Clobetasol (BioDeep_00000019023)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

化学式: C22H28ClFO4 (410.16600500000004)
中文名称: 氯倍他索
谱图信息: 最多检出来源 Mus musculus(blood) 33.33%

分子结构信息

SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C)C3(F)C(O)CC2(C)C1(O)C(=O)CCl
InChI: InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

描述信息

Clobetasol is only found in individuals that have used or taken this drug. It is a derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in treatment of psoriasis but may cause marked adrenocortical suppression. [PubChem]The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Initially, however, clobetasol, like other corticosteroids, bind to the glucocorticoid receptor, which complexes, enteres the cell nucleus and modifies genetic transcription (transrepression/transactivation).
D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07A - Corticosteroids, plain > D07AD - Corticosteroids, very potent (group iv)
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D005938 - Glucocorticoids
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid
D000893 - Anti-Inflammatory Agents

同义名列表

19 个代谢物同义名

(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one; (11beta,16beta)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; (11Β,16β)-21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; (11b,16b)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; 21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; Clobetasol 17-propionate; Clobetasol 17 propionate; Clobetasol propionate; Clobecort amex; Clobetasolum; Embeline e; Clobetasol; Clofenazon; Dermovate; Embeline; Temovate; Cormax; Clobex; OLUX



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

  • R Ramessur, N Saffar, B Czako, A Agarwal, K Batta. Cutaneous thrombosis associated with skin necrosis following Oxford-AstraZeneca COVID-19 vaccination. Clinical and experimental dermatology. 2021 Dec; 46(8):1610-1612. doi: 10.1111/ced.14819. [PMID: 34189756]
  • M J Lavery, S Nawimana, R Parslew, L Stewart. A flare of pre-existing erythema multiforme following BNT162b2 (Pfizer-BioNTech) COVID-19 vaccine. Clinical and experimental dermatology. 2021 10; 46(7):1325-1327. doi: 10.1111/ced.14714. [PMID: 33914926]
  • Mingyi Jing, Qianying Yu, Baohua Zhu, Fan Yuan, Jie Zhang, Li Peng, Wenxia Lin, Mingling Chen. Topical 0.05\% clobetasol cream in the treatment of chronic hand eczema: A protocol for systematic review and meta-analysis. Medicine. 2021 Mar; 100(10):e24418. doi: 10.1097/md.0000000000024418. [PMID: 33725820]
  • Ankita Dadwal, Neeraj Mishra, Raj K Narang. Development and Characterization of a Clobetasol Propionate Nanostructured Lipid Carrier-Based Gel for the Treatment of Plaque Psoriasis. Current molecular pharmacology. 2021; 14(3):399-411. doi: 10.2174/1874467213666200628135552. [PMID: 32598275]
  • Dario Didona, Luca Scarsella, Milad Fehresti, Farzan Solimani, Hazem A Juratli, Manuel Göbel, Stefan Mühlenbein, Lily Holiangu, Josquin Pieper, Vera Korff, Thomas Schmidt, Cassian Sitaru, Rüdiger Eming, Michael Hertl, Robert Pollmann. Autoreactive Peripheral Blood T Helper Cell Responses in Bullous Pemphigoid and Elderly Patients With Pruritic Disorders. Frontiers in immunology. 2021; 12(?):569287. doi: 10.3389/fimmu.2021.569287. [PMID: 33841390]
  • Si Wen, Jiangmei Wu, Li Ye, Bin Yang, Lizhi Hu, Mao-Qiang Man. Topical Applications of a Heparinoid-Containing Product Attenuate Glucocorticoid-Induced Alterations in Epidermal Permeability Barrier in Mice. Skin pharmacology and physiology. 2021; 34(2):86-93. doi: 10.1159/000513724. [PMID: 33652434]
  • Ömer Kutlu, Abdullah Demirbaş, Ömer F Elmas, Ulaş Güvenç, Ahmet Metin. Fixed drug eruption: A new side effect of bromelain. Contact dermatitis. 2021 Jan; 84(1):51-52. doi: 10.1111/cod.13658. [PMID: 32648609]
  • Sudeep Sudesh Pukale, Saurabh Sharma, Manu Dalela, Arihant Kumar Singh, Sujata Mohanty, Anupama Mittal, Deepak Chitkara. Multi-component clobetasol-loaded monolithic lipid-polymer hybrid nanoparticles ameliorate imiquimod-induced psoriasis-like skin inflammation in Swiss albino mice. Acta biomaterialia. 2020 10; 115(?):393-409. doi: 10.1016/j.actbio.2020.08.020. [PMID: 32846238]
