Perphenazine (BioDeep_00000002090)

 

Secondary id: BioDeep_00000398776

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol

化学式: C21H26ClN3OS (403.1485)
中文名称: 奋乃静
谱图信息: 最多检出来源 Homo sapiens(blood) 88.08%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Perphenazine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/perphenazine (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002090). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c1ccc2c(c1)N(CCCN1CCN(CC1)CCO)c1cc(ccc1S2)Cl
InChI: InChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2

描述信息

Perphenazine is only found in individuals that have used or taken this drug. It is an antipsychotic phenothiazine derivative with actions and uses similar to those of chlorpromazine. [PubChem]Binds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone and vomiting centre. Perphenazine also binds the alpha andrenergic receptor. This receptors action is mediated by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.
N - Nervous system > N05 - Psycholeptics > N05A - Antipsychotics > N05AB - Phenothiazines with piperazine structure
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents
D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents > D018492 - Dopamine Antagonists
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants
C78272 - Agent Affecting Nervous System > C29710 - Antipsychotic Agent
Perphenazine is an orally active dopamine receptor and histamine-1 receptor antagonist, with Ki values of 0.56 nM (D2), 0.43 nM (D3), 6 nM (5-HT2A), respectively. Perphenazine also binds to Alpha-1A adrenergic receptor. Perphenazine inhibits cancer cell proliferation, and induces apoptosis. Perphenazine can be used in the research of mental disease, cancer, inflammation[1][3][5].

同义名列表

22 个代谢物同义名

2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol; gamma-(4-(beta-Hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine; 2-(4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazinyl)ethanol; 2-Chloro-10-(3-(4-(2-hydroxyethyl)piperazin-1-yl)propyl)phenothiazine; 4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethanol; Γ-(4-(β-hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine; g-(4-(b-Hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine; 4-[3-(2-Chlorophenothiazin-10-yl)propyl]-1-piperazineethanol; 4-(3-(2-Chlorophenothiazin-10-yl)propyl)-1-piperazineethanol; Chlorperphenazine; Chlorpiprazine; Perphenazinum; perphenazine; Ethaperazine; Etaperazine; Perfenazina; Perphenazin; Perfenazine; Etaperazin; Trilafon; PZC; Perphenazine



