Hydrocodone (BioDeep_00000002446)

 

Secondary id: BioDeep_00000397858

human metabolite blood metabolite Chemicals and Drugs natural product Volatile Flavor Compounds


代谢物信息卡片


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

化学式: C18H21NO3 (299.1521356)
中文名称: 氢可酮
谱图信息: 最多检出来源 Homo sapiens(blood) 27.37%

分子结构信息

SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(=O)CC4
InChI: InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3

描述信息

Hydrocodone is only found in individuals that have used or taken this drug. It is a narcotic analgesic related to codeine, but more potent and more addicting by weight. It is used also as cough suppressant. [PubChem]Hydrocodone acts as a weak agonist at OP1, OP2, and OP3 opiate receptors within the central nervous system (CNS). Hydrocodone primarily affects OP3 receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, 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 such as hydrocodone also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
R - Respiratory system > R05 - Cough and cold preparations > R05D - Cough suppressants, excl. combinations with expectorants > R05DA - Opium alkaloids and derivatives
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist
C78273 - Agent Affecting Respiratory System > C66917 - Antitussive Agent
D019141 - Respiratory System Agents > D000996 - Antitussive Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics

同义名列表

29 个代谢物同义名

(1S,5R,13R,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one; 4,5-alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one; 4,5-a-Epoxy-3-methoxy-17-methylmorphinan-6-one; 4,5-Α-epoxy-3-methoxy-17-methylmorphinan-6-one; Nourypharma brand OF hydrocodone tartrate; Hydrocodone tartrate (1:1), hydrate (2:5); Du pont brand OF hydrocodone tartrate; Robins brand OF hydrocodone tartrate; Wyeth brand OF hydrocodone tartrate; Knoll brand OF hydrocodone tartrate; Hydrocodeinonebitartrate; hydrocodone bitartrate; (-)-Dihydrocodeinone; Dihydrocodeinone; Hydrocodonum; Hydrocodone; Hidrocodona; Idrocodone; Hydrocodon; Multacodin; Hydroconum; Hydrocone; Hydrocon; Robidone; Codinovo; Dicodid; Hycodan; Hycon; Hydrocodone



数据库引用编号

20 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)