  • Ankita Dadwal, Neeraj Mishra, Ravindra K Rawal, Raj Kumar Narang. Development and characterisation of clobetasol propionate loaded Squarticles as a lipid nanocarrier for treatment of plaque psoriasis. Journal of microencapsulation. 2020 Aug; 37(5):341-354. doi: 10.1080/02652048.2020.1756970. [PMID: 32293928]
  • Paulina Carvajal-Vidal, Roberto González-Pizarro, Carolina Araya, Marta Espina, Lyda Halbaut, Immaculada Gómez de Aranda, M Luisa García, Ana C Calpena. Nanostructured lipid carriers loaded with Halobetasol propionate for topical treatment of inflammation: Development, characterization, biopharmaceutical behavior and therapeutic efficacy of gel dosage forms. International journal of pharmaceutics. 2020 Jul; 585(?):119480. doi: 10.1016/j.ijpharm.2020.119480. [PMID: 32479897]
  • Yu-Ting Lu, Rong Guan, Jia-Run Zheng, Tai-Jun Hang, Min Song. Determination of clobetasol propionate, tazarotene and tazarotenic acid in Bama mini-pig skin by UPLC-MS/MS: Application to pharmacokinetic and drug-drug interaction studies. Journal of pharmaceutical and biomedical analysis. 2020 Jul; 186(?):113322. doi: 10.1016/j.jpba.2020.113322. [PMID: 32380355]
  • Andrew S Fischer, Susan Pei, Bridget E Shields, Misha Rosenbach, Adam I Rubin. Dermatomal necrotizing infundibular crystalline folliculitis following herpes zoster in a patient on PD-1 inhibitor therapy. Journal of cutaneous pathology. 2020 Jun; 47(6):501-505. doi: 10.1111/cup.13653. [PMID: 32428371]
  • Zahra Beygom Moosavi, Maryam Aliabdi, Fereshteh Golfakhrabadi, Foroogh Namjoyan. The comparison of therapeutic effect of Clobetasol propionate lotion and squill extract in alopecia areata: a randomized, double-blind clinical trial. Archives of dermatological research. 2020 Apr; 312(3):173-178. doi: 10.1007/s00403-019-02004-w. [PMID: 31707498]
  • Tamara Angelo, Nesma El-Sayed, Marijas Jurisic, Aljoscha Koenneke, Guilherme M Gelfuso, Marcilio Cunha-Filho, Stephania F Taveira, Robert Lemor, Marc Schneider, Tais Gratieri. Effect of physical stimuli on hair follicle deposition of clobetasol-loaded Lipid Nanocarriers. Scientific reports. 2020 01; 10(1):176. doi: 10.1038/s41598-019-56760-w. [PMID: 31932640]
  • Paulina Carvajal-Vidal, María-José Fábrega, Marta Espina, Ana Cristina Calpena, M Luisa García. Development of Halobetasol-loaded nanostructured lipid carrier for dermal administration: Optimization, physicochemical and biopharmaceutical behavior, and therapeutic efficacy. Nanomedicine : nanotechnology, biology, and medicine. 2019 08; 20(?):102026. doi: 10.1016/j.nano.2019.102026. [PMID: 31170512]
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  • Kyosuke Satake, Toru Amano, Tadao Okamoto. Low systemic exposure and calcemic effect of calcipotriol/betamethasone ointment in rats with imiquimod-induced psoriasis-like dermatitis. European journal of pharmacology. 2018 May; 826(?):31-38. doi: 10.1016/j.ejphar.2018.02.032. [PMID: 29476878]
  • Mads A Røpke, Cristina Alonso, Sora Jung, Hanne Norsgaard, Claudia Richter, Maxim E Darvin, Thomas Litman, Annika Vogt, Jürgen Lademann, Ulrike Blume-Peytavi, Jan Kottner. Effects of glucocorticoids on stratum corneum lipids and function in human skin-A detailed lipidomic analysis. Journal of dermatological science. 2017 Dec; 88(3):330-338. doi: 10.1016/j.jdermsci.2017.08.009. [PMID: 28911799]
  • Maicon Roberto Kviecinski, Isabela Machado Barbosa David, Flávia de Souza Fernandes, Marina Dos Reis Correa, Morgana Miranda Clarinda, Amanda Fernandes Freitas, Jane da Silva, Marta Gava, Simony Davet Müller, Drielly Florentino, Fabrícia Petronilho, Diego Moterle, Luiz Alberto Kanis, Rozangela Curi Pedrosa. Healing effect of Dillenia indica fruit extracts standardized to betulinic acid on ultraviolet radiation-induced psoriasis-like wounds in rats. Pharmaceutical biology. 2017 Dec; 55(1):641-648. doi: 10.1080/13880209.2016.1266672. [PMID: 27951742]
  • Lígia Marquez Andrade, Luis Antônio Dantas Silva, Anna Paula Krawczyk-Santos, Isabella Cristina de S M Amorim, Priscila Bianca Rodrigues da Rocha, Eliana Martins Lima, Jorge Luiz V Anjos, Antonio Alonso, Ricardo Neves Marreto, Stephânia Fleury Taveira. Improved tacrolimus skin permeation by co-encapsulation with clobetasol in lipid nanoparticles: Study of drug effects in lipid matrix by electron paramagnetic resonance. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2017 Oct; 119(?):142-149. doi: 10.1016/j.ejpb.2017.06.014. [PMID: 28627400]
