Cinnarizine (BioDeep_00000017965)

   

human metabolite blood metabolite Chemicals and Drugs Volatile Flavor Compounds


代谢物信息卡片


1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine

化学式: C26H28N2 (368.2252368)
中文名称: 桂利嗪
谱图信息: 最多检出来源 Homo sapiens(urine) 66.67%

分子结构信息

SMILES: C(=Cc1ccccc1)CN1CCN(C(c2ccccc2)c2ccccc2)CC1
InChI: InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2

描述信息

Cinnarizine is an anti-histaminic drug which is mainly used for the control of vomiting due to motion sickness. Cinnarizine was first synthesized by Janssen Pharmaceutica in 1955. It acts by interfering with the signal transmission between vestibular apparatus of the inner ear and the vomiting centre of the hypothalamus. The disparity of signal processing between inner ear motion receptors and the visual senses is abolished, so that the confusion of brain whether the individual is moving or standing is reduced. Vomiting in motion sickness is actually a physiological compensatory mechanism of the brain to keep the individual from moving so that it can adjust to the signal perception. Cinnarizine could be also viewed as a nootropic drug because of its vasorelaxating abilities (due to calcium channel blockage), which happen mostly in brain. It is also effectively combined with other nootropics, primarily piracetam; in such combination each drug potentiate the other in boosting brain oxygen supply.
N - Nervous system > N07 - Other nervous system drugs > N07C - Antivertigo preparations > N07CA - Antivertigo preparations
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
C308 - Immunotherapeutic Agent > C29578 - Histamine-1 Receptor Antagonist
D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers
D000077264 - Calcium-Regulating Hormones and Agents
D049990 - Membrane Transport Modulators
Cinnarizine is an antihistamine and a calcium channel blocker, promote cerebral blood flow, used to treat cerebral apoplexy, post-trauma cerebral symptoms, and cerebral arteriosclerosis.

同义名列表

6 个代谢物同义名

1-(diphenylmethyl)-4-(3-phenylprop-2-en-1-yl)piperazine; 1-(Diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine; (E)-1-Benzhydryl-4-Cinnamylpiperazine; cinnarizine; Cinnarizine-d8; Cinnarizine



