Noroxycodone (BioDeep_00000018230)

   

human metabolite Endogenous


代谢物信息卡片


(1S,5R,13R,17S)-17-hydroxy-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one

化学式: C17H19NO4 (301.1314014)
中文名称:
谱图信息: 最多检出来源 Bos taurus(endogenous) 50%

分子结构信息

SMILES: COC1=C2C3=C(CC4C5(C3(CCN4)C(O2)C(=O)CC5)O)C=C1
InChI: InChI=1S/C17H19NO4/c1-21-11-3-2-9-8-12-17(20)5-4-10(19)15-16(17,6-7-18-12)13(9)14(11)22-15/h2-3,12,15,18,20H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1

描述信息

Noroxycodone belongs to the family of Morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids

同义名列表

3 个代谢物同义名

(1S,5R,13R,17S)-17-hydroxy-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one; SCHEMBL10033226; Noroxycodone



数据库引用编号

8 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(0)

PharmGKB(1)

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

  • Aymen A Al-Qurain, Desmond B Williams, Lorraine Mackenzie, Michael S Roberts, Michael D Wiese. Simultaneous LC-MS/MS quantification of oxycodone, tramadol and fentanyl and their metabolites (noroxycodone, oxymorphone, O- desmethyltramadol, N- desmethyltramadol, and norfentanyl) in human plasma and whole blood collected via venepuncture and volumetric absorptive micro sampling. Journal of pharmaceutical and biomedical analysis. 2021 Sep; 203(?):114171. doi: 10.1016/j.jpba.2021.114171. [PMID: 34087551]
  • John R Cashman, Mark Gohdes, Annelies de Kater, Grant Schoenhard. N-Oxygenation of Oxycodone and Retro-reduction of Oxycodone N-Oxide. Drug metabolism and disposition: the biological fate of chemicals. 2020 02; 48(2):106-115. doi: 10.1124/dmd.119.089300. [PMID: 31727673]
  • Michael N Kammer, Amanda Kussrow, Ilavarasi Gandhi, Rafal Drabek, Robert H Batchelor, George W Jackson, Darryl J Bornhop. Quantification of Opioids in Urine Using an Aptamer-Based Free-Solution Assay. Analytical chemistry. 2019 08; 91(16):10582-10588. doi: 10.1021/acs.analchem.9b01638. [PMID: 31314489]
  • Anne Leuppi-Taegtmeyer, Urs Duthaler, Felix Hammann, Yasmin Schmid, Michael Dickenmann, Patricia Amico, Andreas W Jehle, Stefan Kalbermatter, Christoph Lenherr, Henriette E Meyer Zu Schwabedissen, Manuel Haschke, Matthias E Liechti, Stephan Krähenbühl. Pharmacokinetics of oxycodone/naloxone and its metabolites in patients with end-stage renal disease during and between haemodialysis sessions. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2019 04; 34(4):692-702. doi: 10.1093/ndt/gfy285. [PMID: 30189012]
  • Michele Protti, Maria Carmen Catapano, Boaz Gedaliahu Samolsky Dekel, James Rudge, Gilberto Gerra, Lorenzo Somaini, Roberto Mandrioli, Laura Mercolini. Determination of oxycodone and its major metabolites in haematic and urinary matrices: Comparison of traditional and miniaturised sampling approaches. Journal of pharmaceutical and biomedical analysis. 2018 Apr; 152(?):204-214. doi: 10.1016/j.jpba.2018.01.043. [PMID: 29414014]
  • Flaminia Pantano, Stefano Brauneis, Alexandre Forneris, Roberta Pacifici, Enrico Marinelli, Chrystalla Kyriakou, Simona Pichini, Francesco Paolo Busardò. Determination of oxycodone and its major metabolites noroxycodone and oxymorphone by ultra-high-performance liquid chromatography tandem mass spectrometry in plasma and urine: application to real cases. Clinical chemistry and laboratory medicine. 2017 Aug; 55(9):1324-1331. doi: 10.1515/cclm-2016-0990. [PMID: 28080998]
