Ciclopirox (BioDeep_00000026844)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolamine salt

化学式: C12H17NO2 (207.12592220000002)
中文名称: 环吡酮胺
谱图信息: 最多检出来源 Homo sapiens(blood) 43.1%

分子结构信息

SMILES: CC1=CC(=O)N(C(=C1)C2CCCCC2)O
InChI: InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3

描述信息

Ciclopirox is only found in individuals that have used or taken this drug. It is a synthetic antifungal agent for topical dermatologic use. [Wikipedia] Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe3+ and Al3+. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. Ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.
G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids
D - Dermatologicals > D01 - Antifungals for dermatological use > D01A - Antifungals for topical use
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
C254 - Anti-Infective Agent > C514 - Antifungal Agent

同义名列表

20 个代谢物同义名

6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolamine salt; 6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one; 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone; Ciclopirox Olamine; Cyclopyroxolamine; Ciclopirox olamin; Ciclopiroxolamine; Ciclopirox-olamin; Ciclopiroxum; Dafnegin CSC; Dafnegin-CSC; Cyclopirox; CICLOPIROX; Batrafen; HOE-296b; HOE 296b; HOE 296; HOE-296; Loprox; Penlac



数据库引用编号

11 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

  • Yiying Zhu, Zhangxun Zhao, Minggao Xue, Dan Wang, Guifeng Su, Xiaoman Ju, Qihong Yang, Shaohua Zhang, Dongmei Fan, Huifang Zhu, Min Yu, Yan Li, Lingmei Kong, Hongyu Zhou. Ciclopirox olamine sensitizes leukemia cells to natural killer cell-mediated cytolysis by upregulating NKG2DLs via the Akt signaling pathway. Biochemical and biophysical research communications. 2023 06; 659(?):10-19. doi: 10.1016/j.bbrc.2023.03.062. [PMID: 37030020]
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  • Tom Bellmann, Ruth Luber, Lisa Kischio, Berit Karl, Yvette Pötzinger, Uwe Beekmann, Dana Kralisch, Cornelia Wiegand, Dagmar Fischer. Bacterial nanocellulose patches as a carrier for hydrating formulations to improve the topical treatment of nail diseases. International journal of pharmaceutics. 2022 Nov; 628(?):122267. doi: 10.1016/j.ijpharm.2022.122267. [PMID: 36209980]
  • Paulo H F Carmo, Gustavo J C Freitas, João C M Dornelas, Bruna C T Almeida, Ludmila M Baltazar, Gabriella F Ferreira, Nalu T A Peres, Daniel A Santos. Reactive oxygen and nitrogen species are crucial for the antifungal activity of amorolfine and ciclopirox olamine against the dermatophyte Trichophyton interdigitale. Medical mycology. 2022 Aug; 60(8):. doi: 10.1093/mmy/myac058. [PMID: 35896502]
  • 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]
  • Priyanka S Radadiya, Mackenzie M Thornton, Rajni V Puri, Sireesha Yerrathota, Johnny Dinh-Phan, Brenda Magenheimer, Dharmalingam Subramaniam, Pamela V Tran, Hao Zhu, Subhashini Bolisetty, James P Calvet, Darren P Wallace, Madhulika Sharma. Ciclopirox olamine induces ferritinophagy and reduces cyst burden in polycystic kidney disease. JCI insight. 2021 03; 6(8):. doi: 10.1172/jci.insight.141299. [PMID: 33784251]
  • Markéta Gajdošová, David Vetchý, Jan Muselík, Jan Gajdziok, Jan Juřica, Martina Vetchá, Karel Hauptman, Vladimír Jekl. Bilayer mucoadhesive buccal films with prolonged release of ciclopirox olamine for the treatment of oral candidiasis: In vitro development, ex vivo permeation testing, pharmacokinetic and efficacy study in rabbits. International journal of pharmaceutics. 2021 Jan; 592(?):120086. doi: 10.1016/j.ijpharm.2020.120086. [PMID: 33188896]
  • Mariusz Dyląg, Ewa Leniak, Sebastian Gnat, Jacek C Szepietowski, Lukasz Kozubowski. A case of anti- pityriasis versicolor therapy that preserves healthy mycobiome. BMC dermatology. 2020 09; 20(1):9. doi: 10.1186/s12895-020-00106-x. [PMID: 32993612]
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  • Scott J Weir, Robyn Wood, Karl Schorno, Amanda E Brinker, Prabhu Ramamoorthy, Kathy Heppert, Lian Rajewski, Mehmet Tanol, Tammy Ham, Michael J McKenna, William McCulloch, Michael Dalton, Gregory A Reed, Roy A Jensen, Michael J Baltezor, Shrikant Anant, John A Taylor. Preclinical Pharmacokinetics of Fosciclopirox, a Novel Treatment of Urothelial Cancers, in Rats and Dogs. The Journal of pharmacology and experimental therapeutics. 2019 08; 370(2):148-159. doi: 10.1124/jpet.119.257972. [PMID: 31113837]
  • Shari R Lipner, Richard K Scher. Onychomycosis: Treatment and prevention of recurrence. Journal of the American Academy of Dermatology. 2019 Apr; 80(4):853-867. doi: 10.1016/j.jaad.2018.05.1260. [PMID: 29959962]
  • Aditya K Gupta, Sarah G Versteeg. Topical Treatment of Facial Seborrheic Dermatitis: A Systematic Review. American journal of clinical dermatology. 2017 Apr; 18(2):193-213. doi: 10.1007/s40257-016-0232-2. [PMID: 27804089]
