Clodronate (BioDeep_00000033258)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(Dichloro-phosphono-methyl)-phosphonic acid

化学式: CH4Cl2O6P2 (243.88602040000004)
中文名称: 氯屈瞵酸
谱图信息: 最多检出来源 Homo sapiens(blood) 8.33%

分子结构信息

SMILES: C(P(=O)(O)O)(P(=O)(O)O)(Cl)Cl
InChI: InChI=1S/CH4Cl2O6P2/c2-1(3,10(4,5)6)11(7,8)9/h(H2,4,5,6)(H2,7,8,9)

描述信息

Clodronate is only found in individuals that have used or taken this drug. It is a diphosphonate which affects calcium metabolism. It inhibits bone resorption and soft tissue calcification. [PubChem]The bisphosphonate group binds strongly to the bone mineral, hydroxyapatite. This explains the specific pharmacological action of these compounds on mineralized tissues, especially bone. The exact mechanism of action of clodronate is not known, however it is known that it does not inhibit protein isoprenylation but can be metabolized intracellularly to a β-γ-methylene (AppCp-type) analog of ATP (AppCCl2p), which is cytotoxic to macrophages in vitro. Inhibition of the ADP/ATP translocase by the metabolite AppCCl2p is a likely route by which clodronate causes osteoclast apoptosis and inhibits bone resorption. Recently, the slime mold Dictyostelium discoideum was shown to take up bisphosphonates by pinocytosis. In these cells, clodronate, but not other pharmacologically active bisphosphonates, was incorporated into adenine nucleotides, which could potentially explain why this bisphosphonate sometimes seems to act differently than the other bisphosphonates. Clodronate, like all biphosphonates, also binds protein-tyrosine-phosphatase.
M - Musculo-skeletal system > M05 - Drugs for treatment of bone diseases > M05B - Drugs affecting bone structure and mineralization > M05BA - Bisphosphonates
C78281 - Agent Affecting Musculoskeletal System > C67439 - Bone Resorption Inhibitor
D050071 - Bone Density Conservation Agents > D004164 - Diphosphonates

同义名列表

36 个代谢物同义名

(Dichloro-phosphono-methyl)-phosphonic acid; [dichloro(phosphono)methyl]phosphonic acid; Dichloromethylene-1,1-bisphosphonic acid; (Dichloro-phosphono-methyl)-phosphonate; Dichloromethylene-1,1-diphosphonic acid; (Dichloromethylene)bisphosphonic acid; Dichloromethylidene diphosphonic acid; Dichloromethylene-1,1-bisphosphonate; (Dichloromethylene)diphosphonic acid; Dichloromethylene-1,1-diphosphonate; Acid, dichloromethanediphosphonic; (Dichloromethylene)bisphosphonate; Dichloromethylidene diphosphonate; (Dichloromethylene)diphosphonate; Diphosphonate, dichloromethylene; Dichloromethanediphosphonic acid; Biphosphonate, dichloromethylene; Dichloromethylenebisphosphonate; Dichloromethylene biphosphonate; Dichloromethylene diphosphonate; Diphosphonate, dichloromethane; Dichloromethane diphosphonate; Dichloromethanediphosphonate; Disodium, clodronate; Clodronate Disodium; Acidum clodronicum; Sodium, clodronate; Acide clodronique; Clodronate sodium; Acido clodronico; Acid, clodronic; Clodronic Acid; Clodronsaeure; Clodronate; Bonefos; CL2MDP



