benfotiamine (BioDeep_00000386645)

   


代谢物信息卡片


S-Benzoylthiamine O-monophosphate

化学式: C19H23N4O6PS (466.10758680000004)
中文名称: 苯磷硫胺
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=C(CCOP(=O)(O)O)SC(=O)c1ccccc1)N(C=O)Cc1cnc(C)[nH]c1=N
InChI: InChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)

描述信息

A - Alimentary tract and metabolism > A11 - Vitamins > A11D - Vitamin b1, plain and in combination with vitamin b6 and b12 > A11DA - Vitamin b1, plain
D064449 - Sequestering Agents > D002614 - Chelating Agents
D007155 - Immunologic Factors

同义名列表

2 个代谢物同义名

S-Benzoylthiamine O-monophosphate; benfotiamine



数据库引用编号

12 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)

0 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

  • Kieran V Allowitz, John J Yoo, Justin R Taylor, Omar A Baloch, Kyra Harames, Kota V Ramana. Therapeutic potential of vitamin B1 derivative benfotiamine from diabetes to COVID-19. Future medicinal chemistry. 2022 06; 14(11):809-826. doi: 10.4155/fmc-2022-0040. [PMID: 35535731]
  • Ruchika Bhawal, Qin Fu, Elizabeth T Anderson, Gary E Gibson, Sheng Zhang. Serum Metabolomic and Lipidomic Profiling Reveals Novel Biomarkers of Efficacy for Benfotiamine in Alzheimer's Disease. International journal of molecular sciences. 2021 Dec; 22(24):. doi: 10.3390/ijms222413188. [PMID: 34947984]
  • 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]
  • Malkanthi Evans, Abdul M Sulley, David C Crowley, Jamie Langston, Najla Guthrie. Pain Bloc-R Alleviates Unresolved, Non-Pathological Aches and Discomfort in Healthy Adults-A Randomized, Double-Blind, Placebo-Controlled, Crossover Study. Nutrients. 2020 Jun; 12(6):. doi: 10.3390/nu12061831. [PMID: 32575480]
  • 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]
  • V Raj, S Ojha, F C Howarth, P D Belur, S B Subramanya. Therapeutic potential of benfotiamine and its molecular targets. European review for medical and pharmacological sciences. 2018 05; 22(10):3261-3273. doi: 10.26355/eurrev_201805_15089. [PMID: 29863274]
  • Mehmet Alperen Ustuner, Dilara Kaman, Neriman Colakoglu. Effects of benfotiamine and coenzyme Q10 on kidney damage induced gentamicin. Tissue & cell. 2017 Dec; 49(6):691-696. doi: 10.1016/j.tice.2017.10.001. [PMID: 29066103]
  • Guilherme Vannucchi Portari, Paula Payão Ovidio, Rafael Deminice, Alceu Afonso Jordão. Protective effect of treatment with thiamine or benfotiamine on liver oxidative damage in rat model of acute ethanol intoxication. Life sciences. 2016 Oct; 162(?):21-4. doi: 10.1016/j.lfs.2016.08.017. [PMID: 27545821]
  • Wan-Su Park, Jongtae Lee, Taegon Hong, Gabjin Park, Sunil Youn, Youngwhan Seo, Sanghun Lee, Seunghoon Han. Comparative Pharmacokinetic Analysis of Thiamine and Its Phosphorylated Metabolites Administered as Multivitamin Preparations. Clinical therapeutics. 2016 Oct; 38(10):2277-2285. doi: 10.1016/j.clinthera.2016.08.009. [PMID: 27707509]
  • Ann M Manzardo, Tiffany Pendleton, Albert Poje, Elizabeth C Penick, Merlin G Butler. Change in psychiatric symptomatology after benfotiamine treatment in males is related to lifetime alcoholism severity. Drug and alcohol dependence. 2015 Jul; 152(?):257-63. doi: 10.1016/j.drugalcdep.2015.03.032. [PMID: 25908323]