10 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

  • Loralie J Langman, Jeremy Gaskins, Erik Korte, Cynthia Maluf, Whitney L Wooderchak-Donahue, Gwendolyn A McMillin, Paul J Jannetto, Brandi Hartley, Arthur Malkani, Madhusudhan Yakkanti, Saeed A Jortani. Endogenous and iatrogenic sources of variability in response to opioid therapy in Post-Surgical and injured orthopedic patients. Clinica chimica acta; international journal of clinical chemistry. 2021 Nov; 522(?):105-113. doi: 10.1016/j.cca.2021.08.004. [PMID: 34384754]
  • Christian Gentzsch, Kerstin Seier, Antonios Drakopoulos, Marie-Lise Jobin, Yann Lanoiselée, Zsombor Koszegi, Damien Maurel, Rémy Sounier, Harald Hübner, Peter Gmeiner, Sébastien Granier, Davide Calebiro, Michael Decker. Selective and Wash-Resistant Fluorescent Dihydrocodeinone Derivatives Allow Single-Molecule Imaging of μ-Opioid Receptor Dimerization. Angewandte Chemie (International ed. in English). 2020 04; 59(15):5958-5964. doi: 10.1002/anie.201912683. [PMID: 31808251]
  • Brooke L Deatherage Kaiser, Jon M Jacobs, Athena A Schepmoes, Heather M Brewer, Bobbie-Jo M Webb-Robertson, Sandra Valtier, Vikhyat S Bebarta, Joshua N Adkins. Assessment of the Utility of the Oral Fluid and Plasma Proteomes for Hydrocodone Exposure. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2020 01; 16(1):49-60. doi: 10.1007/s13181-019-00731-0. [PMID: 31677050]
  • 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]
  • Keivan Hosseinnejad, Tyler Yin, Jeremy T Gaskins, M Elaine Stauble, Yanhong Wu, Paul Jannetto, Loralie L Langman, Saeed A Jortani. Lack of Influence by CYP3A4 and CYP3A5 Genotypes on Pain Relief by Hydrocodone in Postoperative Cesarean Section Pain Management. The journal of applied laboratory medicine. 2019 05; 3(6):954-964. doi: 10.1373/jalm.2018.026070. [PMID: 31639687]
  • Mehran Dastmalchi, Xue Chen, Jillian M Hagel, Limei Chang, Rongji Chen, Sukanya Ramasamy, Sam Yeaman, Peter J Facchini. Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy. Nature chemical biology. 2019 04; 15(4):384-390. doi: 10.1038/s41589-019-0247-0. [PMID: 30886433]
  • Mark A Cervinski, Paul J Jannetto. A Question of Opioid Diversion or Compliance. Clinical chemistry. 2019 02; 65(2):236-240. doi: 10.1373/clinchem.2018.294140. [PMID: 30692135]
  • Matthew Feldhammer, Alec Saitman, Ly Nguyen, Bryan Milstid. Dilution of Urine Followed by Adulteration in an Attempt to Deceive the Laboratory. Journal of analytical toxicology. 2019 Jan; 43(1):e7-e9. doi: 10.1093/jat/bky059. [PMID: 30192938]
  • Robert West, Charles Mikel, Doriane Hofilena, Maria Guevara. Positivity rates of drugs in patients treated for opioid dependence with buprenorphine: A comparison of oral fluid and urine using paired collections and LC-MS/MS. Drug and alcohol dependence. 2018 12; 193(?):183-191. doi: 10.1016/j.drugalcdep.2018.07.023. [PMID: 30391868]
  • Travis C Mickle, Sven M Guenther, Andrew C Barrett, Kathryn Ann Roupe, Jing Zhou, Daniel Dickerson, Lynn R Webster. Pharmacokinetics and Abuse Potential of Benzhydrocodone, a Novel Prodrug of Hydrocodone, After Intranasal Administration in Recreational Drug Users. Pain medicine (Malden, Mass.). 2018 12; 19(12):2438-2449. doi: 10.1093/pm/pnx247. [PMID: 29092079]
  • Jean Michel Cardot, John C Lukas, Paula Muniz. Time Scaling for In Vitro-In Vivo Correlation: the Inverse Release Function (IRF) Approach. The AAPS journal. 2018 08; 20(6):95. doi: 10.1208/s12248-018-0250-5. [PMID: 30159772]
  • Mary Bond, Kerri A Schoedel, Laura Rabinovich-Guilatt, Maciej Gasior, William Tracewell, Richard Malamut, Yuju Ma, Lynn R Webster. Evaluation of the Relative Intranasal Abuse Potential of a Hydrocodone Extended-Release Tablet Formulated with Abuse-Deterrence Technology in Nondependent, Recreational Opioid Users. Pain medicine (Malden, Mass.). 2018 08; 19(8):1597-1612. doi: 10.1093/pm/pnx133. [PMID: 29016880]
