Brimonidine (BioDeep_00000006624)

 

Secondary id: BioDeep_00001867998

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine

化学式: C11H10BrN5 (291.012)
中文名称: 溴莫尼定
谱图信息: 最多检出来源 Rattus norvegicus(blood) 4.19%

分子结构信息

SMILES: BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12
InChI: InChI=1S/C11H10BrN5/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8/h1-4H,5-6H2,(H2,15,16,17)

描述信息

Brimonidine is only found in individuals that have used or taken this drug. It is a drug used to treat glaucoma. It acts via decreasing aqueous humor synthesis. [Wikipedia]Brimonidine is an alpha adrenergic receptor agonist (primarily alpha-2). It has a peak ocular hypotensive effect occurring at two hours post-dosing. Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow.
S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EA - Sympathomimetics in glaucoma therapy
S - Sensory organs > S01 - Ophthalmologicals > S01G - Decongestants and antiallergics > S01GA - Sympathomimetics used as decongestants
C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D000322 - Adrenergic Agonists
C78283 - Agent Affecting Organs of Special Senses > C29705 - Anti-glaucoma Agent
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents
D - Dermatologicals
Brimonidine (UK 14304) is a full α2-adrenergic receptor (α2-AR) agonist.

同义名列表

26 个代谢物同义名

5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine; 5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline D-tartrate; 5-Bromo-6-(imidazolidinylideneamino)quinoxaline; Brimonidine tartrate (1:1), (S-(r*,r*))-isomer; 5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline; 5-Bromo-6-(imidazolin-2-ylamino)quinoxaline; Brimonidine tartrate, (R-(r*,r*))-isomer; Brimonidine tartrate (1:1); Tartrate, brimonidine; Brimonidine tartrate; Purite, brimonidine; Brimonidine purite; Ratio brimonidine; Ratio-brimonidine; RatioBrimonidine; Brimonidinum; brimonidine; Bromoxidine; Brimonidina; Alphagan p; Alphagan; Sanrosa; Mirvaso; UK 14304; AGN190342; Brimonidine



