Valproic acid glucuronide (BioDeep_00000027665)

   

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid

化学式: C14H24O8 (320.1471)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 16.28%

分子结构信息

SMILES: CCCC(CCC)C(=O)OC1C(C(C(C(O1)C(=O)O)O)O)O
InChI: InChI=1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19)/t8-,9-,10+,11-,14-/m0/s1

描述信息

Valproic acid glucuronide is the glucuronidation product of valproic acid. Valproic acid or 2-Propylpentanoic acid, is a chemical compound that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy and bipolar disorder, but also used to treat migraine headaches and schizophrenia. In epileptics, valproic acid is used to control absence seizures, tonic-clonic seizures (grand mal), complex partial seizures, and the seizures associated with Lennox-Gastaut syndrome. Glucuronidation is a vital phase 2 metabolic (conjugative) process by which a wide range of drugs and other xenobiotics may be rendered water-soluble, detoxified and excreted. Acyl (ester) glucuronides (AGs) of carboxylic acids are potentially reactive metabolites. In particular, AGs are important phase 2 metabolites for a wide range of carboxylic acid-containing drugs. (PMID: 18201150, 17496767, 17496206) [HMDB]
Valproic acid glucuronide is the glucuronidation product of valproic acid. Valproic acid, or 2-Propylpentanoic acid, is a chemical compound that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy and bipolar disorder, but also used to treat migraine headaches and schizophrenia. In epileptics, valproic acid is used to control absence seizures, tonic-clonic seizures (grand mal), complex partial seizures, and the seizures associated with Lennox-Gastaut syndrome. Glucuronidation is a vital phase 2 metabolic (conjugative) process by which a wide range of drugs and other xenobiotics may be rendered water-soluble, detoxified and excreted. Acyl (ester) glucuronides (AGs) of carboxylic acids are potentially reactive metabolites. In particular, AGs are important phase 2 metabolites for a wide range of carboxylic acid-containing drugs. (PMID: 18201150, 17496767, 17496206).

同义名列表

20 个代谢物同义名

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid; 3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid; 3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylate; 1-(2-Propylpentanoate) beta-delta-glucopyranuronic acid; 1-(2-Propylpentanoate) beta-delta-glucopyranuronate; 1-(2-Propylpentanoate) beta-D-glucopyranuronic acid; 1-(2-Propylpentanoate) beta-D-glucopyranuronate; 1-O-Valproyl-beta-delta-glucopyranuronic acid; 1-O-Valproyl-b-D-glucopyranuronic acid; Dipropylacetate glucuronide; 1-(2-Propylpentanoic acid; Valproic acid glucuronide; Valproate glucuronide; 1-(2-Propylpentanoate; VALPROIC ACID; Myproic acid; Valproate; Myproate; VPA-g; VPAG



数据库引用编号

7 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

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)

