norfentanyl (BioDeep_00000018043)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


N-Phenyl-N-(piperidin-4-yl)propionamide

化学式: C14H20N2O (232.157555)
中文名称: N-苯基-N-(4-哌啶基)哌啶酰胺
谱图信息: 最多检出来源 Homo sapiens(blood) 75%

分子结构信息

SMILES: CCC(=O)N(c1ccccc1)C1CCNCC1
InChI: InChI=1S/C14H20N2O/c1-2-14(17)16(12-6-4-3-5-7-12)13-8-10-15-11-9-13/h3-7,13,15H,2,8-11H2,1H3

描述信息

norfentanyl is a metabolite of fentanyl. Fentanyl (also known as fentanil, brand names Sublimaze, Actiq, Durogesic, Duragesic, Fentora, Matrifen, Haldid, Onsolis, Instanyl, Abstral, Lazanda and others) is a potent, synthetic narcotic analgesic with a rapid onset and short duration of action. It is a strong agonist at the μ-opioid receptors. Historically it has been used to treat breakthrough pain and is commonly used in pre-procedures as a pain reliever as well as an anesthetic in combination with a benzodiazepine. (Wikipedia)

同义名列表

9 个代谢物同义名

N-Phenyl-N-(piperidin-4-yl)propionamide; 4-(N-phenyl-n-propionyl)aminopiperidine; N-phenyl-N-(piperidin-4-yl)propanamide; N-Phenyl-N-(4-piperidinyl)propanamide; N-Phenyl-N-4-piperidinylpropionamide; N-Phenyl-N-4-piperidinylpropanamide; 4-(N-Propionylanilino)piperidine; Norfentanyl monohydrochloride; Norfentanyl