数据库引用编号

20 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 12 ADRA1A, ADRA2A, AKT1, BCL2, BDNF, CNTF, EGFR, GFAP, MAPK1, NOS3, TNK1, VEGFA
Peripheral membrane protein 1 TNK1
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 2 BCL2, EGFR
Nucleus 7 ADRA1A, AKT1, BCL2, EGFR, MAPK1, NOS3, VEGFA
cytosol 8 ADRA1A, AKT1, BCL2, GFAP, MAPK1, NOS3, PRKCQ, SST
dendrite 1 BDNF
centrosome 1 MAPK1
nucleoplasm 4 ADRA1A, AKT1, MAPK1, NOS3
Cell membrane 6 ADRA1A, ADRA2A, ADRB3, AKT1, EGFR, TNF
lamellipodium 1 AKT1
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 4 ADRA1A, ADRA2A, ADRB3, CACNA1I
Synapse 1 MAPK1
cell cortex 1 AKT1
cell junction 1 EGFR
cell surface 3 EGFR, TNF, VEGFA
glutamatergic synapse 3 ADRA2A, AKT1, EGFR
Golgi apparatus 3 MAPK1, NOS3, VEGFA
Golgi membrane 3 EGFR, INS, NOS3
lysosomal membrane 1 EGF
neuronal cell body 3 ADRA2A, SST, TNF
postsynapse 1 AKT1
synaptic vesicle 1 BDNF
endosome 1 EGFR
plasma membrane 13 ADRA1A, ADRA2A, ADRB3, AKT1, CACNA1I, EGF, EGFR, KNG1, MAPK1, NOS3, PRKCQ, TNF, TNK1
Membrane 8 AKT1, BCL2, BDNF, CACNA1I, EGF, EGFR, TNK1, VEGFA
apical plasma membrane 1 EGFR
axon 2 BDNF, CNTF
basolateral plasma membrane 2 ADRA2A, EGFR
caveola 3 ADRA1A, MAPK1, NOS3
extracellular exosome 2 EGF, KNG1
endoplasmic reticulum 2 BCL2, VEGFA
extracellular space 9 BDNF, CNTF, EGF, EGFR, INS, KNG1, SST, TNF, VEGFA
perinuclear region of cytoplasm 3 BDNF, EGFR, NOS3
adherens junction 1 VEGFA
mitochondrion 2 BCL2, MAPK1
protein-containing complex 3 AKT1, BCL2, EGFR
intracellular membrane-bounded organelle 1 ADRA1A
Single-pass type I membrane protein 1 EGFR
Secreted 4 BDNF, INS, SST, VEGFA
extracellular region 9 BDNF, CNTF, EGF, INS, KNG1, MAPK1, SST, TNF, VEGFA
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
astrocyte end-foot 1 GFAP
centriolar satellite 1 PRKCQ
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 MAPK1
Nucleus membrane 2 ADRA1A, BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 3 ADRA1A, BCL2, EGFR
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
microtubule cytoskeleton 1 AKT1
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 1 MAPK1
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
presynaptic active zone membrane 1 ADRA2A
Membrane raft 2 EGFR, TNF
pore complex 1 BCL2
Cell junction, focal adhesion 1 MAPK1
Cytoplasm, cytoskeleton, spindle 1 MAPK1
focal adhesion 2 EGFR, MAPK1
spindle 2 AKT1, MAPK1
GABA-ergic synapse 2 ADRA2A, SST
extracellular matrix 1 VEGFA
intracellular vesicle 1 EGFR
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 KNG1
secretory granule 1 VEGFA
intermediate filament 1 GFAP
Late endosome 1 MAPK1
receptor complex 3 ADRA2A, ADRB3, EGFR
ciliary basal body 1 AKT1
cell projection 1 GFAP
phagocytic cup 1 TNF
mitotic spindle 1 MAPK1
cytoskeleton 2 MAPK1, NOS3
Secreted, extracellular space 1 KNG1
blood microparticle 1 KNG1
endosome lumen 1 INS
Membrane, caveola 2 ADRA1A, MAPK1
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
cell body 1 GFAP
myelin sheath 1 BCL2
pseudopodium 1 MAPK1
intermediate filament cytoskeleton 1 GFAP
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 1 MAPK1
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 BDNF, INS, KNG1, MAPK1
platelet alpha granule lumen 3 EGF, KNG1, VEGFA
axon terminus 1 ADRA2A
voltage-gated calcium channel complex 1 CACNA1I
endocytic vesicle membrane 1 NOS3
transport vesicle 1 INS
azurophil granule lumen 1 MAPK1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 ADRA2A
immunological synapse 1 PRKCQ
neuronal dense core vesicle 1 SST
aggresome 1 PRKCQ
clathrin-coated endocytic vesicle membrane 2 EGF, EGFR
dopaminergic synapse 1 ADRA2A
cytoplasmic side of lysosomal membrane 1 GFAP
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
BAD-BCL-2 complex 1 BCL2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Taiichiro Chikama, Koichiro Shinji, Chika Yokota, Ken Hayashi, Yoshiaki Kiuchi. Inflammatory Cells and Lipid Deposits Detected by in Vivo Confocal Microscopy in Brimonidine Tartrate Ophthalmic Solution-Related Corneal Disorders: A Case Series. Ocular immunology and inflammation. 2023 Nov; 31(9):1842-1847. doi: 10.1080/09273948.2022.2137045. [PMID: 36306423]
  • Xiaohui Wang, Rui Zhang, Bin Chen, Ting Zhang, Xinghua Jin, Ping Gao. Preliminary evaluation of the efficacy and safety of brimonidine for deep sedation. Fundamental & clinical pharmacology. 2023 Aug; ?(?):. doi: 10.1111/fcp.12944. [PMID: 37612481]
  • Yunli Xu, Hongyi Li. In vitro and in vivo evaluation of brimonidine loaded silica nanoparticles-laden silicone contact lenses to manage glaucoma. Journal of biomaterials applications. 2022 08; 37(2):333-343. doi: 10.1177/08853282221090880. [PMID: 35482359]
  • Iria Brocos-Mosquera, Ane M Gabilondo, Rebeca Diez-Alarcia, Carolina Muguruza, Amaia M Erdozain, J Javier Meana, Luis F Callado. α2A- and α2C-adrenoceptor expression and functionality in postmortem prefrontal cortex of schizophrenia subjects. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. 2021 11; 52(?):3-11. doi: 10.1016/j.euroneuro.2021.05.012. [PMID: 34237656]
