Mycophenolic acid glucuronide (BioDeep_00000054181)
human metabolite Endogenous blood metabolite
代谢物信息卡片
6-({5-[(2Z)-5-carboxy-3-methylpent-2-en-1-yl]-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
化学式: C23H28O12 (496.1580688)
中文名称:
谱图信息:
最多检出来源 Danio rerio(blood) 20%
分子结构信息
SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)O)OC3C(C(C(C(O3)C(=O)O)O)O)O
InChI: InChI=1S/C23H28O12/c1-9(5-7-13(24)25)4-6-11-18(32-3)10(2)12-8-33-22(31)14(12)19(11)34-23-17(28)15(26)16(27)20(35-23)21(29)30/h4,15-17,20,23,26-28H,5-8H2,1-3H3,(H,24,25)(H,29,30)/b9-4-
描述信息
Mycophenolic acid glucuronide is a metabolite of mycophenolate mofetil. Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine. It is a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH) in purine biosynthesis which is necessary for the growth of T cells and B cells. Other cells are able to recover purines via a separate, scavenger, pathway and are, thus, able to escape the effect. MMF is a less toxic alternative to azathioprine. (Wikipedia)
同义名列表
7 个代谢物同义名
6-({5-[(2Z)-5-carboxy-3-methylpent-2-en-1-yl]-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid; 6-({5-[(2Z)-5-carboxy-3-methylpent-2-en-1-yl]-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid; 6-[[5-[(Z)-5-carboxy-3-methylpent-2-enyl]-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-4-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; Mycophenolic acid 7-O-glucuronide; mycophenolic acid glucuronide; Mycophenolate glucuronide; MPAG CPD
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
1 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(1)
- Mycophenolic Acid Metabolism Pathway:
Adenosine triphosphate + Mycophenolic acid + Water ⟶ Adenosine diphosphate + Mycophenolic acid + Phosphate
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。
文献列表
- Joseph Berthier, Mehdi Benmameri, François-Ludovic Sauvage, Gabin Fabre, Benjamin Chantemargue, Hélène Arnion, Pierre Marquet, Patrick Trouillas, Nicolas Picard, Franck Saint-Marcoux. MRP4 is responsible for the efflux transport of mycophenolic acid β-d glucuronide (MPAG) from hepatocytes to blood.
Xenobiotica; the fate of foreign compounds in biological systems.
2021 Jan; 51(1):105-114. doi:
10.1080/00498254.2020.1813352. [PMID: 32820679] - Dionysius Subali, Mi Hye Kwon, Won Seok Bang, Hee Eun Kang. The pharmacokinetics of mycophenolic acid in rats with orotic acid induced nonalcoholic fatty liver disease.
Canadian journal of physiology and pharmacology.
2020 Mar; 98(3):169-176. doi:
10.1139/cjpp-2019-0383. [PMID: 31652406] - Yan Rong, Tony K L Kiang. Mechanisms of Metabolism Interaction Between p-Cresol and Mycophenolic Acid.
Toxicological sciences : an official journal of the Society of Toxicology.
2020 02; 173(2):267-279. doi:
10.1093/toxsci/kfz231. [PMID: 31742356] - Pâmela C Lukasewicz Ferreira, Flavia Valladao Thiesen, Thaina Tavares de Araujo, Domingos Otávio D'Ávila, Giovani Gadonski, Carmem Silvana A de Oliveira, Aline Rigon Zimmer, Pedro Eduardo Fröehlich. Comparison of plasma and oral fluid concentrations of mycophenolic acid and its glucuronide metabolite by LC-MS in kidney transplant patients.
European journal of clinical pharmacology.
2019 Apr; 75(4):553-559. doi:
10.1007/s00228-018-02614-9. [PMID: 30610275] - Jennifer E Slovak, Sol M Rivera-Velez, Julianne K Hwang, Nicolas F Villarino. Pharmacokinetics and pharmacodynamics of mycophenolic acid in healthy cats after twice-daily intravenous infusion of mycophenolate mofetil for three days.
American journal of veterinary research.
2018 Oct; 79(10):1093-1099. doi:
10.2460/ajvr.79.10.1093. [PMID: 30256137] - Lu-Yang Xu, Zheng Jiao, Fei-Yan Liu, Xiao-Yan Qiu, Li Ji, Ming Zhang. Pharmacokinetics Evaluation of Mycophenolic Acid and Its Glucuronide Metabolite in Chinese Renal Transplant Recipients Receiving Enteric-Coated Mycophenolate Sodium and Tacrolimus.
Therapeutic drug monitoring.
2018 10; 40(5):572-580. doi:
10.1097/ftd.0000000000000533. [PMID: 29847459] - Uttam Garg, Ada Munar, Clinton Frazee. Determination of Mycophenolic Acid and Mycophenolic Acid Glucuronide Using Liquid Chromatography Tandem Mass Spectrometry (LC/MS/MS).
