Tazarotene (BioDeep_00000009354)

 

Secondary id: BioDeep_00000398924

human metabolite blood metabolite Chemicals and Drugs Volatile Flavor Compounds


代谢物信息卡片


ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate

化学式: C21H21NO2S (351.12929260000004)
中文名称: 他扎罗汀
谱图信息: 最多检出来源 Escherichia coli(natural_products) 66.67%

分子结构信息

SMILES: CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1
InChI: InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3

描述信息

Tazarotene is only found in individuals that have used or taken this drug. It is a prescription topical retinoid sold as a cream or gel. This medication is approved for treatment of psoriasis, acne, and sun damaged skin (photodamage). [Wikipedia]Although the exact mechanism of tazarotene action is not known, studies have shown that the active form of the drug (tazarotenic acid) binds to all three members of the retinoic acid receptor (RAR) family: RARa, RARb, and RARg, but shows relative selectivity for RARb, and RARg and may modify gene expression. It also has affinity for RXR receptors.
C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent
D - Dermatologicals > D05 - Antipsoriatics > D05A - Antipsoriatics for topical use
C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent
D003879 - Dermatologic Agents > D007641 - Keratolytic Agents
D009676 - Noxae > D013723 - Teratogens
Same as: D01132

同义名列表

9 个代谢物同义名

ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate; Tazarotenum; Tazarotene; Tazaroteno; Tazorac; Fabior; Avage; Zorac; Tazarotene



