Miconazole (BioDeep_00000017940)

Main id: BioDeep_00000016586

 

human metabolite blood metabolite Chemicals and Drugs natural product


代谢物信息卡片


1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole

化学式: C18H14Cl4N2O (413.9860194)
中文名称: 1-[2-(24-二氯苯基)-2-[(24-二氯苯基)甲氧基]乙基]-1H-咪唑
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl
InChI: InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2

描述信息

Miconazole is only found in individuals that have used or taken this drug. It is an imidazole antifungal agent that is used topically and by intravenous infusion. [PubChem]Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids > G01AF - Imidazole derivatives
A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents > A07A - Intestinal antiinfectives > A07AC - Imidazole derivatives
A - Alimentary tract and metabolism > A01 - Stomatological preparations > A01A - Stomatological preparations > A01AB - Antiinfectives and antiseptics for local oral treatment
D - Dermatologicals > D01 - Antifungals for dermatological use > D01A - Antifungals for topical use > D01AC - Imidazole and triazole derivatives
J - Antiinfectives for systemic use > J02 - Antimycotics for systemic use > J02A - Antimycotics for systemic use > J02AB - Imidazole derivatives
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D065088 - Steroid Synthesis Inhibitors
D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065688 - Cytochrome P-450 CYP2C9 Inhibitors
D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065692 - Cytochrome P-450 CYP3A Inhibitors
D004791 - Enzyme Inhibitors > D065088 - Steroid Synthesis Inhibitors > D058888 - 14-alpha Demethylase Inhibitors
S - Sensory organs > S02 - Otologicals > S02A - Antiinfectives > S02AA - Antiinfectives
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
C254 - Anti-Infective Agent > C514 - Antifungal Agent

同义名列表

17 个代谢物同义名

1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole; Johnston and johnston brand OF miconazole nitrate; Janssen-cilag brand OF miconazole; Janssen cilag brand OF miconazole; Miconazole janssen-cilag brand; Esteve brand OF miconazole; Miconazole esteve brand; Nitrate, miconazole; Miconazole Nitrate; Nitrate, miconasil; Miconasil nitrate; miconazole; Dactarin; Monistat; Brentan; Oravig; MCZ



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(4)

PlantCyc(1)

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)