Current protocols in toxicology.
2018 02; 75(?):18.21.1-18.21.8. doi:
10.1002/cptx.42. [PMID: 29512127] - Yasuaki Mino, Takafumi Naito, Kumiko Shimoyama, Noriyoshi Ogawa, Junichi Kawakami. Mycophenolic acid exposure and complement fraction C3 influence inosine 5'-monophosphate dehydrogenase activity in systemic lupus erythematosus.
Annals of clinical biochemistry.
2017 Jul; 54(4):490-494. doi:
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Genetics and molecular research : GMR.
2017 May; 16(2):. doi:
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Scandinavian journal of clinical and laboratory investigation.
2016 Dec; 76(8):612-619. doi:
10.1080/00365513.2016.1230775. [PMID: 27676419] - Camille Girard-Bock, Marie-Odile Benoit-Biancamano, Lyne Villeneuve, Sylvie Desjardins, Chantal Guillemette. A Rare UGT2B7 Variant Creates a Novel N-Glycosylation Site at Codon 121 with Impaired Enzyme Activity.
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2016 12; 44(12):1867-1871. doi:
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British journal of clinical pharmacology.
2015 Nov; 80(5):1086-96. doi:
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Annals of transplantation.
2015 Aug; 20(?):483-92. doi:
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Acta pharmacologica Sinica.
2015 May; 36(5):644-50. doi:
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Clinical pharmacokinetics.
2015 Apr; 54(4):423-34. doi:
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Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2015; 135(10):1123-7. doi:
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Molecular pharmaceutics.
2014 Feb; 11(2):568-79. doi:
10.1021/mp400513k. [PMID: 24320552] - Amitava Dasgupta, Myrtle Johnson, Gertie Tso. Mathematical equations to calculate true mycophenolic acid concentration in human plasma by using two immunoassays with different cross-reactivities with acyl glucuronide metabolite: comparison of calculated values with values obtained by using an HPLC-UV method.
Journal of clinical laboratory analysis.
2013 Jul; 27(4):290-3. doi:
10.1002/jcla.21599. [PMID: 23852786] - Chirag G Patel, Ken Ogasawara, Fatemeh Akhlaghi. Mycophenolic acid glucuronide is transported by multidrug resistance-associated protein 2 and this transport is not inhibited by cyclosporine, tacrolimus or sirolimus.
Xenobiotica; the fate of foreign compounds in biological systems.
2013 Mar; 43(3):229-35. doi:
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Therapeutic drug monitoring.
2012 Dec; 34(6):652-9. doi:
10.1097/ftd.0b013e3182706ef1. [PMID: 23131696] - M G Kees, T Steinke, S Moritz, K Rupprecht, E M Paulus, F Kees, M Bucher, L Faerber. Omeprazole impairs the absorption of mycophenolate mofetil but not of enteric-coated mycophenolate sodium in healthy volunteers.
Journal of clinical pharmacology.
2012 Aug; 52(8):1265-72. doi:
10.1177/0091270011412968. [PMID: 21903891] - Martin H J Wiesen, Fedja Farowski, Markus Feldkötter, Bernd Hoppe, Carsten Müller. Liquid chromatography-tandem mass spectrometry method for the quantification of mycophenolic acid and its phenolic glucuronide in saliva and plasma using a standardized saliva collection device.
Journal of chromatography. A.
2012 Jun; 1241(?):52-9. doi:
10.1016/j.chroma.2012.04.008. [PMID: 22552204] - Y Mino, T Naito, K Shimoyama, N Ogawa, J Kawakami. Effective plasma concentrations of mycophenolic acid and its glucuronide in systemic lupus erythematosus patients in the remission-maintenance phase.
Journal of clinical pharmacy and therapeutics.
2012 Apr; 37(2):217-20. doi:
10.1111/j.1365-2710.2011.01269.x. [PMID: 21517926] - Jacek Klepacki, Jelena Klawitter, Jamie Bendrick-Peart, Bjorn Schniedewind, Svenja Heischmann, Touraj Shokati, Uwe Christians, Jost Klawitter. A high-throughput U-HPLC-MS/MS assay for the quantification of mycophenolic acid and its major metabolites mycophenolic acid glucuronide and mycophenolic acid acyl-glucuronide in human plasma and urine.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2012 Feb; 883-884(?):113-9. doi:
10.1016/j.jchromb.2011.07.021. [PMID: 21839692] - Erica D Greanya, Eric Poulin, Nilufar Partovi, R Jean Shapiro, Mai Al-Khatib, Mary H H Ensom. Pharmacokinetics of tacrolimus and mycophenolate mofetil in renal transplant recipients on a corticosteroid-free regimen.
