Phenylacetylglutamine (BioDeep_00000002938)
Secondary id: BioDeep_00000404022
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
代谢物信息卡片
(2S)-5-amino-5-oxo-2-[(2-phenylacetyl)amino]pentanoic acid
化学式: C13H16N2O4 (264.111)
中文名称: N-苯乙酰基-L-谷氨酰胺, 苯乙酰谷氨酰胺
谱图信息:
最多检出来源 Homo sapiens(blood) 28.17%
Reviewed
Last reviewed on 2024-09-13.
Cite this Page
Phenylacetylglutamine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/phenylacetylglutamine (retrieved
2024-12-22) (BioDeep RN: BioDeep_00000002938). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: C1=CC=C(C=C1)CC(=O)NC(CCC(=O)N)C(=O)O
InChI: InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)
描述信息
Phenylacetylglutamine is a product formed from the conjugation of phenylacetate and glutamine. Technically, it is the amino acid acetylation product of phenylacetate (or phenylbutyrate after beta-oxidation). Phenylacetylglutamine is a normal constituent of human urine, but other mammals such as the dog, cat, rat, monkey, sheep, and horse do not excrete this compound. Phenylacetyl-CoA and L-glutamine react to form phenylacetylglutamine and coenzyme A. The enzyme (glutamine N-acetyl transferase) that catalyzes this reaction has been purified from human liver mitochondria and shown to be a polypeptide species distinct from glycine-N-acyltransferase. Phenylacetylglutamine is a major nitrogenous metabolite that accumulates in uremia (PMID: 2791363, 8972626). It has been shown that over 50\\\% of urine phenylacetylglutamine may be derived from kidney conjugation of free plasma phenylacetic acid and/or from the kidneys preferential filtration of conjugated phenylacetic acid (PMID: 6420430). Phenylacetylglutamine is a microbial metabolite found in Christensenellaceae, Lachnospiraceae and Ruminococcaceae (PMID: 26241311).
Phenylacetylglutamine is a product formed by the conjugation of phenylacetate and glutamine. Technically it is the amino acid acetylation product of phenylacetate (or phenylbutyrate after beta-oxidation). Phenylacetylglutamine is a normal constituent of human urine, but other mammals including the dog, cat, rat, monkey, sheep and horse do not excrete this compound. Phenylacetyl CoA and glutamine react to form phenylacetyl glutamine and Coenzyme A. The enzyme (Glutamine N-acetyl transferase) that catalyzes this reaction has been purified from human liver mitochondria and shown to be a distinct polypeptide species from glycine-N-acyltransferase. Phenylacetylglutamine is a major nitrogenous metabolite that accumulates in uremia. (PMID: 2791363; PMID: 8972626). It has been shown that over 50\\\% of urine phenylacetylglutamine may be derived from kidney conjugation of free plasma phenylacetic acid and/or from the kidneys preferential filtration of conjugated phenylacetic acid (PMID: 6420430)
Phenylacetylglutamine is a colonic microbial metabolite from amino acid fermentation.
同义名列表
20 个代谢物同义名
(2S)-5-amino-5-oxo-2-[(2-phenylacetyl)amino]pentanoic acid; (2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid; N-[(4-Hydroxyphenyl)acetyl]glutamic acid; L-N(sup 2)-(Phenylacetyl)glutamine; N(2)-(2-Phenylacetyl)-L-glutamine; alpha-N-Phenylacetyl-L-glutamine; N2-(2-Phenylacetyl)-L-glutamine; N(2)-(Phenylacetyl)-L-glutamine; alpha-N-Phenylacetylglutamine; N2-(Phenylacetyl)-L-glutamine; a-N-Phenylacetyl-L-glutamine; Α-N-phenylacetyl-L-glutamine; N(2)-phenylacetylglutamine; α-N-Phenylacetylglutamine; Phenylacetyl-L-glutamine; N-Phenylacetylglutamine; Phenylacetylglutamine; Phenylacetylglutamine; NSC 203800; Phenylacetylglutamine
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:17884
- ChEBI: CHEBI:8087
- KEGG: C04148
- PubChem: 306137
- PubChem: 92258
- HMDB: HMDB0006344
- Metlin: METLIN58397
- ChEMBL: CHEMBL2219677
- ChEMBL: CHEMBL4303372
- Wikipedia: Phenylacetylglutamine
- MetaCyc: CPD-1097
- KNApSAcK: C00052383
- foodb: FDB023896
- chemspider: 83292
- CAS: 28047-15-6
- PMhub: MS000007246
- PubChem: 6833
- 3DMET: B00684
- NIKKAJI: J75.641E
- RefMet: alpha-N-Phenylacetylglutamine
- medchemexpress: HY-W050026
- KNApSAcK: 17884
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
4 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(4)
- Phenylacetate Metabolism:
Adenosine triphosphate + Coenzyme A + Phenylacetic acid ⟶ Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate - Phenylacetate Metabolism:
Adenosine triphosphate + Coenzyme A + Phenylacetic acid ⟶ Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate - Phenylacetate Metabolism:
Adenosine triphosphate + Coenzyme A + Phenylacetic acid ⟶ Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate - Phenylacetate Metabolism:
Adenosine triphosphate + Coenzyme A + Phenylacetic acid ⟶ Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate
PharmGKB(0)
2 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
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
- Xiaofeng Chen, Hua Zhang, Sichong Ren, Yangnan Ding, Naznin Sultana Remex, Md Shenuarin Bhuiyan, Jiahua Qu, Xiaoqiang Tang. Gut microbiota and microbiota-derived metabolites in cardiovascular diseases.