6 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

  • Galal Magdy, Eman Aboelkassim, Ramadan A El-Domany, Fathalla Belal. Green synthesis, characterization, and antimicrobial applications of silver nanoparticles as fluorescent nanoprobes for the spectrofluorimetric determination of ornidazole and miconazole. Scientific reports. 2022 Dec; 12(1):21395. doi: 10.1038/s41598-022-25830-x. [PMID: 36496441]
  • Khaled M Hosny, Amal M Sindi, Sarah Ali, Waleed S Alharbi, Maher S Hajjaj, Haitham A Bukhary, Moutaz Y Badr, Rayan Y Mushtaq, Samar S A Murshid, Alshaimaa M Almehmady, Rana B Bakhaidar, Eman Alfayez, Mallesh Kurakula. Development, optimization, and evaluation of a nanostructured lipid carrier of sesame oil loaded with miconazole for the treatment of oral candidiasis. Drug delivery. 2022 Dec; 29(1):254-262. doi: 10.1080/10717544.2021.2023703. [PMID: 35014929]
  • Rania S Abdel-Rashid, Doaa A Helal, Ahmed Adel Alaa-Eldin, Raghda Abdel-Monem. Polymeric versus lipid nanocapsules for miconazole nitrate enhanced topical delivery: in vitro and ex vivo evaluation. Drug delivery. 2022 Dec; 29(1):294-304. doi: 10.1080/10717544.2022.2026535. [PMID: 35037528]
  • Lifen Gong, Tao Zhu, Chen Chen, Ningxiao Xia, Yinping Yao, Junchao Ding, Peng Xu, Shufen Li, Zengxian Sun, Xinyan Dong, Weida Shen, Peng Sun, Linghui Zeng, Yicheng Xie, Peifang Jiang. Miconazole exerts disease-modifying effects during epilepsy by suppressing neuroinflammation via NF-κB pathway and iNOS production. Neurobiology of disease. 2022 10; 172(?):105823. doi: 10.1016/j.nbd.2022.105823. [PMID: 35878745]
  • Ding Lijuan, Yin Lu, Wang Liping, Sun Yaya, Liu Xiaoyun, L I Xiangrong. Effectiveness of redcore lotion in patients with vulvovaginal candidiasis: a systematic review and Meta-analysis. Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan. 2022 08; 42(4):487-492. doi: 10.19852/j.cnki.jtcm.2022.04.001. [PMID: 35848964]
  • Yuanyuan Zhu, Lina Wang, Guoxian Guo, Jing Tang, Jia Yu. Development of a novel HPLC-ESI-MS/MS method to analyze the stereoselective pharmacokinetics and tissue distribution of isoconazole enantiomers in rats. Chirality. 2022 06; 34(6):901-912. doi: 10.1002/chir.23442. [PMID: 35322467]
  • Emmanuel Maduabuchi Uronnachi, Anthony Attama, Franklin Kenechukwu, Chukwuebuka Umeyor, Thaddeus Gugu, Calistus Nwakile, Chidalu Ikeotuonye. Solidified Reverse Micellar Solution- (SRMS-) Based Microparticles for Enhanced Oral Bioavailability and Systemic Antifungal Efficacy of Miconazole Nitrate in Immunocompromised Mice. BioMed research international. 2022; 2022(?):8930709. doi: 10.1155/2022/8930709. [PMID: 35118159]
  • Hong-Mei Yin, Qiong He, Jia Chen, Zhen Li, Wanli Yang, Xiaobo Hu. Drug metabolism-related eight-gene signature can predict the prognosis of gastric adenocarcinoma. Journal of clinical laboratory analysis. 2021 Dec; 35(12):e24085. doi: 10.1002/jcla.24085. [PMID: 34773716]
  • Monica Mazzarino, Fabio Comunità, Xavier de la Torre, Francesco Molaioni, Francesco Botrè. Effects of the administration of miconazole by different routes on the biomarkers of the "steroidal module" of the Athlete Biological Passport. Drug testing and analysis. 2021 Oct; 13(10):1712-1726. doi: 10.1002/dta.3121. [PMID: 34212529]
  • Wei Li, Zhen Wang, Xiaoyu Wang, Xiaowei Cao, Caili Bi, Lili Jiang, Shuna Cui, Yong Liu. Risk prediction of drug-drug interaction potential of phenytoin and miconazole topical formulations. Chemico-biological interactions. 2021 Jul; 343(?):109498. doi: 10.1016/j.cbi.2021.109498. [PMID: 33961833]
