Vanoxerine (BioDeep_00000184910)
human metabolite blood metabolite
代谢物信息卡片
1-(2 (Bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride
化学式: C28H32F2N2O (450.2483)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1CN(CCN1CCCC2=CC=CC=C2)CCOC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F
InChI: InChI=1S/C28H32F2N2O/c29-26-12-8-24(9-13-26)28(25-10-14-27(30)15-11-25)33-22-21-32-19-17-31(18-20-32)16-4-7-23-5-2-1-3-6-23/h1-3,5-6,8-15,28H,4,7,16-22H2
描述信息
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018765 - Dopamine Uptake Inhibitors
C78272 - Agent Affecting Nervous System > C66884 - Dopamine Agonist
D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents
D049990 - Membrane Transport Modulators
同义名列表
9 个代谢物同义名
1-(2 (Bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride; 1-(2 (Bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine; 1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine; Vanoxeamine; Vanoxerinum; Vanoxerine; Vanoxerina; GBR 12909; GBR12909
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:64089
- PubChem: 3455
- HMDB: HMDB0259764
- DrugBank: DB03701
- ChEMBL: CHEMBL281594
- Wikipedia: Vanoxerine
- chemspider: 3337
- CAS: 110872-73-6
- CAS: 67469-69-6
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
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Cellular and molecular neurobiology.
2007 Sep; 27(6):757-70. doi:
10.1007/s10571-007-9162-0. [PMID: 17680357] - Georgianna G Gould, Bryan W Brooks, Alan Frazer. [(3)H] citalopram binding to serotonin transporter sites in minnow brains.
Basic & clinical pharmacology & toxicology.
2007 Sep; 101(3):203-10. doi:
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Bioorganic & medicinal chemistry.
2007 Jul; 15(13):4511-9. doi:
10.1016/j.bmc.2007.04.019. [PMID: 17467995] - Alberto Ambesi-Impiombato, Fabio Panariello, Carmela Dell'aversano, Carmine Tomasetti, Giovanni Muscettola, Andrea de Bartolomeis. Differential expression of Homer 1 gene by acute and chronic administration of antipsychotics and dopamine transporter inhibitors in the rat forebrain.
Synapse (New York, N.Y.).
2007 Jun; 61(6):429-39. doi:
10.1002/syn.20385. [PMID: 17372981] - Nobuyuki Maruoka, Tetsuhito Murata, Naoto Omata, Yasuhiro Takashima, Yasuhisa Fujibayashi, Yuji Wada. Biphasic mechanism of the toxicity induced by 1-methyl-4-phenylpyridinium ion (MPP+) as revealed by dynamic changes in glucose metabolism in rat brain slices.
Neurotoxicology.
2007 May; 28(3):672-8. doi:
10.1016/j.neuro.2007.02.008. [PMID: 17391768] - Nianhang Chen, Maarten E A Reith. Substrates and inhibitors display different sensitivity to expression level of the dopamine transporter in heterologously expressing cells.
Journal of neurochemistry.
2007 Apr; 101(2):377-88. doi:
10.1111/j.1471-4159.2006.04384.x. [PMID: 17250655] - Kathleen M Gilbert, Terrence L Boos, Christina M Dersch, Elisabeth Greiner, Arthur E Jacobson, David Lewis, Dorota Matecka, Thomas E Prisinzano, Ying Zhang, Richard B Rothman, Kenner C Rice, Carol A Venanzi. DAT/SERT selectivity of flexible GBR 12909 analogs modeled using 3D-QSAR methods.
Bioorganic & medicinal chemistry.
2007 Jan; 15(2):1146-59. doi:
10.1016/j.bmc.2006.09.070. [PMID: 17127069] - Lisa S Middleton, Subbu Apparsundaram, Kelley A King-Pospisil, Linda P Dwoskin. Nicotine increases dopamine transporter function in rat striatum through a trafficking-independent mechanism.
European journal of pharmacology.
2007 Jan; 554(2-3):128-36. doi:
10.1016/j.ejphar.2006.09.074. [PMID: 17141211] - Anthony S L Chan, Linda W C Ng, Lydia S W Poon, Winnie W Y Chan, Yung H Wong. Dopaminergic and adrenergic toxicities on SK-N-MC human neuroblastoma cells are mediated through G protein signaling and oxidative stress.
Apoptosis : an international journal on programmed cell death.
