Levomethadyl Acetate (BioDeep_00000006646)

 

Secondary id: BioDeep_00001868310

human metabolite blood metabolite Chemicals and Drugs natural product


代谢物信息卡片


(1S,4S)-4-(Dimethylamino)-1-ethyl-2,2-diphenylpentyl acetic acid

化学式: C23H31NO2 (353.2354666)
中文名称: 左醋美沙朵, 醋美沙朵
谱图信息: 最多检出来源 Macaca mulatta(otcml) 1.8%

分子结构信息

SMILES: CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C
InChI: InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3

描述信息

Levomethadyl Acetate is only found in individuals that have used or taken this drug. It is a narcotic analgesic with a long onset and duration of action. It is used mainly in the treatment of narcotic dependence. [PubChem]Opiate receptors (Mu, Kappa, Delta) are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Levomethadyl acetate effectively opens calcium-dependent inwardly rectifying potassium channels (OP1 receptor agonist), resulting in hyperpolarization and reduced neuronal excitability.
N - Nervous system > N07 - Other nervous system drugs > N07B - Drugs used in addictive disorders > N07BC - Drugs used in opioid dependence
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist
D002491 - Central Nervous System Agents > D000700 - Analgesics

同义名列表

34 个代谢物同义名

(1S,4S)-4-(Dimethylamino)-1-ethyl-2,2-diphenylpentyl acetic acid; (1S,4S)-4-(Dimethylamino)-1-ethyl-2,2-diphenylpentyl acetate; (3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate; (3R,6R)-3-Acetoxy-6-dimethylamino-4,4-diphenylheptane; [6-(dimethylamino)-4,4-diphenylheptan-3-yl] acetate; 6-(Dimethylamino)-4,4-diphenyl-3-heptanol acetate; Levomethadyl acetate hydrochloride; Levo-alpha-acetylmethadol; Levo alpha acetylmethadol; Levomethadyl acetic acid; (-)-alpha-Acetylmethadol; Levo-alphacetylmethadol; 1-alpha-Acetylmethadol; Levo-methadyl acetate; Levomethadyl Acetate; (-)-Α-acetylmethadol; (-)-a-Acetylmethadol; Levacetylmethadolum; Alphacetylmethadol; Levoacetylmethadol; 1-a-Acetylmethadol; 1-Α-acetylmethadol; Levacetylmethadol; Levacetilmetadol; Methadyl acetate; Acetylmethadol; Amidolacetate; Dimepheptanol; Acemethadone; Levomethadyl; Methadol; Nor-laam; Orlaam; LAAM



数据库引用编号

23 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)

