Cytisinicline (BioDeep_00000229787)

Main id: BioDeep_00000001941

 

PANOMIX_OTCML-2023


代谢物信息卡片


(1R,5S)-1,2,3,4,5,6-HEXAHYDRO-8H-1,5-METHANOPYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE (CYTISINE)

化学式: C11H14N2O (190.1106074)
中文名称: 金雀花碱, 野靛碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C2CNCC1C3=CC=CC(=O)N3C2
InChI: InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1

描述信息

Cytisine is an organic heterotricyclic compound that is the toxic principle in Laburnum seeds and is found in many members of the Fabaceae (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as an aid to giving up smoking. It has a role as a nicotinic acetylcholine receptor agonist, a phytotoxin and a plant metabolite. It is an alkaloid, an organic heterotricyclic compound, a secondary amino compound, a lactam and a bridged compound.
Cytisine is an alkaloid naturally derived from the Fabaceae family of plants including the genera Laburnum and Cytisus. Recent studies have shown it to be a more effective and significantly more affordable smoking cessation treatment than nicotine replacement therapy. Also known as baptitoxine or sophorine, cytisine has been used as a smoking cessation treatment since 1964, and is relatively unknown in regions outside of central and Eastern Europe. Cytisine is a partial nicotinic acetylcholine agonist with a half-life of 4.8 hours. Recent Phase III clinical trials using Tabex (a brand of Cytisine marketed by Sopharma AD) have shown similar efficacy to varenicline, but at a fraction of the cost.
Cytisine is a natural product found in Viscum cruciatum, Thermopsis chinensis, and other organisms with data available.
See also: Cytisus scoparius flowering top (part of); Thermopsis lanceolata whole (part of).
An organic heterotricyclic compound that is the toxic principle in Laburnum seeds and is found in many members of the Fabaceae (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as an aid to giving up smoking.
N - Nervous system > N07 - Other nervous system drugs > N07B - Drugs used in addictive disorders > N07BA - Drugs used in nicotine dependence
C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist > C73579 - Nicotinic Agonist
Cytisinicline (Cytisine) is an alkaloid. Cytisinicline (Cytisine) is a partial agonist of α4β2 nAChRs[1], and partial to full agonist at β4 containing receptors and α7 receptors[2]. Has been used medically to help with smoking cessation[3].
Cytisinicline (Cytisine) is an alkaloid. Cytisinicline (Cytisine) is a partial agonist of α4β2 nAChRs[1], and partial to full agonist at β4 containing receptors and α7 receptors[2]. Has been used medically to help with smoking cessation[3].
Cytisinicline (Cytisine) is an alkaloid. Cytisinicline (Cytisine) is a partial agonist of α4β2 nAChRs[1], and partial to full agonist at β4 containing receptors and α7 receptors[2]. Has been used medically to help with smoking cessation[3].

同义名列表

73 个代谢物同义名

(1R,5S)-1,2,3,4,5,6-HEXAHYDRO-8H-1,5-METHANOPYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE (CYTISINE); 1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-; 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-; (1R,5S)-1,2,3,4,5,6-hexahydro-1,5-m ethano-8H-pyrido[1,2-a][1,5]diazocin-8-one; (1R,5S)-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANO-8H-PYRIDO-(1,2-A)(1,5)DIAZOCIN-8-ONE; (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-Methano-8H-Pyrido[1,2-A][1,5]Diazocin-8-One; (1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one; 1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one (cytisine); (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one; (1r,5s)-1,2,3,4,5,6-Hexahydro-8h-1,5-Methanopyrido[1,2-A][1,5]diazocin-8-One; (1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido(1,2-a)(1,5)diazocin-8-one; (1R)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido-(1,2-a)(1,5)diazocin-8-one; Cytisine1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one; (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one; 1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one; (1R,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one; (1R,9S)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one; (1R,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one; (1S,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one; (1R,9S)-7,11-diazatricyclo[7.3.1.0,2,7]trideca-2,4-dien-6-one; (1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one; 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R-cis)-; 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R)-; 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-; 5-24-02-00535 (Beilstein Handbook Reference); cytisine tetrahydrochloride, trihydrate; cytisine dihydrochloride, trihydrate; Cytisine, >=99.0\\% (HPLC), >=99\\%; cytisine hydrochloride, hydrate; ANJTVLIZGCUXLD-DTWKUNHWSA-N; Cytisine, >=99\\%, powder; 3-hydroxy-11-norcytisine; CYTISINICLINE [WHO-DD]; cytisine hydrochloride; Cytisinicline [USAN]; CYTISINICLINE [INN]; Prestwick3_000624; CYTISINE (MART.); CYTISINE [MART.]; CYTISINE [HSDB]; UNII-53S5U404NU; Cytisine- Bio-X; Cytisine ((+)-); cytisiniclinum; Cytisinicline; BPBio1_000648; CYTISINE [MI]; citisiniclina; (-)-Cytisine; PDSP1_000461; Cytisine (-); Baphitoxine; Baptitoxine; 53S5U404NU; Baptitoxin; C11H14N2O; Sophorine; Cystisine; citizine; Laburnin; Cytisine; Tsitizin; Cytitone; cystisin; Citizin; Ulexine; Cytizin; Cytisin; cytiton; Ulexin; Tabex; Tabax; C5E



