodochlorhydroxyquin in dogs. Journal of pharmaceutical sciences. 1984 Oct; 73(10):1369-72. doi: 10.1002/jps.2600731011. [PMID: 6239025]
  • H Kotaki, Y Yamamura, Y Tanimura, Y Saitoh, F Nakagawa, Z Tamura. Enterohepatic circulation of clioquinol in the rat. Journal of pharmacobio-dynamics. 1984 Jun; 7(6):420-5. doi: 10.1248/bpb1978.7.420. [PMID: 6237189]
  • K Hayakawa, T Ogai, Y Irikura, M Miyazaki, Z Tamura. Effect of clioquinol on metals in rabbit. Chemical & pharmaceutical bulletin. 1984 May; 32(5):1973-9. doi: 10.1248/cpb.32.1973. [PMID: 6235939]
  • H Kotaki, K Nakajima, Y Tanimura, Y Saitoh, F Nakagawa, K Nagashima, TamuraZ. [Appearance of intoxication, and plasma and tissue clioquinol concentrations after intravenous administration of clioquinol to rabbits]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1984 Apr; 104(4):413-7. doi: 10.1248/yakushi1947.104.4_413. [PMID: 6238155]
  • M Jurima, W Kalow, T Inaba. Metabolism of 14C-iodochlorhydroxyquin in the dog and the rat. Journal of pharmacobio-dynamics. 1984 Mar; 7(3):164-70. doi: 10.1248/bpb1978.7.164. [PMID: 6235361]
  • S J Stohs, F W Ezzedeen, A K Anderson, J N Baldwin, M C Makoid. Percutaneous absorption of iodochlorhydroxyquin in humans. The Journal of investigative dermatology. 1984 Feb; 82(2):195-8. doi: 10.1111/1523-1747.ep12259839. [PMID: 6229586]
  • H Kotaki, Y Yamamura, Y Tanimura, Y Saitoh, F Nakagawa, Z Tamura. Intestinal absorption and metabolism of clioquinol in the rat. Journal of pharmacobio-dynamics. 1983 Nov; 6(11):881-7. doi: 10.1248/bpb1978.6.881. [PMID: 6230438]
  • H Kotaki, K Nakajima, Y Tanimura, Y Saitoh, F Nakagawa, Z Tamura, K Nagashima. Appearance of intoxication in rats by intraperitoneal administration of clioquinol. Journal of pharmacobio-dynamics. 1983 Oct; 6(10):773-83. doi: 10.1248/bpb1978.6.773. [PMID: 6229623]
  • F W Ezzedeen, S J Stohs, M Stublar. Analysis of iodochlorhydroxyquin in biological materials by high-performance liquid chromatography. Journal of chromatography. 1983 Aug; 276(1):121-8. doi: 10.1016/s0378-4347(00)85072-0. [PMID: 6231303]
  • H Kotaki, Y Yamamura, Y Tanimura, Y Saitoh, F Nakagawa, Z Tamura. Determination of chinoform and its metabolites in plasma by gas chromatography--mass spectrometry. Chemical & pharmaceutical bulletin. 1983 Jan; 31(1):299-304. doi: 10.1248/cpb.31.299. [PMID: 6221810]
  • K Ohtsuka, N Ohishi, G Eguchi, K Yagi. Degeneration of retinal neuroblasts by chinoform-ferric chelate. Experientia. 1982 Jan; 38(1):120-2. doi: 10.1007/bf01944564. [PMID: 6173256]
  • Y Egashira, H Matsuyama. Subacute myelo-optico-neuropathy (SMON) in Japan. With special reference to the autopsy cases. Acta pathologica japonica. 1982; 32 Suppl 1(?):101-16. doi: NULL. [PMID: 6316716]
  • A Sioufi, F Pommier. Gas chromatographic determination of clioquinol (Vioform) in human plasma. Journal of chromatography. 1981 Nov; 226(1):219-23. doi: 10.1016/s0378-4347(00)84225-5. [PMID: 6459333]
  • D M Hoover, W W Carlton. The subacute neurotoxicity of excess pyridoxine HCl and clioquinol (5-chloro-7-iodo-8-hydroxyquinoline) in beagle dogs. I. Clinical disease. Veterinary pathology. 1981 Nov; 18(6):745-56. doi: 10.1177/030098588101800605. [PMID: 6457437]
  • F W Ezzedeen, A N Masoud, S J Stohs, S J Lerman. High-performance liquid chromatographic analysis of iodochlorhydroxyquin in plasma. Journal of pharmaceutical sciences. 1981 Aug; 70(8):889-91. doi: 10.1002/jps.2600700814. [PMID: 6458695]
  • H P Minder, A M Merritt, W Chalupa. In vitro fermentation of feces from normal and chronically diarrheal horses. American journal of veterinary research. 1980 Apr; 41(4):564-7. doi: NULL. [PMID: 6447466]
  • T Suzuki, T Kohno, S Takeyama, K Kotera, K Tsubaki. Analysis of gas chromatography/electron capture detector sensitive substances in human serum in relation to the determination of iodochlorhydroxyquin concentration. Clinica chimica acta; international journal of clinical chemistry. 1980 Jan; 100(1):75-9. doi: 10.1016/0009-8981(80)90189-8. [PMID: 6444282]
  • M Mumenthaler, H E Kaeser, A Meyer, T Hess. Transient global amnesia after clioquinol: five personal observations from outside Japan. Journal of neurology, neurosurgery, and psychiatry. 1979 Dec; 42(12):1084-90. doi: 10.1136/jnnp.42.12.1084. [PMID: 160443]
  • B Inouye, M Ogata. Effect of chinoform on the function of biological membranes. Physiological chemistry and physics. 1979; 11(1):49-57. doi: NULL. [PMID: 159463]
  • P H Degen, J Moppert, K Schmid, E G Weirich. Percutaneous absorption of clioquinol (Vioform). Dermatologica. 1979; 159(4):295-301. doi: 10.1159/000250618. [PMID: 157893]
  • T Fischer, C Fagerlund, P Hartvig. Absorption of 8-hydroxyquinolines through the human skin. Acta dermato-venereologica. 1978; 58(5):407-11. doi: NULL. [PMID: 82350]
  • P Hartvig, C Fagerlund. Extractive alkylation of biological samples of clioquinol or chloroquinaldol and determination by electron capture gas chromatography. Journal of chromatography. 1977 Oct; 140(2):170-3. doi: 10.1016/s0021-9673(00)88410-1. [PMID: 144142]
  • P Del Soldato. TLC determination of iodochlorhydroxyquin and its conjugate in plasma. Journal of pharmaceutical sciences. 1977 Sep; 66(9):1334-6. doi: 10.1002/jps.2600660934. [PMID: 143525]
  • K Hayakawa, T Imanari, Z Tamura, S Kuroda, H Ikeda, J Tateishi. Relationship between neurological symptoms and concentrations of clioquinol in serum and nervous systems of beagle dogs. Chemical & pharmaceutical bulletin. 1977 Aug; 25(8):2013-8. doi: 10.1248/cpb.25.2013. [PMID: 144569]