Ketotifen (BioDeep_00000018014)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),4,10,12-pentaen-8-one

化学式: C19H19NOS (309.1187284)
中文名称: 酮替芬
谱图信息: 最多检出来源 Homo sapiens(blood) 20.83%

分子结构信息

SMILES: CN1CCC(=C2C3=C(C(=O)CC4=CC=CC=C42)SC=C3)CC1
InChI: InChI=1S/C19H19NOS/c1-20-9-6-13(7-10-20)18-15-5-3-2-4-14(15)12-17(21)19-16(18)8-11-22-19/h2-5,8,11H,6-7,9-10,12H2,1H3

描述信息

Ketotifen is only found in individuals that have used or taken this drug. It is a cycloheptathiophene blocker of histamine H1 receptors and release of inflammatory mediators. It has been proposed for the treatment of asthma, rhinitis, skin allergies, and anaphylaxis. [PubChem]Ketotifen is a relatively selective, non-competitive histamine antagonist (H1-receptor) and mast cell stabilizer. Ketotifen inhibits the release of mediators from mast cells involved in hypersensitivity reactions. Decreased chemotaxis and activation of eosinophils have also been demonstrated. Ketotifen also inhibits cAMP phosphodiesterase. Properties of ketotifen which may contribute to its antiallergic activity and its ability to affect the underlying pathology of asthma include inhibition of the development of airway hyper-reactivity associated with activation of platelets by PAF (Platelet Activating Factor), inhibition of PAF-induced accumulation of eosinophils and platelets in the airways, suppression of the priming of eosinophils by human recombinant cytokines and antagonism of bronchoconstriction due to leukotrienes. Ketotifen inhibits of the release of allergic mediators such as histamine, leukotrienes C4 and D4(SRS-A) and PAF.
R - Respiratory system > R06 - Antihistamines for systemic use > R06A - Antihistamines for systemic use
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
S - Sensory organs > S01 - Ophthalmologicals > S01G - Decongestants and antiallergics
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
C308 - Immunotherapeutic Agent > C29578 - Histamine-1 Receptor Antagonist
D003879 - Dermatologic Agents > D000982 - Antipruritics
D018926 - Anti-Allergic Agents
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS

同义名列表

15 个代谢物同义名

2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),4,10,12-pentaen-8-one; 4,9-Dihydro-4-(1-methyl-4-piperidylidene)-10H-benzo(4,5)-cyclohepta(1,2-b)thiophen-10-one; 10-(1-methylpiperidin-4-ylidene)-5H-benzo[1,2]cyclohepta[3,4-b]thiophen-4-one; 10-(1-Methyl-4-piperidinylidene)-5H-benzo[1,2]cyclohepta[3,4-b]thiophen-4-one; Fumarate, ketotifen; Ketotifene fumarate; Ketotifen fumarate; Ketotifenum; Ketotiphene; Ketotifene; Ketotifeno; Ketotiphen; ketotifen; Zaditen; Alaway

数据库引用编号

11 个数据库交叉引用编号

ChEBI: CHEBI:92511
PubChem: 3827
HMDB: HMDB0015056
DrugBank: DB00920
ChEMBL: CHEMBL534
Wikipedia: Ketotifen
MeSH: Ketotifen
chemspider: 3695
CAS: 116655-76-6
CAS: 34580-13-7
PMhub: MS000001659

