Fosinopril (BioDeep_00000002441)

 

Secondary id: BioDeep_00000397579

human metabolite blood metabolite


代谢物信息卡片


(2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-(1-oxopropoxy)propoxy]-(4-phenylbutyl)phosphoryl]-1-oxoethyl]-2-pyrrolidinecarboxylic acid

化学式: C30H46NO7P (563.3012)
中文名称: 福辛普利
谱图信息: 最多检出来源 Homo sapiens(blood) 24.42%

分子结构信息

SMILES: CCC(=O)OC(C(C)C)OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N2CC(CC2C(=O)O)C3CCCCC3
InChI: InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)

描述信息

Fosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.
C - Cardiovascular system > C09 - Agents acting on the renin-angiotensin system > C09A - Ace inhibitors, plain > C09AA - Ace inhibitors, plain
D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D000806 - Angiotensin-Converting Enzyme Inhibitors
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3324

同义名列表

36 个代谢物同义名

(2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-(1-oxopropoxy)propoxy]-(4-phenylbutyl)phosphoryl]-1-oxoethyl]-2-pyrrolidinecarboxylic acid; (2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid; (2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylate; (S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid; (2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid; (2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid; (S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylate; (2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate; 4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid; Fosinopril, (1(s*(r*)),2 alpha,4 alpha)-(D-pro)-isomer; Bristol myers squibb brand OF fosinopril sodium; Bristol-myers squibb brand OF fosinopril sodium; Fosinopril, (1(s*(r*)),2 alpha,4 beta)-isomer; Fosinopril, (1(s*(s*)),2 alpha,4 beta)-isomer; Merck lipha santé brand OF fosinopril; Schwarz brand OF fosinopril sodium; Squibb brand OF fosinopril sodium; Esteve brand OF fosinopril sodium; Ferrer brand OF fosinopril sodium; Sanol brand OF fosinopril sodium; Sodium, fosinopril; Fosinopril sodium; Tensocardil; Tenso stop; Fosenopril; fosinopril; Fositens; Fosinorm; Hiperlex; Monopril; Dynacil; Fozitec; Fosinil; Staril; Newace; Fosinopril



数据库引用编号

37 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

2 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(2)

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 6 ACE, ALB, EDN1, MME, NOS3, VEGFA
Peripheral membrane protein 1 GORASP1
Nucleus 3 ALB, NOS3, VEGFA
cytosol 3 ALB, NOS3, NRK
dendrite 1 MME
trans-Golgi network 1 MME
centrosome 1 ALB
nucleoplasm 1 NOS3
Cell membrane 6 ACE, AGTR1, AGTR2, MME, TNF, VCAM1
Cytoplasmic side 1 GORASP1
Multi-pass membrane protein 3 AGTR1, AGTR2, CACNA1I
Golgi apparatus membrane 1 GORASP1
Synapse 1 MME
cell surface 4 MME, TNF, VCAM1, VEGFA
Golgi apparatus 5 ALB, GORASP1, NOS3, VCAM1, VEGFA
Golgi membrane 3 GORASP1, INS, NOS3
neuronal cell body 2 MME, TNF
sarcolemma 1 VCAM1
synaptic vesicle 1 MME
Lysosome 1 ACE
Presynapse 1 MME
endosome 1 ACE
plasma membrane 11 ACE, AGTR1, AGTR2, CACNA1I, KL, KNG1, MME, NOS3, REN, TNF, VCAM1
Membrane 9 ACE, AGTR1, CACNA1I, KL, MME, NRK, REN, VCAM1, VEGFA
apical plasma membrane 1 KL
axon 1 MME
brush border 1 MME
caveola 1 NOS3
extracellular exosome 6 ACE, ALB, KL, KNG1, MME, VCAM1
endoplasmic reticulum 3 ALB, VCAM1, VEGFA
extracellular space 13 ACE, ALB, CRP, EDN1, IL6, INS, KL, KNG1, LPA, REN, TNF, VCAM1, VEGFA
perinuclear region of cytoplasm 1 NOS3
adherens junction 1 VEGFA
protein-containing complex 1 ALB
filopodium 1 VCAM1
Single-pass type I membrane protein 3 ACE, KL, VCAM1
Secreted 8 ACE, ALB, CRP, EDN1, IL6, INS, REN, VEGFA
extracellular region 12 ACE, ALB, CRP, EDN1, IL6, INS, KL, KNG1, LPA, REN, TNF, VEGFA
basal part of cell 1 EDN1
[Isoform 2]: Secreted 1 KL
anchoring junction 1 ALB
external side of plasma membrane 3 ACE, TNF, VCAM1
Secreted, extracellular space, extracellular matrix 1 VEGFA
cytoplasmic vesicle 1 MME
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 2 MME, VCAM1
apical part of cell 2 REN, VCAM1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 MME, TNF
Apical cell membrane 1 KL
Membrane raft 2 MME, TNF
focal adhesion 1 MME
cis-Golgi network 1 GORASP1
extracellular matrix 1 VEGFA
collagen-containing extracellular matrix 1 KNG1
secretory granule 1 VEGFA
ciliary basal body 1 ALB
phagocytic cup 1 TNF
cytoskeleton 1 NOS3
podosome 1 VCAM1
centriole 1 ALB
Secreted, extracellular space 1 KNG1
brush border membrane 1 ACE
spindle pole 1 ALB
blood microparticle 2 ALB, KNG1
sperm midpiece 1 ACE
endosome lumen 1 INS
microvillus 1 VCAM1
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
basal plasma membrane 1 ACE
secretory granule lumen 1 INS
secretory granule membrane 1 MME
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 ALB, IL6, INS, KNG1
platelet alpha granule lumen 3 ALB, KNG1, VEGFA
voltage-gated calcium channel complex 1 CACNA1I
endocytic vesicle membrane 1 NOS3
transport vesicle 2 EDN1, INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
[Isoform 1]: Cell membrane 1 KL
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
rough endoplasmic reticulum lumen 1 EDN1
Weibel-Palade body 1 EDN1
interleukin-6 receptor complex 1 IL6
neuron projection terminus 1 MME
plasma lipoprotein particle 1 LPA
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
[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
[Vascular cell adhesion protein 1]: Cell membrane 1 VCAM1
[Soluble Vascular Cell Adhesion Molecule-1]: Secreted 1 VCAM1
alpha9-beta1 integrin-vascular cell adhesion molecule-1 complex 1 VCAM1
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Klotho peptide]: Secreted 1 KL


