O-Desmethyl tramadol (BioDeep_00000408587)

   


代谢物信息卡片


(+)-(1R,2R)-O-DESMETHYL TRAMADOL HCL

化学式: C15H23NO2 (249.1728698)
中文名称: (+)-O-去甲基曲马多
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN(C)CC1CCCCC1(C2=CC(=CC=C2)O)O
InChI: InChI=1S/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3/t13-,15+/m1/s1

描述信息

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 > C241 - Analgesic Agent
D002491 - Central Nervous System Agents > D000700 - Analgesics
CONFIDENCE standard compound; INTERNAL_ID 2287

同义名列表

3 个代谢物同义名

(+)-(1R,2R)-O-DESMETHYL TRAMADOL HCL; O-Desmethyl tramadol; N,O-Desmethyltramadol



数据库引用编号

16 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)

0 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

  • Tim Boogaerts, Maarten Quireyns, Hans De Loof, Xander Bertels, Natan Van Wichelen, Bram Pussig, Jan Saevels, Lies Lahousse, Pauline Bonmariage, Wouter Hamelinck, Bert Aertgeerts, Adrian Covaci, Alexander L N van Nuijs. Do the lockdown-imposed changes in a wastewater treatment plant catchment's socio-demographics impact longitudinal temporal trends in psychoactive pharmaceutical use?. The Science of the total environment. 2023 Feb; ?(?):162342. doi: 10.1016/j.scitotenv.2023.162342. [PMID: 36842581]
  • O Yoo, E K Y Tang, M N Nguyen, S Salman, A J Hua, B S von Ungern Sternberg, L Y Lim. HPLC-UV assay of tramadol and O-desmethyltramadol in human plasma containing other drugs potentially co-administered to participants in a paediatric population pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Nov; 1184(?):122971. doi: 10.1016/j.jchromb.2021.122971. [PMID: 34649173]
  • 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]
  • Piotr J Rudzki, Katarzyna Jarus-Dziedzic, Monika Filist, Edyta Gilant, Katarzyna Buś-Kwaśnik, Andrzej Leś, Małgorzata Sasinowska-Motyl, Łukasz Nagraba, Magdalena Bujalska-Zadrożny. Evaluation of tramadol human pharmacokinetics and safety after co-administration of magnesium ions in randomized, single- and multiple-dose studies. Pharmacological reports : PR. 2021 Apr; 73(2):604-614. doi: 10.1007/s43440-021-00239-x. [PMID: 33686610]
  • Koji Suzuki, Takafumi Naito, Hironari Tanaka, Kaito Shibata, Yasuhide Yamada, Kunihiko Itoh, Junichi Kawakami. Impact of CYP2D6 activity and cachexia progression on enantiomeric alteration of plasma tramadol and its demethylated metabolites and their relationships with central nervous system symptoms in head and neck cancer patients. Basic & clinical pharmacology & toxicology. 2021 Mar; 128(3):472-481. doi: 10.1111/bcpt.13528. [PMID: 33131142]
  • Benjamin Kimble, Larry Vogelnest, Peter Valtchev, Merran Govendir. Pharmacokinetic profile of injectable tramadol in the koala (Phascolarctos cinereus) and prediction of its analgesic efficacy. PloS one. 2021; 16(3):e0247546. doi: 10.1371/journal.pone.0247546. [PMID: 33657107]
  • Koji Suzuki, Takafumi Naito, Hironari Tanaka, Yasuhide Yamada, Kunihiko Itoh, Junichi Kawakami. A Reversed-Phase Mode LC-MS/MS Method Using a Polysaccharide Chiral Selector for Simultaneous Quantitation of Each Enantiomer of Tramadol and its Metabolites in Human Plasma and Evaluation of CYP-Mediated Stereoselective Demethylation. Therapeutic drug monitoring. 2020 06; 42(3):503-511. doi: 10.1097/ftd.0000000000000707. [PMID: 31613803]
  • Sybil Skinner Robertson, Mohamad Samer Mouksassi, France Varin. Population Pharmacokinetic/Pharmacodynamic Modeling of O-Desmethyltramadol in Young and Elderly Healthy Volunteers. Drugs & aging. 2019 08; 36(8):747-758. doi: 10.1007/s40266-019-00681-w. [PMID: 31161580]
  • Joanna Porażka, Edyta Szałek, Wojciech Połom, Mateusz Czajkowski, Tomasz Grabowski, Marcin Matuszewski, Edmund Grześkowiak. Influence of Obesity and Type 2 Diabetes Mellitus on the Pharmacokinetics of Tramadol After Single Oral Dose Administration. European journal of drug metabolism and pharmacokinetics. 2019 Aug; 44(4):579-584. doi: 10.1007/s13318-019-00543-1. [PMID: 30778911]