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)

104 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

  • Xuezhen Wang, Jiaming Yang, Peifeng Huang, Dong Wang, Zhibin Zhang, Zehua Zhou, Leiqin Liang, Rongmei Yao, Long Yang. Cytisine: State of the art in pharmacological activities and pharmacokinetics. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2024 Jan; 171(?):116210. doi: 10.1016/j.biopha.2024.116210. [PMID: 38271893]
  • Qing-Qing Zhou, Xiao-Yan Xie, Jia-Wen Zhu, Wei-Wei Pan, Bao-Gang Xie, Wu Zhou, Jin-Biao Xu. Hosimosines A-E, structurally diverse cytisine derivatives from the seeds of Ormosia hosiei Hemsl. et Wils. Fitoterapia. 2023 Aug; 170(?):105661. doi: 10.1016/j.fitote.2023.105661. [PMID: 37648030]
  • Wojciech Świątkowski, Barbara Budzyńska, Monika Maciąg, Agnieszka Świątkowska, Przemko Tylżanowski, Mansur Rahnama-Hezavah, Piotr Stachurski, Renata Chałas. Nicotine and Cytisine Embryotoxicity in the Experimental Zebrafish Model. International journal of molecular sciences. 2023 Jul; 24(15):. doi: 10.3390/ijms241512094. [PMID: 37569468]
  • Nancy A Rigotti, Neal L Benowitz, Judith Prochaska, Scott Leischow, Mitchell Nides, Brent Blumenstein, Anthony Clarke, Daniel Cain, Cindy Jacobs. Cytisinicline for Smoking Cessation: A Randomized Clinical Trial. JAMA. 2023 07; 330(2):152-160. doi: 10.1001/jama.2023.10042. [PMID: 37432430]
  • Qing-Qing Zhou, Xiao-Yan Xie, Yan-Xia Zhang, Wu Zhou, Zha-Jun Zhan, Jin-Biao Xu. [Research progress on chemical structures and pharmacological effects of natural cytisine and its derivatives]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 May; 48(10):2679-2698. doi: 10.19540/j.cnki.cjcmm.20220623.202. [PMID: 37282929]
  • Peng Zhang, Ji-Bin Zou, Qiao An, Ping Yi, Chun-Mao Yuan, Lie-Jun Huang, Wei Gu, Zhan-Xing Hu, Xiao-Jiang Hao. Two new cytisine-type alkaloids from the seeds of Thermopsis lanceolata. Journal of Asian natural products research. 2022 Dec; 24(12):1141-1149. doi: 10.1080/10286020.2021.2020759. [PMID: 34984943]
  • Yanqing Wang, Xiaoying Yin, Lingyan Chen, Zhixiang Yin, Zhicheng Zuo. Discovery and evaluation of cytisine N-isoflavones as novel EGFR/HER2 dual inhibitors. Bioorganic chemistry. 2022 10; 127(?):105868. doi: 10.1016/j.bioorg.2022.105868. [PMID: 35816874]
  • Aaron L Nichols, Zack Blumenfeld, Chengcheng Fan, Laura Luebbert, Annet E M Blom, Bruce N Cohen, Jonathan S Marvin, Philip M Borden, Charlene H Kim, Anand K Muthusamy, Amol V Shivange, Hailey J Knox, Hugo Rego Campello, Jonathan H Wang, Dennis A Dougherty, Loren L Looger, Timothy Gallagher, Douglas C Rees, Henry A Lester. Fluorescence activation mechanism and imaging of drug permeation with new sensors for smoking-cessation ligands. eLife. 2022 01; 11(?):. doi: 10.7554/elife.74648. [PMID: 34982029]
  • Linjing Zhang, Lijun Zheng, Qin Wang, Zhenze Pana, Xiaoqin Zhang, Mingqing Huang, Huiyou Xu, Lin Ni. Cytisine-like alkaloids from the seeds of Ormosia hosiei Hemsl. et Wils. Natural product research. 2021 Dec; ?(?):1-7. doi: 10.1080/14786419.2021.2005591. [PMID: 34933632]
  • Xuanrong Sun, Tianwei Zhang, Yue Cai, Ke Yang, Tingting Peng, Renhao Liu, Xing-Nuo Li. Tonkinensine B induces apoptosis through mitochondrial dysfunction and inactivation of the PI3K/AKT pathway in triple-negative breast cancer cells. The Journal of pharmacy and pharmacology. 2021 Sep; 73(10):1397-1404. doi: 10.1093/jpp/rgab108. [PMID: 34313786]