2007 Jan; 12(1):167-79. doi:
10.1007/s10495-006-0524-8. [PMID: 17136323] - A Storch, Y-I Hwang, G Bringmann, D Feineis, S Ott, R Brückner, J Schwarz. Cytotoxicity of chloral-derived beta-carbolines is not specific towards neuronal nor dopaminergic cells.
Journal of neural transmission (Vienna, Austria : 1996).
2006 Dec; 113(12):1895-901. doi:
10.1007/s00702-006-0495-5. [PMID: 16868795] - Nagendra V Chemuturi, Jon E Haraldsson, Thomas Prisinzano, Maureen Donovan. Role of dopamine transporter (DAT) in dopamine transport across the nasal mucosa.
Life sciences.
2006 Aug; 79(14):1391-8. doi:
10.1016/j.lfs.2006.04.021. [PMID: 16733058] - Keith Chiasson, Benoît Daoust, Daniel Levesque, Maria-Grazia Martinoli. Dopamine D2 agonists, bromocriptine and quinpirole, increase MPP+ -induced toxicity in PC12 cells.
Neurotoxicity research.
2006 Aug; 10(1):31-42. doi:
10.1007/bf03033332. [PMID: 17000468] - Shijun Zhang, Fernando Fernandez, Stuart Hazeldine, Jeffrey Deschamps, Juan Zhen, Maarten E A Reith, Aloke K Dutta. Further structural exploration of trisubstituted asymmetric pyran derivatives (2S,4R,5R)-2-benzhydryl-5-benzylamino-tetrahydropyran-4-ol and their corresponding disubstituted (3S,6S) pyran derivatives: a proposed pharmacophore model for high-affinity interaction with the dopamine, serotonin, and norepinephrine transporters.
Journal of medicinal chemistry.
2006 Jul; 49(14):4239-47. doi:
10.1021/jm0601699. [PMID: 16821783] - Terrence L Boos, Elisabeth Greiner, W Jason Calhoun, Thomas E Prisinzano, Barbara Nightingale, Christina M Dersch, Richard B Rothman, Arthur E Jacobson, Kenner C Rice. Structure-activity relationships of substituted N-benzyl piperidines in the GBR series: Synthesis of 4-(2-(bis(4-fluorophenyl)methoxy)ethyl)-1-(2-trifluoromethylbenzyl)piperidine, an allosteric modulator of the serotonin transporter.
Bioorganic & medicinal chemistry.
2006 Jun; 14(11):3967-73. doi:
10.1016/j.bmc.2006.01.065. [PMID: 16563775] - Sylvie Chalon, Hakan Hall, Wadad Saba, Lucette Garreau, Frédéric Dollé, Christer Halldin, Patrick Emond, Michel Bottlaender, Jean-Bernard Deloye, Julie Helfenbein, Jean-Claude Madelmont, Sylvie Bodard, Zoïa Mincheva, Jean-Claude Besnard, Denis Guilloteau. Pharmacological characterization of (E)-N-(4-fluorobut-2-enyl)-2beta-carbomethoxy-3beta-(4'-tolyl)nortropane (LBT-999) as a highly promising fluorinated ligand for the dopamine transporter.
The Journal of pharmacology and experimental therapeutics.
2006 Apr; 317(1):147-52. doi:
10.1124/jpet.105.096792. [PMID: 16339913] - Ezio Carboni, Alessandra Silvagni, Cinzia Vacca, Gaetano Di Chiara. Cumulative effect of norepinephrine and dopamine carrier blockade on extracellular dopamine increase in the nucleus accumbens shell, bed nucleus of stria terminalis and prefrontal cortex.
Journal of neurochemistry.
2006 Jan; 96(2):473-81. doi:
10.1111/j.1471-4159.2005.03556.x. [PMID: 16336224] - Gennady B Lapa, Gary D Byrd, Alla A Lapa, Evgeny A Budygin, Steven R Childers, Sara R Jones, Jill J Harp. The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines.
Bioorganic & medicinal chemistry letters.
2005 Nov; 15(22):4915-8. doi:
10.1016/j.bmcl.2005.08.028. [PMID: 16165350] - Balachandra K Gorentla, Roxanne A Vaughan. Differential effects of dopamine and psychoactive drugs on dopamine transporter phosphorylation and regulation.
Neuropharmacology.