  • Amit D Raval, Divyesh Thakker, Arohi N Rangoonwala, Deval Gor, Rama Walia. Vitamin B and its derivatives for diabetic kidney disease. The Cochrane database of systematic reviews. 2015 Jan; 1(?):CD009403. doi: 10.1002/14651858.cd009403.pub2. [PMID: 25579852]
  • Feifan Xie, Zeneng Cheng, Sanwang Li, Xingling Liu, Xin Guo, Peng Yu, Zhenkun Gu. Pharmacokinetic study of benfotiamine and the bioavailability assessment compared to thiamine hydrochloride. Journal of clinical pharmacology. 2014 Jun; 54(6):688-95. doi: 10.1002/jcph.261. [PMID: 24399744]
  • Gamaleldin I Harisa. Benfotiamine enhances antioxidant defenses and protects against cisplatin-induced DNA damage in nephrotoxic rats. Journal of biochemical and molecular toxicology. 2013 Aug; 27(8):398-405. doi: 10.1002/jbt.21501. [PMID: 23716490]
  • Shabnam Garg, Ashit Syngle, Kanchan Vohra. Efficacy and tolerability of advanced glycation end-products inhibitor in osteoarthritis: a randomized, double-blind, placebo-controlled study. The Clinical journal of pain. 2013 Aug; 29(8):717-24. doi: 10.1097/ajp.0b013e318272ebec. [PMID: 23354008]
  • Guilherme Vannucchi Portari, Helio Vannucchi, Alceu Afonso Jordao. Liver, plasma and erythrocyte levels of thiamine and its phosphate esters in rats with acute ethanol intoxication: a comparison of thiamine and benfotiamine administration. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2013 Mar; 48(4-5):799-802. doi: 10.1016/j.ejps.2013.01.010. [PMID: 23369791]
  • V A Sergienko, V B Segin, A Samir, A A Sergienko. [The effect of long-chain polyunsaturated higher ω-3 fatty acids, benfotiamine and α-lipoic acid on the lipid metabolism in patients with diabetes mellitus type 2 and cardiovascular autonomic neuropathy]. Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova. 2013; 113(11):54-8. doi: ". [PMID: 24429949]
  • Samina Kousar, Munir Ahmad Sheikh, Muhammad Asghar. Antiglycation activity of thiamin-HCl and benfotiamine in diabetic condition. JPMA. The Journal of the Pakistan Medical Association. 2012 Oct; 62(10):1033-8. doi: NULL. [PMID: 23866441]
  • D A Fraser, N P Hessvik, N Nikolić, V Aas, K F Hanssen, S K Bøhn, G H Thoresen, A C Rustan. Benfotiamine increases glucose oxidation and downregulates NADPH oxidase 4 expression in cultured human myotubes exposed to both normal and high glucose concentrations. Genes & nutrition. 2012 Jul; 7(3):459-69. doi: 10.1007/s12263-011-0252-8. [PMID: 21984258]
  • Raphael de Souza Pinto, Gabriela Castilho, Bruno Alves Paim, Adriana Machado-Lima, Natalia M Inada, Edna Regina Nakandakare, Aníbal Eugênio Vercesi, Marisa Passarelli. Inhibition of macrophage oxidative stress prevents the reduction of ABCA-1 transporter induced by advanced glycated albumin. Lipids. 2012 May; 47(5):443-50. doi: 10.1007/s11745-011-3647-9. [PMID: 22271422]
  • Teruo Miyazawa, Kiyotaka Nakagawa, Satoko Shimasaki, Ryoji Nagai. Lipid glycation and protein glycation in diabetes and atherosclerosis. Amino acids. 2012 Apr; 42(4):1163-70. doi: 10.1007/s00726-010-0772-3. [PMID: 20957396]
  • S Müller-Krebs, W Zhang, L P Kihm, J Reiser, P P Nawroth, V Schwenger. Glucose effects on the peritoneum: what can we learn from rodent models?. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2012 Apr; 120(4):197-8. doi: 10.1055/s-0032-1304572. [PMID: 22402947]