分类词条

Cycloheptathiophenes

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

9606 - Homo sapiens: -

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

Jia-Zi Dong, Pei-Jing Rong, Tie-Ming Ma, Dan Wang, Xiao-Tong Wang, Ye Qiao. [Influence of electroacupuncture of"Zusanli"(ST36)on mast cells/TRPV1 signaling pathway in visceral hypersensitivity rats with functional dyspepsia]. Zhen ci yan jiu = Acupuncture research. 2022 Jul; 47(7):592-7. doi: 10.13702/j.1000-0607.20210937. [PMID: 35880275]
Ziye Huang, Guang Wang, Bowei Yang, Pei Li, Tongxin Yang, Yuyun Wu, Xing Yang, Jianhe Liu, Jiongming Li. Mechanism of ketotifen fumarate inhibiting renal calcium oxalate stone formation in SD rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Jul; 151(?):113147. doi: 10.1016/j.biopha.2022.113147. [PMID: 35643070]
Huanan Li, Wei Zhang, Fei Ma, Xiaofan Zhang, Yuyan Wang, Jingui Wang. Abdominal Massage Improves the Symptoms of Irritable Bowel Syndrome by Regulating Mast Cells via the Trypase-PAR2-PKCε Pathway in Rats. Pain research & management. 2022; 2022(?):8331439. doi: 10.1155/2022/8331439. [PMID: 36213180]
Tomohiro Nizawa, Imran A Bhutto, Anupama Tiwari, Rhonda R Grebe, Jesse Alt, Rana Rais, Malia M Edwards, Gerard A Lutty. Topical Ketotifen Fumarate Inhibits Choroidal Mast Cell Degranulation and Loss of Retinal Pigment Epithelial Cells in Rat Model for Geographic Atrophy. Translational vision science & technology. 2021 12; 10(14):37. doi: 10.1167/tvst.10.14.37. [PMID: 34967831]
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]
Pantea Kiani, Andrew Scholey, Thomas A Dahl, Lauren McMann, Jacqueline M Iversen, Joris C Verster. In Vitro Assessment of the Antiviral Activity of Ketotifen, Indomethacin and Naproxen, Alone and in Combination, against SARS-CoV-2. Viruses. 2021 03; 13(4):. doi: 10.3390/v13040558. [PMID: 33810356]
Nur Zahirah Abd Rani, Kok Wai Lam, Juriyati Jalil, Hazni Falina Mohamad, Mohd Shukri Mat Ali, Khairana Husain. Mechanistic Studies of the Antiallergic Activity of Phyllanthus amarus Schum. & Thonn. and Its Compounds. Molecules (Basel, Switzerland). 2021 Jan; 26(3):. doi: 10.3390/molecules26030695. [PMID: 33525733]
Walaa Yehia Abdelzaher, Abdel Hamid Sayed AboBakr Ali, Nashwa Fathy Gamal El-Tahawy. Mast cell stabilizer modulates Sirt1/Nrf2/TNF pathway and inhibits oxidative stress, inflammation, and apoptosis in rat model of cyclophosphamide hepatotoxicity. Immunopharmacology and immunotoxicology. 2020 Apr; 42(2):101-109. doi: 10.1080/08923973.2020.1727499. [PMID: 32066295]
Feifei Feng, J Paul Fawcett, Hu Zhang, Ian G Tucker. Cell-based, animal and H1 receptor binding studies relative to the sedative effects of ketotifen and norketotifen atropisomers. The Journal of pharmacy and pharmacology. 2020 Apr; 72(4):507-518. doi: 10.1111/jphp.13220. [PMID: 32030755]
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]
Dalia El Baihary, Rihab Osman, Hend Mohamed Abdel-Bar, Omaima A Sammour. Pharmacokinetic/pulmokinetic analysis of optimized lung targeted spray dried ketotifen-dextran core shell nanocomplexes-in-microparticles. International journal of biological macromolecules. 2019 Oct; 139(?):678-687. doi: 10.1016/j.ijbiomac.2019.08.011. [PMID: 31381926]
Xian Zhang, Qin Huang, Xin Wang, Zhiyong Deng, Jie Li, Xiang Yan, Matti Jauhiainen, Jari Metso, Peter Libby, Jian Liu, Guo-Ping Shi. Dietary cholesterol is essential to mast cell activation and associated obesity and diabetes in mice. Biochimica et biophysica acta. Molecular basis of disease. 2019 06; 1865(6):1690-1700. doi: 10.1016/j.bbadis.2019.04.006. [PMID: 30978390]
