Griseofulvin (BioDeep_00000001594)

 

Secondary id: BioDeep_00000398549

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs


代谢物信息卡片


(2S,6R)-7-chloro-2,4,6-trimethoxy-6-methyl-3H-spiro[1-benzofuran-2,1-cyclohexan]-2-ene-3,4-dione

化学式: C17H17ClO6 (352.0713612)
中文名称: 灰黄霉素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 61.11%

分子结构信息

SMILES: CC1CC(=O)C=C(C12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC
InChI: InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3

描述信息

Griseofulvin is only found in individuals that have used or taken this drug. It is an antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections. [PubChem]Griseofulvin is fungistatic, however the exact mechanism by which it inhibits the growth of dermatophytes is not clear. It is thought to inhibit fungal cell mitosis and nuclear acid synthesis. It also binds to and interferes with the function of spindle and cytoplasmic microtubules by binding to alpha and beta tubulin. It binds to keratin in human cells, then once it reaches the fungal site of action, it binds to fungal microtubes thus altering the fungal process of mitosis.
D - Dermatologicals > D01 - Antifungals for dermatological use > D01B - Antifungals for systemic use > D01BA - Antifungals for systemic use
D - Dermatologicals > D01 - Antifungals for dermatological use > D01A - Antifungals for topical use > D01AA - Antibiotics
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
C254 - Anti-Infective Agent > C514 - Antifungal Agent
Griseofulvin(Gris-PEG; Grifulvin) is a spirocyclic fungal natural product used in treatment of fungal dermatophytes; Antifungal drug.

同义名列表

30 个代谢物同义名

(2S,6R)-7-chloro-2,4,6-trimethoxy-6-methyl-3H-spiro[1-benzofuran-2,1-cyclohexan]-2-ene-3,4-dione; (+)-Griseofulvin; Curling factor; Griseofulvinum; Griseofulvina; Griseofulvine; Fulvicin u F; Griseofulvin; Fulvicin-u-F; V, Grifulvin; Spirofulvin; Grifulvin V; Grisefuline; sporostatin; Grisactin V; FulvicinUF; Grifulvin; Grisactin; Grisovin; Fulvicin; Gris peg; Gris-peg; Amudane; GrisPEG; Lamoryl; Likuden; Poncyl; Fulcin; Grysio; GRE



数据库引用编号

25 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)