数据库引用编号

6 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

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

  • Grace Mahowald, Tahira Khaliq, Sankha Basu, David Griggs, Molly Siegel, Lisa Leffert, Sarah Bernstein, James G Flood, Sacha Uljon. Bupivacaine Metabolite Can Interfere with Norfentanyl Measurement by LC-MS/MS. The journal of applied laboratory medicine. 2022 06; 7(4):854-862. doi: 10.1093/jalm/jfac009. [PMID: 35259249]
  • Lu Li, Xuejiao Yu, Lihong Lyu, Hongbin Duan, Yao Chen, Jing Bian, Zhiru Xu, Li Liu, Yurong Zhang. Determination of Fentanyl, Alpha-Methylfentanyl, Beta-Hydroxyfentanyl and the Metabolite Norfentanyl in Rat Urine by LC-MS-MS. Journal of analytical toxicology. 2022 Apr; 46(4):421-431. doi: 10.1093/jat/bkab021. [PMID: 33647104]
  • 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]
  • Jean Jung, Allan Kolodziej, Elise Pape, Michael Bisch, Lucie Javot, Valérie Gibaja, Jean-Yves Jouzeau, Julien Scala-Bertola, Nicolas Gambier. Multiplex detection of 14 fentanyl analogues and U-47700 in biological samples: Application to a panel of French hospitalized patients. Forensic science international. 2020 Dec; 317(?):110437. doi: 10.1016/j.forsciint.2020.110437. [PMID: 33007729]
  • Amita Wanar, Kelley Saia, Thomas A Field. Delayed Norfentanyl Clearance During Pregnancy. Obstetrics and gynecology. 2020 11; 136(5):905-907. doi: 10.1097/aog.0000000000004106. [PMID: 33030873]
  • Andrew S Huhn, J Gregory Hobelmann, George A Oyler, Eric C Strain. Protracted renal clearance of fentanyl in persons with opioid use disorder. Drug and alcohol dependence. 2020 09; 214(?):108147. doi: 10.1016/j.drugalcdep.2020.108147. [PMID: 32650192]
  • Kaitlyn B Palmquist, Madeleine J Swortwood. Quantification of Furanylfentanyl and its Metabolites in Human and Rat Plasma Using LC-MS-MS. Journal of analytical toxicology. 2020 Jul; 44(6):589-595. doi: 10.1093/jat/bkaa013. [PMID: 32064536]
  • Zhao Li, Hui Chen, Sheng Feng, Kengku Liu, Ping Wang. Development and Clinical Validation of a Sensitive Lateral Flow Assay for Rapid Urine Fentanyl Screening in the Emergency Department. Clinical chemistry. 2020 02; 66(2):324-332. doi: 10.1093/clinchem/hvz023. [PMID: 32040576]
  • Marcus J P Geist, Victoria C Ziesenitz, Hubert J Bardenheuer, Juergen Burhenne, Gisela Skopp, Gerd Mikus. Minor contribution of cytochrome P450 3A activity on fentanyl exposure in palliative care cancer patients. Scientific reports. 2019 10; 9(1):14635. doi: 10.1038/s41598-019-51279-6. [PMID: 31601999]
  • Alonja Reiter, Alexander Mueller, Benjamin Otto, Sven Anders, Maja Falckenberg, Stefanie Iwersen-Bergmann, Hilke Andresen-Streichert. Fast increase of postmortem fentanyl blood concentrations after transdermal application: A call to careful interpretation. Forensic science international. 2019 Sep; 302(?):109896. doi: 10.1016/j.forsciint.2019.109896. [PMID: 31426021]
  • J S Smith, J F Coetzee, I W G Fisher, D J Borts, J P Mochel. Pharmacokinetics of fentanyl citrate and norfentanyl in Holstein calves and effect of analytical performances on fentanyl parameter estimation. Journal of veterinary pharmacology and therapeutics. 2018 Aug; 41(4):555-561. doi: 10.1111/jvp.12501. [PMID: 29603262]
  • Gregory W Vandergrift, Arden J Hessels, Jan Palaty, Erik T Krogh, Chris G Gill. Paper spray mass spectrometry for the direct, semi-quantitative measurement of fentanyl and norfentanyl in complex matrices. Clinical biochemistry. 2018 Apr; 54(?):106-111. doi: 10.1016/j.clinbiochem.2018.02.005. [PMID: 29432758]
  • Melissa M Goggin, An Nguyen, Gregory C Janis. Identification of Unique Metabolites of the Designer Opioid Furanyl Fentanyl. Journal of analytical toxicology. 2017 Jun; 41(5):367-375. doi: 10.1093/jat/bkx022. [PMID: 28369517]
  • Xiulu Ruan, Srinivas Chiravuri, Alan D Kaye. Fentanyl-Norfentanyl Concentrations During Transdermal Patch Application: LC-MS-MS Urine Analysis. Journal of analytical toxicology. 2017 03; 41(2):163-164. doi: 10.1093/jat/bkw115. [PMID: 27744372]
  • Oneka T Cummings, J Enders, G L McIntire. Response to: Fentanyl-Norfentanyl Concentrations During Transdermal Patch Application: LC-MS-MS Urine Analysis. Journal of analytical toxicology. 2017 03; 41(2):165-166. doi: 10.1093/jat/bkw117. [PMID: 27744370]
  • Xiulu Ruan, Srinivas Chiravuri, Alan D Kaye. Using postmortem blood and urine norfentanyl/fentanyl ratios in the investigation of fentanyl-related deaths. Clinical toxicology (Philadelphia, Pa.). 2016 Nov; 54(9):893. doi: 10.1080/15563650.2016.1199030. [PMID: 27314754]
  • Brandon Stamper, Waseem Gul, Murrell Godfrey, Shahbaz W Gul, Mahmoud A ElSohly. LC-MS-MS Method for the Analysis of Miscellaneous Drugs in Wastewater During Football Games III. Journal of analytical toxicology. 2016 Oct; 40(8):694-699. doi: 10.1093/jat/bkw081. [PMID: 27562966]
