Diflunisal (BioDeep_00000002715)

 

Secondary id: BioDeep_00000408865

human metabolite blood metabolite


代谢物信息卡片


2,4-Difluoro-4-hydroxy-3-biphenylcarboxylic acid

化学式: C13H8F2O3 (250.0441)
中文名称: 二氟尼柳D3, 二氟苯水杨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 52.41%

分子结构信息

SMILES: C1=CC(=C(C=C1C2=C(C=C(C=C2)F)F)C(=O)O)O
InChI: InChI=1S/C13H8F2O3/c14-8-2-3-9(11(15)6-8)7-1-4-12(16)10(5-7)13(17)18/h1-6,16H,(H,17,18)

描述信息

Diflunisal, a salicylate derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with pharmacologic actions similar to other prototypical NSAIAs. Diflunisal possesses anti-inflammatory, analgesic and antipyretic activity. Though its mechanism of action has not been clearly established, most of its actions appear to be associated with inhibition of prostaglandin synthesis via the arachidonic acid pathway. Diflunisal is used to relieve pain accompanied with inflammation and in the symptomatic treatment of rheumatoid arthritis and osteoarthritis.
N - Nervous system > N02 - Analgesics > N02B - Other analgesics and antipyretics > N02BA - Salicylic acid and derivatives
D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors
D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D004791 - Enzyme Inhibitors
KEIO_ID D058

同义名列表

31 个代谢物同义名

2,4-Difluoro-4-hydroxy-3-biphenylcarboxylic acid; 2-(Hydroxy)-5-(2,4-difluorophenyl)benzoic acid; 2,4-Difluoro-4-hydroxy-3-biphenylcarboxylate; 5-(2,4-difluorophenyl)-2-hydroxybenzoic acid; 2-(Hydroxy)-5-(2,4-difluorophenyl)benzoate; Merck sharp and dohme brand OF diflunisal; Cahill may roberts brand OF diflunisal; 5-(2,4-Difluorophenyl)salicylic acid; 5-(2,4-Difluorophenyl)salicylate; Novopharm brand OF diflunisal; Frosst sa brand OF diflunisal; Nu-pharm brand OF diflunisal; Nu pharm brand OF diflunisal; Diflunisal novopharm brand; Apotex brand OF diflunisal; Merck brand OF diflunisal; Novo diflunisal; Novo-diflunisal; NovoDiflunisal; Apo diflunisal; Apo-diflunisal; ApoDiflunisal; Nu-diflunisal; Diflunisal-d3; Nu diflunisal; NuDiflunisal; diflunisal; Dolobid; Dolobis; Dolocid; Diflunisal