  • 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]
  • Chenwen Xiao, Jiaoyu Wang, Zhenfeng Liao, Yee Huang, Quanan Ji, Yan Liu, Fei Su, Lijun Xu, Qiang Wei, Yao Pan, Ke Li, Guolian Bao. Assessment of the mechanism of drug resistance in Trichophyton mentagrophytes in response to various substances. BMC genomics. 2021 Apr; 22(1):250. doi: 10.1186/s12864-021-07520-6. [PMID: 33827426]
  • Witor Ribeiro Ferraz, Renan Augusto Gomes, Andre Luis S Novaes, Gustavo Henrique Goulart Trossini. Ligand and structure-based virtual screening applied to the SARS-CoV-2 main protease: an in silico repurposing study. Future medicinal chemistry. 2020 10; 12(20):1815-1828. doi: 10.4155/fmc-2020-0165. [PMID: 32787684]
  • Jana Tits, Freya Cools, Kaat De Cremer, Katrijn De Brucker, Judith Berman, Kristof Verbruggen, Bert Gevaert, Paul Cos, Bruno P A Cammue, Karin Thevissen. Combination of Miconazole and Domiphen Bromide Is Fungicidal against Biofilms of Resistant Candida spp. Antimicrobial agents and chemotherapy. 2020 09; 64(10):. doi: 10.1128/aac.01296-20. [PMID: 32690639]
  • Fei Mo, Jia Ma, Xianwei Yang, Peipei Zhang, Qingqing Li, Jiye Zhang. In vitro and in vivo effects of the combination of myricetin and miconazole nitrate incorporated to thermosensitive hydrogels, on C. albicans biofilms. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Jun; 71(?):153223. doi: 10.1016/j.phymed.2020.153223. [PMID: 32460204]
  • Mohamed Tarek, Hebatallah A Wagdy, Eman S Elzanfaly, Sawsan M Amer. A Validated Ultra-Performance Liquid Chromatographic Method for the Simultaneous Determination of Nadifloxacin, Mometasone Furoate and Miconazole Nitrate in Their Combined Dosage Form and Spiked Human Plasma Samples. Journal of chromatographic science. 2020 Jan; 57(10):867-873. doi: 10.1093/chromsci/bmz082. [PMID: 31602483]
  • Wenjing Luan, Xiaolei Liu, Xuefei Wang, Yanan An, Yang Wang, Chao Wang, Keshu Shen, Hongyue Xu, Shulin Li, Mingyuan Liu, L U Yu. Inhibition of Drug Resistance of Staphylococcus aureus by Efflux Pump Inhibitor and Autolysis Inducer to Strengthen the Antibacterial Activity of β-lactam Drugs. Polish journal of microbiology. 2019 Dec; 68(4):477-491. doi: 10.33073/pjm-2019-047. [PMID: 31880892]
  • 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]
  • Cecilie Hurup Munkboel, Tobias Bangsgaard Rasmussen, Camilla Elgaard, Maja-Luna Kingo Olesen, Andreas Christopher Kretschmann, Bjarne Styrishave. The classic azole antifungal drugs are highly potent endocrine disruptors in vitro inhibiting steroidogenic CYP enzymes at concentrations lower than therapeutic Cmax. Toxicology. 2019 09; 425(?):152247. doi: 10.1016/j.tox.2019.152247. [PMID: 31330226]
  • M Chevalier, A Doglio, R Rajendran, G Ramage, I Prêcheur, S Ranque. Inhibition of adhesion-specific genes by Solidago virgaurea extract causes loss of Candida albicans biofilm integrity. Journal of applied microbiology. 2019 Jul; 127(1):68-77. doi: 10.1111/jam.14289. [PMID: 31013388]
  • Stephen Boulton, Rajeevan Selvaratnam, Rashik Ahmed, Katherine Van, Xiaodong Cheng, Giuseppe Melacini. Mechanisms of Specific versus Nonspecific Interactions of Aggregation-Prone Inhibitors and Attenuators. Journal of medicinal chemistry. 2019 05; 62(10):5063-5079. doi: 10.1021/acs.jmedchem.9b00258. [PMID: 31074269]
  • James Simpson, Adrienn Pálvölgyi, Ferenc A Antoni. Direct stimulation of adenylyl cyclase 9 by the fungicide imidazole miconazole. Naunyn-Schmiedeberg's archives of pharmacology. 2019 04; 392(4):497-504. doi: 10.1007/s00210-018-01610-1. [PMID: 30607468]