Chinese medical journal.
2023 Jul; ?(?):. doi:
10.1097/cm9.0000000000002206. [PMID: 37442759] - J Xu, M Cai, Z Wang, Q Chen, X Han, J Tian, S Jin, Z Yan, Y Li, B Lu, H Lu. Phenylacetylglutamine as a novel biomarker of type 2 diabetes with distal symmetric polyneuropathy by metabolomics.
Journal of endocrinological investigation.
2022 Oct; ?(?):. doi:
10.1007/s40618-022-01929-w. [PMID: 36282471] - Xiao Zong, Qin Fan, Qian Yang, Roubai Pan, Lingfang Zhuang, Rong Tao. Phenylacetylglutamine as a risk factor and prognostic indicator of heart failure.
ESC heart failure.
2022 08; 9(4):2645-2653. doi:
10.1002/ehf2.13989. [PMID: 35624536] - Mitchelle Katemauswa, Ekram Hossain, Zongyuan Liu, Mahbobeh Lesani, Adwaita R Parab, Danya A Dean, Laura-Isobel McCall. Enabling Quantitative Analysis of Surface Small Molecules for Exposomics and Behavioral Studies.
Journal of the American Society for Mass Spectrometry.
2022 Mar; 33(3):412-419. doi:
10.1021/jasms.1c00263. [PMID: 35084848] - Quentin Leyrolle, Renata Cserjesi, Romane Demeure, Audrey M Neyrinck, Camille Amadieu, Julie Rodriguez, Olli Kärkkäinen, Kati Hanhineva, Nicolas Paquot, Miriam Cnop, Patrice D Cani, Jean-Paul Thissen, Laure B Bindels, Olivier Klein, Olivier Luminet, Nathalie M Delzenne. Microbiota and Metabolite Profiling as Markers of Mood Disorders: A Cross-Sectional Study in Obese Patients.
Nutrients.
2021 Dec; 14(1):. doi:
10.3390/nu14010147. [PMID: 35011021] - Xiaofeng Wang, Jack Tseng, Carmen Mak, Nagaraju Poola, Regis A Vilchez. Exposures of Phenylacetic Acid and Phenylacetylglutamine Across Different Subpopulations and Correlation with Adverse Events.
Clinical pharmacokinetics.
2021 12; 60(12):1557-1567. doi:
10.1007/s40262-021-01047-5. [PMID: 34125423] - Robert D Mair, Seolhyun Lee, Natalie S Plummer, Tammy L Sirich, Timothy W Meyer. Impaired Tubular Secretion of Organic Solutes in Advanced Chronic Kidney Disease.
Journal of the American Society of Nephrology : JASN.
2021 11; 32(11):2877-2884. doi:
10.1681/asn.2021030336. [PMID: 34408065] - Yang Liu, Shaoyan Liu, Zhizhuang Zhao, Xiang Song, Haixian Qu, Hongbin Liu. Phenylacetylglutamine is associated with the degree of coronary atherosclerotic severity assessed by coronary computed tomographic angiography in patients with suspected coronary artery disease.
Atherosclerosis.
2021 09; 333(?):75-82. doi:
10.1016/j.atherosclerosis.2021.08.029. [PMID: 34438323] - Filip Ottosson, Louise Brunkwall, Einar Smith, Marju Orho-Melander, Peter M Nilsson, Céline Fernandez, Olle Melander. The gut microbiota-related metabolite phenylacetylglutamine associates with increased risk of incident coronary artery disease.
Journal of hypertension.
2020 12; 38(12):2427-2434. doi:
10.1097/hjh.0000000000002569. [PMID: 32665522] - Kiana Ashley West, Chidimma Kanu, Tanya Maric, Julie Anne Kathryn McDonald, Jeremy K Nicholson, Jia V Li, Mark R Johnson, Elaine Holmes, Makrina D Savvidou. Longitudinal metabolic and gut bacterial profiling of pregnant women with previous bariatric surgery.
Gut.
2020 08; 69(8):1452-1459. doi:
10.1136/gutjnl-2019-319620. [PMID: 31964751] - Marco Witkowski, Taylor L Weeks, Stanley L Hazen. Gut Microbiota and Cardiovascular Disease.
Circulation research.
2020 07; 127(4):553-570. doi:
10.1161/circresaha.120.316242. [PMID: 32762536] - Wendy J Dahl, Wei-Lun Hung, Amanda L Ford, Joon Hyuk Suh, Jerémié Auger, Varuni Nagulesapillai, Yu Wang. In older women, a high-protein diet including animal-sourced foods did not impact serum levels and urinary excretion of trimethylamine-N-oxide.
Nutrition research (New York, N.Y.).