  • Hosam Eldin Dahshan, Mohamed A Helal, Samia M Mostafa, Mohamed Saleh Elgawish. Development and validation of an HPLC-UV method for simultaneous determination of sildenafil and tramadol in biological fluids: Application to drug-drug interaction study. Journal of pharmaceutical and biomedical analysis. 2019 May; 168(?):201-208. doi: 10.1016/j.jpba.2019.02.025. [PMID: 30825803]
  • Joomi Lee, Hee-Doo Yoo, Jung-Woo Bae, Sooyeun Lee, Kwang-Hee Shin. Population pharmacokinetic analysis of tramadol and O-desmethyltramadol with genetic polymorphism of CYP2D6. Drug design, development and therapy. 2019; 13(?):1751-1761. doi: 10.2147/dddt.s199574. [PMID: 31213765]
  • Tania E Perez Jimenez, Butch Kukanich, Hyun Joo, Katrina L Mealey, Tamara L Grubb, Stephen A Greene, Michael H Court. Oral Coadministration of Fluconazole with Tramadol Markedly Increases Plasma and Urine Concentrations of Tramadol and the O-Desmethyltramadol Metabolite in Healthy Dogs. Drug metabolism and disposition: the biological fate of chemicals. 2019 01; 47(1):15-25. doi: 10.1124/dmd.118.083444. [PMID: 30366901]
  • Hironari Tanaka, Takafumi Naito, Hikaru Sato, Takanori Hiraide, Yasuhide Yamada, Junichi Kawakami. Impact of CYP genotype and inflammatory markers on the plasma concentrations of tramadol and its demethylated metabolites and drug tolerability in cancer patients. European journal of clinical pharmacology. 2018 Nov; 74(11):1461-1469. doi: 10.1007/s00228-018-2527-0. [PMID: 30051214]
  • Gregorio Encina, Mercedes Encabo, Marisol Escriche, Mounia Lahjou, Eric Sicard, Kevin Smith, Neus Gascon, Carlos Plata-Salamán, Sebastián Videla. The Effect of Food on Tramadol and Celecoxib Bioavailability Following Oral Administration of Co-Crystal of Tramadol-Celecoxib (CTC): A Randomised, Open-Label, Single-Dose, Crossover Study in Healthy Volunteers. Clinical drug investigation. 2018 Sep; 38(9):819-827. doi: 10.1007/s40261-018-0672-y. [PMID: 30008052]
  • Manar Hamed Arafa, Hebatallah Husseini Atteia. Genetic polymorphisms of cytochrome P450 2D6 (CYP2D6) are associated with long term tramadol treatment-induced oxidative damage and hepatotoxicity. Toxicology and applied pharmacology. 2018 05; 346(?):37-44. doi: 10.1016/j.taap.2018.03.019. [PMID: 29555325]
  • Rocío Evangelista Vaz, Dragomir I Draganov, Christelle Rapp, Frederic Avenel, Guido Steiner, Margarete Arras, Alessandra Bergadano. Preliminary pharmacokinetics of tramadol hydrochloride after administration via different routes in male and female B6 mice. Veterinary anaesthesia and analgesia. 2018 Jan; 45(1):111-122. doi: 10.1016/j.vaa.2016.09.007. [PMID: 29066180]
  • Mohammed I Rasool, Ahsan F Bairam, Katsuhisa Kurogi, Ming-Cheh Liu. On the sulfation of O-desmethyltramadol by human cytosolic sulfotransferases. Pharmacological reports : PR. 2017 Oct; 69(5):953-958. doi: 10.1016/j.pharep.2017.02.014. [PMID: 28802998]
  • Alexandra F Schütter, Julia Tünsmeyer, Sabine B R Kästner. Influence of tramadol on acute thermal and mechanical cutaneous nociception in dogs. Veterinary anaesthesia and analgesia. 2017 Mar; 44(2):309-316. doi: 10.1016/j.vaa.2016.02.003. [PMID: 28215815]
  • Ulrike M Stamer, Frank Musshoff, Frank Stüber, Jürgen Brockmöller, Michael Steffens, Mladen V Tzvetkov. Loss-of-function polymorphisms in the organic cation transporter OCT1 are associated with reduced postoperative tramadol consumption. Pain. 2016 11; 157(11):2467-2475. doi: 10.1097/j.pain.0000000000000662. [PMID: 27541716]
  • Sybil Skinner-Robertson, Caroline Fradette, Sylvie Bouchard, Mohamad-Samer Mouksassi, France Varin. Pharmacokinetics of Tramadol and O-Desmethyltramadol Enantiomers Following Administration of Extended-Release Tablets to Elderly and Young Subjects. Drugs & aging. 2015 Dec; 32(12):1029-43. doi: 10.1007/s40266-015-0315-4. [PMID: 26508138]
  • Markus R Meyer, Staffan Rosenborg, Marta Stenberg, Olof Beck. First report on the pharmacokinetics of tramadol and O-desmethyltramadol in exhaled breath compared to plasma and oral fluid after a single oral dose. Biochemical pharmacology. 2015 Dec; 98(3):502-10. doi: 10.1016/j.bcp.2015.09.008. [PMID: 26388171]