  • Boaz Gedaliahu Samolsky Dekel, Gabriele Donati, Alessio Vasarri, Anna Laura Croci Chiocchini, Alberto Gori, Giuseppe Cavallari, Gianfranco Di Nino, Laura Mercolini, Michele Protti, Roberto Mandrioli, Rita Maria Melotti, Gaetano La Manna. Dialyzability of Oxycodone and Its Metabolites in Chronic Noncancer Pain Patients with End-Stage Renal Disease. Pain practice : the official journal of World Institute of Pain. 2017 06; 17(5):604-615. doi: 10.1111/papr.12483. [PMID: 27589376]
  • Merja Kokki, Marja Heikkinen, Pyry Välitalo, Heidi Hautajärvi, Juho Hokkanen, Hanna Pitkänen, Ulla Sankilampi, Veli-Pekka Ranta, Hannu Kokki. Maturation of oxycodone pharmacokinetics in neonates and infants: Oxycodone and its metabolites in plasma and urine. British journal of clinical pharmacology. 2017 04; 83(4):791-800. doi: 10.1111/bcp.13164. [PMID: 27780305]
  • Fleur Gaudette, Andréa Sirhan-Daneau, Maude St-Onge, Jacques Turgeon, Veronique Michaud. Development of a sensitive method for the determination of oxycodone and its major metabolites noroxycodone and oxymorphone in human plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Jan; 1008(?):174-180. doi: 10.1016/j.jchromb.2015.11.035. [PMID: 26655109]
  • Natalie M Elder, Rabia S Atayee, Brookie M Best, Joseph D Ma. Observations of urinary oxycodone and metabolite distributions in pain patients. Journal of analytical toxicology. 2014 Apr; 38(3):129-34. doi: 10.1093/jat/bku007. [PMID: 24523296]
  • Guang-Tao Hao, Hai-Yan Zhou, Hong-Zhi Gao, Heng-Yan Qu, Yu-Guang Liang, Yuan-Yuan Li, Rui-Hua Dong, Li-Juan Zhang, Xiao-Fang Wang, Ze-Yuan Liu. Pharmacokinetics of oxycodone hydrochloride and three of its metabolites after intravenous administration in Chinese patients with pain. Pharmacological reports : PR. 2014 Feb; 66(1):153-8. doi: 10.1016/j.pharep.2013.08.012. [PMID: 24905321]
  • Kathleen V Moy, Joseph D Ma, Candis M Morello, Rabia S Atayee, Brookie M Best. Monitoring oxycodone use in patients with chronic pain: analysis of oxycodone and metabolite excretion in saliva and urine. Journal of opioid management. 2014 Jan; 10(1):47-56. doi: 10.5055/jom.2014.0191. [PMID: 24604569]
  • Yutaka Fujiwara, Masanori Toyoda, Naoko Chayahara, Naomi Kiyota, Takanobu Shimada, Yoshinori Imamura, Toru Mukohara, Hironobu Minami. Effects of aprepitant on the pharmacokinetics of controlled-release oral oxycodone in cancer patients. PloS one. 2014; 9(8):e104215. doi: 10.1371/journal.pone.0104215. [PMID: 25121773]
  • Takafumi Naito, Masaki Tashiro, Takuya Ishida, Kazunori Ohnishi, Junichi Kawakami. Cancer cachexia raises the plasma concentration of oxymorphone through the reduction of CYP3A but not CYP2D6 in oxycodone-treated patients. Journal of clinical pharmacology. 2013 Aug; 53(8):812-8. doi: 10.1002/jcph.112. [PMID: 23733622]
  • Wenfang B Fang, Michelle R Lofwall, Sharon L Walsh, David E Moody. Determination of oxycodone, noroxycodone and oxymorphone by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry in human matrices: in vivo and in vitro applications. Journal of analytical toxicology. 2013 Jul; 37(6):337-44. doi: 10.1093/jat/bkt042. [PMID: 23743505]
  • Edward J Cone, Rebecca Heltsley, David L Black, John M Mitchell, Charles P Lodico, Ronald R Flegel. Prescription opioids. I. Metabolism and excretion patterns of oxycodone in urine following controlled single dose administration. Journal of analytical toxicology. 2013 Jun; 37(5):255-64. doi: 10.1093/jat/bkt031. [PMID: 23609023]
  • Ulrike M Stamer, Lan Zhang, Malte Book, Lutz E Lehmann, Frank Stuber, Frank Musshoff. CYP2D6 genotype dependent oxycodone metabolism in postoperative patients. PloS one. 2013; 8(3):e60239. doi: 10.1371/journal.pone.0060239. [PMID: 23555934]