  • Prakash K Soni, T R Saini. Formulation design and optimization of cationic-charged liposomes of brimonidine tartrate for effective ocular drug delivery by design of experiment (DoE) approach. Drug development and industrial pharmacy. 2021 Nov; 47(11):1847-1866. doi: 10.1080/03639045.2022.2070198. [PMID: 35484943]
  • 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]
  • Sven Schnichels, José Hurst, Jan Willem de Vries, Sami Ullah, Katharina Frößl, Agnieszka Gruszka, Marina Löscher, Karl-Ulrich Bartz-Schmidt, Martin S Spitzer, Andreas Herrmann. Improved Treatment Options for Glaucoma with Brimonidine-Loaded Lipid DNA Nanoparticles. ACS applied materials & interfaces. 2021 Mar; 13(8):9445-9456. doi: 10.1021/acsami.0c18626. [PMID: 33528240]
  • Gen Suzuki, Eriko Kunikane, Wakasa Shigemi, Keisuke Shinno, Seiko Kozai, Masaaki Kurata, Akio Kawamura. Ocular and systemic pharmacokinetics of brimonidine and brinzolamide after topical administration in rabbits: comparison between fixed-combination and single-drug formulations. Current eye research. 2021 03; 46(3):380-386. doi: 10.1080/02713683.2020.1800046. [PMID: 32706598]
  • Yuka Kasuya, Ichiya Sano, Shinji Makino. Interstitial Keratitis with Lipid Keratopathy Mimicking Corneal Opacity Induced by Brimonidine Tartrate Eye Drops. Klinische Monatsblatter fur Augenheilkunde. 2020 12; 237(12):1466-1467. doi: 10.1055/a-1265-7105. [PMID: 33285590]
  • 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]
  • Sang M Lee, Ji-Eun Lee, Sung I Kim, Jae H Jung, Jonghoon Shin. Effect of topical glaucoma medication on tear lipid layer thickness in patients with unilateral glaucoma. Indian journal of ophthalmology. 2019 08; 67(8):1297-1302. doi: 10.4103/ijo.ijo_2100_18. [PMID: 31332113]
  • Xi Han, Yang Liu, Wendy R Kam, David A Sullivan. Effect of brimonidine, an α2 adrenergic agonist, on human meibomian gland epithelial cells. Experimental eye research. 2018 05; 170(?):20-28. doi: 10.1016/j.exer.2018.02.009. [PMID: 29452108]
  • Xiaochen Pang, Jiawei Li, Jiaxin Pi, Dongli Qi, Pan Guo, Nan Li, Yumei Wu, Zhidong Liu. Increasing efficacy and reducing systemic absorption of brimonidine tartrate ophthalmic gels in rabbits. Pharmaceutical development and technology. 2018 Mar; 23(3):231-239. doi: 10.1080/10837450.2017.1328693. [PMID: 28488447]
  • Noha S El-Salamouni, Ragwa M Farid, Amal H El-Kamel, Safaa S El-Gamal. Nanostructured lipid carriers for intraocular brimonidine localisation: development, in-vitro and in-vivo evaluation. Journal of microencapsulation. 2018 Jan; 35(1):102-113. doi: 10.1080/02652048.2018.1425753. [PMID: 29310481]
  • Alexandra Robciuc, Joanna Witos, Suvi-Katriina Ruokonen, Antti H Rantamäki, Pierre-Jean Pisella, Susanne K Wiedmer, Juha M Holopainen. Pure Glaucoma Drugs Are Toxic to Immortalized Human Corneal Epithelial Cells, but They Do Not Destabilize Lipid Membranes. Cornea. 2017 Oct; 36(10):1249-1255. doi: 10.1097/ico.0000000000001322. [PMID: 28825921]
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  • Noha S El-Salamouni, Ragwa M Farid, Amal H El-Kamel, Safaa S El-Gamal. Effect of sterilization on the physical stability of brimonidine-loaded solid lipid nanoparticles and nanostructured lipid carriers. International journal of pharmaceutics. 2015 Dec; 496(2):976-83. doi: 10.1016/j.ijpharm.2015.10.043. [PMID: 26498372]
  • Ko Eun Kim, Inseok Jang, Hyungwon Moon, Yu Jeong Kim, Jin Wook Jeoung, Ki Ho Park, Hyuncheol Kim. Neuroprotective Effects of Human Serum Albumin Nanoparticles Loaded With Brimonidine on Retinal Ganglion Cells in Optic Nerve Crush Model. Investigative ophthalmology & visual science. 2015 Aug; 56(9):5641-9. doi: 10.1167/iovs.15-16538. [PMID: 26313300]
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  • Maria Petersson, Zaida Diaz-Cabiale, José Angel Narváez, Kjell Fuxe, Kerstin Uvnäs-Moberg. Oxytocin increases the density of high affinity alpha(2)-adrenoceptors within the hypothalamus, the amygdala and the nucleus of the solitary tract in ovariectomized rats. Brain research. 2005 Jul; 1049(2):234-9. doi: 10.1016/j.brainres.2005.05.034. [PMID: 15967417]
  • Qing Yang, Regina Alemany, Jesús Casas, Klára Kitajka, Stephen M Lanier, Pablo V Escribá. Influence of the membrane lipid structure on signal processing via G protein-coupled receptors. Molecular pharmacology. 2005 Jul; 68(1):210-7. doi: 10.1124/mol.105.011692. [PMID: 15837842]
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  • Ullrich Hoffmann, Saskia Kuno, Gerd Franke, Christoph Fusch, Johannes P Haas. Adrenoceptor agonist poisoning after accidental oral ingestion of brimonidine eye drops. Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies. 2004 May; 5(3):282-5. doi: 10.1097/01.pcc.0000123548.73664.18. [PMID: 15115569]
  • Janaina P Dina, Teresa Feres, Antonio C M Paiva, Therezinha B Paiva. Role of membrane potential and expression of endothelial factors in restenosis after angioplasty in SHR. Hypertension (Dallas, Tex. : 1979). 2004 Jan; 43(1):131-5. doi: 10.1161/01.hyp.0000105300.74809.4f. [PMID: 14638626]
  • José Melena, Neville N Osborne. Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs. Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie. 2003 Oct; 241(10):827-33. doi: 10.1007/s00417-003-0726-5. [PMID: 12898280]
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