2005 Nov; 49(6):759-68. doi:
10.1016/j.neuropharm.2005.08.011. [PMID: 16181646] - Barbara Nightingale, Christina M Dersch, Terrence L Boos, Elisabeth Greiner, William J Calhoun, Arthur E Jacobson, Kenner C Rice, Richard B Rothman. Studies of the biogenic amine transporters. XI. Identification of a 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR12909) analog that allosterically modulates the serotonin transporter.
The Journal of pharmacology and experimental therapeutics.
2005 Aug; 314(2):906-15. doi:
10.1124/jpet.105.084376. [PMID: 15860577] - Tatyana D Sotnikova, Jean-Martin Beaulieu, Larry S Barak, William C Wetsel, Marc G Caron, Raul R Gainetdinov. Dopamine-independent locomotor actions of amphetamines in a novel acute mouse model of Parkinson disease.
PLoS biology.
2005 Aug; 3(8):e271. doi:
10.1371/journal.pbio.0030271. [PMID: 16050778] - Shijun Zhang, Juan Zhen, Maarten E A Reith, Aloke K Dutta. Discovery of novel trisubstituted asymmetric derivatives of (2S,4R,5R)-2-benzhydryl-5-benzylaminotetrahydropyran-4-ol, exhibiting high affinity for serotonin and norepinephrine transporters in a stereospecific manner.
Journal of medicinal chemistry.
2005 Jul; 48(15):4962-71. doi:
10.1021/jm049021k. [PMID: 16033275] - Maarten E A Reith, Lijuan C Wang, Aloke K Dutta. Pharmacological profile of radioligand binding to the norepinephrine transporter: instances of poor indication of functional activity.
Journal of neuroscience methods.
2005 Apr; 143(1):87-94. doi:
10.1016/j.jneumeth.2004.09.015. [PMID: 15763140] - Julie Broadbent, Kathryn M Kampmueller, Sharon A Koonse. Role of dopamine in behavioral sensitization to ethanol in DBA/2J mice.
Alcohol (Fayetteville, N.Y.).
2005 Feb; 35(2):137-48. doi:
10.1016/j.alcohol.2005.03.006. [PMID: 15963427] - Juan Zhen, Soumen Maiti, Nianhang Chen, Aloke K Dutta, Maarten E A Reith. Interaction between a hydroxypiperidine analogue of 4-(2-benzhydryloxy-ethyl)-1-(4-fluorobenzyl)piperidine and Aspartate 68 in the human dopamine transporter.
European journal of pharmacology.
2004 Dec; 506(1):17-26. doi:
10.1016/j.ejphar.2004.10.028. [PMID: 15588620] - Jianjing Cao, John R Lever, Theresa Kopajtic, Jonathan L Katz, Anh T Pham, Muhsinah L Holmes, Joseph B Justice, Amy Hauck Newman. Novel azido and isothiocyanato analogues of [3-(4-phenylalkylpiperazin-1-yl)propyl]bis(4-fluorophenyl)amines as potential irreversible ligands for the dopamine transporter.
Journal of medicinal chemistry.
2004 Dec; 47(25):6128-36. doi:
10.1021/jm049670w. [PMID: 15566284] - Sárka Manáková, Katja A Puttonen, Atso Raasmaja, Pekka T Männistö. The roles of dopamine transporter and Bcl-2 protein in the protection of CV1-P cells from 6-OHDA-induced toxicity.
Toxicology letters.
2004 Dec; 154(1-2):117-23. doi:
10.1016/j.toxlet.2004.07.007. [PMID: 15475185] - Paul W Czoty, Chinnasamy R Ramanathan, Nicole H Mutschler, Alexandros Makriyannis, Jack Bergman. Drug discrimination in methamphetamine-trained monkeys: effects of monoamine transporter inhibitors.
The Journal of pharmacology and experimental therapeutics.
2004 Nov; 311(2):720-7. doi:
10.1124/jpet.104.071035. [PMID: 15240827] - Norihiro Harada, Hiroyuki Ohba, Dai Fukumoto, Takeharu Kakiuchi, Hideo Tsukada. Potential of [(18)F]beta-CFT-FE (2beta-carbomethoxy-3beta-(4-fluorophenyl)-8-(2-[(18)F]fluoroethyl)nortropane) as a dopamine transporter ligand: A PET study in the conscious monkey brain.
Synapse (New York, N.Y.).