  • Marian E Benitez, James K Roush, Butch KuKanich, Rose McMurphy. Pharmacokinetics of hydrocodone and tramadol administered for control of postoperative pain in dogs following tibial plateau leveling osteotomy. American journal of veterinary research. 2015 Sep; 76(9):763-70. doi: 10.2460/ajvr.76.9.763. [PMID: 26309104]
  • E Bortolami, G Della Rocca, A Di Salvo, M Giorgi, T W Kim, M Isola, G M De Benedictis. Pharmacokinetics and antinociceptive effects of tramadol and its metabolite O-desmethyltramadol following intravenous administration in sheep. Veterinary journal (London, England : 1997). 2015 Sep; 205(3):404-9. doi: 10.1016/j.tvjl.2015.04.011. [PMID: 26166406]
  • Jennifer L Boonstra, Lorraine Barbosa, William G Van Bonn, Shawn P Johnson, Frances M D Gulland, Sherry K Cox, Tomas Martin-Jimenez. PHARMACOKINETICS OF TRAMADOL HYDROCHLORIDE AND ITS METABOLITE O-DESMETHYLTRAMADOL FOLLOWING A SINGLE, ORALLY ADMINISTERED DOSE IN CALIFORNIA SEA LIONS (ZALOPHUS CALIFORNIANUS). Journal of zoo and wildlife medicine : official publication of the American Association of Zoo Veterinarians. 2015 Sep; 46(3):476-81. doi: 10.1638/2014-0183.1. [PMID: 26352950]
  • Bilal Yilmaz, Ali Fuat Erdem. Simultaneous Determination of Tramadol and Its Metabolite in Human Urine by the Gas Chromatography-Mass Spectrometry Method. Journal of chromatographic science. 2015 Aug; 53(7):1037-43. doi: 10.1093/chromsci/bmu214. [PMID: 25616987]
  • Terry M Norton, Sherry Cox, Steven E Nelson, Michelle Kaylor, Rachel Thomas, Amy Hupp, Kurt K Sladky. PHARMACOKINETICS OF TRAMADOL AND O-DESMETHYLTRAMADOL IN LOGGERHEAD SEA TURTLES (CARETTA CARETTA). Journal of zoo and wildlife medicine : official publication of the American Association of Zoo Veterinarians. 2015 Jun; 46(2):262-5. doi: 10.1638/2014-0158r1.1. [PMID: 26056877]
  • Kanako Miyano, Kouichiro Minami, Toru Yokoyama, Katsuya Ohbuchi, Takuhiro Yamaguchi, Satoshi Murakami, Seiji Shiraishi, Masahiro Yamamoto, Motohiro Matoba, Yasuhito Uezono. Tramadol and its metabolite m1 selectively suppress transient receptor potential ankyrin 1 activity, but not transient receptor potential vanilloid 1 activity. Anesthesia and analgesia. 2015 Apr; 120(4):790-8. doi: 10.1213/ane.0000000000000625. [PMID: 25642661]
  • Qiaoli Wang, Xiaotong Han, Jian Li, Xinghui Gao, Yan Wang, Mingzhou Liu, Guicheng Dong, Jiang Yue. Regulation of cerebral CYP2D alters tramadol metabolism in the brain: interactions of tramadol with propranolol and nicotine. Xenobiotica; the fate of foreign compounds in biological systems. 2015 Apr; 45(4):335-44. doi: 10.3109/00498254.2014.981609. [PMID: 25387586]
  • Yong-Jin Im, Ji-Young Jeon, Eun-Young Kim, Yunjeong Kim, Dong-Joon Oh, Ji-Seok Yoo, Dae-Hee Shin, Soo-Wan Chae, Min-Gul Kim. An assessment of the pharmacokinetics of a sustained-release formulation of a tramadol/acetaminophen combination in healthy subjects. Clinical therapeutics. 2015 Feb; 37(2):376-89. doi: 10.1016/j.clinthera.2014.12.007. [PMID: 25618318]
  • Bılal Yılmaz, Alı Fuat Erdem. Simultaneous Determination of Tramadol and its Metabolite in Human Plasma by GC/MS. Journal of AOAC International. 2015 Jan; 98(1):56-61. doi: 10.5740/jaoacint.14-085. [PMID: 25857879]
  • C Vullo, T-W Kim, M Meligrana, C Marini, M Giorgi. Pharmacokinetics of tramadol and its major metabolite after intramuscular administration in piglets. Journal of veterinary pharmacology and therapeutics. 2014 Dec; 37(6):603-6. doi: 10.1111/jvp.12133. [PMID: 24806910]
  • Maha A Hilal, Khaled M Mohamed. Simultaneous determination of tramadol and O-desmethyltramadol in human plasma using HPLC-DAD. Journal of chromatographic science. 2014 Nov; 52(10):1186-92. doi: 10.1093/chromsci/bmt174. [PMID: 24297526]
  • Theresa M Scott, Jillian K Yeakel, Barry K Logan. Identification of mitragynine and O-desmethyltramadol in Kratom and legal high products sold online. Drug testing and analysis. 2014 Sep; 6(9):959-63. doi: 10.1002/dta.1673. [PMID: 24962931]
  • Treena R Wiebe, James H Watterson. Analysis of tramadol and O-desmethyltramadol in decomposed skeletal tissues following acute and repeated tramadol exposure by gas chromatography mass spectrometry. Forensic science international. 2014 Sep; 242(?):261-265. doi: 10.1016/j.forsciint.2014.07.010. [PMID: 25112198]