2020 06; 78(?):72-81. doi:
10.1016/j.nutres.2020.05.004. [PMID: 32544852] - Ina Nemet, Prasenjit Prasad Saha, Nilaksh Gupta, Weifei Zhu, Kymberleigh A Romano, Sarah M Skye, Tomas Cajka, Maradumane L Mohan, Lin Li, Yuping Wu, Masanori Funabashi, Amanda E Ramer-Tait, Sathyamangla Venkata Naga Prasad, Oliver Fiehn, Federico E Rey, W H Wilson Tang, Michael A Fischbach, Joseph A DiDonato, Stanley L Hazen. A Cardiovascular Disease-Linked Gut Microbial Metabolite Acts via Adrenergic Receptors.
Cell.
2020 03; 180(5):862-877.e22. doi:
10.1016/j.cell.2020.02.016. [PMID: 32142679] - Fernando Andrade, Isidro Vitoria, Elena Martín Hernández, Guillem Pintos-Morell, Patricia Correcher, Rocío Puig-Piña, Pilar Quijada-Fraile, Luis Peña-Quintana, Ana Mª Marquez, Olatz Villate, Mª Teresa García Silva, Javier de Las Heras, Leticia Ceberio, Esmeralda Rodrigues, Teresa Almeida Campos, Raquel Yahyaoui, Javier Blasco, Inmaculada Vives-Piñera, David Gil, Mireia Del Toro, Mónica Ruiz-Pons, Elvira Cañedo, Miguel Angel Barba Romero, Mª Concepción García-Jiménez, Luis Aldámiz-Echevarría. Quantification of urinary derivatives of Phenylbutyric and Benzoic acids by LC-MS/MS as treatment compliance biomarkers in Urea Cycle disorders.
Journal of pharmaceutical and biomedical analysis.
2019 Nov; 176(?):112798. doi:
10.1016/j.jpba.2019.112798. [PMID: 31394303] - Tiffany A Freed, Josef Coresh, Lesley A Inker, Douglas R Toal, Regis Perichon, Jingsha Chen, Kelli D Goodman, Qibo Zhang, Jessie K Conner, Deirdre M Hauser, Kate E T Vroom, Maria L Oyaski, Jacob E Wulff, Gudný Eiríksdóttir, Vilmundur Gudnason, Vicente E Torres, Lisa A Ford, Andrew S Levey. Validation of a Metabolite Panel for a More Accurate Estimation of Glomerular Filtration Rate Using Quantitative LC-MS/MS.
Clinical chemistry.
2019 03; 65(3):406-418. doi:
10.1373/clinchem.2018.288092. [PMID: 30647123] - Nadezda V Khodorova, Douglas N Rutledge, Marion Oberli, David Mathiron, Paulo Marcelo, Robert Benamouzig, Daniel Tomé, Claire Gaudichon, Serge Pilard. Urinary Metabolomics Profiles Associated to Bovine Meat Ingestion in Humans.
Molecular nutrition & food research.
2019 01; 63(1):e1700834. doi:
10.1002/mnfr.201700834. [PMID: 29468821] - Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics.
Scientific reports.
2018 07; 8(1):10056. doi:
10.1038/s41598-018-28477-9. [PMID: 29968805] - Sheldon C Leong, Justin N Sao, Abigail Taussig, Natalie S Plummer, Timothy W Meyer, Tammy L Sirich. Residual Function Effectively Controls Plasma Concentrations of Secreted Solutes in Patients on Twice Weekly Hemodialysis.
Journal of the American Society of Nephrology : JASN.
2018 07; 29(7):1992-1999. doi:
10.1681/asn.2018010081. [PMID: 29728422] - Mai Hazekawa, Kazuhiko Ono, Takuya Nishinakagawa, Tomoyo Kawakubo-Yasukochi, Manabu Nakashima. In Vitro Anti-inflammatory Effects of the Phenylbutyric Acid Metabolite Phenylacetyl Glutamine.
Biological & pharmaceutical bulletin.
2018 Jun; 41(6):961-966. doi:
10.1248/bpb.b17-00799. [PMID: 29526885] - R Todd Stravitz, Michelle Gottfried, Valerie Durkalski, Robert J Fontana, A James Hanje, David Koch, Bilal Hameed, Daniel Ganger, Ram M Subramanian, Stan Bukofzer, William R Ravis, Kristen Clasen, Averell Sherker, Lanna Little, William M Lee. Safety, tolerability, and pharmacokinetics of l-ornithine phenylacetate in patients with acute liver injury/failure and hyperammonemia.
Hepatology (Baltimore, Md.).
2018 03; 67(3):1003-1013. doi:
10.1002/hep.29621. [PMID: 29080224] - Hai-Tao Yu, Xiao-Yi Fu, Bin Xu, Li-Li Zuo, Hong-Bo Ma, Shu-Ran Wang. Untargeted metabolomics approach (UPLC-Q-TOF-MS) explores the biomarkers of serum and urine in overweight/obese young men.
Asia Pacific journal of clinical nutrition.