2004 Oct; 54(1):37-45. doi:
10.1002/syn.20059. [PMID: 15300883] - Hao-Wei Shen, Yoko Hagino, Hideaki Kobayashi, Keiko Shinohara-Tanaka, Kazutaka Ikeda, Hideko Yamamoto, Toshifumi Yamamoto, Klaus-Peter Lesch, Dennis L Murphy, F Scott Hall, George R Uhl, Ichiro Sora. Regional differences in extracellular dopamine and serotonin assessed by in vivo microdialysis in mice lacking dopamine and/or serotonin transporters.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2004 Oct; 29(10):1790-9. doi:
10.1038/sj.npp.1300476. [PMID: 15226739] - Lesley J Bryan-Lluka, Marisa H Papacostas, Filip A Paczkowski, Janet C Wanstall. Nitric oxide donors inhibit 5-hydroxytryptamine (5-HT) uptake by the human 5-HT transporter (SERT).
British journal of pharmacology.
2004 Sep; 143(1):63-70. doi:
10.1038/sj.bjp.0705904. [PMID: 15302679] - Jason M Williams, Jeffery D Steketee. Characterization of dopamine transport in crude synaptosomes prepared from rat medial prefrontal cortex.
Journal of neuroscience methods.
2004 Aug; 137(2):161-5. doi:
10.1016/j.jneumeth.2004.02.022. [PMID: 15262056] - Yong Yang, Xing Liu, Jian-Hua Ding, Jing Sun, Yan Long, Fang Wang, Hong-Hong Yao, Gang Hu. Effects of iptakalim on rotenone-induced cytotoxicity and dopamine release from PC12 cells.
Neuroscience letters.
2004 Aug; 366(1):53-7. doi:
10.1016/j.neulet.2004.05.009. [PMID: 15265589] - James K Rowlett, Donna M Platt, Roger D Spealman. Cocaine-like discriminative stimulus effects of heroin: modulation by selective monoamine transport inhibitors.
The Journal of pharmacology and experimental therapeutics.
2004 Jul; 310(1):342-8. doi:
10.1124/jpet.104.065631. [PMID: 14985417] - Kimberly P Lindsey, Kristin M Wilcox, John R Votaw, Mark M Goodman, Christophe Plisson, F Ivy Carroll, Kenner C Rice, Leonard L Howell. Effects of dopamine transporter inhibitors on cocaine self-administration in rhesus monkeys: relationship to transporter occupancy determined by positron emission tomography neuroimaging.
The Journal of pharmacology and experimental therapeutics.
2004 Jun; 309(3):959-69. doi:
10.1124/jpet.103.060293. [PMID: 14982963] - Nianhang Chen, Juan Zhen, Maarten E A Reith. Mutation of Trp84 and Asp313 of the dopamine transporter reveals similar mode of binding interaction for GBR12909 and benztropine as opposed to cocaine.
Journal of neurochemistry.
2004 May; 89(4):853-64. doi:
10.1111/j.1471-4159.2004.02386.x. [PMID: 15140185] - Alexander Storch, Yu-I Hwang, Debra A Gearhart, J Warren Beach, Edward J Neafsey, Michael A Collins, Johannes Schwarz. Dopamine transporter-mediated cytotoxicity of beta-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake.
Journal of neurochemistry.
2004 May; 89(3):685-94. doi:
10.1111/j.1471-4159.2004.02397.x. [PMID: 15086525] - Vincent Castagné, Michaël Rougemont, Michel Cuenod, Kim Q Do. Low brain glutathione and ascorbic acid associated with dopamine uptake inhibition during rat's development induce long-term cognitive deficit: relevance to schizophrenia.
Neurobiology of disease.
2004 Feb; 15(1):93-105. doi:
10.1016/j.nbd.2003.09.005. [PMID: 14751774] - V Valentini, R Frau, G Di Chiara. Noradrenaline transporter blockers raise extracellular dopamine in medial prefrontal but not parietal and occipital cortex: differences with mianserin and clozapine.
Journal of neurochemistry.
2004 Feb; 88(4):917-27. doi:
10.1046/j.1471-4159.2003.02238.x. [PMID: 14756813] - V Castagné, M Cuénod, K Q Do. An animal model with relevance to schizophrenia: sex-dependent cognitive deficits in osteogenic disorder-Shionogi rats induced by glutathione synthesis and dopamine uptake inhibition during development.
Neuroscience.
2004; 123(4):821-34. doi:
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