  • Jing Xu, Xiang-Cai Zhang, Xiao-Qin Lv, Ying-Ying Xu, Guo-Xiang Wang, Bo Jiang, Long Cai, Xiu-Jun Cai. Effect of the cytochrome P450 2D6*10 genotype on the pharmacokinetics of tramadol in post-operative patients. Die Pharmazie. 2014 Feb; 69(2):138-41. doi: NULL. [PMID: 24640604]
  • P Cagnardi, C Ferraresi, A Zonca, A Pecile, G Ravasio, D D Zani, R Villa. Clinical pharmacokinetics of tramadol and main metabolites in horses undergoing orchiectomy. The veterinary quarterly. 2014; 34(3):143-51. doi: 10.1080/01652176.2014.963208. [PMID: 25211185]
  • Nunziata Barbera, Marco Fisichella, Andrea Bosco, Francesca Indorato, Giorgio Spadaro, Guido Romano. A suicidal poisoning due to tramadol. A metabolic approach to death investigation. Journal of forensic and legal medicine. 2013 Jul; 20(5):555-8. doi: 10.1016/j.jflm.2013.03.006. [PMID: 23756535]
  • Abdel-Aziz Y El-Sayed, Khaled M Mohamed, Ahmed Y Nasser, Jennifer Button, David W Holt. Simultaneous determination of tramadol, O-desmethyltramadol and N-desmethyltramadol in human urine by gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 May; 926(?):9-15. doi: 10.1016/j.jchromb.2013.02.019. [PMID: 23542669]
  • Nora M Hagelberg, Tuukka Saarikoski, Teijo I Saari, Mikko Neuvonen, Pertti J Neuvonen, Miia Turpeinen, Mika Scheinin, Kari Laine, Klaus T Olkkola. Ticlopidine inhibits both O-demethylation and renal clearance of tramadol, increasing the exposure to it, but itraconazole has no marked effect on the ticlopidine-tramadol interaction. European journal of clinical pharmacology. 2013 Apr; 69(4):867-75. doi: 10.1007/s00228-012-1433-0. [PMID: 23099620]
  • Janet K Coller, Jennifer R Michalakas, Heather M James, Aaron L Farquharson, Joel Colvill, Jason M White, Andrew A Somogyi. Inhibition of CYP2D6-mediated tramadol O-demethylation in methadone but not buprenorphine maintenance patients. British journal of clinical pharmacology. 2012 Nov; 74(5):835-41. doi: 10.1111/j.1365-2125.2012.04256.x. [PMID: 22369095]
  • Tarek Mahdy, Taha H El-Shihi, Mostafa M Emara, Silvio Chericoni, Mario Giusiani, Mario Giorgi. Development and validation of a new GC-MS method for the detection of tramadol, O-desmethyltramadol, 6-acetylmorphine and morphine in blood, brain, liver and kidney of Wistar rats treated with the combination of heroin and tramadol. Journal of analytical toxicology. 2012 Oct; 36(8):548-59. doi: 10.1093/jat/bks069. [PMID: 22933659]
  • Binh T Ly, Stephen L Thornton, Colleen Buono, Judith A Stone, Alan H B Wu. False-positive urine phencyclidine immunoassay screen result caused by interference by tramadol and its metabolites. Annals of emergency medicine. 2012 Jun; 59(6):545-7. doi: 10.1016/j.annemergmed.2011.08.013. [PMID: 21924518]
  • Paola C Rúa-Gómez, Wilhelm Püttmann. Impact of wastewater treatment plant discharge of lidocaine, tramadol, venlafaxine and their metabolites on the quality of surface waters and groundwater. Journal of environmental monitoring : JEM. 2012 May; 14(5):1391-9. doi: 10.1039/c2em10950f. [PMID: 22446514]
  • 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]
  • Natália Valadares de Moraes, Gabriela Rocha Lauretti, Marcio Nogueira Napolitano, Naiane Ribeiro Santos, Ana Leonor Pardo Campos Godoy, Vera Lucia Lanchote. Enantioselective analysis of unbound tramadol, O-desmethyltramadol and N-desmethyltramadol in plasma by ultrafiltration and LC-MS/MS: application to clinical pharmacokinetics. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jan; 880(1):140-7. doi: 10.1016/j.jchromb.2011.11.033. [PMID: 22173007]
  • Sam Salman, Sherwin K B Sy, Kenneth F Ilett, Madhu Page-Sharp, Michael J Paech. Population pharmacokinetic modeling of tramadol and its O-desmethyl metabolite in plasma and breast milk. European journal of clinical pharmacology. 2011 Sep; 67(9):899-908. doi: 10.1007/s00228-011-1023-6. [PMID: 21394525]