数据库引用编号

9 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

  • Dhaval Oza, Fernando Ivich, Joshua Pace, Mikyung Yu, Mark Niedre, Mansoor Amiji. Lipid nanoparticle encapsulated large peritoneal macrophages migrate to the lungs via the systemic circulation in a model of clodronate-mediated lung-resident macrophage depletion. Theranostics. 2024; 14(6):2526-2543. doi: 10.7150/thno.91062. [PMID: 38646640]
  • Rudragouda Channappanavar, Muneeswaran Selvaraj, Sunil More, Stanley Perlman. Alveolar macrophages protect mice from MERS-CoV-induced pneumonia and severe disease. Veterinary pathology. 2022 07; 59(4):627-638. doi: 10.1177/03009858221095270. [PMID: 35499307]
  • Daiki Goto, Soichiro Nagata, Yoshitaka Naito, Shinsuke Isobe, Takamasa Iwakura, Tomoyuki Fujikura, Naro Ohashi, Akihiko Kato, Hiroaki Miyajima, Ken Sugimoto, Hideo Yasuda. Nicotinic acetylcholine receptor agonist reduces acute lung injury after renal ischemia-reperfusion injury by acting on splenic macrophages in mice. American journal of physiology. Renal physiology. 2022 05; 322(5):F540-F552. doi: 10.1152/ajprenal.00334.2021. [PMID: 35311383]
  • Alexander Jacob, Michael Phelps, Shane Fraher, Marcos Lopez, Anthony Chang, Richard J Quigg, Jessy J Alexander. Macrophage Depletion Reduces Disease Pathology in Factor H-Dependent Immune Complex-Mediated Glomerulonephritis. Journal of immunology research. 2022; 2022(?):1737419. doi: 10.1155/2022/1737419. [PMID: 35097132]
  • Patrice Garcia, Isabelle Perot, Benoit Loup, Frederic Balssa, Murielle Jaubert, Vivian Delcourt, Chris Dujardin, Marie-Agnes Popot, Ludovic Bailly-Chouriberry. Long-term detection of clodronate in equine plasma by liquid chromatography-tandem mass spectrometry. Drug testing and analysis. 2021 Aug; 13(8):1527-1534. doi: 10.1002/dta.3050. [PMID: 33870655]
  • Atsushi Miura, Takashi Hosono, Taiichiro Seki. Macrophage potentiates the recovery of liver zonation and metabolic function after acute liver injury. Scientific reports. 2021 05; 11(1):9730. doi: 10.1038/s41598-021-88989-9. [PMID: 33958644]
  • Madoka Koyanagi, Satoshi Imai, Mayuna Matsumoto, Yoko Iguma, Nobuko Kawaguchi-Sakita, Takeshi Kotake, Yuki Iwamitsu, Mpumelelo Ntogwa, Ren Hiraiwa, Kazuki Nagayasu, Mamiko Saigo, Takashi Ogihara, Atsushi Yonezawa, Tomohiro Omura, Shunsaku Nakagawa, Takayuki Nakagawa, Kazuo Matsubara. Pronociceptive Roles of Schwann Cell-Derived Galectin-3 in Taxane-Induced Peripheral Neuropathy. Cancer research. 2021 04; 81(8):2207-2219. doi: 10.1158/0008-5472.can-20-2799. [PMID: 33608316]
  • Shuang-Quan Yu, Shuangtao Ma, Donna H Wang. Ablation of TRPV1-positive nerves exacerbates salt-induced hypertension and tissue injury in rats after renal ischemia-reperfusion via infiltration of macrophages. Clinical and experimental hypertension (New York, N.Y. : 1993). 2021 Apr; 43(3):254-262. doi: 10.1080/10641963.2020.1860078. [PMID: 33327798]
  • Yang Ye, Hua-Wei Zhang, Hong-Xia Mei, Hao-Ran Xu, Shu-Yang Xiang, Qian Yang, Sheng-Xing Zheng, Fang Gao Smith, Sheng-Wei Jin, Qian Wang. PDX regulates inflammatory cell infiltration via resident macrophage in LPS-induced lung injury. Journal of cellular and molecular medicine. 2020 09; 24(18):10604-10614. doi: 10.1111/jcmm.15679. [PMID: 32735065]
  • Clarisa R Krueger, Colin F Mitchell, Britta S Leise, Heather K Knych. Pharmacokinetics and pharmacodynamics of clodronate disodium evaluated in plasma, synovial fluid and urine. Equine veterinary journal. 2020 Sep; 52(5):725-732. doi: 10.1111/evj.13244. [PMID: 32003488]