21 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

  • Si-Qiong Teng, Jiao-Xian Du, Meng-Xi Wang, Ming-Xuan Gao, Juan He, Yan-Ling Yang, Ji-Kai Liu, Tao Feng. Polyketides from the fungus Pochonia chlamydosporia and their bioactivities. Phytochemistry. 2023 Jun; 213(?):113747. doi: 10.1016/j.phytochem.2023.113747. [PMID: 37295632]
  • Yanjing Guo, Jingjing Li, Jiale Shi, Liru Mi, Jing Zhang, Su Han, Wei Liu, Dan Cheng, Sheng Qiang, Hazem M Kalaji, Shiguo Chen. Griseofulvin Inhibits Root Growth by Targeting Microtubule-Associated Proteins Rather Tubulins in Arabidopsis. International journal of molecular sciences. 2023 May; 24(10):. doi: 10.3390/ijms24108692. [PMID: 37240033]
  • Hongke Huang, Dongxue Li, Shilong Jiang, Rui Yang, Yuqing Yang, Zhongqiu Xia, Xinyue Jiang, Yongtian Zhao, Delu Wang, Baoan Song, Zhuo Chen. Integrated Transcriptome and Proteome Analysis Reveals that the Antimicrobial Griseofulvin Targets Didymella segeticola Beta-Tubulin to Control Tea Leaf Spot. Phytopathology. 2023 Feb; ?(?):PHYTO02220061R. doi: 10.1094/phyto-02-22-0061-r. [PMID: 36173282]
  • Manjunatha Chandana, Aditya Anand, Sourav Ghosh, Rahul Das, Subhashree Beura, Sarita Jena, Amol Ratnakar Suryawanshi, Govindarajan Padmanaban, Viswanathan Arun Nagaraj. Malaria parasite heme biosynthesis promotes and griseofulvin protects against cerebral malaria in mice. Nature communications. 2022 07; 13(1):4028. doi: 10.1038/s41467-022-31431-z. [PMID: 35821013]
  • Parisa Aris, Masoud Mohamadzadeh, Yulong Wei, Xuhua Xia. In Silico Molecular Dynamics of Griseofulvin and Its Derivatives Revealed Potential Therapeutic Applications for COVID-19. International journal of molecular sciences. 2022 Jun; 23(13):. doi: 10.3390/ijms23136889. [PMID: 35805893]
  • Franklin Chimaobi Kenechukwu, Marcos Lopes Dias, Eduardo Ricci-Júnior. Biodegradable nanoparticles from prosopisylated cellulose as a platform for enhanced oral bioavailability of poorly water-soluble drugs. Carbohydrate polymers. 2021 Mar; 256(?):117492. doi: 10.1016/j.carbpol.2020.117492. [PMID: 33483021]
  • Narjes Saheb Sharif-Askari, Fatemeh Saheb Sharif-Askari, Bushra Mdkhana, Saba Al Heialy, Elaref Ratemi, Malak Alghamdi, Salah Abusnana, Tarek Kashour, Qutayba Hamid, Rabih Halwani. Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Archives of toxicology. 2020 12; 94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. [PMID: 32808185]
  • Joscha Brinkmann, Frauke Rest, Christian Luebbert, Gabriele Sadowski. Solubility of Pharmaceutical Ingredients in Natural Edible Oils. Molecular pharmaceutics. 2020 07; 17(7):2499-2507. doi: 10.1021/acs.molpharmaceut.0c00215. [PMID: 32369379]
  • A Geronikaki, V Kartsev, A Petrou, M G Akrivou, I S Vizirianakis, F M Chatzopoulou, B Lichitsky, S Sirakanyan, M Kostic, M Smiljkovic, M Soković, D Druzhilovskiy, V Poroikov. Antibacterial activity of griseofulvin analogues as an example of drug repurposing. International journal of antimicrobial agents. 2020 Mar; 55(3):105884. doi: 10.1016/j.ijantimicag.2020.105884. [PMID: 31931149]
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  • Adrian Dobrowolski, Ramona Strob, Jan Felix Dräger-Gillessen, Damian Pieloth, Gerhard Schaldach, Helmut Wiggers, Markus Thommes. Preparation of submicron drug particles via spray drying from organic solvents. International journal of pharmaceutics. 2019 Aug; 567(?):118501. doi: 10.1016/j.ijpharm.2019.118501. [PMID: 31288055]