  • Yuanyuan Zhang, Min Lv, Hui Xu. Insecticidal activity of twin compounds from podophyllotoxin and cytisine. Bioorganic & medicinal chemistry letters. 2021 07; 43(?):128104. doi: 10.1016/j.bmcl.2021.128104. [PMID: 33984477]
  • 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]
  • Anna Petruczynik, Karol Wróblewski, Justyna Misiurek, Tomasz Plech, Karolina Szalast, Krzysztof Wojtanowski, Tomasz Mroczek, Grażyna Szymczak, Monika Waksmundzka-Hajnos, Piotr Tutka. Determination of Cytisine and N-Methylcytisine from Selected Plant Extracts by High-Performance Liquid Chromatography and Comparison of Their Cytotoxic Activity. Toxins. 2020 08; 12(9):. doi: 10.3390/toxins12090557. [PMID: 32872484]
  • Fangmei Chen, Xiaoying Yin, Yanqing Wang, Yixin Lv, Si Sheng, Sheng Ouyang, Youquan Zhong. Pharmacokinetics, Tissue Distribution, and Druggability Prediction of the Natural Anticancer Active Compound Cytisine N-Isoflavones Combined with Computer Simulation. Biological & pharmaceutical bulletin. 2020 Jun; 43(6):976-984. doi: 10.1248/bpb.b20-00004. [PMID: 32188833]
  • Xiaobo Huang, Hui Xu. Advances on the Bioactivities, Total Synthesis, Structural Modification, and Structure-Activity Relationships of Cytisine Derivatives. Mini reviews in medicinal chemistry. 2020; 20(5):369-395. doi: 10.2174/1389557519666191104121821. [PMID: 31686638]
  • Andrea Ariano, Alessandro Costagliola, Massimiliano D'Ambola, Laura Cortese, Luigi Pietrobattista, Gabriella Di Francesco, Stefania Salucci, Valentina Iovane, Orlando Paciello, Lorella Severino. Spartium junceum L. poisoning in small ruminants. Veterinaria italiana. 2019 12; 55(4):369-373. doi: 10.12834/vetit.1696.8973.2. [PMID: 31955560]
  • Piotr Tutka, Denis Vinnikov, Ryan J Courtney, Neal L Benowitz. Cytisine for nicotine addiction treatment: a review of pharmacology, therapeutics and an update of clinical trial evidence for smoking cessation. Addiction (Abingdon, England). 2019 11; 114(11):1951-1969. doi: 10.1111/add.14721. [PMID: 31240783]
  • 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]
  • Soo Hee Jeong, Janie Sheridan, Chris Bullen, David Newcombe, Natalie Walker, Malcolm Tingle. Ascending single dose pharmacokinetics of cytisine in healthy adult smokers. Xenobiotica; the fate of foreign compounds in biological systems. 2019 Nov; 49(11):1332-1337. doi: 10.1080/00498254.2018.1557760. [PMID: 30526213]
  • Xiaobo Huang, Min Lv, Hui Xu. Semisynthesis of novel N-acyl/sulfonyl derivatives of 5(3,5)-(di)halogenocytisines/cytisine and their pesticidal activities against Mythimna separata Walker, Tetranychus cinnabarinus Boisduval, and Sitobion avenae Fabricius. Pest management science. 2019 Oct; 75(10):2598-2609. doi: 10.1002/ps.5375. [PMID: 30740869]
  • Karol Wróblewski, Anna Petruczynik, Tomasz Tuzimski, Dominika Przygodzka, Grzegorz Buszewicz, Patrycjusz Kołodziejczyk, Piotr Tutka. Comparison of Various Chromatographic Systems for Analysis of Cytisine in Human Serum, Saliva and Pharmaceutical Formulation by HPLC with Diode Array, Fluorescence or Mass Spectrometry Detection. Molecules (Basel, Switzerland). 2019 Jul; 24(14):. doi: 10.3390/molecules24142580. [PMID: 31315205]
  • Dennis Thomas, Michael Farrell, Hayden McRobbie, Piotr Tutka, Dennis Petrie, Robert West, Mohammad Siahpush, Coral Gartner, Natalie Walker, Colin P Mendelsohn, Wayne Hall, Christine Paul, Nicholas Zwar, Stuart G Ferguson, Veronica C Boland, Robyn Richmond, Christopher M Doran, Anthony Shakeshaft, Richard P Mattick, Ryan J Courtney. The effectiveness, safety and cost-effectiveness of cytisine versus varenicline for smoking cessation in an Australian population: a study protocol for a randomized controlled non-inferiority trial. Addiction (Abingdon, England). 2019 05; 114(5):923-933. doi: 10.1111/add.14541. [PMID: 30589984]