  • Jérémie Joffre, Che-Chung Yeh, Erika Wong, Mayuri Thete, Fengyun Xu, Ivana Zlatanova, Elliot Lloyd, Lester Kobzik, Matthieu Legrand, Judith Hellman. Activation of CB1R Promotes Lipopolysaccharide-Induced IL-10 Secretion by Monocytic Myeloid-Derived Suppressive Cells and Reduces Acute Inflammation and Organ Injury. Journal of immunology (Baltimore, Md. : 1950). 2020 06; 204(12):3339-3350. doi: 10.4049/jimmunol.2000213. [PMID: 32385136]
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  • Satoshi Nishiwaki, Shigeki Saito, Kyosuke Takeshita, Hidefumi Kato, Ryuzo Ueda, Akiyoshi Takami, Tomoki Naoe, Mika Ogawa, Takayuki Nakayama. In vivo tracking of transplanted macrophages with near infrared fluorescent dye reveals temporal distribution and specific homing in the liver that can be perturbed by clodronate liposomes. PloS one. 2020; 15(12):e0242488. doi: 10.1371/journal.pone.0242488. [PMID: 33301448]
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  • Yoshinori Ozono, Kotaro Shide, Fumiyo Toyoshima, Yuuka Takaishi, Mai Tsuchimochi, Ayako Kamiunten, Takuro Kameda, Kenichi Nakamura, Tadashi Miike, Kazunori Kusumoto, Hisayoshi Iwakiri, Satoru Hasuike, Kenji Nagata, Akira Sawaguchi, Kazuya Shimoda. Monocyte-derived fibrocytes elimination had little contribution on liver fibrosis. Hepatobiliary & pancreatic diseases international : HBPD INT. 2019 Aug; 18(4):348-353. doi: 10.1016/j.hbpd.2019.02.002. [PMID: 30826294]
  • Sivaramakrishnan Ramadurai, Nirod Kumar Sarangi, Sean Maher, Nicola MacConnell, Alan M Bond, Dennis McDaid, Damien Flynn, Tia E Keyes. Microcavity-Supported Lipid Bilayers; Evaluation of Drug-Lipid Membrane Interactions by Electrochemical Impedance and Fluorescence Correlation Spectroscopy. Langmuir : the ACS journal of surfaces and colloids. 2019 06; 35(24):8095-8109. doi: 10.1021/acs.langmuir.9b01028. [PMID: 31120755]
  • Congcong Wu, Wenjun Chen, Jian Wu, Xi Zhang, Xuanzhang Huang, Ruifang Lin, Baoling Zhu, Hua Jiang. Effect of bisphosphonates on overall survival in subgroups of patients with prostate cancer. Clinical & experimental metastasis. 2019 06; 36(3):199-209. doi: 10.1007/s10585-019-09963-4. [PMID: 30963355]
  • M N Michalski, L E Zweifler, B P Sinder, A J Koh, J Yamashita, H Roca, L K McCauley. Clodronate-Loaded Liposome Treatment Has Site-Specific Skeletal Effects. Journal of dental research. 2019 04; 98(4):459-467. doi: 10.1177/0022034518821685. [PMID: 30626255]
  • Jackie E Bader, Reilly T Enos, Kandy T Velázquez, Meredith S Carson, Alex T Sougiannis, Owen P McGuinness, Cory M Robinson, E Angela Murphy. Repeated clodronate-liposome treatment results in neutrophilia and is not effective in limiting obesity-linked metabolic impairments. American journal of physiology. Endocrinology and metabolism. 2019 03; 316(3):E358-E372. doi: 10.1152/ajpendo.00438.2018. [PMID: 30576244]
  • Eun Jeong Jeon, Dong Young Kim, Na Hyun Lee, Hye-Eun Choi, Hyae Gyeong Cheon. Telmisartan induces browning of fully differentiated white adipocytes via M2 macrophage polarization. Scientific reports. 2019 02; 9(1):1236. doi: 10.1038/s41598-018-38399-1. [PMID: 30718686]
  • Yuhui Li, Hongda Lu, Xiaojuan Lv, Qiu Tang, Wangxia Li, Hongfei Zhu, Yuan Long. Blockade of Aquaporin 4 Inhibits Irradiation-Induced Pulmonary Inflammation and Modulates Macrophage Polarization in Mice. Inflammation. 2018 Dec; 41(6):2196-2205. doi: 10.1007/s10753-018-0862-z. [PMID: 30091034]