  • Allison J Stewart, Dawn M Boothe, Crisanta Cruz-Espindola, Emily J Mitchum, Jenny Springfield. Pharmacokinetics of tramadol and metabolites O-desmethyltramadol and N-desmethyltramadol in adult horses. American journal of veterinary research. 2011 Jul; 72(7):967-74. doi: 10.2460/ajvr.72.7.967. [PMID: 21728858]
  • Torsten Arndt, Ulrich Claussen, Brunhilde Güssregen, Stefanie Schröfel, Birgit Stürzer, Annika Werle, Gerald Wolf. Kratom alkaloids and O-desmethyltramadol in urine of a "Krypton" herbal mixture consumer. Forensic science international. 2011 May; 208(1-3):47-52. doi: 10.1016/j.forsciint.2010.10.025. [PMID: 21112167]
  • Robert Kronstrand, Markus Roman, Gunilla Thelander, Anders Eriksson. Unintentional fatal intoxications with mitragynine and O-desmethyltramadol from the herbal blend Krypton. Journal of analytical toxicology. 2011 May; 35(4):242-7. doi: 10.1093/anatox/35.4.242. [PMID: 21513619]
  • Ana Leonor Pardo Campos Godoy, Natália Valadares De Moraes, Edson Zangiacomi Martinez, Teresa Maria De Jesus Ponte Carvalho, Maria Paula Marques, Vera Lucia Lanchote. Simultaneous analysis of tramadol, O-desmethyltramadol, and N-desmethyltramadol enantiomers in rat plasma by high-performance liquid chromatography-tandem mass spectrometry: application to pharmacokinetics. Chirality. 2011 Apr; 23(4):287-93. doi: 10.1002/chir.20914. [PMID: 21384434]
  • Peter A Black, Sherry K Cox, Michael Macek, Anne Tieber, Randall E Junge. Pharmacokinetics of tramadol hydrochloride and its metabolite O-desmethyltramadol in peafowl (Pavo cristatus). Journal of zoo and wildlife medicine : official publication of the American Association of Zoo Veterinarians. 2010 Dec; 41(4):671-6. doi: 10.1638/2010-0054.1. [PMID: 21370649]
  • Suhas S Khandave, Satish V Sawant, Santosh S Joshi, Yatish K Bansal, Sonal S Kadam. Comparative bioequivalence studies of tramadol hydrochloride sustained-release 200 mg tablets. Drug design, development and therapy. 2010 Nov; 4(?):367-74. doi: 10.2147/dddt.s15133. [PMID: 21151623]
  • B De Backer, F Renardy, R Denooz, C Charlier. Quantification in postmortem blood and identification in urine of tramadol and its two main metabolites in two cases of lethal tramadol intoxication. Journal of analytical toxicology. 2010 Nov; 34(9):599-604. doi: 10.1093/jat/34.9.599. [PMID: 21073815]
  • Anette Green Nielsen, Rasmus Steen Pedersen, Lene Noehr-Jensen, Per Damkier, Kim Brosen. Two separate dose-dependent effects of paroxetine: mydriasis and inhibition of tramadol's O-demethylation via CYP2D6. European journal of clinical pharmacology. 2010 Jul; 66(7):655-60. doi: 10.1007/s00228-010-0803-8. [PMID: 20354688]
  • Q Li, R Wang, Y Guo, S Wen, L Xu, S Wang. Relationship of CYP2D6 genetic polymorphisms and the pharmacokinetics of tramadol in Chinese volunteers. Journal of clinical pharmacy and therapeutics. 2010 Apr; 35(2):239-47. doi: 10.1111/j.1365-2710.2009.01102.x. [PMID: 20456744]
  • Lukás Chytil, Olga Matousková, Olga Cerná, Pavla Pokorná, Václav Vobruba, Frantisek Perlík, Ondrej Slanar. Enantiomeric determination of tramadol and O-desmethyltramadol in human plasma by fast liquid chromatographic technique coupled with mass spectrometric detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Feb; 878(3-4):481-6. doi: 10.1016/j.jchromb.2009.12.005. [PMID: 20018572]
  • G Groenewoud, T Cronje, M A Potgieter, D Karhu. Comparative bioavailability of two once-daily tramadol HCl 200 mg extended-release products in healthy volunteers. International journal of clinical pharmacology and therapeutics. 2010 Feb; 48(2):146-57. doi: 10.5414/cpp48146. [PMID: 20137767]
  • L Noehr-Jensen, S T Zwisler, F Larsen, S H Sindrup, P Damkier, K Brosen. Escitalopram is a weak inhibitor of the CYP2D6-catalyzed O-demethylation of (+)-tramadol but does not reduce the hypoalgesic effect in experimental pain. Clinical pharmacology and therapeutics. 2009 Dec; 86(6):626-33. doi: 10.1038/clpt.2009.154. [PMID: 19710642]
  • Lukás Chytil, Martin Stícha, Olga Matousková, Frantisek Perlík, Ondrej Slanar. Enatiomeric determination of tramadol and O-desmethyltramadol in human urine by gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Jul; 877(20-21):1937-42. doi: 10.1016/j.jchromb.2009.04.042. [PMID: 19482526]