数据库引用编号

24 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 11 ACMSD, ALB, ALOX5, AXIN2, CLU, EGFR, FAP, FGR, PTGS1, PTGS2, XDH
Peripheral membrane protein 5 ACHE, ALOX5, CLU, PTGS1, PTGS2
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 7 EGFR, PTGS1, PTGS2, SLN, UGT1A1, UGT1A9, UGT2B7
Mitochondrion membrane 1 CLU
Nucleus 5 ACHE, ALB, AXIN2, CLU, EGFR
cytosol 7 ACMSD, ALB, ALOX5, AXIN2, CLU, FGR, XDH
mitochondrial membrane 1 CLU
centrosome 2 ALB, AXIN2
nucleoplasm 1 ALOX5
Cell membrane 5 ACHE, EGFR, FAP, FGR, TNF
Lipid-anchor 1 FGR
Cytoplasmic side 2 CLU, FGR
lamellipodium 1 FAP
ruffle membrane 3 EGFR, FAP, FGR
Early endosome membrane 1 EGFR
Synapse 2 ACHE, CLU
cell junction 1 EGFR
cell surface 5 ACHE, CLU, EGFR, FAP, TNF
glutamatergic synapse 1 EGFR
Golgi apparatus 4 ACHE, ALB, CLU, PTGS1
Golgi membrane 1 EGFR
mitochondrial inner membrane 2 CLU, FGR
neuromuscular junction 1 ACHE
neuronal cell body 1 TNF
Cytoplasm, cytosol 2 ALOX5, CLU
endosome 1 EGFR
plasma membrane 8 ACHE, AXIN2, EGFR, F2, FAP, FGR, TNF, UGT1A1
Membrane 8 ACHE, ACMSD, EGFR, FAP, SLN, UGT1A1, UGT1A9, UGT2B7
apical plasma membrane 1 EGFR
basolateral plasma membrane 1 EGFR
caveola 1 PTGS2
extracellular exosome 7 ALB, CLU, F2, FGR, PTGS1, SERPINA7, TTR
endoplasmic reticulum 5 ALB, CLU, PTGS2, UGT1A1, UGT1A9
extracellular space 11 ACHE, ALB, ALOX5, CLU, EGFR, F2, FAP, SERPINA7, TNF, TTR, XDH
perinuclear region of cytoplasm 5 ACHE, ALOX5, CLU, EGFR, UGT1A1
mitochondrion 1 CLU
protein-containing complex 4 ALB, CLU, EGFR, PTGS2
intracellular membrane-bounded organelle 2 CLU, PTGS1
Microsome membrane 2 PTGS1, PTGS2
Single-pass type I membrane protein 1 EGFR
Secreted 5 ACHE, ALB, CLU, F2, TTR
extracellular region 9 ACHE, ALB, ALOX5, CLU, F2, FGR, SERPINA7, TNF, TTR
Single-pass membrane protein 4 SLN, UGT1A1, UGT1A9, UGT2B7
basal part of cell 1 FAP
Extracellular side 1 ACHE
anchoring junction 2 ALB, FAP
photoreceptor outer segment 1 PTGS1
Nucleus membrane 1 ALOX5
nuclear membrane 2 ALOX5, EGFR
external side of plasma membrane 1 TNF
actin cytoskeleton 1 FGR
beta-catenin destruction complex 1 AXIN2
apical part of cell 1 FAP
recycling endosome 1 TNF
Single-pass type II membrane protein 2 FAP, TNF
Cell projection, ruffle membrane 1 FAP
Cytoplasm, perinuclear region 3 ALOX5, CLU, UGT1A1
Mitochondrion inner membrane 1 FGR
Membrane raft 2 EGFR, TNF
focal adhesion 2 EGFR, FAP
Peroxisome 1 XDH
basement membrane 1 ACHE
intracellular vesicle 1 EGFR
sarcoplasmic reticulum 2 SLN, XDH
Mitochondrion intermembrane space 1 FGR
mitochondrial intermembrane space 1 FGR
collagen-containing extracellular matrix 2 CLU, F2
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 EGFR
neuron projection 2 PTGS1, PTGS2
ciliary basal body 1 ALB
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 3 ALB, CLU, F2
Lipid-anchor, GPI-anchor 1 ACHE
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Endomembrane system 1 PTGS1
side of membrane 1 ACHE
basal plasma membrane 1 EGFR
[Isoform 4]: Cytoplasm 1 CLU
synaptic membrane 1 EGFR
Microsome 1 CLU
ficolin-1-rich granule lumen 1 ALOX5
secretory granule lumen 2 ALOX5, FGR
Golgi lumen 1 F2
endoplasmic reticulum lumen 3 ALB, F2, PTGS2
nuclear matrix 1 ALOX5
platelet alpha granule lumen 2 ALB, CLU
azurophil granule lumen 1 TTR
Sarcoplasmic reticulum membrane 1 SLN
aggresome 1 FGR
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
[Isoform 2]: Cytoplasm 1 FAP
clathrin-coated endocytic vesicle membrane 1 EGFR
synaptic cleft 1 ACHE
apical dendrite 1 CLU
spherical high-density lipoprotein particle 1 CLU
lamellipodium membrane 1 FAP
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 CLU
Cell projection, lamellipodium membrane 1 FAP
Cell projection, invadopodium membrane 1 FAP
neurofibrillary tangle 1 CLU
endoplasmic reticulum chaperone complex 1 UGT1A1
Cytoplasmic vesicle, secretory vesicle, chromaffin granule 1 CLU
chromaffin granule 1 CLU
Nucleus intermembrane space 1 ALOX5
[Isoform 6]: Cytoplasm 1 CLU
perinuclear endoplasmic reticulum lumen 1 CLU
[Isoform H]: Cell membrane 1 ACHE
cytochrome complex 1 UGT1A1
ciliary transition fiber 1 ALB
[Prolyl endopeptidase FAP]: Cell surface 1 FAP
[Antiplasmin-cleaving enzyme FAP, soluble form]: Secreted 1 FAP
peptidase complex 1 FAP
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Omar K Siddiqi, Yuliya Y Mints, John L Berk, Lawreen Connors, Gheorghe Doros, Deepa M Gopal, Shivangi Kataria, Graham Lohrmann, Alexandra R Pipilas, Frederick L Ruberg. Diflunisal treatment is associated with improved survival for patients with early stage wild-type transthyretin (ATTR) amyloid cardiomyopathy: the Boston University Amyloidosis Center experience. Amyloid : the international journal of experimental and clinical investigation : the official journal of the International Society of Amyloidosis. 2022 Jun; 29(2):71-78. doi: 10.1080/13506129.2021.2000388. [PMID: 35083944]