Zimiao Chen, Hongwei Sun, Jian Wang, Liansong Ni, Xuejiang Gu, Shengjie Ge, Qiong Chen, Liangshan Mu, Xingbo Cheng. Role of Ketotifen on metabolic profiles, inflammation and oxidative stress in diabetic rats. Endocrine journal. 2017 Apr; 64(4):411-416. doi: 10.1507/endocrj.ej16-0458. [PMID: 28321031]
Kayoko Kanamitsu, Yoshitane Nozaki, Yoko Nagaya, Yuichi Sugiyama, Hiroyuki Kusuhara. Quantitative prediction of histamine H1 receptor occupancy by the sedative and non-sedative antagonists in the human central nervous system based on systemic exposure and preclinical data. Drug metabolism and pharmacokinetics. 2017 Apr; 32(2):135-144. doi: 10.1016/j.dmpk.2016.11.007. [PMID: 28190755]
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Laia Tolosa, M José Gómez-Lechón, Nuria Jiménez, David Hervás, Ramiro Jover, M Teresa Donato. Advantageous use of HepaRG cells for the screening and mechanistic study of drug-induced steatosis. Toxicology and applied pharmacology. 2016 07; 302(?):1-9. doi: 10.1016/j.taap.2016.04.007. [PMID: 27089845]
Asuka Baba, Masahiro Tachi, Yutaka Ejima, Yasuhiro Endo, Hiroaki Toyama, Mitsunobu Matsubara, Kazutomo Saito, Masanori Yamauchi, Chieko Miura, Itsuro Kazama. Anti-Allergic Drugs Tranilast and Ketotifen Dose-Dependently Exert Mast Cell-Stabilizing Properties. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2016; 38(1):15-27. doi: 10.1159/000438605. [PMID: 26741745]
Fei Tong, Lei Luo, Daojun Liu. Effect of Intervention in Mast Cell Function Before Reperfusion on Renal Ischemia-Reperfusion Injury in Rats. Kidney & blood pressure research. 2016; 41(3):335-44. doi: 10.1159/000443437. [PMID: 27304487]
Ali Mokhtari, Mehrgan Ghazaeian, Mahdieh Maghsoudi, Mohsen Keyvanfard, Iraj Emami. Simple chemiluminescence determination of ketotifen using tris(1,10 phenanthroline)ruthenium(II)- Ce(IV) system. Luminescence : the journal of biological and chemical luminescence. 2015 Nov; 30(7):1094-100. doi: 10.1002/bio.2864. [PMID: 25691393]
Nagla A El-Shitany, Karema El-Desoky. Cromoglycate, not ketotifen, ameliorated the injured effect of warm ischemia/reperfusion in rat liver: role of mast cell degranulation, oxidative stress, proinflammatory cytokine, and inducible nitric oxide synthase. Drug design, development and therapy. 2015; 9(?):5237-46. doi: 10.2147/dddt.s88337. [PMID: 26396497]
Pin-Jie Huang, Xiao-Liang Gan, Jian-Pei Liu, De-Zhao Liu, Yan-Ling Wang, Zi-Qing Hei. Effects of anti-histamine treatment on liver injury triggered by small intestinal ischemia reperfusion in rats. The Chinese journal of physiology. 2014 Oct; 57(5):271-8. doi: 10.4077/cjp.2014.bac230. [PMID: 25241987]
Jian-hong Li, Zhi-fei Wang, Yan-ming Xie, Wei Zhao. [Clinical characteristics and combined use of medicine analysis of 2 991 hospitalized patients with psoriasis based on real world database]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Sep; 39(18):3442-7. doi: . [PMID: 25532375]
Frida Gustafsson, Alison J Foster, Sunil Sarda, Matthew H Bridgland-Taylor, J Gerry Kenna. A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. Toxicological sciences : an official journal of the Society of Toxicology. 2014 Jan; 137(1):189-211. doi: 10.1093/toxsci/kft223. [PMID: 24085192]
Hong Li, Long-feng Zhao, Yan-qin Hao, De-wu Han. [Effects of antihistamine treatment on immune function in rats with experimental hepatitis]. Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology. 2013 Oct; 21(10):764-8. doi: 10.3760/cma.j.issn.1007-3418.2013.10.010. [PMID: 24331635]