2018 ; 27(5):1067-1076. doi:
10.6133/apjcn.052018.07. [PMID: 30272855] - Tariq Shafi, Tammy L Sirich, Timothy W Meyer, Thomas H Hostetter, Natalie S Plummer, Seungyoung Hwang, Michal L Melamed, Tanushree Banerjee, Josef Coresh, Neil R Powe. Results of the HEMO Study suggest that p-cresol sulfate and indoxyl sulfate are not associated with cardiovascular outcomes.
Kidney international.
2017 12; 92(6):1484-1492. doi:
10.1016/j.kint.2017.05.012. [PMID: 28739139] - Yi Jiang, Mohammed Almannai, V Reid Sutton, Qin Sun, Sarah H Elsea. Quantitation of phenylbutyrate metabolites by UPLC-MS/MS demonstrates inverse correlation of phenylacetate:phenylacetylglutamine ratio with plasma glutamine levels.
Molecular genetics and metabolism.
2017 11; 122(3):39-45. doi:
10.1016/j.ymgme.2017.08.011. [PMID: 28888854] - Enrique Almanza-Aguilera, Mireia Urpi-Sarda, Rafael Llorach, Rosa Vázquez-Fresno, Mar Garcia-Aloy, Francesc Carmona, Alex Sanchez, Francisco Madrid-Gambin, Ramon Estruch, Dolores Corella, Cristina Andres-Lacueva. Microbial metabolites are associated with a high adherence to a Mediterranean dietary pattern using a 1H-NMR-based untargeted metabolomics approach.
The Journal of nutritional biochemistry.
2017 10; 48(?):36-43. doi:
10.1016/j.jnutbio.2017.06.001. [PMID: 28692847] - Ruben Poesen, Kathleen Claes, Pieter Evenepoel, Henriette de Loor, Patrick Augustijns, Dirk Kuypers, Björn Meijers. Microbiota-Derived Phenylacetylglutamine Associates with Overall Mortality and Cardiovascular Disease in Patients with CKD.
Journal of the American Society of Nephrology : JASN.
2016 Nov; 27(11):3479-3487. doi:
10.1681/asn.2015121302. [PMID: 27230658] - Julia Kuligowski, Daniel Sanjuan-Herráez, María A Vázquez-Sánchez, Anna Brunet-Vega, Carles Pericay, María José Ramírez-Lázaro, Sergio Lario, Lourdes Gombau, Félix Junquera, Xavier Calvet, Guillermo Quintás. Metabolomic Analysis of Gastric Cancer Progression within the Correa's Cascade Using Ultraperformance Liquid Chromatography-Mass Spectrometry.
Journal of proteome research.
2016 08; 15(8):2729-38. doi:
10.1021/acs.jproteome.6b00281. [PMID: 27384260] - Tariq Shafi, Timothy W Meyer, Thomas H Hostetter, Michal L Melamed, Rulan S Parekh, Seungyoung Hwang, Tanushree Banerjee, Josef Coresh, Neil R Powe. Free Levels of Selected Organic Solutes and Cardiovascular Morbidity and Mortality in Hemodialysis Patients: Results from the Retained Organic Solutes and Clinical Outcomes (ROSCO) Investigators.
PloS one.
2015; 10(5):e0126048. doi:
10.1371/journal.pone.0126048. [PMID: 25938230] - Clara Barrios, Michelle Beaumont, Tess Pallister, Judith Villar, Julia K Goodrich, Andrew Clark, Julio Pascual, Ruth E Ley, Tim D Spector, Jordana T Bell, Cristina Menni. Gut-Microbiota-Metabolite Axis in Early Renal Function Decline.
PloS one.
2015; 10(8):e0134311. doi:
10.1371/journal.pone.0134311. [PMID: 26241311] - Tammy L Sirich, Benjamin A Funk, Natalie S Plummer, Thomas H Hostetter, Timothy W Meyer. Prominent accumulation in hemodialysis patients of solutes normally cleared by tubular secretion.
Journal of the American Society of Nephrology : JASN.
2014 Mar; 25(3):615-22. doi:
10.1681/asn.2013060597. [PMID: 24231664] - Don C Rockey, John M Vierling, Parvez Mantry, Marwan Ghabril, Robert S Brown, Olga Alexeeva, Igor A Zupanets, Vladimir Grinevich, Andrey Baranovsky, Larysa Dudar, Galyna Fadieienko, Nataliya Kharchenko, Iryna Klaryts'ka, Vyacheslav Morozov, Priya Grewal, Timothy McCashland, K Gautham Reddy, K Rajender Reddy, Vasyl Syplyviy, Nathan M Bass, Klara Dickinson, Catherine Norris, Dion Coakley, Masoud Mokhtarani, Bruce F Scharschmidt. Randomized, double-blind, controlled study of glycerol phenylbutyrate in hepatic encephalopathy.
Hepatology (Baltimore, Md.).
2014 Mar; 59(3):1073-83. doi:
10.1002/hep.26611. [PMID: 23847109] - M Mokhtarani, G A Diaz, W Rhead, S A Berry, U Lichter-Konecki, A Feigenbaum, A Schulze, N Longo, J Bartley, W Berquist, R Gallagher, W Smith, S E McCandless, C Harding, D C Rockey, J M Vierling, P Mantry, M Ghabril, R S Brown, K Dickinson, T Moors, C Norris, D Coakley, D A Milikien, S C Nagamani, C Lemons, B Lee, B F Scharschmidt. Elevated phenylacetic acid levels do not correlate with adverse events in patients with urea cycle disorders or hepatic encephalopathy and can be predicted based on the plasma PAA to PAGN ratio.