  • Galal Magdy, Ahmed F Abdel Hakiem, Fathalla Belal, Ahmed M Abdel-Megied. A novel quality by design approach for development and validation of a green reversed-phase HPLC method with fluorescence detection for the simultaneous determination of lesinurad, febuxostat, and diflunisal: Application to human plasma. Journal of separation science. 2021 Jun; 44(11):2177-2188. doi: 10.1002/jssc.202100016. [PMID: 33773042]
  • 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]
  • Luke T Nelson, Ryan J Paxman, Jin Xu, Bill Webb, Evan T Powers, Jeffery W Kelly. Blinded potency comparison of transthyretin kinetic stabilisers by subunit exchange in human plasma. Amyloid : the international journal of experimental and clinical investigation : the official journal of the International Society of Amyloidosis. 2021 Mar; 28(1):24-29. doi: 10.1080/13506129.2020.1808783. [PMID: 32811187]
  • Takeshi Yokoyama, Mineyuki Mizuguchi. Transthyretin Amyloidogenesis Inhibitors: From Discovery to Current Developments. Journal of medicinal chemistry. 2020 12; 63(23):14228-14242. doi: 10.1021/acs.jmedchem.0c00934. [PMID: 32914975]
  • Lidia Ciccone, Susanna Nencetti, Nicolo Tonali, Carole Fruchart-Gaillard, William Shepard, Elisa Nuti, Caterina Camodeca, Armando Rossello, Elisabetta Orlandini. Monoaryl derivatives as transthyretin fibril formation inhibitors: Design, synthesis, biological evaluation and structural analysis. Bioorganic & medicinal chemistry. 2020 09; 28(18):115673. doi: 10.1016/j.bmc.2020.115673. [PMID: 32828431]
  • Graham Lohrmann, Alexandra Pipilas, Roberta Mussinelli, Deepa M Gopal, John L Berk, Lawreen H Connors, Nirupama Vellanki, Jennifer Hellawell, Omar K Siddiqi, Jonathan Fox, Mathew S Maurer, Frederick L Ruberg. Stabilization of Cardiac Function With Diflunisal in Transthyretin (ATTR) Cardiac Amyloidosis. Journal of cardiac failure. 2020 Sep; 26(9):753-759. doi: 10.1016/j.cardfail.2019.11.024. [PMID: 31805416]
  • Michael R Duff, Scott A Gabel, Lars C Pedersen, Eugene F DeRose, Juno M Krahn, Elizabeth E Howell, Robert E London. The Structural Basis for Nonsteroidal Anti-Inflammatory Drug Inhibition of Human Dihydrofolate Reductase. Journal of medicinal chemistry. 2020 08; 63(15):8314-8324. doi: 10.1021/acs.jmedchem.0c00546. [PMID: 32658475]
  • Gergő Dargó, Dávid Bajusz, Kristóf Simon, Judit Müller, György T Balogh. Human Serum Albumin Binding in a Vial: A Novel UV-pH Titration Method To Assist Drug Design. Journal of medicinal chemistry. 2020 02; 63(4):1763-1774. doi: 10.1021/acs.jmedchem.0c00046. [PMID: 31995375]
  • 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]
  • Xabier Rios, Vanessa Gómez-Vallejo, Abraham Martín, Unai Cossío, Miguel Ángel Morcillo, Mobina Alemi, Isabel Cardoso, Jordi Quintana, Jesús Jiménez-Barbero, Ellen Y Cotrina, Gregorio Valencia, Gemma Arsequell, Jordi Llop. Radiochemical examination of transthyretin (TTR) brain penetration assisted by iododiflunisal, a TTR tetramer stabilizer and a new candidate drug for AD. Scientific reports. 2019 09; 9(1):13672. doi: 10.1038/s41598-019-50071-w. [PMID: 31541162]
  • Joel N Buxbaum. Treatment of hereditary and acquired forms of transthyretin amyloidosis in the era of personalized medicine: the role of randomized controlled trials. Amyloid : the international journal of experimental and clinical investigation : the official journal of the International Society of Amyloidosis. 2019 Jun; 26(2):55-65. doi: 10.1080/13506129.2019.1575201. [PMID: 30907141]
  • Stephen Boulton, Rajeevan Selvaratnam, Rashik Ahmed, Katherine Van, Xiaodong Cheng, Giuseppe Melacini. Mechanisms of Specific versus Nonspecific Interactions of Aggregation-Prone Inhibitors and Attenuators. Journal of medicinal chemistry. 2019 05; 62(10):5063-5079. doi: 10.1021/acs.jmedchem.9b00258. [PMID: 31074269]
  • Bhawna Chaubey, Samanwita Pal. Binding Interaction of Organofluorine-Serum Albumin: A Comparative Ligand-Detected 19F NMR Analysis. The journal of physical chemistry. B. 2018 10; 122(40):9409-9418. doi: 10.1021/acs.jpcb.8b06583. [PMID: 30222347]
  • Mark Miller, Arindom Pal, Wabel Albusairi, Hyun Joo, Beverly Pappas, Md Tariqul Haque Tuhin, Dengpan Liang, Raghavendra Jampala, Fang Liu, Jared Khan, Marjon Faaij, Miki Park, William Chan, Isabella Graef, Robert Zamboni, Neil Kumar, Jonathan Fox, Uma Sinha, Mamoun Alhamadsheh. Enthalpy-Driven Stabilization of Transthyretin by AG10 Mimics a Naturally Occurring Genetic Variant That Protects from Transthyretin Amyloidosis. Journal of medicinal chemistry. 2018 09; 61(17):7862-7876. doi: 10.1021/acs.jmedchem.8b00817. [PMID: 30133284]
  • Göknil Pelin Coşkun, Teodora Djikic, Taha Bartu Hayal, Nezaket Türkel, Kemal Yelekçi, Fikrettin Şahin, Ş Güniz Küçükgüzel. Synthesis, Molecular Docking and Anticancer Activity of Diflunisal Derivatives as Cyclooxygenase Enzyme Inhibitors. Molecules (Basel, Switzerland). 2018 Aug; 23(8):. doi: 10.3390/molecules23081969. [PMID: 30082676]