数据库引用编号

14 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

  • Sunita Thakur, Md Meraj Anjum, Shweta Jaiswal, Anand Kumar, Payal Deepak, Sneha Anand, Sanjay Singh, Paruvathanahalli Siddalingam Rajinikanth. Novel Synergistic Approach: Tazarotene-Calcipotriol-Loaded-PVA/PVP-Nanofibers Incorporated in Hydrogel Film for Management and Treatment of Psoriasis. Molecular pharmaceutics. 2023 Feb; 20(2):997-1014. doi: 10.1021/acs.molpharmaceut.2c00713. [PMID: 36630478]
  • Lei Li, Xing-Fei Zhang, Guo-Ping Yang, Jie Huang, Xiao-Yan Yang, Ling Ye, Can Guo, Shuang Yang, Xiao-Min Wang. Safety, Tolerability, and Pharmacokinetics of Tazarotene Clindamycin Cream: A Single-Dose, 3-Period Crossover Study. Clinical pharmacology in drug development. 2021 06; 10(6):598-606. doi: 10.1002/cpdd.890. [PMID: 33241616]
  • 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]
  • Chunxia He, Hongzhong Jin, Xiguang Liu, Fengming Hu, Litao Zhang, Shifa Zhang, Yanling He, Xiumin Yang, Hao Chen, Xiaohua Wang, Chao Ji, Chengzhi Lv, Guoying Miao, Xiaojing Li, Qingchun Diao, Linfeng Li, Xuefei Li, Yuzhen Li, Rupeng Wang, Lijuan Zhang, Xiaoyong Zhou, Xiujuan Xia, Min Yan, Jiquan Song, Ruzhi Zhang, Long Geng, Min Zheng, Qianjin Lu, Tao Lu, Yuling Shi, Haixia Jing, Xiaojie Zhang, Jianqiang Shi, Jue Xia, Yu Gao, Yun Wang. Tazarotene/Betamethasone Dipropionate Cream in Patients with Plaque Psoriasis: Results of a Prospective, Multicenter, Observational Study. Dermatology (Basel, Switzerland). 2021; 237(4):603-610. doi: 10.1159/000511891. [PMID: 33352561]
  • 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]
  • Arisha Mahmood, Vamshi Krishna Rapalli, Tejashree Waghule, Srividya Gorantla, Sunil Kumar Dubey, Ranendra Narayan Saha, Gautam Singhvi. UV spectrophotometric method for simultaneous estimation of betamethasone valerate and tazarotene with absorption factor method: Application for in-vitro and ex-vivo characterization of lipidic nanocarriers for topical delivery. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2020 Jul; 235(?):118310. doi: 10.1016/j.saa.2020.118310. [PMID: 32251894]
  • 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]
  • Luana Niculescu, Cristel Ruini, Jerome Srour, Suzanna Salzer, Ines Schönbuchner, Tanja von Braunmühl, Thomas Ruzicka, Ulrich Hohenleutner, Kathrin A Giehl, Judith Fischer, Andreas Wollenberg. Tazarotene 0.015\% Cream as a Potential Topical Agent for Management of Ichthyosis in Dorfman-Chanarin Syndrome. Acta dermato-venereologica. 2019 Mar; 99(3):345-346. doi: 10.2340/00015555-3087. [PMID: 30460372]
  • Beata Nowak, Agnieszka Matuszewska, Jarosław Filipiak, Anna Nikodem, Anna Merwid-Ląd, Małgorzata Pieśniewska, Lidia Fereniec-Gołębiewska, Joanna Kwiatkowska, Adam Szeląg. The influence of bexarotene, a selective agonist of the retinoid receptor X (RXR), and tazarotene, a selective agonist of the retinoid acid receptor (RAR), on bone metabolism in rats. Advances in medical sciences. 2016 Mar; 61(1):85-9. doi: 10.1016/j.advms.2015.09.001. [PMID: 26569440]
  • Beata Nowak, Agnieszka Matuszewska, Jarosław Filipiak, Anna Nikodem, Anna Merwid-Ląd, Małgorzata Pieśniewska, Joanna Kwiatkowska, Bartosz Grotthus, Adam Szeląg. The Negative Impact of Selective Activation of Retinoic Acid Receptors on Bone Metabolism and Bone Mechanical Properties in Rats. Advances in clinical and experimental medicine : official organ Wroclaw Medical University. 2016 Mar; 25(2):213-8. doi: 10.17219/acem/41860. [PMID: 27627552]
  • Ying Tong, Hong Pan, Chenglong Sun, Xiaofei Xin, Li Ding, Pengcheng Ma. Simultaneous determination of tazarotene and its active metabolite tazarotenic acid in minipig plasma by LC-MS/MS and its application in pharmacokinetic study after topical administration of tazarotene gel. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Jan; 978-979(?):173-8. doi: 10.1016/j.jchromb.2014.11.030. [PMID: 25550192]
  • Rui-Xing Yu, Yun Hui, Cheng-Rang Li. Köebner phenomenon induced by cupping therapy in a psoriasis patient. Dermatology online journal. 2013 Jun; 19(6):18575. doi: ". [PMID: 24011324]