  • Kalle Sigfridsson, Aixiang Xue, Kelly Goodwin, Adrian J Fretland, Torbjörn Arvidsson. Sustained release and improved bioavailability in mice after subcutaneous administration of griseofulvin as nano- and microcrystals. International journal of pharmaceutics. 2019 Jul; 566(?):565-572. doi: 10.1016/j.ijpharm.2019.06.015. [PMID: 31181305]
  • Yu-Bin Bai, Yu-Qi Gao, Xiao-Di Nie, Thi-Mai-Luong Tuong, Ding Li, Jin-Ming Gao. Antifungal Activity of Griseofulvin Derivatives against Phytopathogenic Fungi in Vitro and in Vivo and Three-Dimensional Quantitative Structure-Activity Relationship Analysis. Journal of agricultural and food chemistry. 2019 Jun; 67(22):6125-6132. doi: 10.1021/acs.jafc.9b00606. [PMID: 31083998]
  • Yuji Saito, Tomoaki Usami, Miki Katoh, Masayuki Nadai. Effects of Thylakoid-Rich Spinach Extract on the Pharmacokinetics of Drugs in Rats. Biological & pharmaceutical bulletin. 2019; 42(1):103-109. doi: 10.1248/bpb.b18-00632. [PMID: 30606982]
  • Jingyi Ye, Huiyi Wu, Chuanli Huang, Wanting Lin, Caifeng Zhang, Bei Huang, Banyi Lu, Hongyu Xu, Xiaoling Li, Xiaoying Long. Comparisons of in vitro Fick's first law, lipolysis, and in vivo rat models for oral absorption on BCS II drugs in SNEDDS. International journal of nanomedicine. 2019; 14(?):5623-5636. doi: 10.2147/ijn.s203911. [PMID: 31440045]
  • Victor Kartsev, Athina Geronikaki, Anthi Petrou, Boris Lichitsky, Marina Kostic, Marija Smiljkovic, Marina Soković, Samvel Sirakanyan. Griseofulvin Derivatives: Synthesis, Molecular Docking and Biological Evaluation. Current topics in medicinal chemistry. 2019; 19(13):1145-1161. doi: 10.2174/1568026619666190523080136. [PMID: 31119999]
  • Alany Ingrid Ribeiro, Eveline Soares Costa, Sergio Scherrer Thomasi, Dayson Fernando Ribeiro Brandão, Paulo Cesar Vieira, João Batista Fernandes, Moacir Rossi Forim, Antonio Gilberto Ferreira, Sérgio Florentino Pascholati, Luis Fernando Pascholati Gusmão, Maria Fátima das Graças Fernandes da Silva. Biological and Chemical Control of Sclerotinia sclerotiorum using Stachybotrys levispora and Its Secondary Metabolite Griseofulvin. Journal of agricultural and food chemistry. 2018 Jul; 66(29):7627-7632. doi: 10.1021/acs.jafc.7b04197. [PMID: 29944364]
  • Pei-Lun Sun, Yang-Chih Lin, Yu-Hung Wu, Pei-Han Kao, Yu-Ming Ju, Yun-Chen Fan. Tinea folliculorum complicating tinea of the glabrous skin: an important yet neglected entity. Medical mycology. 2018 Jul; 56(5):521-530. doi: 10.1093/mmy/myx086. [PMID: 29087496]
  • Asger B Petersen, Nikolaj S Andersen, Gleb Konotop, Nur Hafzan Md Hanafiah, Marc S Raab, Alwin Krämer, Mads H Clausen. Synthesis and formulation studies of griseofulvin analogues with improved solubility and metabolic stability. European journal of medicinal chemistry. 2017 Apr; 130(?):240-247. doi: 10.1016/j.ejmech.2017.02.055. [PMID: 28258034]
  • Dewu Zhang, Lili Zhao, Lining Wang, Xiaomei Fang, Jianyuan Zhao, Xinwei Wang, Li Li, Hongyu Liu, Yuzhen Wei, Xuefu You, Shan Cen, Liyan Yu. Griseofulvin Derivative and Indole Alkaloids from Penicillium griseofulvum CPCC 400528. Journal of natural products. 2017 02; 80(2):371-376. doi: 10.1021/acs.jnatprod.6b00829. [PMID: 28117586]
  • Joana Marto, Catarina Vitor, Ana Guerreiro, Cristiana Severino, Carla Eleutério, Andreia Ascenso, Sandra Simões. Ethosomes for enhanced skin delivery of griseofulvin. Colloids and surfaces. B, Biointerfaces. 2016 Oct; 146(?):616-23. doi: 10.1016/j.colsurfb.2016.07.021. [PMID: 27429295]