  • Oneka T Cummings, Jeffrey R Enders, Gregory L McIntire, R Backer, A Poklis. Fentanyl-Norfentanyl Concentrations During Transdermal Patch Application: LC-MS-MS Urine Analysis. Journal of analytical toxicology. 2016 Oct; 40(8):595-600. doi: 10.1093/jat/bkw067. [PMID: 27405369]
  • Xiulu Ruan, Srinivas Chiravuri, Alan D Kaye. Toxicological testing when evaluating fatal cases suspected of acute fentanyl toxicity. Forensic science, medicine, and pathology. 2016 Sep; 12(3):363-5. doi: 10.1007/s12024-016-9789-6. [PMID: 27383255]
  • Justin Poklis, Alphonse Poklis, Carl Wolf, Mary Mainland, Laura Hair, Kelly Devers, Leszek Chrostowski, Elise Arbefeville, Michele Merves, Julia Pearson. Postmortem tissue distribution of acetyl fentanyl, fentanyl and their respective nor-metabolites analyzed by ultrahigh performance liquid chromatography with tandem mass spectrometry. Forensic science international. 2015 Dec; 257(?):435-441. doi: 10.1016/j.forsciint.2015.10.021. [PMID: 26583960]
  • Sudeep R Bista, Alison Haywood, Ross Norris, Phillip Good, Angela Tapuni, Michael Lobb, Janet Hardy. Saliva versus Plasma for Pharmacokinetic and Pharmacodynamic Studies of Fentanyl in Patients with Cancer. Clinical therapeutics. 2015 Nov; 37(11):2468-75. doi: 10.1016/j.clinthera.2015.09.002. [PMID: 26404396]
  • Victoria C Ziesenitz, Sonja K König, Nina S Mahlke, Gisela Skopp, Walter E Haefeli, Gerd Mikus. Pharmacokinetic interaction of intravenous fentanyl with ketoconazole. Journal of clinical pharmacology. 2015 Jun; 55(6):708-17. doi: 10.1002/jcph.469. [PMID: 25651378]
  • Sudeep Raj Bista, Alison Haywood, Janet Hardy, Michael Lobb, Angela Tapuni, Ross Norris. Protein binding of fentanyl and its metabolite nor-fentanyl in human plasma, albumin and α-1 acid glycoprotein. Xenobiotica; the fate of foreign compounds in biological systems. 2015 Mar; 45(3):207-12. doi: 10.3109/00498254.2014.971093. [PMID: 25314012]
  • Nina Sophia Mahlke, Victoria Ziesenitz, Gerd Mikus, Gisela Skopp. Quantitative low-volume assay for simultaneous determination of fentanyl, norfentanyl, and minor metabolites in human plasma and urine by liquid chromatography-tandem mass spectrometry (LC-MS/MS). International journal of legal medicine. 2014 Sep; 128(5):771-8. doi: 10.1007/s00414-014-1040-y. [PMID: 24997532]
  • Noriaki Tanaka, Takafumi Naito, Tatsuya Yagi, Matsuyuki Doi, Shigehito Sato, Junichi Kawakami. Impact of CYP3A5*3 on plasma exposure and urinary excretion of fentanyl and norfentanyl in the early postsurgical period. Therapeutic drug monitoring. 2014 Jun; 36(3):345-52. doi: 10.1097/ftd.0000000000000029. [PMID: 24365989]
  • Sudeep R Bista, Michael Lobb, Alison Haywood, Janet Hardy, Angela Tapuni, Ross Norris. Development, validation and application of an HPLC-MS/MS method for the determination of fentanyl and nor-fentanyl in human plasma and saliva. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jun; 960(?):27-33. doi: 10.1016/j.jchromb.2014.04.019. [PMID: 24780703]
  • Amy L Patton, Kathryn A Seely, Sharon Pulla, Nancy J Rusch, Cindy L Moran, William E Fantegrossi, Laura D Knight, Jeanna M Marraffa, Paul D Kennedy, Laura P James, Gregory W Endres, Jeffery H Moran. Quantitative measurement of acetyl fentanyl and acetyl norfentanyl in human urine by LC-MS/MS. Analytical chemistry. 2014 Feb; 86(3):1760-6. doi: 10.1021/ac4036197. [PMID: 24354295]
  • Ruth Verplaetse, Jan Tytgat. Development and validation of a sensitive UPLC-MS/MS method for the analysis of narcotic analgesics in urine and whole blood in forensic context. Forensic science international. 2012 Feb; 215(1-3):136-45. doi: 10.1016/j.forsciint.2011.01.047. [PMID: 21356580]
  • Claudia F Clavijo, James Joseph Thomas, Meghan Cromie, Björn Schniedewind, Keith L Hoffman, Uwe Christians, Jeffrey L Galinkin. A low blood volume LC-MS/MS assay for the quantification of fentanyl and its major metabolites norfentanyl and despropionyl fentanyl in children. Journal of separation science. 2011 Dec; 34(24):3568-77. doi: 10.1002/jssc.201100422. [PMID: 21916010]
  • Sabina Strano-Rossi, Iván Alvarez, María Jesús Tabernero, Pamela Cabarcos, Purificación Fernández, Ana María Bermejo. Determination of fentanyl, metabolite and analogs in urine by GC/MS. Journal of applied toxicology : JAT. 2011 Oct; 31(7):649-54. doi: 10.1002/jat.1613. [PMID: 21132842]
  • Ruth Verplaetse, Jan Tytgat. Development and validation of a sensitive ultra performance liquid chromatography tandem mass spectrometry method for the analysis of fentanyl and its major metabolite norfentanyl in urine and whole blood in forensic context. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Jul; 878(22):1987-96. doi: 10.1016/j.jchromb.2010.05.033. [PMID: 20542478]