  • Michael Jarratt, Cary P Werner, Alessandra B Alió Saenz. Tazarotene foam versus tazarotene gel: a randomized relative bioavailability study in acne vulgaris. Clinical drug investigation. 2013 Apr; 33(4):283-9. doi: 10.1007/s40261-013-0065-1. [PMID: 23456673]
  • S P Dhanabal, L Priyanka Dwarampudi, N Muruganantham, R Vadivelan. Evaluation of the antipsoriatic activity of Aloe vera leaf extract using a mouse tail model of psoriasis. Phytotherapy research : PTR. 2012 Apr; 26(4):617-9. doi: 10.1002/ptr.3589. [PMID: 21915932]
  • Jessica Wong, Robert Phelps, Jacob Levitt. Treatment of acquired perforating dermatosis with cantharidin. Archives of dermatology. 2012 Feb; 148(2):160-2. doi: 10.1001/archdermatol.2011.350. [PMID: 22351815]
  • Emma Mormeneo, Cecilia Jimenez-Mallebrera, Xavier Palomer, Valeria De Nigris, Manuel Vázquez-Carrera, Anna Orozco, Andrés Nascimento, Jaume Colomer, Carles Lerín, Anna M Gómez-Foix. PGC-1α induces mitochondrial and myokine transcriptional programs and lipid droplet and glycogen accumulation in cultured human skeletal muscle cells. PloS one. 2012; 7(1):e29985. doi: 10.1371/journal.pone.0029985. [PMID: 22272266]
  • Hyun Jung Kim, Hyun Jung Park, Jae Nam Yun, Se Kyoo Jeong, Sung Ku Ahn, Seung Hun Lee. Pseudoceramide-containing physiological lipid mixture reduces adverse effects of topical steroids. Allergy, asthma & immunology research. 2011 Apr; 3(2):96-102. doi: 10.4168/aair.2011.3.2.96. [PMID: 21461248]
  • María Pilar Sánchez-Salas, Francisco Javier García Latasa de Aranibar, Rosa Oncíns Torres, Paula Gambó Grasa. Bullous-hemorrhagic Darier disease. Skinmed. 2011 Jan; 9(1):65-6. doi: . [PMID: 21409967]
  • Wee Kuan Kek, Wallace S Foulds, Gail McConnell, Amanda J Wright, John M Girkin, Clive G Wilson. Two-photon fluorescence excitation microscopy to assess transscleral diffusional pathways in an isolated perfused bovine eye model. Investigative ophthalmology & visual science. 2010 Oct; 51(10):5182-9. doi: 10.1167/iovs.09-3854. [PMID: 20445125]
  • Yin-Ku Lin, Zih-Rou Huang, Rou-Zi Zhuo, Jia-You Fang. Combination of calcipotriol and methotrexate in nanostructured lipid carriers for topical delivery. International journal of nanomedicine. 2010 Mar; 5(?):117-28. doi: 10.2147/ijn.s9155. [PMID: 20309398]
  • ". Childhood psoriasis: often favorable outcome. Prescrire international. 2009 Dec; 18(104):275. doi: ". [PMID: 20027717]
  • Angèle Tingaud-Sequeira, François Chauvigné, Juanjo Lozano, María J Agulleiro, Esther Asensio, Joan Cerdà. New insights into molecular pathways associated with flatfish ovarian development and atresia revealed by transcriptional analysis. BMC genomics. 2009 Sep; 10(?):434. doi: 10.1186/1471-2164-10-434. [PMID: 19754951]
  • B Seruga, H K Gan, J J Knox. Managing toxicities and optimal dosing of targeted drugs in advanced kidney cancer. Current oncology (Toronto, Ont.). 2009 May; 16 Suppl 1(?):S52-9. doi: 10.3747/co.v16i0.402. [PMID: 19478903]
  • M E Lacouture, L M Reilly, P Gerami, J Guitart. Hand foot skin reaction in cancer patients treated with the multikinase inhibitors sorafenib and sunitinib. Annals of oncology : official journal of the European Society for Medical Oncology. 2008 Nov; 19(11):1955-61. doi: 10.1093/annonc/mdn389. [PMID: 18550575]
  • T Kogai, K Taki, G A Brent. Enhancement of sodium/iodide symporter expression in thyroid and breast cancer. Endocrine-related cancer. 2006 Sep; 13(3):797-826. doi: 10.1677/erc.1.01143. [PMID: 16954431]
  • Kristjan Karason, Margareta Jernås, Daniel A Hägg, Per-Arne Svensson. Evaluation of CXCL9 and CXCL10 as circulating biomarkers of human cardiac allograft rejection. BMC cardiovascular disorders. 2006 Jun; 6(?):29. doi: 10.1186/1471-2261-6-29. [PMID: 16780603]
  • Mayssa Attar, Dale Yu, Jinsong Ni, Zhiling Yu, Kah-Hiing John Ling, Diane D-S Tang-Liu. Disposition and biotransformation of the acetylenic retinoid tazarotene in humans. Journal of pharmaceutical sciences. 2005 Oct; 94(10):2246-55. doi: 10.1002/jps.20427. [PMID: 16136553]
  • G Deplanque, S Madhusudan, P H Jones, S Wellmann, K Christodoulos, D C Talbot, T S Ganesan, A Blann, A L Harris. Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma. British journal of cancer. 2004 Nov; 91(9):1645-50. doi: 10.1038/sj.bjc.6602126. [PMID: 15354209]