Molecular genetics and metabolism.
2013 Dec; 110(4):446-53. doi:
10.1016/j.ymgme.2013.09.017. [PMID: 24144944] - Meritxell Ventura-Cots, José A Arranz, Macarena Simón-Talero, Maria Torrens, Albert Blanco, Encarnació Riudor, Inma Fuentes, Pilar Suñé, German Soriano, Juan Córdoba. Safety of ornithine phenylacetate in cirrhotic decompensated patients: an open-label, dose-escalating, single-cohort study.
Journal of clinical gastroenterology.
2013 Nov; 47(10):881-7. doi:
10.1097/mcg.0b013e318299c789. [PMID: 23751856] - Jonathan R Swann, Konstantina Spagou, Matthew Lewis, Jeremy K Nicholson, Dana A Glei, Teresa E Seeman, Christopher L Coe, Noreen Goldman, Carol D Ryff, Maxine Weinstein, Elaine Holmes. Microbial-mammalian cometabolites dominate the age-associated urinary metabolic phenotype in Taiwanese and American populations.
Journal of proteome research.
2013 Jul; 12(7):3166-80. doi:
10.1021/pr4000152. [PMID: 23701591] - Jon P R Monteleone, M Mokhtarani, G A Diaz, W Rhead, U Lichter-Konecki, S A Berry, C Lemons, K Dickinson, D Coakley, B Lee, B F Scharschmidt. Population pharmacokinetic modeling and dosing simulations of nitrogen-scavenging compounds: disposition of glycerol phenylbutyrate and sodium phenylbutyrate in adult and pediatric patients with urea cycle disorders.
Journal of clinical pharmacology.
2013 Jul; 53(7):699-710. doi:
10.1002/jcph.92. [PMID: 23775211] - Wendy Smith, George A Diaz, Uta Lichter-Konecki, Susan A Berry, Cary O Harding, Shawn E McCandless, Cindy LeMons, Joe Mauney, Klara Dickinson, Dion F Coakley, Tristen Moors, Masoud Mokhtarani, Bruce F Scharschmidt, Brendan Lee. Ammonia control in children ages 2 months through 5 years with urea cycle disorders: comparison of sodium phenylbutyrate and glycerol phenylbutyrate.
The Journal of pediatrics.
2013 Jun; 162(6):1228-34, 1234.e1. doi:
10.1016/j.jpeds.2012.11.084. [PMID: 23324524] - M Mokhtarani, G A Diaz, W Rhead, U Lichter-Konecki, J Bartley, A Feigenbaum, N Longo, W Berquist, S A Berry, R Gallagher, D Bartholomew, C O Harding, M S Korson, S E McCandless, W Smith, J Vockley, S Bart, D Kronn, R Zori, S Cederbaum, N Dorrani, J L Merritt, Sandesh Sreenath-Nagamani, M Summar, C Lemons, K Dickinson, D F Coakley, T L Moors, B Lee, B F Scharschmidt. Urinary phenylacetylglutamine as dosing biomarker for patients with urea cycle disorders.
Molecular genetics and metabolism.
2012 Nov; 107(3):308-14. doi:
10.1016/j.ymgme.2012.08.006. [PMID: 22958974] - Marc Oria, Jordi Romero-Giménez, José Antonio Arranz, Encarnació Riudor, Núria Raguer, Juan Córdoba. Ornithine phenylacetate prevents disturbances of motor-evoked potentials induced by intestinal blood in rats with portacaval anastomosis.
Journal of hepatology.
2012 Jan; 56(1):109-14. doi:
10.1016/j.jhep.2011.06.026. [PMID: 21835138] - Hanne Christine Bertram, Christian Clement Yde, Xumin Zhang, Niels Bastian Kristensen. Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics.
Journal of agricultural and food chemistry.
2011 Dec; 59(23):12499-505. doi:
10.1021/jf204201f. [PMID: 22059599] - Aifric O'Sullivan, Michael J Gibney, Lorraine Brennan. Dietary intake patterns are reflected in metabolomic profiles: potential role in dietary assessment studies.
The American journal of clinical nutrition.
2011 Feb; 93(2):314-21. doi:
10.3945/ajcn.110.000950. [PMID: 21177801] - G Wright, A Chattree, R Jalan. Management of hepatic encephalopathy.
International journal of hepatology.
2011; 2011(?):841407. doi:
10.4061/2011/841407. [PMID: 21994873] - Ivan K S Yap, Ian J Brown, Queenie Chan, Anisha Wijeyesekera, Isabel Garcia-Perez, Magda Bictash, Ruey Leng Loo, Marc Chadeau-Hyam, Timothy Ebbels, Maria De Iorio, Elaine Maibaum, Liancheng Zhao, Hugo Kesteloot, Martha L Daviglus, Jeremiah Stamler, Jeremy K Nicholson, Paul Elliott, Elaine Holmes. Metabolome-wide association study identifies multiple biomarkers that discriminate north and south Chinese populations at differing risks of cardiovascular disease: INTERMAP study.