American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists.
2012 Jan; 69(2):134-42. doi:
10.2146/ajhp110287. [PMID: 22215359] - Monica Cortinovis, Eliana Gotti, Silvia Pradini, Flavio Gaspari, Norberto Perico. Renal graft function and low-dose cyclosporine affect mycophenolic acid pharmacokinetics in kidney transplantation.
Transplantation.
2011 Sep; 92(5):550-6. doi:
10.1097/tp.0b013e318225dbd0. [PMID: 21709602] - Kathleen M Tornatore, Patcharaporn Sudchada, Kiran Dole, Robin DiFrancesco, Nicolae Leca, Aijaz C Gundroo, Ryan T Danison, Kris Attwood, Gregory E Wilding, Julia Zack, Alan Forrest, Rocco C Venuto. Mycophenolic acid pharmacokinetics during maintenance immunosuppression in African American and Caucasian renal transplant recipients.
Journal of clinical pharmacology.
2011 Aug; 51(8):1213-22. doi:
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Journal of clinical pharmacy and therapeutics.
2011 Apr; 36(2):217-24. doi:
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Clinica chimica acta; international journal of clinical chemistry.
2011 Jan; 412(1-2):59-65. doi:
10.1016/j.cca.2010.09.041. [PMID: 20937266] - Jun-wei Gao, Zhi-hai Peng, Xiao-yu Li, Bo Sun, Yan-kun Guo, Gao-lin Liu. Simultaneous determination of mycophenolic acid and its metabolites by HPLC and pharmacokinetic studies in rat plasma and bile.
Archives of pharmacal research.
2011 Jan; 34(1):59-69. doi:
10.1007/s12272-011-0107-2. [PMID: 21468916] - Takafumi Naito. [Optimal immunosuppressive therapy based on pharmacokinetics and pharmacodynamics of antimetabolites in clinical practice].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2010 Dec; 130(12):1695-700. doi:
10.1248/yakushi.130.1695. [PMID: 21139397] - M C Raggi, S B Siebert, D K Abendroth, W Steimer, H Friess, S G Thorban. Neither mycophenolate acyl-glucuronide levels nor their areas under the curve are responsible for the gastrointestinal side effects in kidney transplant recipients receiving EC-MPA: a prospective trial.
Transplantation proceedings.
2010 Dec; 42(10):4049-52. doi:
10.1016/j.transproceed.2010.09.029. [PMID: 21168624] - Bing Chen, ZhiDong Gu, Hao Chen, WeiXia Zhang, XiaoJing Fen, WeiMin Cai, QiShi Fan. Establishment of high-performance liquid chromatography and enzyme multiplied immunoassay technology methods for determination of free mycophenolic acid and its application in Chinese liver transplant recipients.
Therapeutic drug monitoring.
2010 Oct; 32(5):653-60. doi:
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Talanta.
2010 Mar; 80(5):1894-8. doi:
10.1016/j.talanta.2009.10.040. [PMID: 20152429] - Katherine A Barraclough, Katie J Lee, Christine E Staatz. Pharmacogenetic influences on mycophenolate therapy.
Pharmacogenomics.
2010 Mar; 11(3):369-90. doi:
10.2217/pgs.10.9. [PMID: 20235793] - Pamala A Jacobson, Jiayin Huang, Juan Wu, Miae Kim, Brent Logan, Amin Alousi, Michael Grimley, Javier Bolaños-Meade, Vincent Ho, John E Levine, Daniel Weisdorf. Mycophenolate pharmacokinetics and association with response to acute graft-versus-host disease treatment from the Blood and Marrow Transplant Clinical Trials Network.
Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation.
2010 Mar; 16(3):421-9. doi:
10.1016/j.bbmt.2009.11.010. [PMID: 19925875] - Maria Shipkova, Ekkehard Schütz, Ingo Besenthal, Peter Fraunberger, Eberhard Wieland. Investigation of the crossreactivity of mycophenolic acid glucuronide metabolites and of mycophenolate mofetil in the Cedia MPA assay.
Therapeutic drug monitoring.
2010 Feb; 32(1):79-85. doi:
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Methods in molecular biology (Clifton, N.J.).
2010; 603(?):379-87. doi:
10.1007/978-1-60761-459-3_37. [PMID: 20077090] - Michal J Figurski, Magdalena Korecka, Leona Fields, Teresa Waligórska, Leslie M Shaw. High-performance liquid chromatography-mass spectroscopy/mass spectroscopy method for simultaneous quantification of total or free fraction of mycophenolic acid and its glucuronide metabolites.
Therapeutic drug monitoring.
2009 Dec; 31(6):717-26. doi:
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Journal of pharmacokinetics and pharmacodynamics.