  • Zhiling Yu, Dale Yu, Patricia S Walker, Diane D-S Tang-Liu. Tazarotene does not affect the pharmacokinetics and efficacy of a norethindrone/ethinylestradiol oral contraceptive. Clinical pharmacokinetics. 2004; 43(10):673-84. doi: 10.2165/00003088-200443100-00003. [PMID: 15244497]
  • P H Jones, R D Burnett, I Fainaru, P Nadolny, P Walker, Z Yu, D Tang-Liu, T S Ganesan, D C Talbot, A L Harris, G J S Rustin. A phase 1 study of tazarotene in adults with advanced cancer. British journal of cancer. 2003 Sep; 89(5):808-15. doi: 10.1038/sj.bjc.6601169. [PMID: 12942109]
  • Zhiling Yu, John Sefton, Deborah Lew-Kaya, Patricia Walker, Dale Yu, Diane D-S Tang-Liu. Pharmacokinetics of tazarotene cream 0.1\% after a single dose and after repeat topical applications at clinical or exaggerated application rates in patients with acne vulgaris or photodamaged skin. Clinical pharmacokinetics. 2003; 42(10):921-9. doi: 10.2165/00003088-200342100-00004. [PMID: 12885265]
  • Tania J Phillips, Alice B Gottlieb, James J Leyden, Nicholas J Lowe, Deborah A Lew-Kaya, John Sefton, Patricia S Walker, John R Gibson. Efficacy of 0.1\% tazarotene cream for the treatment of photodamage: a 12-month multicenter, randomized trial. Archives of dermatology. 2002 Nov; 138(11):1486-93. doi: 10.1001/archderm.138.11.1486. [PMID: 12437455]
  • Narin Apisarnthanarax, Rakshandra Talpur, Madeleine Duvic. Treatment of cutaneous T cell lymphoma: current status and future directions. American journal of clinical dermatology. 2002; 3(3):193-215. doi: 10.2165/00128071-200203030-00006. [PMID: 11978140]
  • Q Wang, D Lee, V Sysounthone, Chandraratna RAS, S Christakos, R Korah, R Wieder. 1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects. Breast cancer research and treatment. 2001 May; 67(2):157-68. doi: 10.1023/a:1010643323268. [PMID: 11519864]
  • T N Helm, J Lee, K F Helm. Spiny keratoderma. Cutis. 2000 Sep; 66(3):191-2. doi: ". [PMID: 11006853]
  • A Menter. Pharmacokinetics and safety of tazarotene. Journal of the American Academy of Dermatology. 2000 Aug; 43(2 Pt 3):S31-5. doi: 10.1067/mjd.2000.108321. [PMID: 10898827]
  • D D Tang-Liu, R M Matsumoto, J I Usansky. Clinical pharmacokinetics and drug metabolism of tazarotene: a novel topical treatment for acne and psoriasis. Clinical pharmacokinetics. 1999 Oct; 37(4):273-87. doi: 10.2165/00003088-199937040-00001. [PMID: 10554045]
  • R Marks. The role of tazarotene in the treatment of psoriasis. The British journal of dermatology. 1999 Apr; 140 Suppl 54(?):24-8. doi: 10.1046/j.1365-2133.1999.140s54024.x. [PMID: 10731131]
  • R Marks. Pharmacokinetics and safety review of tazarotene. Journal of the American Academy of Dermatology. 1998 Oct; 39(4 Pt 2):S134-8. doi: 10.1016/s0190-9622(98)70310-x. [PMID: 9777791]
  • J Y Koo. Tazarotene in combination with phototherapy. Journal of the American Academy of Dermatology. 1998 Oct; 39(4 Pt 2):S144-8. doi: 10.1016/s0190-9622(98)70312-3. [PMID: 9777793]
  • NULL. Two new retinoids for psoriasis. The Medical letter on drugs and therapeutics. 1997 Nov; 39(1013):105-6. doi: NULL. [PMID: 9391501]
  • S Nagpal, S M Thacher, S Patel, S Friant, M Malhotra, J Shafer, G Krasinski, A T Asano, M Teng, M Duvic, R A Chandraratna. Negative regulation of two hyperproliferative keratinocyte differentiation markers by a retinoic acid receptor-specific retinoid: insight into the mechanism of retinoid action in psoriasis. Cell growth & differentiation : the molecular biology journal of the American Association for Cancer Research. 1996 Dec; 7(12):1783-91. doi: . [PMID: 8959347]
  • S Tsuji, K Nakagawa, T Fukushima. Genetically controlled quantitative variation of ornithine transcarbamylase in the chick kidney. Biochemical genetics. 1983 Oct; 21(9-10):857-69. doi: 10.1007/bf00483945. [PMID: 6419722]
  • H H Borden, R W Harris, W E Mosher. A waterborne outbreak of gastroenteritis in western New York State. American journal of public health and the nation's health. 1970 Feb; 60(2):283-8. doi: 10.2105/ajph.60.2.283. [PMID: 5460971]