  • Ivana Lukášová, Jan Muselík, David Vetchý, Jan Gajdziok, Markéta Gajdošová, Jan Juřica, Zdeněk Knotek, Karel Hauptman, Vladimír Jekl. Pharmacokinetics of Ciclopirox Olamine after Buccal Administration in Rabbits. Current drug delivery. 2017; 14(1):99-108. doi: 10.2174/1567201813666160502142856. [PMID: 27138296]
  • Hongyu Zhou, Chaowei Shang, Min Wang, Tao Shen, Lingmei Kong, Chunlei Yu, Zhennan Ye, Yan Luo, Lei Liu, Yan Li, Shile Huang. Ciclopirox olamine inhibits mTORC1 signaling by activation of AMPK. Biochemical pharmacology. 2016 09; 116(?):39-50. doi: 10.1016/j.bcp.2016.07.005. [PMID: 27396756]
  • L Long, C Hager, M Ghannoum. Evaluation of the Efficacy of ME1111 in the Topical Treatment of Dermatophytosis in a Guinea Pig Model. Antimicrobial agents and chemotherapy. 2016 Apr; 60(4):2343-5. doi: 10.1128/aac.03073-15. [PMID: 26833160]
  • Hongyu Zhou, Tao Shen, Chaowei Shang, Yan Luo, Lei Liu, Juming Yan, Yan Li, Shile Huang. Ciclopirox induces autophagy through reactive oxygen species-mediated activation of JNK signaling pathway. Oncotarget. 2014 Oct; 5(20):10140-50. doi: 10.18632/oncotarget.2471. [PMID: 25294812]
  • Sarah Annette Von Schulz-Hausmann, Leonard Christopher Schmeel, Frederic Carsten Schmeel, Ingo G H Schmidt-Wolf. Targeting the Wnt/beta-catenin pathway in renal cell carcinoma. Anticancer research. 2014 08; 34(8):4101-8. doi: NULL. [PMID: 25075035]
  • Farhaan Hafeez, Xiaoying Hui, Marc Selner, Bert Rosenthal, Howard Maibach. Ciclopirox delivery into the human nail plate using novel lipid diffusion enhancers. Drug development and industrial pharmacy. 2014 Jun; 40(6):838-44. doi: 10.3109/03639045.2013.788016. [PMID: 23600655]
  • Mark D Minden, Donna E Hogge, Scott J Weir, Jim Kasper, Debra A Webster, Lavonne Patton, Yulia Jitkova, Rose Hurren, Marcela Gronda, Carolyn A Goard, Lian G Rajewski, John L Haslam, Kathleen E Heppert, Kevin Schorno, Hong Chang, Joseph M Brandwein, Vikas Gupta, Andre C Schuh, Suzanne Trudel, Karen W L Yee, Gregory A Reed, Aaron D Schimmer. Oral ciclopirox olamine displays biological activity in a phase I study in patients with advanced hematologic malignancies. American journal of hematology. 2014 Apr; 89(4):363-8. doi: 10.1002/ajh.23640. [PMID: 24273151]
  • Anroop B Nair, Kishan Singh, Bandar E Al-Dhubiab, Mahesh Attimarad, Sree Harsha, Ibrahim A Alhaider. Skin uptake and clearance of ciclopirox following topical application. Biopharmaceutics & drug disposition. 2013 Dec; 34(9):540-9. doi: 10.1002/bdd.1866. [PMID: 24123146]
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  • Christian Diehl, Alicia Ferrari. Efficacy of topical 4\% Quassia amara gel in facial seborrheic dermatitis:a randomized, double-blind, comparative study. Journal of drugs in dermatology : JDD. 2013 Mar; 12(3):312-5. doi: ". [PMID: 23545914]
  • Anja Schüffler, Beate Wollinsky, Timm Anke, Johannes C Liermann, Till Opatz. Isolactarane and sterpurane sesquiterpenoids from the basidiomycete Phlebia uda. Journal of natural products. 2012 Jul; 75(7):1405-8. doi: 10.1021/np3000552. [PMID: 22746380]
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  • Cibele Massotti Magagnin, Cheila Denise Ottonelli Stopiglia, Fabiane Jamono Vieira, Daiane Heidrich, Madeline Machado, Gerson Vetoratto, Flávia Maria Lamb, Maria Lúcia Scroferneker. Antifungal susceptibility of dermatophytes isolated from patients with chronic renal failure. Anais brasileiros de dermatologia. 2011 Jul; 86(4):694-701. doi: 10.1590/s0365-05962011000400011. [PMID: 21987135]
  • Rayko Becher, Fabian Weihmann, Holger B Deising, Stefan Gr Wirsel. Development of a novel multiplex DNA microarray for Fusarium graminearum and analysis of azole fungicide responses. BMC genomics. 2011 Jan; 12(?):52. doi: 10.1186/1471-2164-12-52. [PMID: 21255412]
  • Magdalena Skóra, Anna B Macura. In vitro antifungal susceptibility testing of Scopulariopsis brevicaulis strains using agar diffusion method. Wiadomosci parazytologiczne. 2011; 57(2):111-6. doi: . [PMID: 21682097]
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  • Markus Niewerth, Donika Kunze, Michael Seibold, Martin Schaller, Hans Christian Korting, Bernhard Hube. Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrobial agents and chemotherapy. 2003 Jun; 47(6):1805-17. doi: 10.1128/aac.47.6.1805-1817.2003. [PMID: 12760852]
  • Tobias Linden, Dörthe M Katschinski, Katrin Eckhardt, Annette Scheid, Horst Pagel, Roland H Wenger. The antimycotic ciclopirox olamine induces HIF-1alpha stability, VEGF expression, and angiogenesis. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2003 Apr; 17(6):761-3. doi: 10.1096/fj.02-0586fje. [PMID: 12594177]
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