2009 Dec; 36(6):541-64. doi:
10.1007/s10928-009-9136-6. [PMID: 19904584] - Korbinian Rupprecht, Christoph Schmidt, Anne Raspé, Frank Schweda, Maria Shipkova, Wolfgang Fischer, Michael Bucher, Frieder Kees, Lothar Faerber. Bioavailability of mycophenolate mofetil and enteric-coated mycophenolate sodium is differentially affected by pantoprazole in healthy volunteers.
Journal of clinical pharmacology.
2009 Oct; 49(10):1196-201. doi:
10.1177/0091270009344988. [PMID: 19783713] - T Baczkowska, A Sadowska, A Perkowska-Ptasinska, Z Lewandowski, T Cieciura, J Pazik, E Wazna, O Przybyl Kozinska, E Nowacka Cieciura, A Chmura, M Durlik. Optimal mycophenolic acid and mycophenolic acid glucuronide levels at the early period after kidney transplantation are the key contributors to improving long-term outcomes.
Transplantation proceedings.
2009 Oct; 41(8):3019-23. doi:
10.1016/j.transproceed.2009.08.009. [PMID: 19857666] - Wai-Ping Yau, Anantharaman Vathsala, Huei-Xin Lou, Shufeng Zhou, Eli Chan. Mechanism-based enterohepatic circulation model of mycophenolic acid and its glucuronide metabolite: assessment of impact of cyclosporine dose in Asian renal transplant patients.
Journal of clinical pharmacology.
2009 Jun; 49(6):684-99. doi:
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Journal of clinical pharmacology.
2009 Jun; 49(6):710-8. doi:
10.1177/0091270009335003. [PMID: 19451405] - Melanie S Joy, Tandrea Hilliard, Yichun Hu, Susan L Hogan, Jinzhao Wang, Ronald J Falk, Philip C Smith. Influence of clinical and demographic variables on mycophenolic acid pharmacokinetics in antineutrophil cytoplasmic antibody-associated vasculitis.
The Annals of pharmacotherapy.
2009 Jun; 43(6):1020-7. doi:
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Clinical biochemistry.
2009 May; 42(7-8):595-601. doi:
10.1016/j.clinbiochem.2008.11.013. [PMID: 19100248] - Flora T Musuamba, Annick Rousseau, Jean-Louis Bosmans, Jean-Jacques Senessael, Jean Cumps, Pierre Marquet, Pierre Wallemacq, Roger K Verbeeck. Limited sampling models and Bayesian estimation for mycophenolic acid area under the curve prediction in stable renal transplant patients co-medicated with ciclosporin or sirolimus.
Clinical pharmacokinetics.
2009; 48(11):745-58. doi:
10.2165/11318060-000000000-00000. [PMID: 19817503] - Joachim Kuhn, Christian Prante, Knut Kleesiek, Christian Götting. Measurement of mycophenolic acid and its glucuronide using a novel rapid liquid chromatography-electrospray ionization tandem mass spectrometry assay.
Clinical biochemistry.
2009 Jan; 42(1-2):83-90. doi:
10.1016/j.clinbiochem.2008.10.004. [PMID: 18996104] - Melanie S Joy, Tandrea Hilliard, Yichun Hu, Susan L Hogan, Mary Anne Dooley, Ronald J Falk, Philip C Smith. Pharmacokinetics of mycophenolic acid in patients with lupus nephritis.
Pharmacotherapy.
2009 Jan; 29(1):7-16. doi:
10.1592/phco.29.1.7. [PMID: 19113793] - Yasuaki Mino, Takafumi Naito, Tomomi Matsushita, Atsushi Otsuka, Tomomi Ushiyama, Seiichiro Ozono, Akira Hishida, Yoshiyuki Kagawa, Junichi Kawakami. Comparison of pharmacokinetics of mycophenolic acid and its glucuronide between patients with lupus nephritis and with kidney transplantation.
Therapeutic drug monitoring.
2008 Dec; 30(6):656-61. doi:
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Xenobiotica; the fate of foreign compounds in biological systems.
2008 Nov; 38(11):1422-36. doi:
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Therapeutic drug monitoring.
2008 Oct; 30(5):559-64. doi:
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Therapeutic drug monitoring.
2008 Aug; 30(4):439-44. doi:
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Journal of pharmaceutical and biomedical analysis.
2008 Jul; 47(3):575-85. doi:
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Transplant immunology.
2008 Jul; 19(3-4):192-6. doi:
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Journal of clinical pharmacology.
2008 May; 48(5):547-52. doi:
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Biochemical pharmacology.
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Pharmacogenetics and genomics.
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European journal of clinical pharmacology.
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Biological & pharmaceutical bulletin.
2006 Feb; 29(2):275-80. doi:
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