数据库引用编号

19 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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 ABCB1, ANXA5, CASP3, CYP2C19, CYP2D6, CYP3A4, ITPR3, MITF
Peripheral membrane protein 2 ACHE, ANXA5
Endoplasmic reticulum membrane 5 CYP1A2, CYP2C19, CYP2D6, CYP3A4, ITPR3
Nucleus 3 ACHE, CASP3, MITF
cytosol 3 ANXA5, CASP3, MITF
dendrite 3 DRD2, HTR2A, HTR7
nucleoplasm 4 ATP2B1, CASP3, ITPR3, MITF
Cell membrane 7 ABCB1, ACHE, ATP2B1, DRD2, HTR2A, HTR3A, HTR7
Cleavage furrow 1 HTR3A
Cell projection, axon 1 HTR2A
Multi-pass membrane protein 8 ABCB1, ATP2B1, DRD2, HTR2A, HTR3A, HTR7, ITPR3, NNT
Golgi apparatus membrane 1 DRD2
Synapse 5 ACHE, ATP2B1, DRD2, HTR3A, HTR7
cell surface 2 ABCB1, ACHE
dendritic shaft 1 HTR2A
glutamatergic synapse 4 ATP2B1, CASP3, DRD2, HTR2A
Golgi apparatus 1 ACHE
Golgi membrane 2 DRD2, INS
lysosomal membrane 2 CP, MITF
mitochondrial inner membrane 1 NNT
neuromuscular junction 1 ACHE
neuronal cell body 3 CASP3, HTR2A, ITPR3
postsynapse 1 HTR3A
presynaptic membrane 3 ATP2B1, DRD2, HTR2A
sarcolemma 1 ANXA5
Presynapse 1 HTR2A
acrosomal vesicle 1 DRD2
plasma membrane 10 ABCB1, ACHE, ATP2B1, CP, CYP2C19, DRD2, HTR2A, HTR3A, HTR7, ITPR3
synaptic vesicle membrane 2 ATP2B1, DRD2
Membrane 9 ABCB1, ACHE, ANXA5, ATP2B1, CYP2D6, CYP3A4, HTR3A, ITPR3, NNT
apical plasma membrane 1 ABCB1
axon 2 DRD2, HTR2A
basolateral plasma membrane 1 ATP2B1
brush border 1 ITPR3
caveola 1 HTR2A
extracellular exosome 4 ABCB1, ANXA5, ATP2B1, CP
Lysosome membrane 1 MITF
endoplasmic reticulum 2 CYP2D6, ITPR3
extracellular space 4 ACHE, CP, GNRH1, INS
perinuclear region of cytoplasm 1 ACHE
mitochondrion 2 CYP2D6, NNT
protein-containing complex 1 MITF
intracellular membrane-bounded organelle 5 ATP2B1, CYP1A2, CYP2C19, CYP2D6, CYP3A4
Microsome membrane 3 CYP1A2, CYP2D6, CYP3A4
postsynaptic density 1 CASP3
Secreted 4 ACHE, CP, INS, TRH
extracellular region 6 ACHE, ANXA5, CP, GNRH1, INS, TRH
Single-pass membrane protein 1 CYP2D6
Extracellular side 1 ACHE
ciliary membrane 1 DRD2
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 1 ANXA5
dendritic spine 1 DRD2
perikaryon 1 DRD2
cytoplasmic vesicle 1 HTR2A
nucleolus 1 ITPR3
apical part of cell 1 ITPR3
postsynaptic membrane 3 DRD2, HTR2A, HTR3A
Apical cell membrane 1 ABCB1
Mitochondrion inner membrane 1 NNT
Matrix side 1 NNT
focal adhesion 1 ANXA5
GABA-ergic synapse 1 DRD2
basement membrane 1 ACHE
sarcoplasmic reticulum 1 ITPR3
collagen-containing extracellular matrix 1 ANXA5
secretory granule 1 TRH
lateral plasma membrane 2 ATP2B1, DRD2
nuclear outer membrane 1 ITPR3
Postsynaptic cell membrane 1 HTR3A
receptor complex 1 ITPR3
Zymogen granule membrane 1 ANXA5
neuron projection 1 HTR3A
cilium 1 DRD2
chromatin 1 MITF
cell projection 1 ATP2B1
blood microparticle 1 CP
non-motile cilium 1 DRD2
serotonin-activated cation-selective channel complex 1 HTR3A
transmembrane transporter complex 1 HTR3A
Basolateral cell membrane 1 ATP2B1
Lipid-anchor, GPI-anchor 1 ACHE
sperm flagellum 1 DRD2
endosome lumen 1 INS
Membrane, caveola 1 HTR2A
cell body fiber 1 HTR2A
Cell projection, dendrite 1 HTR2A
respiratory chain complex 1 NNT
Presynaptic cell membrane 1 ATP2B1
side of membrane 1 ACHE
trans-Golgi network membrane 1 HTR7
secretory granule lumen 1 INS
secretory granule membrane 1 ITPR3
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 CP, INS
axon terminus 1 DRD2
endocytic vesicle 1 DRD2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 ATP2B1
neurofilament 1 HTR2A
vesicle membrane 1 ANXA5
platelet dense tubular network membrane 1 ITPR3
synaptic cleft 1 ACHE
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
dopaminergic synapse 1 DRD2
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR3
transport vesicle membrane 1 ITPR3
endothelial microparticle 1 ANXA5
photoreceptor ribbon synapse 1 ATP2B1
G protein-coupled receptor complex 1 DRD2
cytoplasmic side of endoplasmic reticulum membrane 1 ITPR3
[Isoform H]: Cell membrane 1 ACHE
G protein-coupled serotonin receptor complex 1 HTR2A