文献列表

  • Jun Wu, Yingtao Xu, Zikai Geng, Jianqing Zhou, Qingping Xiong, Zhimeng Xu, Hailun Li, Yun Han. Chitosan oligosaccharide alleviates renal fibrosis through reducing oxidative stress damage and regulating TGF-β1/Smads pathway. Scientific reports. 2022 11; 12(1):19160. doi: 10.1038/s41598-022-20719-1. [PMID: 36357407]
  • Giuseppe Mancia, Rita Facchetti, Fosca Quarti-Trevano, Guido Grassi. Antihypertensive drug treatment in white-coat hypertension: data from the Plaque HYpertension Lipid-Lowering Italian Study. Journal of hypertension. 2022 10; 40(10):1909-1917. doi: 10.1097/hjh.0000000000003176. [PMID: 35881420]
  • Junjun Li, Fuxing Ge, Shana Wuken, Shungang Jiao, Panlong Chen, Meiwen Huang, Xiaoli Gao, Juan Liu, Pengfei Tu, Xingyun Chai, Luqi Huang. Zerumbone, a humulane sesquiterpene from Syringa pinnatifolia, attenuates cardiac fibrosis by inhibiting of the TGF-β1/Smad signaling pathway after myocardial infarction in mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jun; 100(?):154078. doi: 10.1016/j.phymed.2022.154078. [PMID: 35405613]
  • Yao Lin, Yaxi Cui, Yue Yuan, Lu Gao, Qirui Li, Xiaolan Huang, Yanyan Liu, Lin Shi. Plasma Fibroblast Growth Factor 23 as a Predictor for Fosinopril Therapeutic Efficacy in Pediatric Primary Hypertension. Journal of the American Heart Association. 2022 04; 11(7):e023182. doi: 10.1161/jaha.121.023182. [PMID: 35322670]
  • Swati D Bhende, Murali Balaram Varanasi, Konde Abbulu. A sensitive and efficient LC-MS/MS method for the bioanalysis of fosinopril diacid from human plasma and its application for a bioequivalence study in humans. Biomedical chromatography : BMC. 2021 May; 35(5):e5047. doi: 10.1002/bmc.5047. [PMID: 33352616]
  • Jia Tang, Chao Wu, Jian Cao, Liang Wang. Fabry disease with early-onset ventricular dilation: A case report. Medicine. 2020 Sep; 99(39):e22326. doi: 10.1097/md.0000000000022326. [PMID: 32991443]
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  • Ping Sun, Ning Xu, Yan Li, Yang Han. Destruction of the blood-retina barrier in diabetic retinopathy depends on angiotensin-converting enzyme-mediated TGF-β1/Smad signaling pathway activation. International immunopharmacology. 2020 Aug; 85(?):106686. doi: 10.1016/j.intimp.2020.106686. [PMID: 32531714]
  • Z Yang, Y W Zhan, Y Y Huang, W Huang, F Zhan, S D Lin. Regulation of epithelial mesenchymal transition by the renin-angiotensin system: a role for klotho in renal tubular epithelial cells. Journal of biological regulators and homeostatic agents. 2020 Jan; 34(1):57-67. doi: 10.23812/19-410-a-27. [PMID: 32466632]
  • Marianne A Mahrouse. Simultaneous ultraperformance liquid chromatography/tandem mass spectrometry determination of four antihypertensive drugs in human plasma using hydrophilic-lipophilic balanced reversed-phase sorbents sample preparation protocol. Biomedical chromatography : BMC. 2018 Dec; 32(12):e4362. doi: 10.1002/bmc.4362. [PMID: 30109716]
  • Kai-Li Zhou, Dong-Qi Pan, Yan-Yue Lou, Jie-Hua Shi. Intermolecular interaction of fosinopril with bovine serum albumin (BSA): The multi-spectroscopic and computational investigation. Journal of molecular recognition : JMR. 2018 08; 31(8):e2716. doi: 10.1002/jmr.2716. [PMID: 29659061]