  • Gui-Guang Cheng, Dan Li, Bo Hou, Xiao-Nian Li, Lu Liu, Ying-Ying Chen, Paul-Keilah Lunga, Afsar Khan, Ya-Ping Liu, Zhi-Li Zuo, Xiao-Dong Luo. Melokhanines A-J, Bioactive Monoterpenoid Indole Alkaloids with Diverse Skeletons from Melodinus khasianus. Journal of natural products. 2016 09; 79(9):2158-66. doi: 10.1021/acs.jnatprod.6b00011. [PMID: 27584856]
  • Zeenat Yousuf Bhat, Neetu Sharma, Unnikrishnana Pillai, Atul Singh. Unusual Cause and Presentation of Collapsing Focal Segmental Glomerulosclerosis. American journal of therapeutics. 2016 May; 23(3):e957-60. doi: 10.1097/mjt.0000000000000115. [PMID: 25420079]
  • Monika Malm-Erjefält, Marianne Ekblom, Jan Vouis, Milan Zdravkovic, Hans Lennernäs. Effect on the Gastrointestinal Absorption of Drugs from Different Classes in the Biopharmaceutics Classification System, When Treating with Liraglutide. Molecular pharmaceutics. 2015 Nov; 12(11):4166-73. doi: 10.1021/acs.molpharmaceut.5b00278. [PMID: 26426736]
  • María Del Carmen Martinez, Silvina Fernanda Ruspini, Susana Graciela Afonso, Roberto Meiss, Ana Maria Buzaleh, Alcira Batlle. Experimental protoporphyria: effect of bile acids on liver damage induced by griseofulvin. BioMed research international. 2015; 2015(?):436319. doi: 10.1155/2015/436319. [PMID: 25945334]
  • Chia-Wen Hsu, Jinghua Zhao, Ruili Huang, Jui-Hua Hsieh, Jon Hamm, Xiaoqing Chang, Keith Houck, Menghang Xia. Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor. Scientific reports. 2014 Sep; 4(?):6437. doi: 10.1038/srep06437. [PMID: 25257666]
  • Nancy B Andrioli, Sonia Soloneski, Marcelo L Larramendy, Marta D Mudry. Induction of microtubule damage in Allium cepa meristematic cells by pharmaceutical formulations of thiabendazole and griseofulvin. Mutation research. Genetic toxicology and environmental mutagenesis. 2014 Sep; 772(?):1-5. doi: 10.1016/j.mrgentox.2014.06.009. [PMID: 25308540]
  • M del C Martinez, S G Afonso, A M Buzaleh, A Batlle. Protective action of antioxidants on hepatic damage induced by griseofulvin. TheScientificWorldJournal. 2014; 2014(?):982358. doi: 10.1155/2014/982358. [PMID: 24523661]
  • Nidhi Aggarwal, Shishu Goindi. Preparation and in vivo evaluation of solid lipid nanoparticles of griseofulvin for dermal use. Journal of biomedical nanotechnology. 2013 Apr; 9(4):564-76. doi: 10.1166/jbn.2013.1569. [PMID: 23621015]
  • Kenneth T Johansen, Sileshi G Wubshet, Nils T Nyberg. HPLC-NMR revisited: using time-slice high-performance liquid chromatography-solid-phase extraction-nuclear magnetic resonance with database-assisted dereplication. Analytical chemistry. 2013 Mar; 85(6):3183-9. doi: 10.1021/ac303455j. [PMID: 23432092]
  • Zhi-Zhen Pan, Yu-Jing Zhu, Xiao-Jie Yu, Qi-Fan Lin, Rong-Feng Xiao, Jian-Yang Tang, Qing-Xi Chen, Bo Liu. Synthesis of 4'-thiosemicarbazonegriseofulvin and its effects on the control of enzymatic browning and postharvest disease of fruits. Journal of agricultural and food chemistry. 2012 Oct; 60(43):10784-8. doi: 10.1021/jf302356x. [PMID: 23025498]
  • Maria E N P Ribeiro, Carolina L de Moura, Mariano G S Vieira, Nilce V Gramosa, Chiraphon Chaibundit, Marcos C de Mattos, David Attwood, Stephen G Yeates, S Keith Nixon, Nágila M P S Ricardo. Solubilisation capacity of Brij surfactants. International journal of pharmaceutics. 2012 Oct; 436(1-2):631-5. doi: 10.1016/j.ijpharm.2012.07.032. [PMID: 22842626]