  • M Giorgi, S Del Carlo, G Saccomanni, B Łebkowska-Wieruszewska, C J Kowalski. Pharmacokinetics of tramadol and its major metabolites following rectal and intravenous administration in dogs. New Zealand veterinary journal. 2009 Jun; 57(3):146-52. doi: 10.1080/00480169.2009.36894. [PMID: 19521463]
  • Mario Giorgi, Giuseppe Saccomanni, Beata Lebkowska-Wieruszewska, Cezary Kowalski. Pharmacokinetic evaluation of tramadol and its major metabolites after single oral sustained tablet administration in the dog: a pilot study. Veterinary journal (London, England : 1997). 2009 May; 180(2):253-5. doi: 10.1016/j.tvjl.2007.12.011. [PMID: 18313955]
  • Marcy J Souza, Cheryl B Greenacre, Sherry K Cox. Pharmacokinetics of orally administered tramadol in domestic rabbits (Oryctolagus cuniculus). American journal of veterinary research. 2008 Aug; 69(8):979-82. doi: 10.2460/ajvr.69.8.979. [PMID: 18672959]
  • Karel Allegaert, Ron H N van Schaik, Steve Vermeersch, Rene Verbesselt, Veerle Cossey, Christine Vanhole, Marianne van Fessem, Jan de Hoon, John N van den Anker. Postmenstrual age and CYP2D6 polymorphisms determine tramadol o-demethylation in critically ill neonates and infants. Pediatric research. 2008 Jun; 63(6):674-9. doi: 10.1203/pdr.0b013e31816ff712. [PMID: 18317231]
  • Laurian Vlase, Sorin E Leucuta, Silvia Imre. Determination of tramadol and O-desmethyltramadol in human plasma by high-performance liquid chromatography with mass spectrometry detection. Talanta. 2008 May; 75(4):1104-9. doi: 10.1016/j.talanta.2008.01.006. [PMID: 18585190]
  • Kenneth F Ilett, Michael J Paech, Madhu Page-Sharp, Sherwin K Sy, Judith H Kristensen, Raymond Goy, Sebastian Chua, Tracey Christmas, Karen L Scott. Use of a sparse sampling study design to assess transfer of tramadol and its O-desmethyl metabolite into transitional breast milk. British journal of clinical pharmacology. 2008 May; 65(5):661-6. doi: 10.1111/j.1365-2125.2008.03117.x. [PMID: 18294329]
  • Yalda H Ardakani, Reza Mehvar, Alireza Foroumadi, Mohammad-Reza Rouini. Enantioselective determination of tramadol and its main phase I metabolites in human plasma by high-performance liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Mar; 864(1-2):109-15. doi: 10.1016/j.jchromb.2008.01.038. [PMID: 18282749]
  • B H Pypendop, J E Ilkiw. Pharmacokinetics of tramadol, and its metabolite O-desmethyl-tramadol, in cats. Journal of veterinary pharmacology and therapeutics. 2008 Feb; 31(1):52-9. doi: 10.1111/j.1365-2885.2007.00921.x. [PMID: 18177319]
  • A B de Sousa, A C D Santos, S G Schramm, V Porta, S L Górniak, J C Florio, H de Souza Spinosa. Pharmacokinetics of tramadol and o-desmethyltramadol in goats after intravenous and oral administration. Journal of veterinary pharmacology and therapeutics. 2008 Feb; 31(1):45-51. doi: 10.1111/j.1365-2885.2007.00916.x. [PMID: 18177318]
  • Julia Kirchheiner, Jan-Tobias H A Keulen, Steffen Bauer, Ivar Roots, Jürgen Brockmöller. Effects of the CYP2D6 gene duplication on the pharmacokinetics and pharmacodynamics of tramadol. Journal of clinical psychopharmacology. 2008 Feb; 28(1):78-83. doi: 10.1097/jcp.0b013e318160f827. [PMID: 18204346]
  • Suvi Ojanperä, Ilpo Rasanen, Johanna Sistonen, Anna Pelander, Erkki Vuori, Ilkka Ojanperä. Quantification of drugs in plasma without primary reference standards by liquid chromatography-chemiluminescence nitrogen detection: application to tramadol metabolite ratios. Therapeutic drug monitoring. 2007 Aug; 29(4):423-8. doi: 10.1097/ftd.0b013e318074de97. [PMID: 17667796]
  • U M Stamer, F Musshoff, M Kobilay, B Madea, A Hoeft, F Stuber. Concentrations of tramadol and O-desmethyltramadol enantiomers in different CYP2D6 genotypes. Clinical pharmacology and therapeutics. 2007 Jul; 82(1):41-7. doi: 10.1038/sj.clpt.6100152. [PMID: 17361124]
  • K Allegaert, R Verbesselt, M Rayyan, A Debeer, J de Hoon. Urinary metabolites to assess in vivo ontogeny of hepatic drug metabolism in early neonatal life. Methods and findings in experimental and clinical pharmacology. 2007 May; 29(4):251-6. doi: 10.1358/mf.2007.29.4.1106408. [PMID: 17609736]