  • Elena S Klimtchuk, Tatiana Prokaeva, Nicholas M Frame, Hassan A Abdullahi, Brian Spencer, Surendra Dasari, Haili Cui, John L Berk, Paul J Kurtin, Lawreen H Connors, Olga Gursky. Unusual duplication mutation in a surface loop of human transthyretin leads to an aggressive drug-resistant amyloid disease. Proceedings of the National Academy of Sciences of the United States of America. 2018 07; 115(28):E6428-E6436. doi: 10.1073/pnas.1802977115. [PMID: 29941560]
  • Amanpreet Kaur, Bhupinder Singh Bhoop, Sanjay Chhibber, Gajanand Sharma, Vijay Singh Gondil, Om Prakash Katare. Supramolecular nano-engineered lipidic carriers based on diflunisal-phospholipid complex for transdermal delivery: QbD based optimization, characterization and preclinical investigations for management of rheumatoid arthritis. International journal of pharmaceutics. 2017 Nov; 533(1):206-224. doi: 10.1016/j.ijpharm.2017.09.041. [PMID: 28943207]
  • Mobina Alemi, Sara C Silva, Isabel Santana, Isabel Cardoso. Transthyretin stability is critical in assisting beta amyloid clearance- Relevance of transthyretin stabilization in Alzheimer's disease. CNS neuroscience & therapeutics. 2017 Jul; 23(7):605-619. doi: 10.1111/cns.12707. [PMID: 28570028]
  • Alketa Tarushi, Chrisoula Kakoulidou, Catherine P Raptopoulou, Vassilis Psycharis, Dimitris P Kessissoglou, Ioanna Zoi, Athanasios N Papadopoulos, George Psomas. Zinc complexes of diflunisal: Synthesis, characterization, structure, antioxidant activity, and in vitro and in silico study of the interaction with DNA and albumins. Journal of inorganic biochemistry. 2017 05; 170(?):85-97. doi: 10.1016/j.jinorgbio.2017.02.010. [PMID: 28231454]
  • Spyros Perontsis, Antonios G Hatzidimitriou, Athanasios N Papadopoulos, George Psomas. Nickel-diflunisal complexes: synthesis, characterization, in vitro antioxidant activity and interaction with DNA and albumins. Journal of inorganic biochemistry. 2016 09; 162(?):9-21. doi: 10.1016/j.jinorgbio.2016.06.003. [PMID: 27318424]
  • Amanpreet Kaur, Shishu Goindi, Om Prakash Katare. Formulation, characterisation and in vivo evaluation of lipid-based nanocarrier for topical delivery of diflunisal. Journal of microencapsulation. 2016 Aug; 33(5):475-86. doi: 10.1080/02652048.2016.1216189. [PMID: 27499126]
  • Sofia Tsiliou, Lida-Aikaterini Kefala, Antonios G Hatzidimitriou, Dimitris P Kessissoglou, Franc Perdih, Athanasios N Papadopoulos, Iztok Turel, George Psomas. Cobalt(II) complexes with non-steroidal anti-inflammatory drugs and α-diimines. Journal of inorganic biochemistry. 2016 07; 160(?):125-39. doi: 10.1016/j.jinorgbio.2015.12.015. [PMID: 26775611]
  • Kotaro Shirakawa, Lan Wang, Na Man, Jasna Maksimoska, Alexander W Sorum, Hyung W Lim, Intelly S Lee, Tadahiro Shimazu, John C Newman, Sebastian Schröder, Melanie Ott, Ronen Marmorstein, Jordan Meier, Stephen Nimer, Eric Verdin. Salicylate, diflunisal and their metabolites inhibit CBP/p300 and exhibit anticancer activity. eLife. 2016 05; 5(?):. doi: 10.7554/elife.11156. [PMID: 27244239]
  • Irina Iakovleva, Afshan Begum, Kristoffer Brännström, Alexandra Wijsekera, Lina Nilsson, Jin Zhang, Patrik L Andersson, A Elisabeth Sauer-Eriksson, Anders Olofsson. Tetrabromobisphenol A Is an Efficient Stabilizer of the Transthyretin Tetramer. PloS one. 2016; 11(4):e0153529. doi: 10.1371/journal.pone.0153529. [PMID: 27093678]
  • Irina Iakovleva, Kristoffer Brännström, Lina Nilsson, Anna L Gharibyan, Afshan Begum, Intissar Anan, Malin Walfridsson, A Elisabeth Sauer-Eriksson, Anders Olofsson. Enthalpic Forces Correlate with the Selectivity of Transthyretin-Stabilizing Ligands in Human Plasma. Journal of medicinal chemistry. 2015 Aug; 58(16):6507-15. doi: 10.1021/acs.jmedchem.5b00544. [PMID: 26214366]
  • Michael J Greene, Elena S Klimtchuk, David C Seldin, John L Berk, Lawreen H Connors. Cooperative stabilization of transthyretin by clusterin and diflunisal. Biochemistry. 2015 Jan; 54(2):268-78. doi: 10.1021/bi5011249. [PMID: 25478940]
  • Paolo Ascenzi, Loris Leboffe, Alessandra di Masi, Viviana Trezza, Gabriella Fanali, Magda Gioia, Massimo Coletta, Mauro Fasano. Ligand binding to the FA3-FA4 cleft inhibits the esterase-like activity of human serum albumin. PloS one. 2015; 10(3):e0120603. doi: 10.1371/journal.pone.0120603. [PMID: 25790235]
  • Takeshi Yokoyama, Yuto Kosaka, Mineyuki Mizuguchi. Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin. Journal of medicinal chemistry. 2014 Nov; 57(21):8928-35. doi: 10.1021/jm500997m. [PMID: 25314129]
  • Takeshi Yokoyama, Yuto Kosaka, Mineyuki Mizuguchi. Crystal structures of human transthyretin complexed with glabridin. Journal of medicinal chemistry. 2014 Feb; 57(3):1090-6. doi: 10.1021/jm401832j. [PMID: 24422526]