  • Luigi Cardia, Gioacchino Calapai, Domenico Quattrone, Cristina Mondello, Vincenzo Arcoraci, Fabrizio Calapai, Carmen Mannucci, Epifanio Mondello. Preclinical and Clinical Pharmacology of Hydrocodone for Chronic Pain: A Mini Review. Frontiers in pharmacology. 2018; 9(?):1122. doi: 10.3389/fphar.2018.01122. [PMID: 30327606]
  • Mary Bond, Laura Rabinovich-Guilatt, Sally Selim, Mona Darwish, William Tracewell, Philmore Robertson, Ronghua Yang, Richard Malamut, Philippe Colucci, Murray P Ducharme, Ofer Spiegelstein. Effect of Food on the Pharmacokinetics of Single- and Multiple-Dose Hydrocodone Extended Release in Healthy Subjects. Clinical drug investigation. 2017 Dec; 37(12):1153-1163. doi: 10.1007/s40261-017-0575-3. [PMID: 28948482]
  • Chang Liu, Germán Augusto Gómez-Ríos, Bradley B Schneider, J C Yves Le Blanc, Nathaly Reyes-Garcés, Don W Arnold, Thomas R Covey, Janusz Pawliszyn. Fast quantitation of opioid isomers in human plasma by differential mobility spectrometry/mass spectrometry via SPME/open-port probe sampling interface. Analytica chimica acta. 2017 Oct; 991(?):89-94. doi: 10.1016/j.aca.2017.08.023. [PMID: 29031302]
  • Shuhua Deng, Wencan Huang, Xiaojia Ni, Ming Zhang, Haoyang Lu, Zhanzhang Wang, Jinqing Hu, Xiuqing Zhu, Chang Qiu, Dewei Shang, Yuefeng Zhang, Linghui Xiong, Yuguan Wen. Pharmacokinetics of guaifenesin, pseudoephedrine and hydrocodone in a combination oral liquid formulation, administered as single and multiple doses in healthy Chinese volunteers, and comparison with data for individual compounds formulated as Antuss®. Xenobiotica; the fate of foreign compounds in biological systems. 2017 Oct; 47(10):870-878. doi: 10.1080/00498254.2016.1241451. [PMID: 27662264]
  • Shannon Haymond, Geeta Nagpal, Heather Heiman. Urine Drug Screens to Monitor Opioid Use for Managing Chronic Pain. JAMA. 2017 Sep; 318(11):1061-1062. doi: 10.1001/jama.2017.10593. [PMID: 28975284]
  • Robert E West, Maria G Guevara, Charles Mikel, Ruben Gamez. Detection of Hydrocodone and Morphine as Metabolites in Oral Fluid by LC-MS/MS in Patients Prescribed Codeine. Therapeutic drug monitoring. 2017 02; 39(1):88-90. doi: 10.1097/ftd.0000000000000365. [PMID: 28081042]
  • Mona Darwish, Mary Bond, Yuju Ma, William Tracewell, Philmore Robertson, Lynn R Webster. Abuse Potential with Oral Route of Administration of a Hydrocodone Extended-Release Tablet Formulated with Abuse-Deterrence Technology in Nondependent, Recreational Opioid Users. Pain medicine (Malden, Mass.). 2017 01; 18(1):61-77. doi: 10.1093/pm/pnw122. [PMID: 27330154]
  • Mark E Sutter, Roy R Gerona, M Thais Davis, Bailey M Roche, Daniel K Colby, James A Chenoweth, Axel J Adams, Kelly P Owen, Jonathan B Ford, Hugh B Black, Timothy E Albertson. Fatal Fentanyl: One Pill Can Kill. Academic emergency medicine : official journal of the Society for Academic Emergency Medicine. 2017 01; 24(1):106-113. doi: 10.1111/acem.13034. [PMID: 27322591]
  • Robert B Dixon, Amitava Dasgupta. Suitability of the DRI Hydrocodone/Hydromorphone Immunoassay in the Clinical Environment at a Lower Cutoff: Validation With LC-MS/MS Analysis. Therapeutic drug monitoring. 2016 12; 38(6):787-790. doi: 10.1097/ftd.0000000000000339. [PMID: 27764026]
  • Sohita Dhillon. Hydrocodone Bitartrate ER (Hysingla® ER): A Review in Chronic Pain. Clinical drug investigation. 2016 Nov; 36(11):969-980. doi: 10.1007/s40261-016-0466-z. [PMID: 27718163]