  • Janet Hardy, Ross Norris, Helen Anderson, Angela O'Shea, Bruce Charles. Is saliva a valid substitute for plasma in pharmacokinetic studies of oxycodone and its metabolites in patients with cancer?. Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer. 2012 Apr; 20(4):767-72. doi: 10.1007/s00520-011-1147-3. [PMID: 21491207]
  • Takafumi Naito, Yoshiaki Takashina, Keisuke Yamamoto, Masaki Tashiro, Kazunori Ohnishi, Yoshiyuki Kagawa, Junichi Kawakami. CYP3A5*3 affects plasma disposition of noroxycodone and dose escalation in cancer patients receiving oxycodone. Journal of clinical pharmacology. 2011 Nov; 51(11):1529-38. doi: 10.1177/0091270010388033. [PMID: 21209234]
  • Trine Naalsund Andreassen, Pål Klepstad, Andrew Davies, Kristin Bjordal, Staffan Lundström, Stein Kaasa, Ola Dale. Influences on the pharmacokinetics of oxycodone: a multicentre cross-sectional study in 439 adult cancer patients. European journal of clinical pharmacology. 2011 May; 67(5):493-506. doi: 10.1007/s00228-010-0948-5. [PMID: 21140139]
  • Antti Liukas, Kristiina Kuusniemi, Riku Aantaa, Petri Virolainen, Mikko Neuvonen, Pertti J Neuvonen, Klaus T Olkkola. Elimination of intravenous oxycodone in the elderly: a pharmacokinetic study in postoperative orthopaedic patients of different age groups. Drugs & aging. 2011 Jan; 28(1):41-50. doi: 10.2165/11586140-000000000-00000. [PMID: 21174486]
  • Edward J Cone, Anne Zichterman, Rebecca Heltsley, David L Black, Beverly Cawthon, Tim Robert, Frank Moser, Yale H Caplan. Urine testing for norcodeine, norhydrocodone, and noroxycodone facilitates interpretation and reduces false negatives. Forensic science international. 2010 May; 198(1-3):58-61. doi: 10.1016/j.forsciint.2009.12.005. [PMID: 20036472]
  • Teijo I Saari, Juha Grönlund, Nora M Hagelberg, Mikko Neuvonen, Kari Laine, Pertti J Neuvonen, Klaus T Olkkola. Effects of itraconazole on the pharmacokinetics and pharmacodynamics of intravenously and orally administered oxycodone. European journal of clinical pharmacology. 2010 Apr; 66(4):387-97. doi: 10.1007/s00228-009-0775-8. [PMID: 20076952]
  • M Wagner, E Bourgogne, E Varesio, G Hopfgartner. Quantitation of polar analytes using column-switching: application to oxycodone and three metabolites in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Mar; 878(7-8):637-44. doi: 10.1016/j.jchromb.2010.01.014. [PMID: 20138595]
  • Juha Grönlund, Teijo Saari, Nora Hagelberg, Ilkka K Martikainen, Pertti J Neuvonen, Klaus T Olkkola, Kari Laine. Effect of telithromycin on the pharmacokinetics and pharmacodynamics of oral oxycodone. Journal of clinical pharmacology. 2010 Jan; 50(1):101-8. doi: 10.1177/0091270009336444. [PMID: 19755414]
  • Ahmed I Al-Asmari, Robert A Anderson, Gail A A Cooper. Oxycodone-related fatalities in the west of Scotland. Journal of analytical toxicology. 2009 Oct; 33(8):423-32. doi: 10.1093/jat/33.8.423. [PMID: 19874648]
  • Mikko Neuvonen, Pertti J Neuvonen. Determination of oxycodone, noroxycodone, oxymorphone, and noroxymorphone in human plasma by liquid chromatography-electrospray-tandem mass spectrometry. Therapeutic drug monitoring. 2008 Jun; 30(3):333-40. doi: 10.1097/ftd.0b013e31816e2d4b. [PMID: 18520605]
  • Samuel Chan, Stephen R Edwards, Bruce D Wyse, Maree T Smith. Sex differences in the pharmacokinetics, oxidative metabolism and oral bioavailability of oxycodone in the Sprague-Dawley rat. Clinical and experimental pharmacology & physiology. 2008 Mar; 35(3):295-302. doi: 10.1111/j.1440-1681.2007.04821.x. [PMID: 17973932]