  • Hong Liang, Feng Yang, Nicole Lee, Xiaoyang Wu. HSA-based anti-inflammatory therapy: a new and improved approach. Future medicinal chemistry. 2014 Feb; 6(2):119-21. doi: 10.4155/fmc.13.195. [PMID: 24467237]
  • Carlos A Ribeiro, Sandra Marisa Oliveira, Luis F Guido, Ana Magalhães, Gregorio Valencia, Gemma Arsequell, Maria João Saraiva, Isabel Cardoso. Transthyretin stabilization by iododiflunisal promotes amyloid-β peptide clearance, decreases its deposition, and ameliorates cognitive deficits in an Alzheimer's disease mouse model. Journal of Alzheimer's disease : JAD. 2014; 39(2):357-70. doi: 10.3233/jad-131355. [PMID: 24169237]
  • Dinesh S Patel, Naveen Sharma, Mukesh C Patel, Bhavin N Patel, Pranav S Shrivastav, Mallika Sanyal. Sensitive and selective determination of diflunisal in human plasma by LC-MS. Journal of chromatographic science. 2013 Oct; 51(9):872-82. doi: 10.1093/chromsci/bms181. [PMID: 23144359]
  • Feng Yang, Zhi Yuan Ma, Yao Zhang, Guo Qing Li, Mei Li, Jiang Ke Qin, Oksana Lockridge, Hong Liang. Human serum albumin-based design of a diflunisal prodrug. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2013 Aug; 84(3):549-54. doi: 10.1016/j.ejpb.2013.01.013. [PMID: 23416065]
  • S A Helmy, H M El Bedaiwy. Comparative in vitro dissolution and in vivo bioavailability of diflunisal/naproxen fixed-dose combination tablets and concomitant administration of diflunisal and naproxen in healthy adult subjects. Drug research. 2013 Mar; 63(3):150-8. doi: 10.1055/s-0033-1333768. [PMID: 23444169]
  • David Adams, Cécile Cauquil, Marie Théaudin. [Familial amyloid polyneuropathies: therapeutic issues]. Bulletin de l'Academie nationale de medecine. 2012 Oct; 196(7):1333-45; discussion 1345. doi: NULL. [PMID: 23815018]
  • Nelson Ferreira, Maria João Saraiva, Maria Rosário Almeida. Epigallocatechin-3-gallate as a potential therapeutic drug for TTR-related amyloidosis: 'in vivo' evidence from FAP mice models. PloS one. 2012; 7(1):e29933. doi: 10.1371/journal.pone.0029933. [PMID: 22253829]
  • B M Hovey, J E Ward, P Soo Hoo, C J O'Hara, L H Connors, D C Seldin. Preclinical development of siRNA therapeutics for AL amyloidosis. Gene therapy. 2011 Dec; 18(12):1150-6. doi: 10.1038/gt.2011.69. [PMID: 21562591]
  • Stella Fountoulaki, Franc Perdih, Iztok Turel, Dimitris P Kessissoglou, George Psomas. Non-steroidal anti-inflammatory drug diflunisal interacting with Cu(II). Structure and biological features. Journal of inorganic biochemistry. 2011 Dec; 105(12):1645-55. doi: 10.1016/j.jinorgbio.2011.09.004. [PMID: 22071090]
  • Mamoun M Alhamadsheh, Stephen Connelly, Ahryon Cho, Natàlia Reixach, Evan T Powers, Dorothy W Pan, Ian A Wilson, Jeffery W Kelly, Isabella A Graef. Potent kinetic stabilizers that prevent transthyretin-mediated cardiomyocyte proteotoxicity. Science translational medicine. 2011 Aug; 3(97):97ra81. doi: 10.1126/scitranslmed.3002473. [PMID: 21865539]
  • Yelda Bilginer, Tekin Akpolat, Seza Ozen. Renal amyloidosis in children. Pediatric nephrology (Berlin, Germany). 2011 Aug; 26(8):1215-27. doi: 10.1007/s00467-011-1797-x. [PMID: 21360109]
  • Ali J Ryan, Jamie Ghuman, Patricia A Zunszain, Chun-wa Chung, Stephen Curry. Structural basis of binding of fluorescent, site-specific dansylated amino acids to human serum albumin. Journal of structural biology. 2011 Apr; 174(1):84-91. doi: 10.1016/j.jsb.2010.10.004. [PMID: 20940056]
  • Sungwook Choi, Jeffery W Kelly. A competition assay to identify amyloidogenesis inhibitors by monitoring the fluorescence emitted by the covalent attachment of a stilbene derivative to transthyretin. Bioorganic & medicinal chemistry. 2011 Feb; 19(4):1505-14. doi: 10.1016/j.bmc.2010.12.050. [PMID: 21273081]
  • David Buttar, Nicola Colclough, Stefan Gerhardt, Philip A MacFaul, Scott D Phillips, Alleyn Plowright, Paul Whittamore, Kin Tam, Klaus Maskos, Stefan Steinbacher, Holger Steuber. A combined spectroscopic and crystallographic approach to probing drug-human serum albumin interactions. Bioorganic & medicinal chemistry. 2010 Nov; 18(21):7486-96. doi: 10.1016/j.bmc.2010.08.052. [PMID: 20869876]
  • Shu-ichi Ikeda. [Therapeutic strategy for familial amyloid polyneuropathy (FAP)]. Rinsho shinkeigaku = Clinical neurology. 2009 Nov; 49(11):953-5. doi: 10.5692/clinicalneurol.49.953. [PMID: 20030258]
  • Kathleen M Knights, Leanne K Winner, David J Elliot, Kushari Bowalgaha, John O Miners. Aldosterone glucuronidation by human liver and kidney microsomes and recombinant UDP-glucuronosyltransferases: inhibition by NSAIDs. British journal of clinical pharmacology. 2009 Sep; 68(3):402-12. doi: 10.1111/j.1365-2125.2009.03469.x. [PMID: 19740398]
  • Stefan Balaz. Modeling kinetics of subcellular disposition of chemicals. Chemical reviews. 2009 May; 109(5):1793-899. doi: 10.1021/cr030440j. [PMID: 19265398]