Journal of proteome research.
2010 Dec; 9(12):6647-54. doi:
10.1021/pr100798r. [PMID: 20853909] - Maurice D Laryea, Diran Herebian, Thomas Meissner, Ertan Mayatepek. Simultaneous LC-MS/MS determination of phenylbutyrate, phenylacetate benzoate and their corresponding metabolites phenylacetylglutamine and hippurate in blood and urine.
Journal of inherited metabolic disease.
2010 Dec; 33 Suppl 3(?):S321-8. doi:
10.1007/s10545-010-9172-9. [PMID: 20694517] - Brendan Lee, William Rhead, George A Diaz, Bruce F Scharschmidt, Asad Mian, Oleg Shchelochkov, J F Marier, Martin Beliveau, Joseph Mauney, Klara Dickinson, Antonia Martinez, Sharron Gargosky, Masoud Mokhtarani, Susan A Berry. Phase 2 comparison of a novel ammonia scavenging agent with sodium phenylbutyrate in patients with urea cycle disorders: safety, pharmacokinetics and ammonia control.
Molecular genetics and metabolism.
2010 Jul; 100(3):221-8. doi:
10.1016/j.ymgme.2010.03.014. [PMID: 20382058] - Brendan M McGuire, Igor A Zupanets, Mark E Lowe, Xunjun Xiao, Vasyliy A Syplyviy, Jon Monteleone, Sharron Gargosky, Klara Dickinson, Antonia Martinez, Masoud Mokhtarani, Bruce F Scharschmidt. Pharmacology and safety of glycerol phenylbutyrate in healthy adults and adults with cirrhosis.
Hepatology (Baltimore, Md.).
2010 Jun; 51(6):2077-85. doi:
10.1002/hep.23589. [PMID: 20512995] - C Persu, V Cauni, S Gutue, Irina Blaj, V Jinga, P Geavlete. From interstitial cystitis to chronic pelvic pain.
Journal of medicine and life.
2010 Apr; 3(2):167-74. doi:
NULL. [PMID: 20968203] - Cristina Barosa, Manuela Almeida, M Madalena Caldeira, Filipe Gomes, John G Jones. Contribution of proteolytic and metabolic sources to hepatic glutamine by (2)H NMR analysis of urinary phenylacetylglutamine (2)H-enrichment from (2)H(2)O.
Metabolic engineering.
2010 Jan; 12(1):53-61. doi:
10.1016/j.ymben.2009.08.009. [PMID: 19733678] - Fernando Scaglia. New insights in nutritional management and amino acid supplementation in urea cycle disorders.
Molecular genetics and metabolism.
2010; 100 Suppl 1(?):S72-6. doi:
10.1016/j.ymgme.2010.02.019. [PMID: 20299258] - Yousuke Fukui, Masao Kato, Yohji Inoue, Akio Matsubara, Kohji Itoh. A metabonomic approach identifies human urinary phenylacetylglutamine as a novel marker of interstitial cystitis.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 Nov; 877(30):3806-12. doi:
10.1016/j.jchromb.2009.09.025. [PMID: 19815468] - Lars Marius Ytrebø, Rune Gangsøy Kristiansen, Hanne Maehre, Ole Martin Fuskevåg, Trine Kalstad, Arthur Revhaug, María Jover Cobos, Rajiv Jalan, Christopher F Rose. L-ornithine phenylacetate attenuates increased arterial and extracellular brain ammonia and prevents intracranial hypertension in pigs with acute liver failure.
Hepatology (Baltimore, Md.).
2009 Jul; 50(1):165-74. doi:
10.1002/hep.22917. [PMID: 19554542] - Nathan A Davies, Gavin Wright, Lars M Ytrebø, Vanessa Stadlbauer, Ole-Martin Fuskevåg, Claudia Zwingmann, D Ceri Davies, Abeba Habtesion, Stephen J Hodges, Rajiv Jalan. L-ornithine and phenylacetate synergistically produce sustained reduction in ammonia and brain water in cirrhotic rats.
Hepatology (Baltimore, Md.).
2009 Jul; 50(1):155-64. doi:
10.1002/hep.22897. [PMID: 19437490] - Luis H Camacho, Jon Olson, William P Tong, Charles W Young, David R Spriggs, Mark G Malkin. Phase I dose escalation clinical trial of phenylbutyrate sodium administered twice daily to patients with advanced solid tumors.
Investigational new drugs.
2007 Apr; 25(2):131-8. doi:
10.1007/s10637-006-9017-4. [PMID: 17053987] - R M Kern, Z Yang, P S Kim, W W Grody, R K Iyer, S D Cederbaum. Arginase induction by sodium phenylbutyrate in mouse tissues and human cell lines.
Molecular genetics and metabolism.
2007 Jan; 90(1):37-41. doi:
10.1016/j.ymgme.2006.07.002. [PMID: 16935537] - Dominique Meynial-Denis, Lionel Verdier, Michelle Mignon, Jean-Noël Leclerc, Gérard Bayle, Dominique Darmaun. Does acute glutamine depletion enhance the response of glutamine synthesis to fasting in muscle in adult and old rats?.