  • Hoskins Clare, Paul Kong Thoo Lin, Laurence Tetley, Woei Ping Cheng. The use of nano polymeric self-assemblies based on novel amphiphilic polymers for oral hydrophobic drug delivery. Pharmaceutical research. 2012 Mar; 29(3):782-94. doi: 10.1007/s11095-011-0602-7. [PMID: 21971828]
  • Sarah Maud Fischer, Stephen Timothy Buckley, Wiebke Kirchmeyer, Gert Fricker, Martin Brandl. Application of simulated intestinal fluid on the phospholipid vesicle-based drug permeation assay. International journal of pharmaceutics. 2012 Jan; 422(1-2):52-8. doi: 10.1016/j.ijpharm.2011.10.026. [PMID: 22027395]
  • Nagaraj Selvaraj, Baskar Lakshmanan, Papiya Mitra Mazumder, Muthukumar Karuppasamy, Simon Santosh Jena, Ashok Kumar Pattnaik. Evaluation of wound healing and antimicrobial potentials of Ixora coccinea root extract. Asian Pacific journal of tropical medicine. 2011 Dec; 4(12):959-63. doi: 10.1016/s1995-7645(11)60226-5. [PMID: 22118031]
  • Alex Avdeef, Kin Y Tam. How well can the Caco-2/Madin-Darby canine kidney models predict effective human jejunal permeability?. Journal of medicinal chemistry. 2010 May; 53(9):3566-84. doi: 10.1021/jm901846t. [PMID: 20373811]
  • Seitaro Kamiya, Takurou Kurita, Atsuo Miyagishima, Shigeru Itai, Masayuki Arakawa. Physical properties of griseofulvin-lipid nanoparticles in suspension and their novel interaction mechanism with saccharide during freeze-drying. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2010 Mar; 74(3):461-6. doi: 10.1016/j.ejpb.2009.12.004. [PMID: 20018239]
  • Xiaofan Sui, Jin Sun, Haiyan Li, Yongjun Wang, Jianfang Liu, Xiaohong Liu, Wenping Zhang, Lijiang Chen, Zhonggui He. Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data. European journal of medicinal chemistry. 2009 Nov; 44(11):4455-60. doi: 10.1016/j.ejmech.2009.06.004. [PMID: 19586686]
  • Seitaro Kamiya, Takurou Kurita, Atsuo Miyagishima, Masayuki Arakawa. Preparation of griseofulvin nanoparticle suspension by high-pressure homogenization and preservation of the suspension with saccharides and sugar alcohols. Drug development and industrial pharmacy. 2009 Aug; 35(8):1022-8. doi: 10.1080/03639040802698786. [PMID: 19466885]
  • M Del C Martinez, S G Afonso, R P Meiss, A M Buzaleh, A Batlle. Hepatic damage and oxidative stress induced by Griseofulvin in mice. Cellular and molecular biology (Noisy-le-Grand, France). 2009 Jul; 55(2):127-39. doi: . [PMID: 19656461]
  • K C Ofokansi, K I Chukwu, S I Ugwuanyi. The use of liquid self-microemulsifying drug delivery systems based on peanut oil/tween 80 in the delivery of griseofulvin. Drug development and industrial pharmacy. 2009 Feb; 35(2):185-91. doi: 10.1080/03639040802244292. [PMID: 18825525]
  • Vikas Agarwal, Akhtar Siddiqui, Hazem Ali, Sami Nazzal. Dissolution and powder flow characterization of solid self-emulsified drug delivery system (SEDDS). International journal of pharmaceutics. 2009 Jan; 366(1-2):44-52. doi: 10.1016/j.ijpharm.2008.08.046. [PMID: 18832019]
  • Pratap S Jadon, Virendra Gajbhiye, Rajesh S Jadon, Kavita R Gajbhiye, Narayanan Ganesh. Enhanced oral bioavailability of griseofulvin via niosomes. AAPS PharmSciTech. 2009; 10(4):1186-92. doi: 10.1208/s12249-009-9325-z. [PMID: 19856107]
  • Yoko Satoh, Reiko Iwadate, Yukino Watanabe, Hiroshi Kawai, Naomi Kudo, Yoichi Kawashima, Atsushi Mitsumoto. Manifestation of psychiatric behaviors in a mouse model of griseofulvin-induced hepatic porphyria. The Journal of toxicological sciences. 2008 Dec; 33(5):599-608. doi: 10.2131/jts.33.599. [PMID: 19043281]
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