9 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

  • David A L Newcombe, Andrew A Somogyi, Felix Bochner, Jason M White. Impaired psychomotor function and plasma methadone and levo-alpha-acetylmethadol (LAAM) concentrations in opioid-substitution patients. Experimental and clinical psychopharmacology. 2017 06; 25(3):223-233. doi: 10.1037/pha0000114. [PMID: 28414496]
  • Silvia Minozzi, Laura Amato, Cristina Bellisario, Marina Davoli. Maintenance treatments for opiate -dependent adolescents. The Cochrane database of systematic reviews. 2014 Jun; ?(6):CD007210. doi: 10.1002/14651858.cd007210.pub3. [PMID: 24957634]
  • B Michel-Lauter, C Maier, A Schwarzer. [Accidental levomethadone intoxication in a palliative patient]. Schmerz (Berlin, Germany). 2012 Dec; 26(6):721-3. doi: 10.1007/s00482-012-1229-2. [PMID: 23093298]
  • Francina Fonseca, Rafael de la Torre, Laura Díaz, Antonio Pastor, Elisabet Cuyàs, Nieves Pizarro, Olha Khymenets, Magí Farré, Marta Torrens. Contribution of cytochrome P450 and ABCB1 genetic variability on methadone pharmacokinetics, dose requirements, and response. PloS one. 2011 May; 6(5):e19527. doi: 10.1371/journal.pone.0019527. [PMID: 21589866]
  • Michael J Mancino, Janette McGaugh, Zachary Feldman, James Poling, Alison Oliveto. Effect of PTSD diagnosis and contingency management procedures on cocaine use in dually cocaine- and opioid-dependent individuals maintained on LAAM: a retrospective analysis. The American journal on addictions. 2010 Mar; 19(2):169-77. doi: 10.1111/j.1521-0391.2009.00025.x. [PMID: 20163389]
  • Silvia Minozzi, Laura Amato, Marina Davoli. Maintenance treatments for opiate dependent adolescent. The Cochrane database of systematic reviews. 2009 Apr; ?(2):CD007210. doi: 10.1002/14651858.cd007210.pub2. [PMID: 19370679]
  • Bradley T Conner, M Douglas Anglin, Jeffery Annon, Douglas Longshore. Effect of religiosity and spirituality on drug treatment outcomes. The journal of behavioral health services & research. 2009 Apr; 36(2):189-98. doi: 10.1007/s11414-008-9145-z. [PMID: 18770043]
  • H Wieneke, H Conrads, J Wolstein, F Breuckmann, M Gastpar, R Erbel, Norbert Scherbaum. Levo-alpha-acetylmethadol (LAAM) induced QTc-prolongation - results from a controlled clinical trial. European journal of medical research. 2009 Jan; 14(1):7-12. doi: 10.1186/2047-783x-14-1-7. [PMID: 19258204]
  • J Wolstein, M Gastpar, T Finkbeiner, C Heinrich, R Heitkamp, T Poehlke, N Scherbaum. A randomized, open-label trial comparing methadone and Levo-Alpha-Acetylmethadol (LAAM) in maintenance treatment of opioid addiction. Pharmacopsychiatry. 2009 Jan; 42(1):1-8. doi: 10.1055/s-0028-1083818. [PMID: 19153939]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Nat M J Wright, Laura Sheard, Charlotte N E Tompkins, Clive E Adams, Victoria L Allgar, Nicola S Oldham. Buprenorphine versus dihydrocodeine for opiate detoxification in primary care: a randomised controlled trial. BMC family practice. 2007 Jan; 8(?):3. doi: 10.1186/1471-2296-8-3. [PMID: 17210079]
  • Séverine Crettol, Patricia Digon, Kerry Powell Golay, Marlyse Brawand, Chin B Eap. In vitro P-glycoprotein-mediated transport of (R)-, (S)-, (R,S)-methadone, LAAM and their main metabolites. Pharmacology. 2007; 80(4):304-11. doi: 10.1159/000107104. [PMID: 17690563]
  • Nicolas C Clark, Paul Dietze, Michael G Lenné, Jennifer R Redman. Effect of opioid substitution therapy on alcohol metabolism. Journal of substance abuse treatment. 2006 Apr; 30(3):191-6. doi: 10.1016/j.jsat.2005.11.010. [PMID: 16616162]
  • Douglas Longshore, Jeffrey Annon, M Douglas Anglin, Richard A Rawson. Levo-alpha-acetylmethadol (LAAM) versus methadone: treatment retention and opiate use. Addiction (Abingdon, England). 2005 Aug; 100(8):1131-9. doi: 10.1111/j.1360-0443.2005.01122.x. [PMID: 16042643]
  • Alison Oliveto, James Poling, Kevin A Sevarino, Kishorchandra R Gonsai, Elinore F McCance-Katz, Susan M Stine, Thomas R Kosten. Efficacy of dose and contingency management procedures in LAAM-maintained cocaine-dependent patients. Drug and alcohol dependence. 2005 Aug; 79(2):157-65. doi: 10.1016/j.drugalcdep.2005.01.007. [PMID: 16002025]
  • Malcolm S Reid, Burt Angrist, Sherryl A Baker, Siobhan O'leary, Jennifer Stone, Marion Schwartz, Deborah Leiderman, Ann Montgomery, Ahmed Elkashef, Dorota Majewska, James Robinson, John Rotrosen. A placebo controlled, double-blind study of mecamylamine treatment for cocaine dependence in patients enrolled in an opiate replacement program. Substance abuse. 2005 Jun; 26(2):5-14. doi: 10.1300/j465v26n02_02. [PMID: 16687365]
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  • . Torsades de pointes with methadone. Prescrire international. 2005 Apr; 14(76):61-2. doi: . [PMID: 15875343]
  • Evan D Kharasch, Dale Whittington, Christine Hoffer, Kevin Krudys, Keith Craig, Paolo Vicini, Pam Sheffels, Bojan Lalovic. Paradoxical role of cytochrome P450 3A in the bioactivation and clinical effects of levo-alpha-acetylmethadol: importance of clinical investigations to validate in vitro drug metabolism studies. Clinical pharmacokinetics. 2005; 44(7):731-51. doi: 10.2165/00003088-200544070-00005. [PMID: 15966756]