  • Nadine F J Van Nimmen, Katrien L C Poels, Joannes J Menten, Lode Godderis, Hendrik A F Veulemans. Fentanyl transdermal absorption linked to pharmacokinetic characteristics in patients undergoing palliative care. Journal of clinical pharmacology. 2010 Jun; 50(6):667-78. doi: 10.1177/0091270009347872. [PMID: 20097932]
  • Sara M Thomasy, Khursheed R Mama, Scott D Stanley. Comparison of liquid chromatography-mass spectrometry and radioimmunoassay for measurement of fentanyl and determination of pharmacokinetics in equine plasma. Journal of analytical toxicology. 2008 Nov; 32(9):754-9. doi: 10.1093/jat/32.9.754. [PMID: 19021930]
  • Teijo I Saari, Kari Laine, Mikko Neuvonen, Pertti J Neuvonen, Klaus T Olkkola. Effect of voriconazole and fluconazole on the pharmacokinetics of intravenous fentanyl. European journal of clinical pharmacology. 2008 Jan; 64(1):25-30. doi: 10.1007/s00228-007-0398-x. [PMID: 17987285]
  • Cody J Peer, Diaa M Shakleya, Islam R Younis, James C Kraner, Patrick S Callery. Direct-injection mass spectrometric method for the rapid identification of fentanyl and norfentanyl in postmortem urine of six drug-overdose cases. Journal of analytical toxicology. 2007 Oct; 31(8):515-21. doi: 10.1093/jat/31.8.515. [PMID: 17988466]
  • Vera Coopman, Jan Cordonnier, Karen Pien, Dirk Van Varenbergh. LC-MS/MS analysis of fentanyl and norfentanyl in a fatality due to application of multiple Durogesic transdermal therapeutic systems. Forensic science international. 2007 Jul; 169(2-3):223-7. doi: 10.1016/j.forsciint.2006.03.018. [PMID: 16650707]
  • Chi-Liang Mao, Keith D Zientek, Patrick T Colahan, Mei-Yueh Kuo, Chi-Ho Liu, Kuo-Ming Lee, Chi-Chung Chou. Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation. Journal of pharmaceutical and biomedical analysis. 2006 Jun; 41(4):1332-41. doi: 10.1016/j.jpba.2006.03.009. [PMID: 16621415]
  • F Musshoff, J Trafkowski, U Kuepper, B Madea. An automated and fully validated LC-MS/MS procedure for the simultaneous determination of 11 opioids used in palliative care, with 5 of their metabolites. Journal of mass spectrometry : JMS. 2006 May; 41(5):633-40. doi: 10.1002/jms.1021. [PMID: 16541404]
  • N-H Huynh, N Tyrefors, L Ekman, M Johansson. Determination of fentanyl in human plasma and fentanyl and norfentanyl in human urine using LC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2005 Apr; 37(5):1095-100. doi: 10.1016/j.jpba.2004.09.024. [PMID: 15862690]
  • Alphonse Poklis, Ronald Backer. Urine concentrations of fentanyl and norfentanyl during application of Duragesic transdermal patches. Journal of analytical toxicology. 2004 Sep; 28(6):422-5. doi: 10.1093/jat/28.6.422. [PMID: 15516290]
  • Evan D Kharasch, Christine Hoffer, Dale Whittington. Influence of age on the pharmacokinetics and pharmacodynamics of oral transmucosal fentanyl citrate. Anesthesiology. 2004 Sep; 101(3):738-43. doi: 10.1097/00000542-200409000-00023. [PMID: 15329599]
  • Evan D Kharasch, Dale Whittington, Christine Hoffer. Influence of hepatic and intestinal cytochrome P4503A activity on the acute disposition and effects of oral transmucosal fentanyl citrate. Anesthesiology. 2004 Sep; 101(3):729-37. doi: 10.1097/00000542-200409000-00022. [PMID: 15329598]
  • Evan D Kharasch, Christine Hoffer, T Gul Altuntas, Dale Whittington. Quinidine as a probe for the role of p-glycoprotein in the intestinal absorption and clinical effects of fentanyl. Journal of clinical pharmacology. 2004 Mar; 44(3):224-33. doi: 10.1177/0091270003262075. [PMID: 14973303]
  • D E Koch, R Isaza, J W Carpenter, R P Hunter. Simultaneous extraction and quantitation of fentanyl and norfentanyl from primate plasma with LC/MS detection. Journal of pharmaceutical and biomedical analysis. 2004 Feb; 34(3):577-84. doi: 10.1016/s0731-7085(03)00652-6. [PMID: 15127814]
  • J Day, M Slawson, R A Lugo, D Wilkins. Analysis of fentanyl and norfentanyl in human plasma by liquid chromatography-tandem mass spectrometry using electrospray ionization. Journal of analytical toxicology. 2003 Oct; 27(7):513-6. doi: 10.1093/jat/27.7.513. [PMID: 14607008]
  • A K Valaer, T Huber, S V Andurkar, C R Clark, J DeRuiter. Development of a gas chromatographic-mass spectrometric drug screening method for the N-dealkylated metabolites of fentanyl, sufentanil, and alfentanil. Journal of chromatographic science. 1997 Oct; 35(10):461-6. doi: 10.1093/chromsci/35.10.461. [PMID: 9336954]
  • J H Silverstein, M F Rieders, M McMullin, S Schulman, K Zahl. An analysis of the duration of fentanyl and its metabolites in urine and saliva. Anesthesia and analgesia. 1993 Mar; 76(3):618-21. doi: 10.1213/00000539-199303000-00030. [PMID: 8452277]