  • E-J Choi, B-J Jung, S-H Lee, H-S Yoo, E-A Shin, H-J Ko, S Chang, S-Y Kim, S-M Jeon. A clinical drug library screen identifies clobetasol propionate as an NRF2 inhibitor with potential therapeutic efficacy in KEAP1 mutant lung cancer. Oncogene. 2017 09; 36(37):5285-5295. doi: 10.1038/onc.2017.153. [PMID: 28504720]
  • Vishal Gupta, Somesh Gupta. Genital lichen sclerosus developing around 'ectopic' urethral orifices supports the role of occlusion and urine in its pathogenesis. International journal of STD & AIDS. 2017 08; 28(9):940-942. doi: 10.1177/0956462416688159. [PMID: 28081682]
  • Delphine Giusti, Gregory Gatouillat, Sébastien Le Jan, Julie Plée, Philippe Bernard, Frank Antonicelli, Bach Nga Pham. Eosinophil Cationic Protein (ECP), a predictive marker of bullous pemphigoid severity and outcome. Scientific reports. 2017 07; 7(1):4833. doi: 10.1038/s41598-017-04687-5. [PMID: 28684769]
  • Yisi D Ji, Ali Aboalela, Alessandro Villa. Everolimus-associated stomatitis in a patient who had renal transplant. BMJ case reports. 2016 Oct; 2016(?):. doi: 10.1136/bcr-2016-217513. [PMID: 27797804]
  • Luis Antônio Dantas Silva, Lígia Marquez Andrade, Fernando Augusto Pires de Sá, Ricardo Neves Marreto, Eliana Martins Lima, Tais Gratieri, Stephânia Fleury Taveira. Clobetasol-loaded nanostructured lipid carriers for epidermal targeting. The Journal of pharmacy and pharmacology. 2016 Jun; 68(6):742-50. doi: 10.1111/jphp.12543. [PMID: 27061573]
  • Upendra Nagaich, Neha Gulati. Nanostructured lipid carriers (NLC) based controlled release topical gel of clobetasol propionate: design and in vivo characterization. Drug delivery and translational research. 2016 06; 6(3):289-98. doi: 10.1007/s13346-016-0291-1. [PMID: 27072979]
  • Xiaoming Yao, Tao Su, A S Verkman. Clobetasol promotes remyelination in a mouse model of neuromyelitis optica. Acta neuropathologica communications. 2016 04; 4(1):42. doi: 10.1186/s40478-016-0309-4. [PMID: 27117475]
  • Kei Nakayama, Kentaro Sato, Takazumi Shibano, Tomohiko Isobe, Go Suzuki, Shin-Ichi Kitamura. Occurrence of glucocorticoids discharged from a sewage treatment plant in Japan and the effects of clobetasol propionate exposure on the immune responses of common carp (Cyprinus carpio) to bacterial infection. Environmental toxicology and chemistry. 2016 Apr; 35(4):946-52. doi: 10.1002/etc.3136. [PMID: 26126539]
  • M H Maneli, L Wiesner, C Tinguely, L M Davids, Z Spengane, P Smith, J C van Wyk, A Jardine, N P Khumalo. Combinations of potent topical steroids, mercury and hydroquinone are common in internationally manufactured skin-lightening products: a spectroscopic study. Clinical and experimental dermatology. 2016 Mar; 41(2):196-201. doi: 10.1111/ced.12720. [PMID: 26211494]
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  • Diego Fontana de Andrade, Carine Zuglianello, Adriana Raffin Pohlmann, Silvia Stanisçuaski Guterres, Ruy Carlos Ruver Beck. Assessing the In Vitro Drug Release from Lipid-Core Nanocapsules: a New Strategy Combining Dialysis Sac and a Continuous-Flow System. AAPS PharmSciTech. 2015 Dec; 16(6):1409-17. doi: 10.1208/s12249-015-0330-0. [PMID: 25986595]
  • Müzeyyen Gönül, Engin Gönül. A case of multiple bone fractures due to the use of topical corticosteroid therapy for psoriasis. The Journal of dermatological treatment. 2015 Jun; 26(3):215-6. doi: 10.3109/09546634.2014.933164. [PMID: 24913132]
  • Diego Fontana de Andrade, Márcia Camponogara Fontana, Adriana Raffin Pohlmann, Silvia Stanisçuaski Guterres, Ruy Carlos, Ruver Beck. Nanoencapsulation of Clobetasol Propionate Decreases Its Penetration to Skin Layers Without Changing Its Relative Skin Distribution. Journal of nanoscience and nanotechnology. 2015 Jan; 15(1):875-9. doi: 10.1166/jnn.2015.9183. [PMID: 26328452]
  • Ayeshah Fateemah Beebee Fauzee, Sandile Maswazi Khamanga, Roderick Bryan Walker. The impact of manufacturing variables on in vitro release of clobetasol 17-propionate from pilot scale cream formulations. Drug development and industrial pharmacy. 2014 Dec; 40(12):1683-92. doi: 10.3109/03639045.2013.842579. [PMID: 24102616]
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