  • J A Murillo Pulgarín, A Alañón Molina, I Sánchez-Ferrer Robles. Simultaneous determination of two anti-inflammatory drugs in serum using isopotential fluorimetry. Analytica chimica acta. 2008 Sep; 625(1):47-54. doi: 10.1016/j.aca.2008.07.017. [PMID: 18721539]
  • Hadir M Maher. Simultaneous determination of naproxen and diflunisal using synchronous luminescence spectrometry. Journal of fluorescence. 2008 Sep; 18(5):909-17. doi: 10.1007/s10895-008-0322-5. [PMID: 18256908]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Jonathan S Kingsbury, Thomas M Laue, Elena S Klimtchuk, Roger Théberge, Catherine E Costello, Lawreen H Connors. The modulation of transthyretin tetramer stability by cysteine 10 adducts and the drug diflunisal. Direct analysis by fluorescence-detected analytical ultracentrifugation. The Journal of biological chemistry. 2008 May; 283(18):11887-96. doi: 10.1074/jbc.m709638200. [PMID: 18326041]
  • Elisabet Lázaro, Philip J Lowe, Xavier Briand, Bernard Faller. New approach to measure protein binding based on a parallel artificial membrane assay and human serum albumin. Journal of medicinal chemistry. 2008 Apr; 51(7):2009-17. doi: 10.1021/jm7012826. [PMID: 18348514]
  • Ernest Adeghate, Péter Sótonyi, Huba Kalász. Chronic experimental diabetes accelerates urinary elimination of deprenyl and its metabolites. The open medicinal chemistry journal. 2008 Jan; 2(?):1-5. doi: 10.2174/1874104500802010001. [PMID: 19662137]
  • Clement E Tagoe, Natàlia Reixach, Linsey Friske, David Mustra, David French, Gloria Gallo, Joel N Buxbaum. In vivo stabilization of mutant human transthyretin in transgenic mice. Amyloid : the international journal of experimental and clinical investigation : the official journal of the International Society of Amyloidosis. 2007 Sep; 14(3):227-36. doi: 10.1080/13506120701464396. [PMID: 17701470]
  • J A Murillo Pulgarín, A Alañón Molina, P Fernández López, I Sánchez-Ferrer Robles. Direct determination of closely overlapping drug mixtures of diflunisal and salicylic acid in serum by means of derivative matrix isopotential synchronous fluorescence spectrometry. Analytica chimica acta. 2007 Jan; 583(1):55-62. doi: 10.1016/j.aca.2006.10.009. [PMID: 17386526]
  • Kana Tojo, Yoshiki Sekijima, Jeffery W Kelly, Shu-ichi Ikeda. Diflunisal stabilizes familial amyloid polyneuropathy-associated transthyretin variant tetramers in serum against dissociation required for amyloidogenesis. Neuroscience research. 2006 Dec; 56(4):441-9. doi: 10.1016/j.neures.2006.08.014. [PMID: 17028027]
  • Hege Christensen, Mark Baker, Geoffrey T Tucker, Amin Rostami-Hodjegan. Prediction of plasma protein binding displacement and its implications for quantitative assessment of metabolic drug-drug interactions from in vitro data. Journal of pharmaceutical sciences. 2006 Dec; 95(12):2778-87. doi: 10.1002/jps.20733. [PMID: 16937340]
  • Yoshiki Sekijima, Maria A Dendle, Jeffery W Kelly. Orally administered diflunisal stabilizes transthyretin against dissociation required for amyloidogenesis. Amyloid : the international journal of experimental and clinical investigation : the official journal of the International Society of Amyloidosis. 2006 Dec; 13(4):236-49. doi: 10.1080/13506120600960882. [PMID: 17107884]
  • A Davilas, M Koupparis, P Macheras, G Valsami. In-vitro study on the competitive binding of diflunisal and uraemic toxins to serum albumin and human plasma using a potentiometric ion-probe technique. The Journal of pharmacy and pharmacology. 2006 Nov; 58(11):1467-74. doi: 10.1211/jpp.58.11.0007. [PMID: 17132209]
  • Yuji Mano, Takashi Usui, Hidetaka Kamimura. In vitro drug interaction between diflunisal and indomethacin via glucuronidation in humans. Biopharmaceutics & drug disposition. 2006 Sep; 27(6):267-73. doi: 10.1002/bdd.507. [PMID: 16733833]
  • Francesca Iemma, U Gianfranco Spizzirri, Francesco Puoci, Rita Muzzalupo, Sonia Trombino, Roberta Cassano, Sonia Leta, Nevio Picci. pH-sensitive hydrogels based on bovine serum albumin for oral drug delivery. International journal of pharmaceutics. 2006 Apr; 312(1-2):151-7. doi: 10.1016/j.ijpharm.2006.01.010. [PMID: 16490328]
  • Jian Hua Liu, Philip C Smith. Predicting the pharmacokinetics of acyl glucuronides and their parent compounds in disease states. Current drug metabolism. 2006 Feb; 7(2):147-63. doi: 10.2174/138920006775541589. [PMID: 16472105]
  • F Iemma, U G Spizzirri, F Puoci, R Muzzalupo, S Trombino, N Picci. Radical cross-linked albumin microspheres as potential drug delivery systems: preparation and in vitro studies. Drug delivery. 2005 Jul; 12(4):229-34. doi: 10.1080/10717540590952690. [PMID: 16036717]