数据库引用编号

16 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

  • Felix Paulus, René Holm, Jef Stappaerts, Annette Bauer-Brandl. Absorption of cinnarizine from type II lipid-based formulations: Impact of lipid chain length, supersaturation, digestion, and precipitation inhibition. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2024 Jun; 197(?):106765. doi: 10.1016/j.ejps.2024.106765. [PMID: 38608735]
  • Heta H Desai, Abu T M Serajuddin. Development of lipid-based SEDDS using digestion products of long-chain triglyceride for high drug solubility: Formulation and dispersion testing. International journal of pharmaceutics. 2024 Apr; 654(?):123953. doi: 10.1016/j.ijpharm.2024.123953. [PMID: 38417725]
  • Felix Paulus, Annette Bauer-Brandl, Jef Stappaerts, René Holm. Digestion is a critical element for absorption of cinnarizine from supersaturated lipid-based type I formulations. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2024 Jan; 192(?):106634. doi: 10.1016/j.ejps.2023.106634. [PMID: 37951315]
  • Yuanyuan Zhang, Qian Li, Chunqing Wang, Lin Zhu, Furun Wang, Wencheng Jiao, Xiaomei Zhuang, Fei Xie, Lina Du, Yiguang Jin. Cinnarizine dissolving microneedles against microwave-induced brain injury. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Nov; 155(?):113779. doi: 10.1016/j.biopha.2022.113779. [PMID: 36271560]
  • Carlo Mazzatenta, Vincenzo Piccolo, Giuseppe Argenziano, Andrea Bassi. Oral cinnarizine for the treatment of COVID-19-associated chilblain-like lesions: An old drug for a new disease?. Dermatologic therapy. 2022 05; 35(5):e15365. doi: 10.1111/dth.15365. [PMID: 35137498]
  • Jiaming Zhang, Yu Zhang, Xiaoyu Liu, Xiaolan Xu, Yingchao Li, Tianhong Zhang. Supercritical fluid chromatography tandem mass spectrometry employed with evaporation-free liquid-liquid extraction for the rapid analysis of cinnarizine in rat plasma. Journal of separation science. 2022 Feb; 45(4):968-975. doi: 10.1002/jssc.202100825. [PMID: 34889052]
  • Gisela Ramirez, Anna C Pham, Andrew J Clulow, Malinda Salim, Adrian Hawley, Ben J Boyd. Sustained absorption of delamanid from lipid-based formulations as a path to reduced frequency of administration. Drug delivery and translational research. 2021 06; 11(3):1236-1244. doi: 10.1007/s13346-020-00851-z. [PMID: 32935235]
  • Alexandra-Roxana Ilie, Brendan T Griffin, Maria Vertzoni, Martin Kuentz, Ruzica Kolakovic, Anke Prudic-Paus, Ahmed Malash, Hugo Bohets, Jilly Herman, René Holm. Exploring precipitation inhibitors to improve in vivo absorption of cinnarizine from supersaturated lipid-based drug delivery systems. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2021 Apr; 159(?):105691. doi: 10.1016/j.ejps.2020.105691. [PMID: 33359616]
  • Anthony Lai, Yasemin Sahbaz, Leigh Ford, Tri-Hung Nguyen, Shadabul Haque, Hywel D Williams, Hassan Benameur, Peter J Scammells, Christopher J H Porter. Stabilising disproportionation of lipophilic ionic liquid salts in lipid-based formulations. International journal of pharmaceutics. 2021 Mar; 597(?):120292. doi: 10.1016/j.ijpharm.2021.120292. [PMID: 33581479]
  • Joscha Brinkmann, Isabel Becker, Peter Kroll, Christian Luebbert, Gabriele Sadowski. Predicting the API partitioning between lipid-based drug delivery systems and water. International journal of pharmaceutics. 2021 Feb; 595(?):120266. doi: 10.1016/j.ijpharm.2021.120266. [PMID: 33486017]
  • Huan Wang, Shiji Li, Lili Liu, Jing Wang, Yongli Wang, Wei Guo. Interactions between dipfluzine-based complexes and cytochrome P450 enzymes: Information on salt, cocrystal, and salt cocrystal complexes. Environmental toxicology and pharmacology. 2020 Nov; 80(?):103487. doi: 10.1016/j.etap.2020.103487. [PMID: 32889110]
  • Huan Wang, Shiji Li, Xiaohui Wang, Chaoxing He, Tianshi Wang, Yongli Wang, Wei Guo. Vasodilation activity of dipfluzine metabolites in isolated rat basilar arteries and their underlying mechanisms. Environmental toxicology and pharmacology. 2020 Oct; 79(?):103430. doi: 10.1016/j.etap.2020.103430. [PMID: 32544426]
  • 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]
  • Hong Zhang, Wenzhong Tang, Yushun Chen, Wei Yin. Disinfection threatens aquatic ecosystems. Science (New York, N.Y.). 2020 Apr; 368(6487):146-147. doi: 10.1126/science.abb8905. [PMID: 32273461]
  • Timothy Pas, Alessandra Bergonzi, Emiel Michiels, Frederic Rousseau, Joost Schymkowitz, Robin Koekoekx, Christian Clasen, Bjorn Vergauwen, Guy Van den Mooter. Preparation of Amorphous Solid Dispersions by Cryomilling: Chemical and Physical Concerns Related to Active Pharmaceutical Ingredients and Carriers. Molecular pharmaceutics. 2020 03; 17(3):1001-1013. doi: 10.1021/acs.molpharmaceut.9b01265. [PMID: 31961692]