  • Jaegoo Kim, Thinh Ha Quang Bao, Yu-Kyong Shin, Ki-Young Kim. Antifungal activity of magnoflorine against Candida strains. World journal of microbiology & biotechnology. 2018 Oct; 34(11):167. doi: 10.1007/s11274-018-2549-x. [PMID: 30382403]
  • Mukta Singh, Ratan Kumar Saha, Himadri Saha, Janmejay Parhi. Effect of miconazole nitrate on immunological response and its preventive efficacy in Labeo rohita fingerlings against oomycetes Saprolegnia parasitica. Journal of fish diseases. 2018 Oct; 41(10):1539-1548. doi: 10.1111/jfd.12862. [PMID: 30105863]
  • Jennifer E Balkus, Lisa E Manhart, Jørgen S Jensen, Omu Anzala, Joshua Kimani, Jane Schwebke, Juma Shafi, Charles Rivers, Emanuel Kabare, R Scott McClelland. Mycoplasma genitalium Infection in Kenyan and US Women. Sexually transmitted diseases. 2018 08; 45(8):514-521. doi: 10.1097/olq.0000000000000799. [PMID: 29465649]
  • B Veeraswamy, D Madhu, G Jitender Dev, Y Poornachandra, G Shravan Kumar, C Ganesh Kumar, B Narsaiah. Studies on synthesis of novel pyrido[2,3-d]pyrimidine derivatives, evaluation of their antimicrobial activity and molecular docking. Bioorganic & medicinal chemistry letters. 2018 05; 28(9):1670-1675. doi: 10.1016/j.bmcl.2018.03.022. [PMID: 29602683]
  • Yoshinori Asakawa, Agnieszka Ludwiczuk. Chemical Constituents of Bryophytes: Structures and Biological Activity. Journal of natural products. 2018 03; 81(3):641-660. doi: 10.1021/acs.jnatprod.6b01046. [PMID: 29019405]
  • Franklin C Kenechukwu, Anthony A Attama, Emmanuel C Ibezim, Petra O Nnamani, Chukwuebuka E Umeyor, Emmanuel M Uronnachi, Thaddeus H Gugu, Mumuni A Momoh, Kenneth C Ofokansi, Paul A Akpa. Surface-modified mucoadhesive microgels as a controlled release system for miconazole nitrate to improve localized treatment of vulvovaginal candidiasis. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Jan; 111(?):358-375. doi: 10.1016/j.ejps.2017.10.002. [PMID: 28986195]
  • Rüdiger Nave, Stefan Klein, André Müller, Xinying Chang, Joachim Höchel. Absence of Effect of Intravaginal Miconazole, Clindamycin, Nonoxynol-9, and Tampons on the Pharmacokinetics of an Anastrozole/Levonorgestrel Intravaginal Ring. Journal of clinical pharmacology. 2018 Jan; 58(1):97-106. doi: 10.1002/jcph.984. [PMID: 28783867]
  • Franklin Chimaobi Kenechukwu, Anthony Amaechi Attama, Emmanuel Chinedum Ibezim, Petra Obioma Nnamani, Chukwuebuka Emmanuel Umeyor, Emmanuel Maduabuchi Uronnachi, Mumuni Audu Momoh, Paul Achile Akpa, Angela Chizoba Ozioko. Novel Intravaginal Drug Delivery System Based on Molecularly PEGylated Lipid Matrices for Improved Antifungal Activity of Miconazole Nitrate. BioMed research international. 2018; 2018(?):3714329. doi: 10.1155/2018/3714329. [PMID: 29977910]
  • María Yolanda Rios, Víctor Navarro, M Ángeles Ramírez-Cisneros, Enrique Salazar-Rios. Sulfur-Containing Aristoloxazines and Other Constituents of the Roots of Aristolochia orbicularis. Journal of natural products. 2017 12; 80(12):3112-3119. doi: 10.1021/acs.jnatprod.7b00226. [PMID: 29210585]
  • Rajitha Bollu, Saleha Banu, Rajashaker Bantu, A Gopi Reddy, Lingaiah Nagarapu, K Sirisha, C Ganesh Kumar, Shravan Kumar Gunda, Kamal Shaik. Potential antimicrobial agents from triazole-functionalized 2H-benzo[b][1,4]oxazin-3(4H)-ones. Bioorganic & medicinal chemistry letters. 2017 12; 27(23):5158-5162. doi: 10.1016/j.bmcl.2017.10.061. [PMID: 29103973]