  • Cai Yue, Guanhong Li, Yubing Wen, Xuemei Li, Ruitong Gao. Early Renin-angiotensin System Blockade Improved Short-term and Longterm Renal Outcomes in Systemic Lupus Erythematosus Patients with Antiphospholipid-associated Nephropathy. The Journal of rheumatology. 2018 05; 45(5):655-662. doi: 10.3899/jrheum.170561. [PMID: 29449503]
  • Cheng Xue, Chenchen Zhou, Bo Yang, Jiayi Lv, Bing Dai, Shengqiang Yu, Yi Wang, Guanren Zhao, Changlin Mei. Comparison of efficacy and safety between benidipine and hydrochlorothiazide in fosinopril-treated hypertensive patients with chronic kidney disease: protocol for a randomised controlled trial. BMJ open. 2017 02; 7(2):e013672. doi: 10.1136/bmjopen-2016-013672. [PMID: 28237959]
  • Rongzhong Huang, Yuxing Feng, Ying Wang, Xiaoxia Qin, Narayan Dhruvaraj Melgiri, Yang Sun, Xingsheng Li. Comparative Efficacy and Safety of Antihypertensive Agents for Adult Diabetic Patients with Microalbuminuric Kidney Disease: A Network Meta-Analysis. PloS one. 2017; 12(1):e0168582. doi: 10.1371/journal.pone.0168582. [PMID: 28045910]
  • Kewen Xue, Gao Li, Xiao Sun, Yang Hu, Lei Hu, Jiangeng Huang, Luqin Si. Simultaneous quantification of fosinopril and its active metabolite fosinoprilat in rat plasma by UFLC-MS/MS: Application of formic acid in the stabilization of an ester-containing drug. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 May; 990(?):141-9. doi: 10.1016/j.jchromb.2015.03.028. [PMID: 25875586]
  • Haifeng Huang, Liping Hu, Jiancong Lin, Xiaoxiao Zhu, Weiling Cui, Wenming Xu. Effect of fosinopril on chemerin and VEGF expression in diabetic nephropathy rats. International journal of clinical and experimental pathology. 2015; 8(9):11470-4. doi: . [PMID: 26617877]
  • Matthew A Weir, Jamie L Fleet, Stephanie N Dixon, Arsh K Jain, Matthew Oliver, Ron Wald, Chris McIntyre, Amit X Garg. Angiotensin Converting Enzyme Inhibitor Dialyzability and Outcomes in Older Patients Receiving Hemodialysis. Blood purification. 2015; 40(3):232-42. doi: 10.1159/000438821. [PMID: 26382240]
  • John E Moulder, Eric P Cohen, Brian L Fish. Mitigation of experimental radiation nephropathy by renin-equivalent doses of angiotensin converting enzyme inhibitors. International journal of radiation biology. 2014 Sep; 90(9):762-8. doi: 10.3109/09553002.2014.938375. [PMID: 24991882]
  • Haojun Zhang, Tingting Zhao, Yuewen Gong, Xi Dong, Weiku Zhang, Sifan Sun, Hua Wang, Yanting Gu, Xiaoguang Lu, Meihua Yan, Ping Li. Attenuation of diabetic nephropathy by Chaihuang-Yishen granule through anti-inflammatory mechanism in streptozotocin-induced rat model of diabetics. Journal of ethnopharmacology. 2014; 151(1):556-64. doi: 10.1016/j.jep.2013.11.020. [PMID: 24269779]
  • R G Singh, M Rajak, B Ghosh, A Agrawal, G P Dubey. Comparative evaluation of fosinopril and herbal drug Dioscorea bulbifera in patients of diabetic nephropathy. Saudi journal of kidney diseases and transplantation : an official publication of the Saudi Center for Organ Transplantation, Saudi Arabia. 2013 Jul; 24(4):737-42. doi: 10.4103/1319-2442.113866. [PMID: 23816723]
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  • Ya-chen Zhang, Yong Tang, Min Zhang, Jian Chen, Qing Zhou, Ying-gang Sun, Man-tian Chen, Wei-ping Xu. Fosinopril attenuates the doxorubicin-induced cardiomyopathy by restoring the function of sarcoplasmic reticulum. Cell biochemistry and biophysics. 2012 Dec; 64(3):205-11. doi: 10.1007/s12013-012-9386-6. [PMID: 22729889]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