  • S M Patel, R P Patel, B G Prajapati. Solubility enhancement of benfotiamine, a lipid derivative of thiamine by solid dispersion technique. Journal of pharmacy & bioallied sciences. 2012 Mar; 4(Suppl 1):S104-5. doi: 10.4103/0975-7406.94157. [PMID: 23066179]
  • Ashit Syngle, Kanchan Vohra, Nidhi Garg, Ladbans Kaur, Prem Chand. Advanced glycation end-products inhibition improves endothelial dysfunction in rheumatoid arthritis. International journal of rheumatic diseases. 2012 Feb; 15(1):45-55. doi: 10.1111/j.1756-185x.2011.01679.x. [PMID: 22324946]
  • Mohammad Shoeb, Kota V Ramana. Anti-inflammatory effects of benfotiamine are mediated through the regulation of the arachidonic acid pathway in macrophages. Free radical biology & medicine. 2012 Jan; 52(1):182-90. doi: 10.1016/j.freeradbiomed.2011.10.444. [PMID: 22067901]
  • Yoshiyuki Morishita, Minami Watanabe, Ichiro Hirahara, Tetsu Akimoto, Shigeaki Muto, Eiji Kusano. Level of 8-OHdG in drained dialysate appears to be a marker of peritoneal damage in peritoneal dialysis. International journal of nephrology and renovascular disease. 2012; 5(?):9-14. doi: 10.2147/ijnrd.s27553. [PMID: 22334795]
  • Bruce A Perkins, Naila Rabbani, Andrew Weston, Linda H Ficociello, Antonysunil Adaikalakoteswari, Monika Niewczas, James Warram, Andrzej S Krolewski, Paul Thornalley. Serum levels of advanced glycation endproducts and other markers of protein damage in early diabetic nephropathy in type 1 diabetes. PloS one. 2012; 7(4):e35655. doi: 10.1371/journal.pone.0035655. [PMID: 22558190]
  • Alaa Alkhalaf, Nanne Kleefstra, Klaas H Groenier, Henk J G Bilo, Reinold O B Gans, Peter Heeringa, Jean L Scheijen, Casper G Schalkwijk, Gerjan J Navis, Stephan J L Bakker. Effect of benfotiamine on advanced glycation endproducts and markers of endothelial dysfunction and inflammation in diabetic nephropathy. PloS one. 2012; 7(7):e40427. doi: 10.1371/journal.pone.0040427. [PMID: 22792314]
  • M A Morsy. Protective effect of lisinopril on hepatic ischemia/reperfusion injury in rats. Indian journal of pharmacology. 2011 Nov; 43(6):652-5. doi: 10.4103/0253-7613.89820. [PMID: 22144768]
  • Rong-Rong He, Bun Tsoi, Fang Lan, Nan Yao, Xin-Sheng Yao, Hiroshi Kurihara. Antioxidant properties of lutein contribute to the protection against lipopolysaccharide-induced uveitis in mice. Chinese medicine. 2011 Oct; 6(1):38. doi: 10.1186/1749-8546-6-38. [PMID: 22040935]
  • N Rabbani, P J Thornalley. Emerging role of thiamine therapy for prevention and treatment of early-stage diabetic nephropathy. Diabetes, obesity & metabolism. 2011 Jul; 13(7):577-83. doi: 10.1111/j.1463-1326.2011.01384.x. [PMID: 21342411]
  • Lars P Kihm, Sandra Müller-Krebs, Julia Klein, Gregory Ehrlich, Laura Mertes, Marie-Luise Gross, Antonysunil Adaikalakoteswari, Paul J Thornalley, Hans-Peter Hammes, Peter P Nawroth, Martin Zeier, Vedat Schwenger. Benfotiamine protects against peritoneal and kidney damage in peritoneal dialysis. Journal of the American Society of Nephrology : JASN. 2011 May; 22(5):914-26. doi: 10.1681/asn.2010070750. [PMID: 21511829]