  • Yueying Du, Linda Luo, Shuo Sun, Zhen Jiang, Xingjie Guo. Enantioselective separation and determination of miconazole in rat plasma by chiral LC-MS/MS: application in a stereoselective pharmacokinetic study. Analytical and bioanalytical chemistry. 2017 Nov; 409(27):6315-6323. doi: 10.1007/s00216-017-0551-z. [PMID: 28852798]
  • Franklin Chimaobi Kenechukwu, Anthony Amaechi Attama, Emmanuel Chinedum Ibezim. Novel solidified reverse micellar solution-based mucoadhesive nano lipid gels encapsulating miconazole nitrate-loaded nanoparticles for improved treatment of oropharyngeal candidiasis. Journal of microencapsulation. 2017 Sep; 34(6):592-609. doi: 10.1080/02652048.2017.1370029. [PMID: 28877639]
  • Rohan M Shah, Daniel S Eldridge, Enzo A Palombo, Ian H Harding. Microwave-assisted microemulsion technique for production of miconazole nitrate- and econazole nitrate-loaded solid lipid nanoparticles. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2017 Aug; 117(?):141-150. doi: 10.1016/j.ejpb.2017.04.007. [PMID: 28411057]
  • Simona Nardoni, Angela Grazia Costanzo, Linda Mugnaini, Francesca Pisseri, Guido Rocchigiani, Roberto Papini, Francesca Mancianti. Open-field study comparing an essential oil-based shampoo with miconazole/chlorhexidine for haircoat disinfection in cats with spontaneous microsporiasis. Journal of feline medicine and surgery. 2017 Jun; 19(6):697-701. doi: 10.1177/1098612x15625709. [PMID: 26783019]
  • Yasuyoshi Ishiwata, Masashi Nagata, Takafumi Arai, Misato Makiishi, Maho Yoshikawa, Hiromitsu Takahashi, Hitoshi Kohsaka, Masato Yasuhara. Effects of Miconazole Oral Gel on Blood Concentrations of Tacrolimus and Cyclosporine: A Retrospective Observational Study. Therapeutic drug monitoring. 2016 12; 38(6):717-721. doi: 10.1097/ftd.0000000000000335. [PMID: 27559841]
  • Y Mohini, R B N Prasad, M S L Karuna, Y Poornachandra, C Ganesh Kumar. Synthesis and biological evaluation of ricinoleic acid-based lipoamino acid derivatives. Bioorganic & medicinal chemistry letters. 2016 11; 26(21):5198-5202. doi: 10.1016/j.bmcl.2016.09.063. [PMID: 27707604]
  • Rodrigo Sant'Ana Cabral, Pierre-Marie Allard, Laurence Marcourt, Maria Cláudia Marx Young, Emerson Ferreira Queiroz, Jean-Luc Wolfender. Targeted Isolation of Indolopyridoquinazoline Alkaloids from Conchocarpus fontanesianus Based on Molecular Networks. Journal of natural products. 2016 09; 79(9):2270-8. doi: 10.1021/acs.jnatprod.6b00379. [PMID: 27557347]
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  • Kaat De Cremer, Katrijn De Brucker, Ines Staes, Annelies Peeters, Freija Van den Driessche, Tom Coenye, Bruno P A Cammue, Karin Thevissen. Stimulation of superoxide production increases fungicidal action of miconazole against Candida albicans biofilms. Scientific reports. 2016 06; 6(?):27463. doi: 10.1038/srep27463. [PMID: 27272719]
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  • Yongjing Liu, Miaoduo Deng, Jia Yu, Zhen Jiang, Xingjie Guo. Capillary electrophoretic enantioseparation of basic drugs using a new single-isomer cyclodextrin derivative and theoretical study of the chiral recognition mechanism. Journal of separation science. 2016 May; 39(9):1766-75. doi: 10.1002/jssc.201501026. [PMID: 26935589]
  • Sathyam Reddy Yasa, Shiva Shanker Kaki, Y Poornachandra, C Ganesh Kumar, Vijayalakshmi Penumarthy. Synthesis, characterization, antimicrobial and biofilm inhibitory studies of new esterquats. Bioorganic & medicinal chemistry letters. 2016 Apr; 26(8):1978-82. doi: 10.1016/j.bmcl.2016.03.002. [PMID: 26965863]
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