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


文献列表

  • Eiko Suzuki, Daisuke Nakai, Hidenori Ikenaga, Keiichi Fusegawa, Ryoya Goda, Nobuhiro Kobayashi, Hiroshi Kuga, Takashi Izumi. In vivo inhibition of acylpeptide hydrolase by carbapenem antibiotics causes the decrease of plasma concentration of valproic acid in dogs. Xenobiotica; the fate of foreign compounds in biological systems. 2016; 46(2):126-31. doi: 10.3109/00498254.2015.1054002. [PMID: 26075835]
  • Anu Marahatta, Bidur Bhandary, Seul-Ki Jeong, Hyung-Ryong Kim, Han-Jung Chae. Soybean greatly reduces valproic acid plasma concentrations: a food-drug interaction study. Scientific reports. 2014 Mar; 4(?):4362. doi: 10.1038/srep04362. [PMID: 24618639]
  • Lifang Zhang, Xiaoman Chu, Hong Wang, Hao Xie, Cen Guo, Lijuan Cao, Xueyan Zhou, Guangji Wang, Haiping Hao. Dysregulations of UDP-glucuronosyltransferases in rats with valproic acid and high fat diet induced fatty liver. European journal of pharmacology. 2013 Dec; 721(1-3):277-85. doi: 10.1016/j.ejphar.2013.09.024. [PMID: 24056123]
  • Eiko Suzuki, Naotoshi Yamamura, Yuji Ogura, Daisuke Nakai, Kazuishi Kubota, Nobuhiro Kobayashi, Shin-ichi Miura, Osamu Okazaki. Identification of valproic acid glucuronide hydrolase as a key enzyme for the interaction of valproic acid with carbapenem antibiotics. Drug metabolism and disposition: the biological fate of chemicals. 2010 Sep; 38(9):1538-44. doi: 10.1124/dmd.110.032938. [PMID: 20551238]
  • Min Sun Lee, Young-Joo Lee, Bo Joon Kim, Kye Jung Shin, Bong Chul Chung, Du-Jong Baek, Byung Hwa Jung. The relationship between glucuronide conjugate levels and hepatotoxicity after oral administration of valproic acid. Archives of pharmacal research. 2009 Jul; 32(7):1029-35. doi: 10.1007/s12272-009-1708-x. [PMID: 19641884]
  • Yutaka Nakamura, Keiko Nakahira, Takaharu Mizutani. Decreased valproate level caused by VPA-glucuronidase inhibition by carbapenem antibiotics. Drug metabolism letters. 2008 Dec; 2(4):280-5. doi: 10.2174/187231208786734049. [PMID: 19356106]
  • Harvey Wong, Vincent Tong, K Wayne Riggs, Dan W Rurak, Frank S Abbott, Sanjeev Kumar. Kinetics of valproic acid glucuronidation: evidence for in vivo autoactivation. Drug metabolism and disposition: the biological fate of chemicals. 2007 Aug; 35(8):1380-6. doi: 10.1124/dmd.107.015719. [PMID: 17496206]
  • Hitomi Mori, Kazuhiko Takahashi, Takaharu Mizutani. Interaction between valproic acid and carbapenem antibiotics. Drug metabolism reviews. 2007; 39(4):647-57. doi: 10.1080/03602530701690341. [PMID: 18058328]
  • Hsiu-Ying Yu, Yu-Zen Shen. Concentration-dependent disposition of glucuronide metabolite of valproate. The Journal of pharmacy and pharmacology. 2002 May; 54(5):633-9. doi: 10.1211/0022357021778943. [PMID: 12005358]
  • D M Reith, J Andrews, D McLaughlin. Valproic acid has temporal variability in urinary clearance of metabolites. Chronobiology international. 2001 Jan; 18(1):123-9. doi: 10.1081/cbi-100001176. [PMID: 11247111]
  • H Wong, S Kumar, D W Rurak, E Kwan, F S Abbott, K W Riggs. Ontogeny of valproic acid disposition and metabolism: a developmental study in postnatal lambs and adult sheep. Drug metabolism and disposition: the biological fate of chemicals. 2000 Aug; 28(8):912-9. doi: NULL. [PMID: 10901700]
  • N Azaroual, M Imbenotte, B Cartigny, F Leclerc, L Vallée, M Lhermitte, G Vermeersch. Valproic acid intoxication identified by 1H and 1H-(13)C correlated NMR spectroscopy of urine samples. Magma (New York, N.Y.). 2000 Jul; 10(3):177-82. doi: 10.1016/s1352-8661(00)00086-7. [PMID: 10873209]
  • G D Anderson, A A Acheampong, A J Wilensky, R H Levy. Effect of valproate dose on formation of hepatotoxic metabolites. Epilepsia. 1992 Jul; 33(4):736-42. doi: 10.1111/j.1528-1157.1992.tb02355.x. [PMID: 1628592]
  • E Fisher, H Siemes, R Pund, W Wittfoht, H Nau. Valproate metabolites in serum and urine during antiepileptic therapy in children with infantile spasms: abnormal metabolite pattern associated with reversible hepatotoxicity. Epilepsia. 1992 Jan; 33(1):165-71. doi: 10.1111/j.1528-1157.1992.tb02301.x. [PMID: 1733752]
  • T Kondo, S Kaneko, K Otani, M Ishida, T Hirano, Y Fukushima, H Muranaka, N Koide, M Yokoyama. Associations between risk factors for valproate hepatotoxicity and altered valproate metabolism. Epilepsia. 1992 Jan; 33(1):172-7. doi: 10.1111/j.1528-1157.1992.tb02302.x. [PMID: 1733753]
  • R G Dickinson, W D Hooper, P R Dunstan, M J Eadie. Urinary excretion of valproate and some metabolites in chronically treated patients. Therapeutic drug monitoring. 1989; 11(2):127-33. doi: 10.1097/00007691-198903000-00002. [PMID: 2497561]
  • R G Dickinson, R M Kluck, B T Wood, M J Eadie, W D Hooper. Impaired biliary elimination of beta-glucuronidase-resistant 'glucuronides' of valproic acid after intravenous administration in the rat. Evidence for oxidative metabolism of the resistant isomers. Drug metabolism and disposition: the biological fate of chemicals. 1986 Mar; 14(2):255-62. doi: NULL. [PMID: 2870903]
  • R G Dickinson, R M Kluck, W D Hooper, M Patterson, J B Chalk, M J Eadie. Rearrangement of valproate glucuronide in a patient with drug-associated hepatobiliary and renal dysfunction. Epilepsia. 1985 Nov; 26(6):589-93. doi: 10.1111/j.1528-1157.1985.tb05696.x. [PMID: 3935422]
  • R G Dickinson, R M Kluck, M J Eadie, W D Hooper. Disposition of beta-glucuronidase-resistant 'glucuronides' of valproic acid after intrabiliary administration in the rat: intact absorption, fecal excretion and intestinal hydrolysis. The Journal of pharmacology and experimental therapeutics. 1985 Apr; 233(1):214-21. doi: NULL. [PMID: 3920383]
  • R G Dickinson, W D Hooper, M J Eadie. pH-dependent rearrangement of the biosynthetic ester glucuronide of valproic acid to beta-glucuronidase-resistant forms. Drug metabolism and disposition: the biological fate of chemicals. 1984 Mar; 12(2):247-52. doi: NULL. [PMID: 6144492]