文献列表

  • Ragnhild Birkeland Waade, Vigdis Solhaug, Gudrun Høiseth. Impact of CYP2D6 on serum concentrations of flupentixol, haloperidol, perphenazine and zuclopenthixol. British journal of clinical pharmacology. 2021 05; 87(5):2228-2235. doi: 10.1111/bcp.14626. [PMID: 33118660]
  • 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]
  • Zahra Saghafi, Mojdeh Mohammadi, Mohammad Mehdi Mahboobian, Katayoun Derakhshandeh. Preparation, characterization, and in vivo evaluation of perphenazine-loaded nanostructured lipid carriers for oral bioavailability improvement. Drug development and industrial pharmacy. 2021 Mar; 47(3):509-520. doi: 10.1080/03639045.2021.1892745. [PMID: 33650445]
  • Parnian Mohammadi, Reza Mahjub, Mojdeh Mohammadi, Katayoun Derakhshandeh, Ali Ghaleiha, Mohammad Mehdi Mahboobian. Pharmacokinetics and brain distribution studies of perphenazine-loaded solid lipid nanoparticles. Drug development and industrial pharmacy. 2021 Jan; 47(1):146-152. doi: 10.1080/03639045.2020.1862172. [PMID: 33307865]
  • Parisa Abbasi Farsani, Reza Mahjub, Mojdeh Mohammadi, Seyed Sajad Oliaei, Mohammad Mehdi Mahboobian. Development of Perphenazine-Loaded Solid Lipid Nanoparticles: Statistical Optimization and Cytotoxicity Studies. BioMed research international. 2021; 2021(?):6619195. doi: 10.1155/2021/6619195. [PMID: 33997026]
  • Vikas Shalibhadra Trishla, Pulugurtha Bharadwaja Kirti. Structure-function relationship of Gossypium hirsutum NAC transcription factor, GhNAC4 with regard to ABA and abiotic stress responses. Plant science : an international journal of experimental plant biology. 2021 Jan; 302(?):110718. doi: 10.1016/j.plantsci.2020.110718. [PMID: 33288024]
  • Michał Otręba, Leon Kośmider, Anna Rzepecka-Stojko. Antiviral activity of chlorpromazine, fluphenazine, perphenazine, prochlorperazine, and thioridazine towards RNA-viruses. A review. European journal of pharmacology. 2020 Nov; 887(?):173553. doi: 10.1016/j.ejphar.2020.173553. [PMID: 32949606]
  • Yang Chen, Yunxia Cui, Xiao Sun, Huiwen Wu, Manjiao Ou, Yunzhe Tang, Shuaishuai Ni, Xiaokang Li, Jin Zhu, Fei Mao, Yudong Wang, Jian Li. Repurposing of antipsychotics perphenazine for the treatment of endometrial cancer. Bioorganic & medicinal chemistry letters. 2020 07; 30(14):127239. doi: 10.1016/j.bmcl.2020.127239. [PMID: 32527541]
  • Min-Jeong Heo, Soo Young Choi, Chanmi Lee, Yeong Min Choi, In-Sook An, Seunghee Bae, Sungkwan An, Jin Hyuk Jung. Perphenazine Attenuates the Pro-Inflammatory Responses in Mouse Models of Th2-Type Allergic Dermatitis. International journal of molecular sciences. 2020 May; 21(9):. doi: 10.3390/ijms21093241. [PMID: 32375285]
  • 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]
  • Maryam Shamsayei, Yadollah Yamini, Hamid Asiabi. Electrochemically controlled fiber-in-tube solid-phase microextraction method for the determination of trace amounts of antipsychotic drugs in biological samples. Journal of separation science. 2018 Sep; 41(18):3598-3606. doi: 10.1002/jssc.201800417. [PMID: 30039621]
  • Christopher F McCain, Leah B Namey, Oliver Freudenreich. Lamotrigine Cross-Reactivity With Phencyclidine in Rapid Urine Toxicology in a Research Study. The primary care companion for CNS disorders. 2018 Jul; 20(4):. doi: 10.4088/pcc.17l02192. [PMID: 30084548]