  • Ruiying Wang, Min Wang, Shan Wang, Ke Yang, Ping Zhou, Xueheng Xie, Qi Cheng, Jingxue Ye, Guibo Sun, Xiaobo Sun. An integrated characterization of contractile, electrophysiological, and structural cardiotoxicity of Sophora tonkinensis Gapnep. in human pluripotent stem cell-derived cardiomyocytes. Stem cell research & therapy. 2019 01; 10(1):20. doi: 10.1186/s13287-018-1126-4. [PMID: 30635051]
  • Soo Hee Jeong, Janie Sheridan, David Newcombe, Malcolm Tingle. Plasma concentrations of cytisine, a commercially available plant-based alkaloid, in healthy adult smokers taking recommended doses for smoking cessation. Xenobiotica; the fate of foreign compounds in biological systems. 2018 Dec; 48(12):1245-1248. doi: 10.1080/00498254.2017.1409916. [PMID: 29168931]
  • Richard W Fitch, Barry B Snider, Quan Zhou, Bruce M Foxman, Anshul A Pandya, Jerrel L Yakel, Thao T Olson, Nour Al-Muhtasib, Yingxian Xiao, Kevin D Welch, Kip E Panter. Absolute Configuration and Pharmacology of the Poison Frog Alkaloid Phantasmidine. Journal of natural products. 2018 04; 81(4):1029-1035. doi: 10.1021/acs.jnatprod.8b00062. [PMID: 29671588]
  • Lei Yu, Bo Jiang, Zhifeng Chen, Xin Wang, Dongxue Shang, Xiaopo Zhang, Yongxue Sun, Jinghui Yang, Yubin Ji. Cytisine induces endoplasmic reticulum stress caused by calcium overload in HepG2 cells. Oncology reports. 2018 Mar; 39(3):1475-1484. doi: 10.3892/or.2018.6200. [PMID: 29328482]
  • Qi-Ming Pan, Gui-Jie Zhang, Ri-Zhen Huang, Ying-Ming Pan, Heng-Shan Wang, Dong Liang. Cytisine-type alkaloids and flavonoids from the rhizomes of Sophora tonkinensis. Journal of Asian natural products research. 2016 May; 18(5):429-35. doi: 10.1080/10286020.2015.1131680. [PMID: 26757778]
  • Yu-hang Wu, Zhong-bao Han, Jia-ze Ma, Yan He, Li-yan Liu, Shi-gang Xin, Zhan Yu. [Intermolecular Interactions between Cytisine and Bovine Serum Albumin A Synchronous Fluorescence Spectroscopic Analysis and Molecular Docking Research]. Guang pu xue yu guang pu fen xi = Guang pu. 2016 Mar; 36(3):765-9. doi: NULL. [PMID: 27400521]
  • Tomasz Pieńko, Monika Grudzień, Przemysław Paweł Taciak, Aleksander Paweł Mazurek. Cytisine basicity, solvation, logP, and logD theoretical determination as tool for bioavailability prediction. Journal of molecular graphics & modelling. 2016 Jan; 63(?):15-21. doi: 10.1016/j.jmgm.2015.11.003. [PMID: 26609940]
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  • Isabelle Pouny, Muriel Batut, Laure Vendier, Bruno David, Sirong Yi, François Sautel, Paola B Arimondo, Georges Massiot. Cytisine-like alkaloids from Ormosia hosiei Hemsl. & E.H. Wilson. Phytochemistry. 2014 Nov; 107(?):97-101. doi: 10.1016/j.phytochem.2014.07.022. [PMID: 25172516]
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  • Can Peng, Clare Stokes, Yann S Mineur, Marina R Picciotto, Chengju Tian, Christoph Eibl, Isabelle Tomassoli, Daniela Guendisch, Roger L Papke. Differential modulation of brain nicotinic acetylcholine receptor function by cytisine, varenicline, and two novel bispidine compounds: emergent properties of a hybrid molecule. The Journal of pharmacology and experimental therapeutics. 2013 Nov; 347(2):424-37. doi: 10.1124/jpet.113.206904. [PMID: 23959137]
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