  • Susana Alcázar-Leyva, Noé Alvarado-Vásquez. Could thiamine pyrophosphate be a regulator of the nitric oxide synthesis in the endothelial cell of diabetic patients?. Medical hypotheses. 2011 May; 76(5):629-31. doi: 10.1016/j.mehy.2011.01.015. [PMID: 21288652]
  • Alleboena Satyanarayana, Nagalla Balakrishna, Sujatha Pitla, Paduru Yadagiri Reddy, Sivaprasad Mudili, Pratti Lopamudra, Palla Suryanarayana, Kalluru Viswanath, Radha Ayyagari, Geereddy Bhanuprakash Reddy. Status of B-vitamins and homocysteine in diabetic retinopathy: association with vitamin-B12 deficiency and hyperhomocysteinemia. PloS one. 2011; 6(11):e26747. doi: 10.1371/journal.pone.0026747. [PMID: 22069468]
  • Claudia Luevano-Contreras, Karen Chapman-Novakofski. Dietary advanced glycation end products and aging. Nutrients. 2010 12; 2(12):1247-65. doi: 10.3390/nu2121247. [PMID: 22254007]
  • Cimen Karasu. Glycoxidative stress and cardiovascular complications in experimentally-induced diabetes: effects of antioxidant treatment. The open cardiovascular medicine journal. 2010 Nov; 4(?):240-56. doi: 10.2174/1874192401004010240. [PMID: 21270942]
  • Andries J Smit, Esther G Gerrits. Skin autofluorescence as a measure of advanced glycation endproduct deposition: a novel risk marker in chronic kidney disease. Current opinion in nephrology and hypertension. 2010 Nov; 19(6):527-33. doi: 10.1097/mnh.0b013e32833e9259. [PMID: 20844429]
  • Nicole Schupp, August Heidland, Helga Stopper. Genomic damage in endstage renal disease-contribution of uremic toxins. Toxins. 2010 10; 2(10):2340-58. doi: 10.3390/toxins2102340. [PMID: 22069557]
  • Sanjali Verma, Krishna Reddy, Pitchai Balakumar. The defensive effect of benfotiamine in sodium arsenite-induced experimental vascular endothelial dysfunction. Biological trace element research. 2010 Oct; 137(1):96-109. doi: 10.1007/s12011-009-8567-7. [PMID: 19943121]
  • Alaa Alkhalaf, Astrid Klooster, Willem van Oeveren, Ulrike Achenbach, Nanne Kleefstra, Robbert J Slingerland, G Sophie Mijnhout, Henk J G Bilo, Reinold O B Gans, Gerjan J Navis, Stephan J L Bakker. A double-blind, randomized, placebo-controlled clinical trial on benfotiamine treatment in patients with diabetic nephropathy. Diabetes care. 2010 Jul; 33(7):1598-601. doi: 10.2337/dc09-2241. [PMID: 20413516]
  • N Karachalias, R Babaei-Jadidi, N Rabbani, P J Thornalley. Increased protein damage in renal glomeruli, retina, nerve, plasma and urine and its prevention by thiamine and benfotiamine therapy in a rat model of diabetes. Diabetologia. 2010 Jul; 53(7):1506-16. doi: 10.1007/s00125-010-1722-z. [PMID: 20369223]
  • Pitchai Balakumar, Ankur Rohilla, Pawan Krishan, Ponnu Solairaj, Arunachalam Thangathirupathi. The multifaceted therapeutic potential of benfotiamine. Pharmacological research. 2010 Jun; 61(6):482-8. doi: 10.1016/j.phrs.2010.02.008. [PMID: 20188835]
  • Umesh C S Yadav, Nilesh M Kalariya, Satish K Srivastava, Kota V Ramana. Protective role of benfotiamine, a fat-soluble vitamin B1 analogue, in lipopolysaccharide-induced cytotoxic signals in murine macrophages. Free radical biology & medicine. 2010 May; 48(10):1423-34. doi: 10.1016/j.freeradbiomed.2010.02.031. [PMID: 20219672]