  • Katja F Düsterdieck-Zellmer. [Use of bisphosphonates in horses - a review]. Tierarztliche Praxis. Ausgabe G, Grosstiere/Nutztiere. 2018 Oct; 46(5):323-333. doi: 10.15653/tpg-170804. [PMID: 30340242]
  • Amrutesh S Puranik, Irina A Leaf, Mark A Jensen, Ahmad F Hedayat, Ahmad Saad, Ki-Wook Kim, Abdulrahman M Saadalla, John R Woollard, Sonu Kashyap, Stephen C Textor, Joseph P Grande, Amir Lerman, Robert D Simari, Gwendalyn J Randolph, Jeremy S Duffield, Lilach O Lerman. Kidney-resident macrophages promote a proangiogenic environment in the normal and chronically ischemic mouse kidney. Scientific reports. 2018 09; 8(1):13948. doi: 10.1038/s41598-018-31887-4. [PMID: 30224726]
  • Tine V Karlsen, Elham Nikpey, Jianhua Han, Tore Reikvam, Natalia Rakova, Jorge A Castorena-Gonzalez, Michael J Davis, Jens M Titze, Olav Tenstad, Helge Wiig. High-Salt Diet Causes Expansion of the Lymphatic Network and Increased Lymph Flow in Skin and Muscle of Rats. Arteriosclerosis, thrombosis, and vascular biology. 2018 09; 38(9):2054-2064. doi: 10.1161/atvbaha.118.311149. [PMID: 30354256]
  • Gianantonio Saviola, Lul Abdi-Ali, Maria Rosaria Povino, Lorella Campostrini, Silvano Sacco, Luca Dalle Carbonare, Luca Dalle Carbonare. Intramuscular clodronate in erosive osteoarthritis of the hand is effective on pain and reduces serum COMP: a randomized pilot trial-The ER.O.D.E. study (ERosive Osteoarthritis and Disodium-clodronate Evaluation). Clinical rheumatology. 2017 10; 36(10):2343-2350. doi: 10.1007/s10067-017-3681-y. [PMID: 28536825]
  • Young-Tae Lee, Eun-Ju Ko, Ki-Hye Kim, Hye Suk Hwang, Youri Lee, Young-Man Kwon, Min-Chul Kim, Yu-Na Lee, Yu-Jin Jung, Sang-Moo Kang. Cellular Immune Correlates Preventing Disease Against Respiratory Syncytial Virus by Vaccination with Virus-Like Nanoparticles Carrying Fusion Proteins. Journal of biomedical nanotechnology. 2017 Jan; 13(1):84-98. doi: 10.1166/jbn.2017.2341. [PMID: 29302248]
  • Marta Rusek, Jolanta Elżbieta Pastryk, Jerzy Bełtowski. Modulation of paraoxonase 1 (PON1) activity and protein N-homocysteinylation by bisphosphonates in rats. Chemico-biological interactions. 2016 Nov; 259(Pt B):401-406. doi: 10.1016/j.cbi.2016.07.002. [PMID: 27387541]
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  • David C Woodland, Wei Liu, Jacky Leong, Mallory L Sears, Ping Luo, Xiaojuan Chen. Short-term high-fat feeding induces islet macrophage infiltration and β-cell replication independently of insulin resistance in mice. American journal of physiology. Endocrinology and metabolism. 2016 10; 311(4):E763-E771. doi: 10.1152/ajpendo.00092.2016. [PMID: 27577853]
  • David O Osei-Hwedieh, Tamir Kanias, Claudette St Croix, Morgan Jessup, Zeyu Xiong, Derek Sinchar, Jonathan Franks, Qinzi Xu, Enrico M Novelli, Jonas T Sertorio, Karin Potoka, Robert J Binder, Swati Basu, Andrea M Belanger, Daniel B Kim-Shapiro, Darrell Triulzi, Janet S Lee, Mark T Gladwin. Sickle Cell Trait Increases Red Blood Cell Storage Hemolysis and Post-Transfusion Clearance in Mice. EBioMedicine. 2016 Sep; 11(?):239-248. doi: 10.1016/j.ebiom.2016.08.006. [PMID: 27523807]
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  • Young-Tae Lee, Ki-Hye Kim, Hye Suk Hwang, Youri Lee, Young-Man Kwon, Eun-Ju Ko, Yu-Jin Jung, Yu-Na Lee, Min-Chul Kim, Sang-Moo Kang. Innate and adaptive cellular phenotypes contributing to pulmonary disease in mice after respiratory syncytial virus immunization and infection. Virology. 2015 Nov; 485(?):36-46. doi: 10.1016/j.virol.2015.07.001. [PMID: 26196232]
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