  • Loretta Aureli, Gabriele Cruciani, Maria Candida Cesta, Roberto Anacardio, Lucio De Simone, Alessio Moriconi. Predicting human serum albumin affinity of interleukin-8 (CXCL8) inhibitors by 3D-QSPR approach. Journal of medicinal chemistry. 2005 Apr; 48(7):2469-79. doi: 10.1021/jm049227l. [PMID: 15801837]
  • Maria Rosário Almeida, Bárbara Macedo, Isabel Cardoso, Isabel Alves, Gregorio Valencia, Gemma Arsequell, Antoni Planas, Maria João Saraiva. Selective binding to transthyretin and tetramer stabilization in serum from patients with familial amyloidotic polyneuropathy by an iodinated diflunisal derivative. The Biochemical journal. 2004 Jul; 381(Pt 2):351-6. doi: 10.1042/bj20040011. [PMID: 15080795]
  • Nikhil K Basu, Shigeki Kubota, Meselhy R Meselhy, Marco Ciotti, Bhabadeb Chowdhury, Masao Hartori, Ida S Owens. Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. The Journal of biological chemistry. 2004 Jul; 279(27):28320-9. doi: 10.1074/jbc.m401396200. [PMID: 15117964]
  • Robert L Brent. Utilization of animal studies to determine the effects and human risks of environmental toxicants (drugs, chemicals, and physical agents). Pediatrics. 2004 Apr; 113(4 Suppl):984-95. doi: NULL. [PMID: 15060191]
  • Pekka Suomalainen, Christoffer Johans, Tim Söderlund, Paavo K J Kinnunen. Surface activity profiling of drugs applied to the prediction of blood-brain barrier permeability. Journal of medicinal chemistry. 2004 Mar; 47(7):1783-8. doi: 10.1021/jm0309001. [PMID: 15027870]
  • Sara L Adamski-Werner, Satheesh K Palaninathan, James C Sacchettini, Jeffery W Kelly. Diflunisal analogues stabilize the native state of transthyretin. Potent inhibition of amyloidogenesis. Journal of medicinal chemistry. 2004 Jan; 47(2):355-74. doi: 10.1021/jm030347n. [PMID: 14711308]
  • A T Proudfoot, E P Krenzelok, J A Vale. Position Paper on urine alkalinization. Journal of toxicology. Clinical toxicology. 2004; 42(1):1-26. doi: 10.1081/clt-120028740. [PMID: 15083932]
  • R G Dickinson, A R King. Rearrangement of diflunisal acyl glucuronide into its beta-glucuronidase-resistant isomers facilitates transport through the small intestine to the colon of the rat. Life sciences. 2001 Nov; 70(1):25-36. doi: 10.1016/s0024-3205(01)01371-6. [PMID: 11764004]
  • H Mao, P J Hajduk, R Craig, R Bell, T Borre, S W Fesik. Rational design of diflunisal analogues with reduced affinity for human serum albumin. Journal of the American Chemical Society. 2001 Oct; 123(43):10429-35. doi: 10.1021/ja015955b. [PMID: 11673972]
  • H H Maurer, F X Tauvel, T Kraemer. Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. Journal of analytical toxicology. 2001 May; 25(4):237-44. doi: 10.1093/jat/25.4.237. [PMID: 11386636]
  • C R Mallet, J R Mazzeo, U Neue. Evaluation of several solid phase extraction liquid chromatography/tandem mass spectrometry on-line configurations for high-throughput analysis of acidic and basic drugs in rat plasma. Rapid communications in mass spectrometry : RCM. 2001; 15(13):1075-83. doi: 10.1002/rcm.346. [PMID: 11404844]
  • R S Addison, S L Parker-Scott, M J Eadie, W D Hooper, R G Dickinson. Steady-state dispositions of valproate and diflunisal alone and coadministered to healthy volunteers. European journal of clinical pharmacology. 2000 Dec; 56(9-10):715-21. doi: 10.1007/s002280000211. [PMID: 11214782]
  • A S Mulato, E S Ho, T Cihlar. Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. The Journal of pharmacology and experimental therapeutics. 2000 Oct; 295(1):10-5. doi: . [PMID: 10991954]
  • S S Jacob, M E Franklin, R G Dickinson, W D Hooper. The effect of diflunisal on the elimination of triamterene in human volunteers. Drug metabolism and drug interactions. 2000; 16(3):159-71. doi: 10.1515/dmdi.2000.16.3.159. [PMID: 11116751]
  • F Castelli, P Giunchedi, O La Camera, U Conte. A calorimetric study on diflunisal release from poly(lactide-co-glycolide) microspheres by monitoring the drug effect on dipalmitoylphosphatidylcholine liposomes: temperature and drug loading influence. Drug delivery. 2000 Jan; 7(1):45-53. doi: 10.1080/107175400266786. [PMID: 10895419]
  • R F Squires, J Ai, M R Witt, P Kahnberg, E Saederup, O Sterner, M Nielsen. Honokiol and magnolol increase the number of [3H] muscimol binding sites three-fold in rat forebrain membranes in vitro using a filtration assay, by allosterically increasing the affinities of low-affinity sites. Neurochemical research. 1999 Dec; 24(12):1593-602. doi: 10.1023/a:1021116502548. [PMID: 10591411]
  • C J Meunier, R K Verbeeck. Glucuronidation of R- and S-ketoprofen, acetaminophen, and diflunisal by liver microsomes of adjuvant-induced arthritic rats. Drug metabolism and disposition: the biological fate of chemicals. 1999 Jan; 27(1):26-31. doi: . [PMID: 9884306]
