Dexmethylphenidate (BioDeep_00000033366)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate

化学式: C14H19NO2 (233.1415714)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 3.7%

分子结构信息

SMILES: COC(=O)C(C1CCCCN1)C2=CC=CC=C2
InChI: InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3/t12-,13-/m1/s1

描述信息

Dexmethylphenidate is only found in individuals that have used or taken this drug. It is the dextrorotary form of methylphenidate. It is used for treatment of Attention Deficit Hyperactivity Disorder (ADHD). Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system.Methylphenidate is a catecholamine reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the dopamine transporter (DAT) and norepinephrine transporter (NET), which are responsible for clearing catecholamines from the synapse, particularly in the striatum and meso-limbic system.
N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics > N06BA - Centrally acting sympathomimetics
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018765 - Dopamine Uptake Inhibitors
D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants
C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant
D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents
D049990 - Membrane Transport Modulators

同义名列表

16 个代谢物同义名

methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate; Methyl (R)-phenyl[(R)-piperidin-2-yl]acetic acid; Methyl (R)-phenyl[(R)-piperidin-2-yl]acetate; Hydrochloride, dexmethylphenidate; Dexmethylphenidate hydrochloride; (+)-Threo-methylphenidic acid; D-Threo-methylphenidic acid; (+)-Threo-methylphenidate; D-Threo-methylphenidate; Dexmethylphenidic acid; Dexmethylphenidatum; Dexmethylphenidate; Dexmetilfenidato; XR, Focalin; Focalin XR; Focalin



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

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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。