  • David A L Newcombe, Felix Bochner, Jason M White, Andrew A Somogyi. Evaluation of levo-alpha-acetylmethdol (LAAM) as an alternative treatment for methadone maintenance patients who regularly experience withdrawal: a pharmacokinetic and pharmacodynamic analysis. Drug and alcohol dependence. 2004 Oct; 76(1):63-72. doi: 10.1016/j.drugalcdep.2004.04.004. [PMID: 15380290]
  • David E Moody, Sharon L Walsh, Douglas E Rollins, Jennifer A Neff, Wei Huang. Ketoconazole, a cytochrome P450 3A4 inhibitor, markedly increases concentrations of levo-acetyl-alpha-methadol in opioid-naive individuals. Clinical pharmacology and therapeutics. 2004 Aug; 76(2):154-66. doi: 10.1016/j.clpt.2004.04.004. [PMID: 15289792]
  • C B Eap, G Bouchoux, N Scherbaum, M Gastpar, K Powell Golay, P Baumann. Determination of human plasma levels of levo-alpha-acetylmethadol and its metabolites by gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Jun; 805(1):141-6. doi: 10.1016/j.jchromb.2004.02.034. [PMID: 15113550]
  • Tatiana N Nanovskaya, Sujal V Deshmukh, Rachel Miles, Steve Burmaster, Mahmoud S Ahmed. Transfer of L-alpha-acetylmethadol (LAAM) and L-alpha-acetyl-N-normethadol (norLAAM) by the perfused human placental lobule. The Journal of pharmacology and experimental therapeutics. 2003 Jul; 306(1):205-12. doi: 10.1124/jpet.103.050690. [PMID: 12676878]
  • Irene Kuo, Joseph Brady, Carol Butler, Robert Schwartz, Robert Brooner, David Vlahov, Steffanie A Strathdee. Feasibility of referring drug users from a needle exchange program into an addiction treatment program: experience with a mobile treatment van and LAAM maintenance. Journal of substance abuse treatment. 2003 Jan; 24(1):67-74. doi: 10.1016/s0740-5472(02)00343-4. [PMID: 12646332]
  • Wei Huang, Paul A Bemis, Matthew H Slawson, David E Moody. Determination of l-alpha-acetylmethadol (LAAM), norLAAM, and dinorLAAM in clinical and in vitro samples using liquid chromatography with electrospray ionization and tandem mass spectrometry. Journal of pharmaceutical sciences. 2003 Jan; 92(1):10-20. doi: 10.1002/jps.10263. [PMID: 12486677]
  • Alexander N Katchman, Kelly A McGroary, Michael J Kilborn, Craig A Kornick, Paolo L Manfredi, Raymond L Woosley, Steven N Ebert. Influence of opioid agonists on cardiac human ether-a-go-go-related gene K(+) currents. The Journal of pharmacology and experimental therapeutics. 2002 Nov; 303(2):688-94. doi: 10.1124/jpet.102.038240. [PMID: 12388652]
  • Lisa M Schrott, Mary Irene Baumgart, Xuewei Zhang, Sheldon B Sparber. Prenatal opiate withdrawal activates the chick embryo hypothalamic pituitary-adrenal axis and dilates vitelline blood vessels via serotonin(2) receptors. The Journal of pharmacology and experimental therapeutics. 2002 Oct; 303(1):257-64. doi: 10.1124/jpet.102.037044. [PMID: 12235259]
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  • Raymond G York, Kevin H Denny, David E Moody, Mario E Alburges. Developmental toxicity of levo-alpha-acetylmethadol (LAAM) in tolerant rats. International journal of toxicology. 2002 Mar; 21(2):147-59. doi: 10.1080/10915810252866105. [PMID: 12022632]
  • Lisa Borg, Ann Ho, Aaron Wells, Herman Joseph, Phil Appel, David Moody, Mary Jeanne Kreek. The use of levo-alpha-acetylmethadol (LAAM) in methadone patients who have not achieved heroin abstinence. Journal of addictive diseases. 2002; 21(3):13-22. doi: 10.1300/j069v21n03_02. [PMID: 12094997]
  • B A Schwetz. From the Food and Drug Administration. JAMA. 2001 Jun; 285(21):2705. doi: NULL. [PMID: 11386912]
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  • M L Cheever, G A Armendariz, D E Moody. Detection of methadone, LAAM, and their metabolites by methadone immunoassays. Journal of analytical toxicology. 1999 Oct; 23(6):500-5. doi: 10.1093/jat/23.6.500. [PMID: 10517557]
  • H E Jones, E C Strain, G E Bigelow, S L Walsh, M L Stitzer, T Eissenberg, R E Johnson. Induction with levomethadyl acetate: safety and efficacy. Archives of general psychiatry. 1998 Aug; 55(8):729-36. doi: 10.1001/archpsyc.55.8.729. [PMID: 9707384]
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  • A H Oliveto, C Farren, T R Kosten. Effect of LAAM dose on opiate use in opioid-dependent patients. A pilot study. The American journal on addictions. 1998; 7(4):272-82. doi: NULL. [PMID: 9809131]
  • D G Wilkins, A S Valdez, G G Krueger, D E Rollins. Quantitative analysis of l-alpha-acetylmethadol, l-alpha-acetyl-N-normethadol, and l-alpha-acetyl-N,N-dinormethadol in human hair by positive ion chemical ionization mass spectrometry. Journal of analytical toxicology. 1997 Oct; 21(6):420-6. doi: 10.1093/jat/21.6.420. [PMID: 9323520]
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  • D E Moody, D J Crouch, C O Sakashita, M E Alburges, K Minear, J E Schulthies, R L Foltz. A gas chromatographic-positive ion chemical ionization-mass spectrometric method for the determination of I-alpha-acetylmethadol (LAAM), norLAAM, and dinorLAAM in plasma, urine, and tissue. Journal of analytical toxicology. 1995 Oct; 19(6):343-51. doi: 10.1093/jat/19.6.343. [PMID: 8926727]
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  • G A Casella, G A Deneau, S J Mule. The effect of ethanol on the metabolism of chronically-administered l-alpha-acetylmethadol (LAAM) in the rhesus monkey. Research communications in chemical pathology and pharmacology. 1978 Aug; 21(2):351-4. doi: . [PMID: 99782]
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