Clinical nutrition (Edinburgh, Scotland).
2005 Jun; 24(3):398-406. doi:
10.1016/j.clnu.2004.12.004. [PMID: 15896426] - Robert B MacArthur, Arman Altincatal, Mendel Tuchman. Pharmacokinetics of sodium phenylacetate and sodium benzoate following intravenous administration as both a bolus and continuous infusion to healthy adult volunteers.
Molecular genetics and metabolism.
2004 Apr; 81 Suppl 1(?):S67-73. doi:
10.1016/j.ymgme.2003.12.011. [PMID: 15050977] - Susan M Chang, John G Kuhn, H Ian Robins, S Clifford Schold, Alexander M Spence, Mitchel S Berger, Minesh P Mehta, Ian Pollack, Mark Gilbert, Michael D Prados. A study of a different dose-intense infusion schedule of phenylacetate in patients with recurrent primary brain tumors consortium report.
Investigational new drugs.
2003 Nov; 21(4):429-33. doi:
10.1023/a:1026299118067. [PMID: 14586210] - Patrick Thompson, Frank Balis, Baruti M Serabe, Stacey Berg, Peter Adamson, Renee Klenke, Alberta Aiken, Roger Packer, Daryl J Murry, Regina Jakacki, Susan M Blaney. Pharmacokinetics of phenylacetate administered as a 30-min infusion in children with refractory cancer.
Cancer chemotherapy and pharmacology.
2003 Nov; 52(5):417-23. doi:
10.1007/s00280-003-0674-0. [PMID: 12879279] - Rui Perdigoto, Tiago B Rodrigues, Alexandre L Furtado, Armando Porto, Carlos F G C Geraldes, John G Jones. Integration of [U-13C]glucose and 2H2O for quantification of hepatic glucose production and gluconeogenesis.
NMR in biomedicine.
2003 Jun; 16(4):189-98. doi:
10.1002/nbm.826. [PMID: 14558117] - Blandine Comte, Takhar Kasumov, Bradley A Pierce, Michelle A Puchowicz, Mary-Ellen Scott, Williams Dahms, Douglas Kerr, Itzhak Nissim, Henri Brunengraber. Identification of phenylbutyrylglutamine, a new metabolite of phenylbutyrate metabolism in humans.
Journal of mass spectrometry : JMS.
2002 Jun; 37(6):581-90. doi:
10.1002/jms.316. [PMID: 12112740] - M A Carducci, J Gilbert, M K Bowling, D Noe, M A Eisenberger, V Sinibaldi, Y Zabelina, T L Chen, L B Grochow, R C Donehower. A Phase I clinical and pharmacological evaluation of sodium phenylbutyrate on an 120-h infusion schedule.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2001 Oct; 7(10):3047-55. doi:
NULL. [PMID: 11595694] - J G Jones, M A Solomon, S M Cole, A D Sherry, C R Malloy. An integrated (2)H and (13)C NMR study of gluconeogenesis and TCA cycle flux in humans.
American journal of physiology. Endocrinology and metabolism.
2001 Oct; 281(4):E848-56. doi:
10.1152/ajpendo.2001.281.4.e848. [PMID: 11551863] - D Yang, H Brunengraber. Glutamate, a window on liver intermediary metabolism.
The Journal of nutrition.
2000 04; 130(4S Suppl):991S-4S. doi:
10.1093/jn/130.4.991s. [PMID: 10736368] - J G Jones, M A Solomon, A D Sherry, F M Jeffrey, C R Malloy. 13C NMR measurements of human gluconeogenic fluxes after ingestion of [U-13C]propionate, phenylacetate, and acetaminophen.
The American journal of physiology.
1998 11; 275(5):E843-52. doi:
10.1152/ajpendo.1998.275.5.e843. [PMID: 9815005] - J P Shockcor, S E Unger, I D Wilson, P J Foxall, J K Nicholson, J C Lindon. Combined HPLC, NMR spectroscopy, and ion-trap mass spectrometry with application to the detection and characterization of xenobiotic and endogenous metabolites in human urine.
Analytical chemistry.
1996 Dec; 68(24):4431-5. doi:
10.1021/ac9606463. [PMID: 8972626] - D Yang, S F Previs, C A Fernandez, S Dugelay, M V Soloviev, J W Hazey, K C Agarwal, W C Levine, F David, P Rinaldo, M Beylot, H Brunengraber. Noninvasive probing of citric acid cycle intermediates in primate liver with phenylacetylglutamine.
The American journal of physiology.
1996 May; 270(5 Pt 1):E882-9. doi:
10.1152/ajpendo.1996.270.5.e882. [PMID: 8967478] - B R Landau, V Chandramouli, W C Schumann, K Ekberg, K Kumaran, S C Kalhan, J Wahren. Estimates of Krebs cycle activity and contributions of gluconeogenesis to hepatic glucose production in fasting healthy subjects and IDDM patients.
Diabetologia.