  • Narjes Hendouei, Samaneh Farnia, Farhad Mohseni, Azadeh Salehi, Maedeh Bagheri, Faezeh Shadfar, Fatemeh Barzegar, Seyed Davood Hoseini, Jamshid Yazdani Charati, Fatemeh Shaki. Alterations in oxidative stress markers and its correlation with clinical findings in schizophrenic patients consuming perphenazine, clozapine and risperidone. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jul; 103(?):965-972. doi: 10.1016/j.biopha.2018.04.109. [PMID: 29710513]
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  • Thomas Beresford, Jennifer Buchanan, Elizabeth Brie Thumm, Chad Emrick, David Weitzenkamp, Patrick J Ronan. Late Reduction of Cocaine Cravings in a Randomized, Double-Blind Trial of Aripiprazole vs Perphenazine in Schizophrenia and Comorbid Cocaine Dependence. Journal of clinical psychopharmacology. 2017 Dec; 37(6):657-663. doi: 10.1097/jcp.0000000000000789. [PMID: 28984746]
  • Mehdi Safdarian, Zahra Ramezani, Ata A Ghadiri. Facile synthesis of magnetic molecularly imprinted polymer: Perphenazine template and its application in urine and plasma analysis. Journal of chromatography. A. 2016 Jul; 1455(?):28-36. doi: 10.1016/j.chroma.2016.05.083. [PMID: 27302687]
  • Matthew H Slawson, Kamisha L Johnson-Davis. Quantitation of Haloperidol, Fluphenazine, Perphenazine, and Thiothixene in Serum or Plasma Using Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS). Methods in molecular biology (Clifton, N.J.). 2016; 1383(?):49-57. doi: 10.1007/978-1-4939-3252-8_6. [PMID: 26660173]
  • Hani Raoul Khouzam. Identification and management of tardive dyskinesia: A case series and literature review. Postgraduate medicine. 2015; 127(7):726-37. doi: 10.1080/00325481.2015.1074031. [PMID: 26216578]
  • Kristina Melkersson, Moira Lewitt, Kerstin Hall. Higher serum concentrations of tyrosine and glutamate in schizophrenia patients treated with clozapine, compared to in those treated with conventional antipsychotics. Neuro endocrinology letters. 2015; 36(5):465-80. doi: NULL. [PMID: 26707048]
  • Hiroyoshi Takeuchi, Gagan Fervaha, Hiroyuki Uchida, Takefumi Suzuki, Robert R Bies, David Grönte, Gary Remington. Impact of once- versus twice-daily perphenazine dosing on clinical outcomes: an analysis of the CATIE data. The Journal of clinical psychiatry. 2014 May; 75(5):506-11. doi: 10.4088/jcp.13m08695. [PMID: 24569099]
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  • Lei Xu, Libo Li, Jianshe Huang, Tianyan You. Analysis of perphenazine and fluphenazine by capillary electrophoresis coupled with tris (2,2'-bipyridyl) ruthenium (II) electrochemiluminescence detection. Talanta. 2014 Jan; 118(?):1-6. doi: 10.1016/j.talanta.2013.09.048. [PMID: 24274263]
  • Ling Wang, Yan-Yu Xiao, Ming-Lei Chen, Fan Zeng, Li Zong. Pharmacokinetics of orally disintegrating tablets of perphenazine/hydroxypropyl-beta-cyclodextrin inclusion complex in rabbits. Die Pharmazie. 2013 Oct; 68(10):800-4. doi: NULL. [PMID: 24273883]
  • JoEtta M Juenke, Paul I Brown, Francis M Urry, Kamisha L Johnson-Davis, Gwendolyn A McMillin. Simultaneous UPLC-MS/MS assay for the detection of the traditional antipsychotics haloperidol, fluphenazine, perphenazine, and thiothixene in serum and plasma. Clinica chimica acta; international journal of clinical chemistry. 2013 Aug; 423(?):32-4. doi: 10.1016/j.cca.2013.04.014. [PMID: 23618971]