  • Emilio García Quetglas, Jose Ramón Azanza, Ernesto Cardenas, Belén Sádaba, Miguel Angel Campanero. Stereoselective pharmacokinetic analysis of tramadol and its main phase I metabolites in healthy subjects after intravenous and oral administration of racemic tramadol. Biopharmaceutics & drug disposition. 2007 Jan; 28(1):19-33. doi: 10.1002/bdd.526. [PMID: 17061296]
  • O Slanar, M Nobilis, J Kvetina, R Mikoviny, T Zima, J R Idle, F Perlík. Miotic action of tramadol is determined by CYP2D6 genotype. Physiological research. 2007; 56(1):129-136. doi: 10.33549/physiolres.930872. [PMID: 16497087]
  • Frank Musshoff, Burkhard Madea, Frank Stuber, Ulrike M Stamer. Enantiomeric determination of tramadol and O-desmethyltramadol by liquid chromatography- mass spectrometry and application to postoperative patients receiving tramadol. Journal of analytical toxicology. 2006 Sep; 30(7):463-7. doi: 10.1093/jat/30.7.463. [PMID: 16959140]
  • C Hernandez-Lopez, L Martinez-Farnos, D Karhu, T Perez-Campos, S Rovira, G Encina. Comparative bioavailability between two Tramadol once-daily oral formulations. Methods and findings in experimental and clinical pharmacology. 2006 Jul; 28(6):373-8. doi: 10.1358/mf.2006.28.6.1007674. [PMID: 16894407]
  • K Allegaert, J N Van den Anker, A Debeer, V Cossey, R Verbesselt, D Tibboel, H Devlieger, J de Hoon. Maturational changes in the in vivo activity of CYP3A4 in the first months of life. International journal of clinical pharmacology and therapeutics. 2006 Jul; 44(7):303-8. doi: 10.5414/cpp44303. [PMID: 16961158]
  • Martin Barann, Bernd Urban, Ulrike Stamer, Zita Dorner, Heinz Bönisch, Michael Brüss. Effects of tramadol and O-demethyl-tramadol on human 5-HT reuptake carriers and human 5-HT3A receptors: a possible mechanism for tramadol-induced early emesis. European journal of pharmacology. 2006 Feb; 531(1-3):54-8. doi: 10.1016/j.ejphar.2005.11.054. [PMID: 16427041]
  • Karel Allegaert, J N Van den Anker, R Verbesselt, J de Hoon, C Vanhole, D Tibboel, H Devlieger. O-demethylation of tramadol in the first months of life. European journal of clinical pharmacology. 2005 Dec; 61(11):837-42. doi: 10.1007/s00228-005-0045-3. [PMID: 16283273]
  • Yongchuan Gu, J Paul Fawcett. Improved HPLC method for the simultaneous determination of tramadol and O-desmethyltramadol in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Jul; 821(2):240-3. doi: 10.1016/j.jchromb.2005.05.003. [PMID: 15908287]
  • B KuKanich, M G Papich. Pharmacokinetics of tramadol and the metabolite O-desmethyltramadol in dogs. Journal of veterinary pharmacology and therapeutics. 2004 Aug; 27(4):239-46. doi: 10.1111/j.1365-2885.2004.00578.x. [PMID: 15305853]
  • Li-mei Zhao, Xiao-yan Chen, Jian-jun Cui, Maleku Sunita, Da-fang Zhong. [Determination of tramadol and its active metabolite O-desmethyltramadol in plasma and amniotic fluid using LC/MS/MS]. Yao xue xue bao = Acta pharmaceutica Sinica. 2004 Jun; 39(6):458-62. doi: NULL. [PMID: 15491106]
  • M Bianchi, M Broggini, P Balzarini, E Baratelli, P Ferrario, A E Panerai, P Sacerdote. Effects of tramadol on synovial fluid concentrations of substance P and interleukin-6 in patients with knee osteoarthritis: comparison with paracetamol. International immunopharmacology. 2003 Dec; 3(13-14):1901-8. doi: 10.1016/j.intimp.2003.08.011. [PMID: 14636839]
  • Hui-Chen Liu, Shu-Min Jin, Yong-Li Wang. Gender-related differences in pharmacokinetics of enantiomers of trans-tramadol and its active metabolite, trans-O-demethyltramadol, in rats. Acta pharmacologica Sinica. 2003 Dec; 24(12):1265-9. doi: NULL. [PMID: 14653955]
  • Jürgen Borlak, Robert Hermann, Katharina Erb, Thomas Thum. A rapid and simple CYP2D6 genotyping assay--case study with the analgetic tramadol. Metabolism: clinical and experimental. 2003 Nov; 52(11):1439-43. doi: 10.1016/s0026-0495(03)00256-7. [PMID: 14624403]