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  • Giovambattista De Sarro, Eugenio Donato Di Paola, Santo Gratteri, Pietro Gareri, Vincenzo Rispoli, Antonio Siniscalchi, Giovanni Tripepi, Luca Gallelli, Rita Citraro, Emilio Russo. Fosinopril and zofenopril, two angiotensin-converting enzyme (ACE) inhibitors, potentiate the anticonvulsant activity of antiepileptic drugs against audiogenic seizures in DBA/2 mice. Pharmacological research. 2012 Mar; 65(3):285-96. doi: 10.1016/j.phrs.2011.11.005. [PMID: 22107891]
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  • Shan Tu, Qiaoling Zhou, Rong Tang, Tianfeng Tang, Sai Hu, Xiang Ao. [Proapoptotic effect of angiotensin II on renal tubular epithelial cells and protective effect of Cordyceps sinensis]. Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences. 2012 Jan; 37(1):67-72. doi: 10.3969/j.issn.1672-7347.2012.01.012. [PMID: 22349383]
  • Jun Li, Yi-Xuan Cao, Dong Wang, Ping Zhou, Xiao-Min Yang. [Effect of Astragalus and Salvia's effective components and their compatibility on JAK/STAT pathway]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Sep; 34(9):1388-91. doi: . [PMID: 22260007]
  • Raymond Q Migrino, Mark Bowers, Leanne Harmann, Robert Prost, John F LaDisa. Carotid plaque regression following 6-month statin therapy assessed by 3T cardiovascular magnetic resonance: comparison with ultrasound intima media thickness. Journal of cardiovascular magnetic resonance : official journal of the Society for Cardiovascular Magnetic Resonance. 2011 Aug; 13(?):37. doi: 10.1186/1532-429x-13-37. [PMID: 21812992]
  • Fawzi Elsebaei, Yan Zhu. Fast gradient high performance liquid chromatography method with UV detection for simultaneous determination of seven angiotensin converting enzyme inhibitors together with hydrochlorothiazide in pharmaceutical dosage forms and spiked human plasma and urine. Talanta. 2011 Jul; 85(1):123-9. doi: 10.1016/j.talanta.2011.03.037. [PMID: 21645680]
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  • Gültekin Süleymanlar, Cengiz Utaş, Turgay Arinsoy, Kenan Ateş, Bülent Altun, Mehmet Riza Altiparmak, Tevfik Ecder, Mehmet Emin Yilmaz, Taner Çamsari, Ali Başçi, Ali Riza Odabas, Kamil Serdengeçti. A population-based survey of Chronic REnal Disease In Turkey--the CREDIT study. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2011 Jun; 26(6):1862-71. doi: 10.1093/ndt/gfq656. [PMID: 21051501]
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  • Rong Tang, Qiaoling Zhou, Zhichun Liu, Zhou Xiao, Veeraragoo Pouranan. Effects of fosinopril and losartan on renal Klotho expression and oxidative stress in spontaneously hypertensive rats. Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences. 2011 Jan; 36(1):27-33. doi: 10.3969/j.issn.1672-7347.2011.01.005. [PMID: 21311136]
  • Rong Tang, Qiao-Ling Zhou, Xiang Ao, Wei-Sheng Peng, Pouranan Veeraragoo, Tian-Feng Tang. Fosinopril and losartan regulate klotho gene and nicotinamide adenine dinucleotide phosphate oxidase expression in kidneys of spontaneously hypertensive rats. Kidney & blood pressure research. 2011; 34(5):350-7. doi: 10.1159/000326806. [PMID: 21646815]
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