Hyo Won Jung, Jin Ki Jung, Yong-Ki Park. Comparison of the efficacy of KOB03, ketotifen, and montelukast in an experimental mouse model of allergic rhinitis. International immunopharmacology. 2013 Jun; 16(2):254-60. doi: 10.1016/j.intimp.2013.04.011. [PMID: 23643816]
Ailan Zhang, Xinjin Chi, Gangjian Luo, Ziqing Hei, Hua Xia, Chenfang Luo, Yanling Wang, Xiaowen Mao, Zhengyuan Xia. Mast cell stabilization alleviates acute lung injury after orthotopic autologous liver transplantation in rats by downregulating inflammation. PloS one. 2013; 8(10):e75262. doi: 10.1371/journal.pone.0075262. [PMID: 24116032]
Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
Tatsuo Sakamoto, Michihiro Kamijima, Mio Miyake. Neurogenic airway microvascular leakage induced by toluene inhalation in rats. European journal of pharmacology. 2012 Jun; 685(1-3):180-5. doi: 10.1016/j.ejphar.2012.04.035. [PMID: 22554773]
Laia Tolosa, Sandra Pinto, M Teresa Donato, Agustín Lahoz, José V Castell, J Enrique O'Connor, M José Gómez-Lechón. Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs. Toxicological sciences : an official journal of the Society of Toxicology. 2012 May; 127(1):187-98. doi: 10.1093/toxsci/kfs083. [PMID: 22331495]
Erin Milner, Jason Sousa, Brandon Pybus, Jennifer Auschwitz, Diana Caridha, Sean Gardner, Kristina Grauer, Erin Harris, Mark Hickman, Michael P Kozar, Patricia Lee, Susan Leed, Qigui Li, Victor Melendez, Jay Moon, Franklyn Ngundam, Michael O'Neil, Sandi Parriott, Brittney Potter, Rick Sciotti, Anchalee Tangteung, Geoffrey S Dow. Ketotifen is an antimalarial prodrug of norketotifen with blood schizonticidal and liver-stage efficacy. European journal of drug metabolism and pharmacokinetics. 2012 Mar; 37(1):17-22. doi: 10.1007/s13318-012-0080-2. [PMID: 22314893]
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Sarah Dawson, Simone Stahl, Nikki Paul, Jane Barber, J Gerald Kenna. In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jan; 40(1):130-8. doi: 10.1124/dmd.111.040758. [PMID: 21965623]
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Min Zhou, Yu-Jie Li, Yong-Jun Ma, Wei-Feng Wang, Juan Mi, Hui Chen. Determination of ketotifen fumarate by capillary electrophoresis with tris(2,2'-bipyridyl) ruthenium(II) electrochemiluminescence detection. Luminescence : the journal of biological and chemical luminescence. 2011 Sep; 26(5):319-23. doi: 10.1002/bio.1231. [PMID: 20737650]
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Yasuto Kido, Pär Matsson, Kathleen M Giacomini. Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. Journal of medicinal chemistry. 2011 Jul; 54(13):4548-58. doi: 10.1021/jm2001629. [PMID: 21599003]
Hamish Philpott, Peter Gibson, Frank Thien. Irritable bowel syndrome - An inflammatory disease involving mast cells. Asia Pacific allergy. 2011 Apr; 1(1):36-42. doi: 10.5415/apallergy.2011.1.1.36. [PMID: 22053295]
Jinku Xu, Xinsong Li, Fuqian Sun. In vitro and in vivo evaluation of ketotifen fumarate-loaded silicone hydrogel contact lenses for ocular drug delivery. Drug delivery. 2011 Feb; 18(2):150-8. doi: 10.3109/10717544.2010.522612. [PMID: 21043996]
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Parandis Daneshgar, Parviz Norouzi, Mohammad Reza Ganjali. Application of a continuous square-wave potential program for sub nano molar determination of ketotifen. Chemical & pharmaceutical bulletin. 2009 Feb; 57(2):117-21. doi: 10.1248/cpb.57.117. [PMID: 19182398]
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