  • Stephen R Edwards, Maree T Smith. Low-level quantitation of oxycodone and its oxidative metabolites, noroxycodone, and oxymorphone, in rat plasma by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Apr; 848(2):264-70. doi: 10.1016/j.jchromb.2006.10.039. [PMID: 17098487]
  • Hannu Kokki, Ilpo Rasanen, Merja Lasalmi, Sanna Lehtola, Veli-Pekka Ranta, Kari Vanamo, Ilkka Ojanperä. Comparison of oxycodone pharmacokinetics after buccal and sublingual administration in children. Clinical pharmacokinetics. 2006; 45(7):745-54. doi: 10.2165/00003088-200645070-00009. [PMID: 16802855]
  • Olga Cheremina, Iouri Bachmakov, Antje Neubert, Kay Brune, Martin F Fromm, Burkhard Hinz. Simultaneous determination of oxycodone and its major metabolite, noroxycodone, in human plasma by high-performance liquid chromatography. Biomedical chromatography : BMC. 2005 Dec; 19(10):777-82. doi: 10.1002/bmc.516. [PMID: 15920700]
  • Lillian Huang, Stephen R Edwards, Maree T Smith. Comparison of the pharmacokinetics of oxycodone and noroxycodone in male dark agouti and Sprague--Dawley rats: influence of streptozotocin-induced diabetes. Pharmaceutical research. 2005 Sep; 22(9):1489-98. doi: 10.1007/s11095-005-6154-y. [PMID: 16132361]
  • Andrea Baldacci, Wolfgang Thormann. Analysis of oxycodol and noroxycodol stereoisomers in biological samples by capillary electrophoresis. Electrophoresis. 2005 May; 26(10):1969-77. doi: 10.1002/elps.200410301. [PMID: 15832300]
  • M A Lee, M E F Leng, R M Cooper. Measurements of plasma oxycodone, noroxycodone and oxymorphone levels in a patient with bilateral nephrectomy who is undergoing haemodialysis. Palliative medicine. 2005 Apr; 19(3):259-60. doi: 10.1191/0269216305pm1004cr. [PMID: 15920941]
  • Stephen R Edwards, Maree T Smith. Simultaneous determination of morphine, oxycodone, morphine-3-glucuronide, and noroxycodone concentrations in rat serum by high performance liquid chromatography-electrospray ionization-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Jan; 814(2):241-9. doi: 10.1016/j.jchromb.2004.10.035. [PMID: 15639445]
  • Emma Boström, Britt Jansson, Margareta Hammarlund-Udenaes, Ulrika S H Simonsson. The use of liquid chromatography/mass spectrometry for quantitative analysis of oxycodone, oxymorphone and noroxycodone in Ringer solution, rat plasma and rat brain tissue. Rapid communications in mass spectrometry : RCM. 2004; 18(21):2565-76. doi: 10.1002/rcm.1658. [PMID: 15468158]
  • Karla A Moore, Vera Ramcharitar, Barry Levine, David Fowler. Tentative identification of novel oxycodone metabolites in human urine. Journal of analytical toxicology. 2003 Sep; 27(6):346-52. doi: 10.1093/jat/27.6.346. [PMID: 14516487]
  • J E Stambaugh, R F Reder, M D Stambaugh, H Stambaugh, M Davis. Double-blind, randomized comparison of the analgesic and pharmacokinetic profiles of controlled- and immediate-release oral oxycodone in cancer pain patients. Journal of clinical pharmacology. 2001 May; 41(5):500-6. doi: 10.1177/00912700122010375. [PMID: 11361046]
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  • M Kirvela, L Lindgren, T Seppala, K T Olkkola. The pharmacokinetics of oxycodone in uremic patients undergoing renal transplantation. Journal of clinical anesthesia. 1996 Feb; 8(1):13-8. doi: 10.1016/0952-8180(95)00092-5. [PMID: 8695073]
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