  • Alexandra-Roxana Ilie, Brendan T Griffin, Ruzica Kolakovic, Maria Vertzoni, Martin Kuentz, René Holm. Supersaturated lipid-based drug delivery systems - exploring impact of lipid composition type and drug properties on supersaturability and physical stability. Drug development and industrial pharmacy. 2020 Mar; 46(3):356-364. doi: 10.1080/03639045.2020.1721526. [PMID: 31975613]
  • Kapilkumar Vithani, Alvaro Goyanes, Vincent Jannin, Abdul W Basit, Simon Gaisford, Ben J Boyd. A Proof of Concept for 3D Printing of Solid Lipid-Based Formulations of Poorly Water-Soluble Drugs to Control Formulation Dispersion Kinetics. Pharmaceutical research. 2019 May; 36(7):102. doi: 10.1007/s11095-019-2639-y. [PMID: 31098846]
  • Syaza Y Binte Abu Bakar, Malinda Salim, Andrew J Clulow, Adrian Hawley, Ben J Boyd. Revisiting dispersible milk-drug tablets as a solid lipid formulation in the context of digestion. International journal of pharmaceutics. 2019 Jan; 554(?):179-189. doi: 10.1016/j.ijpharm.2018.10.069. [PMID: 30391337]
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  • Sheshank Sethi, Bhumika Mangla, Sunil Kamboj, Vikas Rana. A QbD approach for the fabrication of immediate and prolong buoyant cinnarizine tablet using polyacrylamide-g-corn fibre gum. International journal of biological macromolecules. 2018 Oct; 117(?):350-361. doi: 10.1016/j.ijbiomac.2018.05.178. [PMID: 29807074]
  • Kapilkumar Vithani, Adrian Hawley, Vincent Jannin, Colin Pouton, Ben J Boyd. Solubilisation behaviour of poorly water-soluble drugs during digestion of solid SMEDDS. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2018 Sep; 130(?):236-246. doi: 10.1016/j.ejpb.2018.07.006. [PMID: 29981444]
  • Ahmad Abdul-Wahhab Shahba, Abid Riaz Ahmed, Fars Kaed Alanazi, Kazi Mohsin, Sayed Ibrahim Abdel-Rahman. Multi-Layer Self-Nanoemulsifying Pellets: an Innovative Drug Delivery System for the Poorly Water-Soluble Drug Cinnarizine. AAPS PharmSciTech. 2018 Jul; 19(5):2087-2102. doi: 10.1208/s12249-018-0990-7. [PMID: 29696614]
  • Paul Joyce, Clive A Prestidge. Synergistic effect of PLGA nanoparticles and submicron triglyceride droplets in enhancing the intestinal solubilisation of a lipophilic weak base. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Jun; 118(?):40-48. doi: 10.1016/j.ejps.2018.03.018. [PMID: 29559402]
  • Suman Jyoti Deka, Ashalata Roy, Debasis Manna, Vishal Trivedi. Integrating virtual screening and biochemical experimental approach to identify potential anti-cancer agents from drug databank. Journal of bioinformatics and computational biology. 2018 06; 16(3):1850002. doi: 10.1142/s0219720018500026. [PMID: 29566637]
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  • Paul Joyce, Rokhsana Yasmin, Achal Bhatt, Ben J Boyd, Anna Pham, Clive A Prestidge. Comparison across Three Hybrid Lipid-Based Drug Delivery Systems for Improving the Oral Absorption of the Poorly Water-Soluble Weak Base Cinnarizine. Molecular pharmaceutics. 2017 11; 14(11):4008-4018. doi: 10.1021/acs.molpharmaceut.7b00676. [PMID: 28950059]
  • Saeed Hajirezaee, Alireza Mirvaghefi, Hamid Farahmand, Naser Agh. NMR-based metabolomic study on the toxicological effects of pesticide, diazinon on adaptation to sea water by endangered Persian sturgeon, Acipenser persicus fingerlings. Chemosphere. 2017 Oct; 185(?):213-226. doi: 10.1016/j.chemosphere.2017.07.016. [PMID: 28697427]
  • Hanady Ajine Bibi, René Holm, Annette Bauer-Brandl. Simultaneous lipolysis/permeation in vitro model, for the estimation of bioavailability of lipid based drug delivery systems. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2017 Aug; 117(?):300-307. doi: 10.1016/j.ejpb.2017.05.001. [PMID: 28478159]
  • A T Larsen, R Holm, A Müllertz. Solution or suspension - Does it matter for lipid based systems? In vivo studies of chase dosing lipid vehicles with aqueous suspensions of a poorly soluble drug. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2017 Aug; 117(?):308-314. doi: 10.1016/j.ejpb.2017.04.023. [PMID: 28465239]
  • Mette D Mosgaard, Philip J Sassene, Huiling Mu, Thomas Rades, Anette Müllertz. High-Throughput Lipolysis in 96-Well Plates for Rapid Screening of Lipid-Based Drug Delivery Systems. Journal of pharmaceutical sciences. 2017 04; 106(4):1183-1186. doi: 10.1016/j.xphs.2016.12.026. [PMID: 28057543]
  • Scheyla D V S Siqueira, Anette Müllertz, Kirsten Gräeser, Georgia Kasten, Huiling Mu, Thomas Rades. Influence of drug load and physical form of cinnarizine in new SNEDDS dosing regimens: in vivo and in vitro evaluations. The AAPS journal. 2017 03; 19(2):587-594. doi: 10.1208/s12248-016-0038-4. [PMID: 28070714]