文献列表

  • Rene Braeckman, Sven Guenther, Travis C Mickle, Andrew C Barrett, Adam Smith, Charles Oh. Dose Proportionality and Steady-State Pharmacokinetics of Serdexmethylphenidate/Dexmethylphenidate, a Novel Prodrug Combination to Treat Attention-Deficit/Hyperactivity Disorder. Journal of child and adolescent psychopharmacology. 2022 Jun; 32(5):288-295. doi: 10.1089/cap.2022.0015. [PMID: 35666231]
  • Hao-Jie Zhu, Kennerly S Patrick, Arthur B Straughn, Owen T Reeves, Hilary Bernstein, Jian Shi, Heather J Johnson, Joshua M Knight, Aaron T Smith, Robert J Malcolm, John S Markowitz. Ethanol Interactions With Dexmethylphenidate and dl-Methylphenidate Spheroidal Oral Drug Absorption Systems in Healthy Volunteers. Journal of clinical psychopharmacology. 2017 Aug; 37(4):419-428. doi: 10.1097/jcp.0000000000000721. [PMID: 28590363]
  • Kennerly S Patrick, Arthur B Straughn. Absorption Differences between Immediate-Release Dexmethylphenidate and dl-Methylphenidate. Drug metabolism and disposition: the biological fate of chemicals. 2016 Mar; 44(3):418-21. doi: 10.1124/dmd.115.067975. [PMID: 26729760]
  • Mark A Stein, Irwin Waldman, Jeffrey Newcorn, Jeffrey Bishop, Rick Kittles, Edwin H Cook. Dopamine transporter genotype and stimulant dose-response in youth with attention-deficit/hyperactivity disorder. Journal of child and adolescent psychopharmacology. 2014 Jun; 24(5):238-44. doi: 10.1089/cap.2013.0102. [PMID: 24813374]
  • Kennerly S Patrick, Arthur B Straughn, Owen T Reeves, Hilary Bernstein, Guinevere H Bell, Erica R Anderson, Robert J Malcolm. Differential influences of ethanol on early exposure to racemic methylphenidate compared with dexmethylphenidate in humans. Drug metabolism and disposition: the biological fate of chemicals. 2013 Jan; 41(1):197-205. doi: 10.1124/dmd.112.048595. [PMID: 23104969]
  • Thomas J Spencer, Ali A Bonab, Darin D Dougherty, Tara Mirto, Jessica Martin, Allison Clarke, Alan J Fischman. Understanding the central pharmacokinetics of spheroidal oral drug absorption system (SODAS) dexmethylphenidate: a positron emission tomography study of dopamine transporter receptor occupancy measured with C-11 altropane. The Journal of clinical psychiatry. 2012 Mar; 73(3):346-52. doi: 10.4088/jcp.10m06393. [PMID: 22154896]
  • Cheryl R Stein, David A Savitz. Serum perfluorinated compound concentration and attention deficit/hyperactivity disorder in children 5-18 years of age. Environmental health perspectives. 2011 Oct; 119(10):1466-71. doi: 10.1289/ehp.1003538. [PMID: 21665566]
  • Kyle C Schmitt, Maarten E A Reith. The atypical stimulant and nootropic modafinil interacts with the dopamine transporter in a different manner than classical cocaine-like inhibitors. PloS one. 2011; 6(10):e25790. doi: 10.1371/journal.pone.0025790. [PMID: 22043293]
  • David J Lapinsky, Ranganadh Velagaleti, Nageswari Yarravarapu, Yi Liu, Yurong Huang, Christopher K Surratt, John R Lever, James D Foster, Rejwi Acharya, Roxanne A Vaughan, Howard M Deutsch. Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling. Bioorganic & medicinal chemistry. 2011 Jan; 19(1):504-12. doi: 10.1016/j.bmc.2010.11.002. [PMID: 21129986]
  • Milind Misra, Qing Shi, Xiaocong Ye, Ewa Gruszecka-Kowalik, Wei Bu, Zhanzhu Liu, Margaret M Schweri, Howard M Deutsch, Carol A Venanzi. Quantitative structure-activity relationship studies of threo-methylphenidate analogs. Bioorganic & medicinal chemistry. 2010 Oct; 18(20):7221-38. doi: 10.1016/j.bmc.2010.08.034. [PMID: 20846865]
  • Robert L Findling. Evolution of the treatment of attention-deficit/hyperactivity disorder in children: a review. Clinical therapeutics. 2008 May; 30(5):942-57. doi: 10.1016/j.clinthera.2008.05.006. [PMID: 18555941]
  • D Tuerck, Y Wang, M Maboudian, Y Wang, G Sedek, F Pommier, S Appel-Dingemanse. Similar bioavailability of dexmethylphenidate extended (bimodal) release, dexmethyl-phenidate immediate release and racemic methylphenidate extended (bimodal) release formulations in man. International journal of clinical pharmacology and therapeutics. 2007 Dec; 45(12):662-8. doi: 10.5414/cpp45662. [PMID: 18184535]
  • Deog-Il Kim, Howard M Deutsch, Xiaocong Ye, Margaret M Schweri. Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate. Journal of medicinal chemistry. 2007 May; 50(11):2718-31. doi: 10.1021/jm061354p. [PMID: 17489581]
  • John S Markowitz, C Lindsay DeVane, Linda K Pestreich, Kennerly S Patrick, Rafael Muniz. A comprehensive in vitro screening of d-, l-, and dl-threo-methylphenidate: an exploratory study. Journal of child and adolescent psychopharmacology. 2006 Dec; 16(6):687-98. doi: 10.1089/cap.2006.16.687. [PMID: 17201613]
  • Dean M Robinson, Gillian M Keating. Dexmethylphenidate extended release: in attention-deficit hyperactivity disorder. Drugs. 2006; 66(5):661-8; discussion 669. doi: 10.2165/00003495-200666050-00006. [PMID: 16620143]
  • Johanna Krause, Klaus-Henning Krause, Stefan H Dresel, Christian la Fougere, Manfred Ackenheil. ADHD in adolescence and adulthood, with a special focus on the dopamine transporter and nicotine. Dialogues in clinical neuroscience. 2006; 8(1):29-36. doi: 10.31887/dcns.2006.8.1/jkrause. [PMID: 16640111]
  • Edmund J S Sonuga-Barke, James M Swanson, David Coghill, Heleen H DeCory, Simon J Hatch. Efficacy of two once-daily methylphenidate formulations compared across dose levels at different times of the day: preliminary indications from a secondary analysis of the COMACS study data. BMC psychiatry. 2004 Sep; 4(?):28. doi: 10.1186/1471-244x-4-28. [PMID: 15458569]
  • Steve K Teo, Michael R Scheffler, Anfan Wu, David I Stirling, Steve D Thomas, Daria Stypinski, Vikram D Khetani. A single-dose, two-way crossover, bioequivalence study of dexmethylphenidate HCl with and without food in healthy subjects. Journal of clinical pharmacology. 2004 Feb; 44(2):173-8. doi: 10.1177/0091270003261899. [PMID: 14747426]
  • Peter C Meltzer, Pinglang Wang, Paul Blundell, Bertha K Madras. Synthesis and evaluation of dopamine and serotonin transporter inhibition by oxacyclic and carbacyclic analogues of methylphenidate. Journal of medicinal chemistry. 2003 Apr; 46(8):1538-45. doi: 10.1021/jm0205292. [PMID: 12672255]
  • N B Modi, B Wang, R J Noveck, S K Gupta. Dose-proportional and stereospecific pharmacokinetics of methylphenidate delivered using an osmotic, controlled-release oral delivery system. Journal of clinical pharmacology. 2000 Oct; 40(10):1141-9. doi: NULL. [PMID: 11028253]
  • S Javanmard, H M Deutsch, D M Collard, M J Kuhar, M M Schweri. Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes. Journal of medicinal chemistry. 1999 Nov; 42(23):4836-43. doi: 10.1021/jm990306k. [PMID: 10579846]