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  • Amit Gupta, Ashish Dhir, Anil Kumar, S K Kulkarni. Protective effect of cyclooxygenase (COX)-inhibitors against drug-induced catatonia and MPTP-induced striatal lesions in rats. Pharmacology, biochemistry, and behavior. 2009 Dec; 94(2):219-26. doi: 10.1016/j.pbb.2009.07.018. [PMID: 19666045]
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  • Elina Turunen, Marko Lehtonen, Tomi Järvinen, Pekka Jarho. Development and validation of a gas chromatographic-mass spectrometric method for quantitative determination of perphenazine in rabbit plasma after sublingual administration. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Sep; 872(1-2):51-7. doi: 10.1016/j.jchromb.2008.07.010. [PMID: 18667368]
  • Jonathan M Meyer, Vicki G Davis, Joseph P McEvoy, Donald C Goff, Henry A Nasrallah, Sonia M Davis, Gail L Daumit, John Hsiao, Marvin S Swartz, T Scott Stroup, Jeffrey A Lieberman. Impact of antipsychotic treatment on nonfasting triglycerides in the CATIE Schizophrenia Trial phase 1. Schizophrenia research. 2008 Aug; 103(1-3):104-9. doi: 10.1016/j.schres.2008.04.023. [PMID: 18534821]
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  • Cecilia Pedernera, José Luis Ruiz, Glòria Castells, Xavier Manteca, Carles Cristòfol. HPLC quantification of perphenazine in sheep plasma: application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Jul; 854(1-2):308-12. doi: 10.1016/j.jchromb.2007.04.038. [PMID: 17512805]
  • Erica Duncan, Boadie W Dunlop, William Boshoven, Sandra L Woolson, Robert M Hamer, Lawrence S Phillips. Relative risk of glucose elevation during antipsychotic exposure in a Veterans Administration population. International clinical psychopharmacology. 2007 Jan; 22(1):1-11. doi: 10.1097/01.yic.0000224792.44276.20. [PMID: 17159454]
  • Weifen Niu, Fei Nie, Jiuru Lu. Chemiluminescence sensor for the determination of perphenazine based on a molecular imprinted polymer. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2006 Jul; 22(7):971-5. doi: 10.2116/analsci.22.971. [PMID: 16837748]
  • Jeffrey A Lieberman, T Scott Stroup, Joseph P McEvoy, Marvin S Swartz, Robert A Rosenheck, Diana O Perkins, Richard S E Keefe, Sonia M Davis, Clarence E Davis, Barry D Lebowitz, Joanne Severe, John K Hsiao. Effectiveness of antipsychotic drugs in patients with chronic schizophrenia. The New England journal of medicine. 2005 Sep; 353(12):1209-23. doi: 10.1056/nejmoa051688. [PMID: 16172203]
  • Chiara Bastianon, Roberta Zanoni, Giorgia Miolo, Sergio Caffieri, Elena Reddi. Mitochondria and plasma membrane as targets of UVA-induced toxicity of neuroleptic drugs fluphenazine, perphenazine and thioridazine. The international journal of biochemistry & cell biology. 2005 Apr; 37(4):901-8. doi: 10.1016/j.biocel.2004.11.016. [PMID: 15694848]
  • Mirjam Talvik, Anna-Lena Nordström, Niels-Erik Larsen, Aurelija Jucaite, Simon Cervenka, Christer Halldin, Lars Farde. A cross-validation study on the relationship between central D2 receptor occupancy and serum perphenazine concentration. Psychopharmacology. 2004 Sep; 175(2):148-53. doi: 10.1007/s00213-004-1802-1. [PMID: 15007534]
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