  • Yusuke Tanaka, Ayaka Kawakami, Ami Nanimatsu, Misaki Horio, Jumpei Matsuoka, Takami Wada, Satoshi Kasaoka, Hiroshi Yoshikawa. In vivo evaluation of supersaturation/precipitation/re-dissolution behavior of cinnarizine, a lipophilic weak base, in the gastrointestinal tract: the key process of oral absorption. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2017 Jan; 96(?):464-471. doi: 10.1016/j.ejps.2016.10.023. [PMID: 27773836]
  • Rokhsana Yasmin, Shasha Rao, Kristen Bremmell, Clive Prestidge. Synergistic role of solid lipid and porous silica in improving the oral delivery of weakly basic poorly water soluble drugs. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2017 Jan; 96(?):508-514. doi: 10.1016/j.ejps.2016.10.026. [PMID: 27793717]
  • Jamal Khan, Thomas Rades, Ben J Boyd. Lipid-Based Formulations Can Enable the Model Poorly Water-Soluble Weakly Basic Drug Cinnarizine To Precipitate in an Amorphous-Salt Form During In Vitro Digestion. Molecular pharmaceutics. 2016 11; 13(11):3783-3793. doi: 10.1021/acs.molpharmaceut.6b00594. [PMID: 27631273]
  • Hussein O Ammar, Mahmoud Ghorab, Rabab Kamel, Alaa H Salama. Design and optimization of gastro-retentive microballoons for enhanced bioavailability of cinnarizine. Drug delivery and translational research. 2016 06; 6(3):210-24. doi: 10.1007/s13346-016-0280-4. [PMID: 26832133]
  • Niels Erik Olesen, Peter Westh, René Holm. A heuristic model to quantify the impact of excess cyclodextrin on oral drug absorption from aqueous solution. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2016 May; 102(?):142-51. doi: 10.1016/j.ejpb.2016.03.011. [PMID: 26969263]
  • Martin Lau Christiansen, Rene Holm, Bertil Abrahamsson, Jette Jacobsen, Jakob Kristensen, Jens Rikardt Andersen, Anette Müllertz. Effect of food intake and co-administration of placebo self-nanoemulsifying drug delivery systems on the absorption of cinnarizine in healthy human volunteers. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2016 Mar; 84(?):77-82. doi: 10.1016/j.ejps.2016.01.011. [PMID: 26775868]
  • Anna C Pham, Linda Hong, Oliver Montagnat, Cameron J Nowell, Tri-Hung Nguyen, Ben J Boyd. In Vivo Formation of Cubic Phase in Situ after Oral Administration of Cubic Phase Precursor Formulation Provides Long Duration Gastric Retention and Absorption for Poorly Water-Soluble Drugs. Molecular pharmaceutics. 2016 Jan; 13(1):280-6. doi: 10.1021/acs.molpharmaceut.5b00784. [PMID: 26567591]
  • Anna C Pham, Tri-Hung Nguyen, Cameron J Nowell, Bim Graham, Ben J Boyd. Examining the gastrointestinal transit of lipid-based liquid crystalline systems using whole-animal imaging. Drug delivery and translational research. 2015 Dec; 5(6):566-74. doi: 10.1007/s13346-015-0253-z. [PMID: 26328930]
  • Philip J Sassene, Mette D Mosgaard, Korbinian Löbmann, Huiling Mu, Flemming H Larsen, Thomas Rades, Anette Müllertz. Elucidating the Molecular Interactions Occurring during Drug Precipitation of Weak Bases from Lipid-Based Formulations: A Case Study with Cinnarizine and a Long Chain Self-Nanoemulsifying Drug Delivery System. Molecular pharmaceutics. 2015 Nov; 12(11):4067-76. doi: 10.1021/acs.molpharmaceut.5b00498. [PMID: 26393273]
  • Mette D Mosgaard, Philip Sassene, Huiling Mu, Thomas Rades, Anette Müllertz. Development of a high-throughput in vitro intestinal lipolysis model for rapid screening of lipid-based drug delivery systems. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2015 Aug; 94(?):493-500. doi: 10.1016/j.ejpb.2015.06.028. [PMID: 26159837]
  • Yasemin Sahbaz, Hywel D Williams, Tri-Hung Nguyen, Jessica Saunders, Leigh Ford, Susan A Charman, Peter J Scammells, Christopher J H Porter. Transformation of poorly water-soluble drugs into lipophilic ionic liquids enhances oral drug exposure from lipid based formulations. Molecular pharmaceutics. 2015 Jun; 12(6):1980-91. doi: 10.1021/mp500790t. [PMID: 25905624]
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  • Philip Carsten Christophersen, Martin Lau Christiansen, Rene Holm, Jakob Kristensen, Jette Jacobsen, Bertil Abrahamsson, Anette Müllertz. Fed and fasted state gastro-intestinal in vitro lipolysis: In vitro in vivo relations of a conventional tablet, a SNEDDS and a solidified SNEDDS. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2014 Jun; 57(?):232-9. doi: 10.1016/j.ejps.2013.09.007. [PMID: 24056027]
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  • Tri-Hung Nguyen, Tracey Hanley, Christopher J H Porter, Ian Larson, Ben J Boyd. Phytantriol and glyceryl monooleate cubic liquid crystalline phases as sustained-release oral drug delivery systems for poorly water soluble drugs I. Phase behaviour in physiologically-relevant media. The Journal of pharmacy and pharmacology. 2010 Jul; 62(7):844-55. doi: 10.1211/jpp.62.06.0005. [PMID: 20636872]
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