  • Murat Olukman, Ebru Demirel Sezer, Sibel Ulker, Eser Y Sözmen, Gülcihan Mehtap Cınar. Fenofibrate treatment enhances antioxidant status and attenuates endothelial dysfunction in streptozotocin-induced diabetic rats. Experimental diabetes research. 2010; 2010(?):828531. doi: 10.1155/2010/828531. [PMID: 21234421]
  • Mihaela Bîcu, Maria Moţa, N M Panduru, Corina Grăunţeanu, E Moţa. Oxidative stress in diabetic kidney disease. Romanian journal of internal medicine = Revue roumaine de medecine interne. 2010; 48(4):307-12. doi: . [PMID: 21528758]
  • Uma Nath Tripathi, Deepak Chandra. The plant extracts of Momordica charantia and Trigonella foenum-graecum have anti-oxidant and anti-hyperglycemic properties for cardiac tissue during diabetes mellitus. Oxidative medicine and cellular longevity. 2009 Nov; 2(5):290-6. doi: 10.4161/oxim.2.5.9529. [PMID: 20716916]
  • Umesh C S Yadav, Sumitra Subramanyam, Kota V Ramana. Prevention of endotoxin-induced uveitis in rats by benfotiamine, a lipophilic analogue of vitamin B1. Investigative ophthalmology & visual science. 2009 May; 50(5):2276-82. doi: 10.1167/iovs.08-2816. [PMID: 19136698]
  • Pitchai Balakumar, Vishal Arvind Chakkarwar, Manjeet Singh. Ameliorative effect of combination of benfotiamine and fenofibrate in diabetes-induced vascular endothelial dysfunction and nephropathy in the rat. Molecular and cellular biochemistry. 2009 Jan; 320(1-2):149-62. doi: 10.1007/s11010-008-9917-z. [PMID: 18830571]
  • Pitchai Balakumar, Ramica Sharma, Manjeet Singh. Benfotiamine attenuates nicotine and uric acid-induced vascular endothelial dysfunction in the rat. Pharmacological research. 2008 Nov; 58(5-6):356-63. doi: 10.1016/j.phrs.2008.09.012. [PMID: 18951979]
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  • Nicole Schupp, Eva Maria Dette, Ursula Schmid, Udo Bahner, Michaela Winkler, August Heidland, Helga Stopper. Benfotiamine reduces genomic damage in peripheral lymphocytes of hemodialysis patients. Naunyn-Schmiedeberg's archives of pharmacology. 2008 Sep; 378(3):283-91. doi: 10.1007/s00210-008-0310-y. [PMID: 18509620]
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  • Ursula Schmid, Helga Stopper, August Heidland, Nicole Schupp. Benfotiamine exhibits direct antioxidative capacity and prevents induction of DNA damage in vitro. Diabetes/metabolism research and reviews. 2008 Jul; 24(5):371-7. doi: 10.1002/dmrr.860. [PMID: 18384109]
  • Marie-Laure Volvert, Sandrine Seyen, Marie Piette, Brigitte Evrard, Marjorie Gangolf, Jean-Christophe Plumier, Lucien Bettendorff. Benfotiamine, a synthetic S-acyl thiamine derivative, has different mechanisms of action and a different pharmacological profile than lipid-soluble thiamine disulfide derivatives. BMC pharmacology. 2008 Jun; 8(?):10. doi: 10.1186/1471-2210-8-10. [PMID: 18549472]
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  • Joachim F Wernicke, Fujun Wang, Yili L Pritchett, Timothy R Smith, Joel Raskin, Deborah N D'Souza, Smriti Iyengar, Amy S Chappell. An open-label 52-week clinical extension comparing duloxetine with routine care in patients with diabetic peripheral neuropathic pain. Pain medicine (Malden, Mass.). 2007 Sep; 8(6):503-13. doi: 10.1111/j.1526-4637.2006.00258.x. [PMID: 17716324]
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