  • Hui-chen Liu, Yang Yu, Na Wang, Yan-ning Hou, Yong-li Wang. [Stereoselectivity in biliary excretion of trans tramadol and trans O-demethyltramadol in rats]. Yao xue xue bao = Acta pharmaceutica Sinica. 2003 Jun; 38(6):412-5. doi: NULL. [PMID: 14513798]
  • Maria J Garrido, Onintza Sayar, Cristina Segura, Javier Rapado, Maria Carmen Dios-Vieitez, Maria Jesus Renedo, Inaki F Troconiz. Pharmacokinetic/pharmacodynamic modeling of the antinociceptive effects of (+)-tramadol in the rat: role of cytochrome P450 2D activity. The Journal of pharmacology and experimental therapeutics. 2003 May; 305(2):710-8. doi: 10.1124/jpet.102.047779. [PMID: 12606644]
  • Q Tao, D J Stone, M R Borenstein, E E Codd, T P Coogan, D Desai-Krieger, S Liao, R B Raffa. Differential tramadol and O-desmethyl metabolite levels in brain vs. plasma of mice and rats administered tramadol hydrochloride orally. Journal of clinical pharmacy and therapeutics. 2002 Apr; 27(2):99-106. doi: 10.1046/j.1365-2710.2002.00384.x. [PMID: 11975693]
  • Hui-Chen Liu, Xi-Jie Zhang, Yan-Yan Yang, Na Wang, Yan-Ning Hou. Stereoselectivity in renal clearance of trans-tramadol and its active metabolite, trans-O-demethyltramadol. Acta pharmacologica Sinica. 2002 Jan; 23(1):83-6. doi: NULL. [PMID: 11860743]
  • H C Liu, N Wang, C S Liu, Y Q Hu, J F Liu, Y N Hou. Distribution of enantiomers of trans-tramadol and trans-O-demethyltramadol in central nervous system of rats. Acta pharmacologica Sinica. 2001 Oct; 22(10):871-5. doi: NULL. [PMID: 11749767]
  • H C Liu, Y Q Hu, J F Liu, N Wang, Y N Hou. [Transportation of the enantiomers of trans tramadol and O-demethyltramadol across blood-brain barrier]. Yao xue xue bao = Acta pharmaceutica Sinica. 2001 Sep; 36(9):644-7. doi: NULL. [PMID: 12580098]
  • S H Gan, R Ismail. Validation of a high-performance liquid chromatography method for tramadol and o-desmethyltramadol in human plasma using solid-phase extraction. Journal of chromatography. B, Biomedical sciences and applications. 2001 Aug; 759(2):325-35. doi: 10.1016/s0378-4347(01)00237-7. [PMID: 11499486]
  • H C Liu, T J Liu, Y Y Yang, Y N Hou. Pharmacokinetics of enantiomers of trans-tramadol and its active metabolite, trans-O-demethyltramadol, in human subjects. Acta pharmacologica Sinica. 2001 Jan; 22(1):91-6. doi: NULL. [PMID: 11730570]
  • M J Garrido, M Valle, M A Campanero, R Calvo, I F Trocóniz. Modeling of the in vivo antinociceptive interaction between an opioid agonist, (+)-O-desmethyltramadol, and a monoamine reuptake inhibitor, (-)-O-desmethyltramadol, in rats. The Journal of pharmacology and experimental therapeutics. 2000 Oct; 295(1):352-9. doi: NULL. [PMID: 10992001]
  • A Ceccato, F Vanderbist, J Y Pabst, B Streel. Enantiomeric determination of tramadol and its main metabolite O-desmethyltramadol in human plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications. 2000 Oct; 748(1):65-76. doi: 10.1016/s0378-4347(00)00318-2. [PMID: 11092587]
  • B V Murthy, K S Pandya, P D Booker, A Murray, W Lintz, R Terlinden. Pharmacokinetics of tramadol in children after i.v. or caudal epidural administration. British journal of anaesthesia. 2000 Mar; 84(3):346-9. doi: 10.1093/oxfordjournals.bja.a013437. [PMID: 10793594]
  • M Valle, J M Pavón, R Calvo, M A Campanero, I F Trocóniz. Simultaneous determination of tramadol and its major active metabolite O-demethyltramadol by high-performance liquid chromatography with electrochemical detection. Journal of chromatography. B, Biomedical sciences and applications. 1999 Mar; 724(1):83-9. doi: 10.1016/s0378-4347(98)00547-7. [PMID: 10202960]
  • B Kurth, G Blaschke. Achiral and chiral determination of tramadol and its metabolites in urine by capillary electrophoresis. Electrophoresis. 1999 Mar; 20(3):555-63. doi: 10.1002/(sici)1522-2683(19990301)20:3<555::aid-elps555>3.0.co;2-b. [PMID: 10217171]
  • B Elsing, G Blaschke. Achiral and chiral high-performance liquid chromatographic determination of tramadol and its major metabolites in urine after oral administration of racemic tramadol. Journal of chromatography. 1993 Feb; 612(2):223-30. doi: 10.1016/0378-4347(93)80167-3. [PMID: 8468380]