  • D Y Hung, G D Mellick, P P Masci, A N Whitaker, M W Whitehouse, M S Roberts. Focused antithrombotic therapy: novel anti-platelet salicylates with reduced ulcerogenic potential and higher first-pass detoxification than aspirin in rats. The Journal of laboratory and clinical medicine. 1998 Dec; 132(6):469-77. doi: 10.1016/s0022-2143(98)90124-x. [PMID: 9851736]
  • M Wang, R G Dickinson. Hepatobiliary transport of diflunisal conjugates and taurocholate by the perfused rat liver: the effect of chronic exposure of rats to diflunisal. Life sciences. 1998; 62(8):751-62. doi: 10.1016/s0024-3205(97)01173-9. [PMID: 9489511]
  • L Gao, J Xing, W Liu. [Determination of diflunisal in plasma by RP-HPLC after solid-liquid extraction]. Yao xue xue bao = Acta pharmaceutica Sinica. 1998; 33(4):286-9. doi: NULL. [PMID: 11939069]
  • F M Brunelle, R K Verbeeck. Conjugation-deconjugation cycling of diflunisal via beta-glucuronidase catalyzed hydrolysis of its acyl glucuronide in the rat. Life sciences. 1997; 60(22):2013-21. doi: 10.1016/s0024-3205(97)00166-5. [PMID: 9180355]
  • R G Dickinson, A R King. Vesico-hepato-renal cycling of acidic drugs via their reactive acyl glucuronide metabolites? Studies with diflunisal in rats. Clinical and experimental pharmacology & physiology. 1996 Aug; 23(8):665-8. doi: 10.1111/j.1440-1681.1996.tb01754.x. [PMID: 8886486]
  • G S Neigh, V S Ananthanarayanan. Ca2+ binding and translocating properties of diflunisal. Biochemistry and molecular biology international. 1996 May; 39(1):53-61. doi: 10.1080/15216549600201051. [PMID: 8799327]
  • M J Bailey, R G Dickinson. Chemical and immunochemical comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma. Chemical research in toxicology. 1996 Apr; 9(3):659-66. doi: 10.1021/tx960017o. [PMID: 8728513]
  • F M Brunelle, R K Verbeeck. Glucuronidation of diflunisal in liver and kidney microsomes of rat and man. Xenobiotica; the fate of foreign compounds in biological systems. 1996 Feb; 26(2):123-31. doi: 10.3109/00498259609046694. [PMID: 8867997]
  • G E Bast, H G Kampffmeyer. No effect of albumin on the dermal absorption rate of hydrocortisone 21-butyrate, permethrin or diflunisal in the isolated, single-pass perfused rabbit ear. Skin pharmacology : the official journal of the Skin Pharmacology Society. 1996; 9(5):327-33. doi: 10.1159/000211438. [PMID: 8990508]
  • J Arias, M Fernández-Rivas, A Moral, M A García, C J Senent. Selective adverse reactions to diflunisal. Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology. 1995 Feb; 74(2):160-2. doi: NULL. [PMID: 7697476]
  • A M Williams, S Worrall, J De Jersey, R G Dickinson. Studies on the reactivity of acyl glucuronides--VIII. Generation of an antiserum for the detection of diflunisal-modified proteins in diflunisal-dosed rats. Biochemical pharmacology. 1995 Jan; 49(2):209-17. doi: 10.1016/s0006-2952(94)00408-0. [PMID: 7840798]
  • J I Macdonald, S M Wallace, R J Herman, R K Verbeeck. Effect of probenecid on the formation and elimination kinetics of the sulphate and glucuronide conjugates of diflunisal. European journal of clinical pharmacology. 1995; 47(6):519-23. doi: 10.1007/bf00193705. [PMID: 7768255]
  • S Worrall, R G Dickinson. Rat serum albumin modified by diflunisal acyl glucuronide is immunogenic in rats. Life sciences. 1995; 56(22):1921-30. doi: 10.1016/0024-3205(95)00167-5. [PMID: 7538189]
  • A Rivero, J I Monreal, M J Gil. Peroxisome enzyme modification and oxidative stress in rat by hypolipidemic and antiinflammatory drugs. Revista espanola de fisiologia. 1994 Dec; 50(4):259-68. doi: . [PMID: 7754169]
  • R G Dickinson, A R King, M A Kelly, I A Kaltashov, C Fenselau. Excretion of 3-hydroxy-diflunisal as a monosulphate conjugate--identification using ESI-MS. Journal of pharmaceutical and biomedical analysis. 1994 Sep; 12(9):1075-8. doi: 10.1016/0731-7085(94)00053-0. [PMID: 7803554]
  • R J Herman, G R Loewen, D M Antosh, M R Taillon, S Hussein, R K Verbeeck. Analysis of polymorphic variation in drug metabolism: III. Glucuronidation and sulfation of diflunisal in man. Clinical and investigative medicine. Medecine clinique et experimentale. 1994 Aug; 17(4):297-307. doi: . [PMID: 7982293]
  • A M Williams, R G Dickinson. Studies on the reactivity of acyl glucuronides--VI. Modulation of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro. Biochemical pharmacology. 1994 Feb; 47(3):457-67. doi: 10.1016/0006-2952(94)90176-7. [PMID: 8117313]
  • E E Sideris, M A Koupparis, P E Macheras. Effect of cyclodextrins on protein binding of drugs: the diflunisal/hydroxypropyl-beta-cyclodextrin model case. Pharmaceutical research. 1994 Jan; 11(1):90-5. doi: 10.1023/a:1018901912619. [PMID: 8140060]
  • C F Lim, J R Stockigt, A J Curtis, K N Wynne, J W Barlow, D J Topliss. A naturally occurring furan fatty acid enhances drug inhibition of thyroxine binding in serum. Metabolism: clinical and experimental. 1993 Nov; 42(11):1468-74. doi: 10.1016/0026-0495(93)90200-8. [PMID: 8231843]