1995 Jul; 38(7):831-8. doi:
10.1007/s001250050360. [PMID: 7556986] - S C Piscitelli, A Thibault, W D Figg, A Tompkins, D Headlee, R Lieberman, D Samid, C E Myers. Disposition of phenylbutyrate and its metabolites, phenylacetate and phenylacetylglutamine.
Journal of clinical pharmacology.
1995 Apr; 35(4):368-73. doi:
10.1002/j.1552-4604.1995.tb04075.x. [PMID: 7650225] - G W Cline, D L Rothman, I Magnusson, L D Katz, G I Shulman. 13C-nuclear magnetic resonance spectroscopy studies of hepatic glucose metabolism in normal subjects and subjects with insulin-dependent diabetes mellitus.
The Journal of clinical investigation.
1994 Dec; 94(6):2369-76. doi:
10.1172/jci117602. [PMID: 7989593] - S Dugelay, D Yang, M V Soloviev, S F Previs, K C Agarwal, C A Fernandez, H Brunengraber. Assay of the concentration and 13C-labeling pattern of phenylacetylglutamine by nuclear magnetic resonance.
Analytical biochemistry.
1994 Sep; 221(2):368-73. doi:
10.1006/abio.1994.1427. [PMID: 7810879] - S W Brusilow, J Finkelstien. Restoration of nitrogen homeostasis in a man with ornithine transcarbamylase deficiency.
Metabolism: clinical and experimental.
1993 Oct; 42(10):1336-9. doi:
10.1016/0026-0495(93)90135-b. [PMID: 8412748] - D Yang, M Beylot, K C Agarwal, M V Soloviev, H Brunengraber. Assay of the human liver citric acid cycle probe phenylacetylglutamine and of phenylacetate in plasma by gas chromatography-mass spectrometry.
Analytical biochemistry.
1993 Jul; 212(1):277-82. doi:
10.1006/abio.1993.1323. [PMID: 8368503] - S W Brusilow. Phenylacetylglutamine may replace urea as a vehicle for waste nitrogen excretion.
Pediatric research.
1991 Feb; 29(2):147-50. doi:
10.1203/00006450-199102000-00009. [PMID: 2014149] - L Zimmerman, H Jörnvall, J Bergström. Phenylacetylglutamine and hippuric acid in uremic and healthy subjects.
Nephron.
1990; 55(3):265-71. doi:
10.1159/000185973. [PMID: 2370926] - L Zimmerman, B Egestad, H Jörnvall, J Bergström. Identification and determination of phenylacetylglutamine, a major nitrogenous metabolite in plasma of uremic patients.
Clinical nephrology.
1989 Sep; 32(3):124-8. doi:
. [PMID: 2791363] - O Simell, I Sipilä, J Rajantie, D L Valle, S W Brusilow. Waste nitrogen excretion via amino acid acylation: benzoate and phenylacetate in lysinuric protein intolerance.
Pediatric research.
1986 Nov; 20(11):1117-21. doi:
10.1203/00006450-198611000-00011. [PMID: 3099249] - K Koide, J Toyama, N Inoue, S Koshikawa, T Akizawa, K Takahashi, S Hidaka, Y Yamane, K Shinoda, M Nakao. [Uremic peak 2a in high performance liquid chromatography--acidic components and their membrane permeability].
Nihon Jinzo Gakkai shi.
1986 Nov; 28(11):1481-9. doi:
NULL. [PMID: 2950263] - P V Mel'nichuk, A P Khokhlov, I M Khailova. Early diagnosis of Tourette's syndrome.
Neuroscience and behavioral physiology.
1985 Jan; 15(1):45-7. doi:
10.1007/bf01186448. [PMID: 3858704] - P V Mel'nichuk, A P Khokhlov, I M Khailova. Pathogenesis of hyperkinesias in children.
Neuroscience and behavioral physiology.
1984 May; 14(3):241-5. doi:
10.1007/bf01191101. [PMID: 6144078] - T N Nenasheva, S P Miaskovskaia, A P Khokhlov. [Method of determining the phenylacetylglutamine content of the urine].
Laboratornoe delo.
1982; ?(2):99-101. doi:
NULL. [PMID: 6174823] - A P Khokhlov, I M Khailova, T I Nenasheva. [Phenylalanine metabolic indices in different forms of hyperkinesis].
Pediatriia.
1980 Oct; ?(10):46-8. doi:
NULL. [PMID: 7432913] - P V Mel'nichuk, A P Khokhlov, I M Khaĭlova. [Early diagnosis of the Tourette syndrome].
Zhurnal nevropatologii i psikhiatrii imeni S.S. Korsakova (Moscow, Russia : 1952).
1980; 80(10):1450-3. doi:
NULL. [PMID: 6933789] - B Fleischer. Localization of some glycolipid glycosylating enzymes in the Golgi apparatus of rat kidney.
Journal of supramolecular structure.
1977; 7(1):79-89. doi:
10.1002/jss.400070108. [PMID: 24139] - K MOLDAVE, A MEISTER. Synthesis of phenylacetylglutamine by human tissue.
The Journal of biological chemistry.
1957 Nov; 229(1):463-76. doi:
NULL. [PMID: 13491597]