  • Pongkwan Sitasuwan, Cathleen Melendez, Margarita Marinova, Kaylee R Mastrianni, Alicia Darragh, Emily Ryan, L Andrew Lee. Degradation of Opioids and Opiates During Acid Hydrolysis Leads to Reduced Recovery Compared to Enzymatic Hydrolysis. Journal of analytical toxicology. 2016 Oct; 40(8):601-607. doi: 10.1093/jat/bkw085. [PMID: 27702939]
  • Renata Nascimento, Alphonse Poklis, Carl E Wolf. Evaluation of a Newly Formulated Enzyme Immunoassay for the Detection of Hydrocodone and Hydromorphone in Pain Management Compliance Testing. Journal of analytical toxicology. 2016 Oct; 40(8):583-587. doi: 10.1093/jat/bkw080. [PMID: 27562969]
  • Oneka T Cummings, Ayodele A Morris, Jeffrey R Enders, Gregory L McIntire. Normalizing Oral Fluid Hydrocodone Data Using Calculated Blood Volume. Journal of analytical toxicology. 2016 Sep; 40(7):486-91. doi: 10.1093/jat/bkw057. [PMID: 27405365]
  • Waseem Gul, Brandon Stamper, Murrell Godfrey, Shahbaz W Gul, Mahmoud A ElSohly. LC-MS-MS Method for Analysis of Opiates in Wastewater During Football Games II. Journal of analytical toxicology. 2016 Jun; 40(5):330-7. doi: 10.1093/jat/bkw022. [PMID: 27052850]
  • Mona Darwish, Ronghua Yang, William Tracewell, Philmore Robertson, Mary Bond. Effects of Renal Impairment and Hepatic Impairment on the Pharmacokinetics of Hydrocodone After Administration of a Hydrocodone Extended-Release Tablet Formulated With Abuse-Deterrence Technology. Clinical pharmacology in drug development. 2016 Mar; 5(2):141-9. doi: 10.1002/cpdd.238. [PMID: 27138027]
  • Akira Nakagawa, Eitaro Matsumura, Takashi Koyanagi, Takane Katayama, Noriaki Kawano, Kayo Yoshimatsu, Kenji Yamamoto, Hidehiko Kumagai, Fumihiko Sato, Hiromichi Minami. Total biosynthesis of opiates by stepwise fermentation using engineered Escherichia coli. Nature communications. 2016 Feb; 7(?):10390. doi: 10.1038/ncomms10390. [PMID: 26847395]
  • Ram P Kapil, Alessandra Cipriano, Warren Wen, Shau Yu Lynch, Ellie He, Salvatore V Colucci, Stephen C Harris. Pharmacokinetic Profile and Sustained 24-hour Analgesia of a Once-daily Hydrocodone Bitartrate Extended-release Tablet with Abuse-deterrent Properties. Clinical therapeutics. 2016 Feb; 38(2):302-14. doi: 10.1016/j.clinthera.2015.12.003. [PMID: 26749219]
  • Oscar A Linares, Jeffrey Fudin, Annemarie L Daly, Raymond C Boston. Individualized Hydrocodone Therapy Based on Phenotype, Pharmacogenetics, and Pharmacokinetic Dosing. The Clinical journal of pain. 2015 Dec; 31(12):1026-35. doi: 10.1097/ajp.0000000000000214. [PMID: 25621429]
  • Krishna Devarakonda, Kenneth Kostenbader, Michael J Giuliani, Jim L Young. Single-dose pharmacokinetics of 2 or 3 tablets of biphasic immediate-release/extended-release hydrocodone bitartrate/acetaminophen (MNK-155) under fed and fasted conditions: two randomized open-label trials. BMC pharmacology & toxicology. 2015 Nov; 16(?):31. doi: 10.1186/s40360-015-0032-y. [PMID: 26614499]
  • Mona Darwish, Mary Bond, Ronghua Yang, William Tracewell, Philmore Robertson. Assessment of Alcohol-Induced Dose Dumping with a Hydrocodone Bitartrate Extended-Release Tablet Formulated with CIMA(®) Abuse Deterrence Technology. Clinical drug investigation. 2015 Oct; 35(10):645-52. doi: 10.1007/s40261-015-0324-4. [PMID: 26369654]
  • 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]
  • Cynthia Y Robinson, Christopher M Rubino, Stephen J Farr. A pharmacokinetic evaluation of single and multiple doses of extended-release hydrocodone bitartrate in subjects experiencing surgical or osteoarthritic pain. Journal of opioid management. 2015 Sep; 11(5):405-15. doi: 10.5055/jom.2015.0290. [PMID: 26535968]
  • K I Stoddard, D B Huggett. Wastewater Effluent Hydrocodone Concentrations as an Indicator of Drug Disposal Program Success. Bulletin of environmental contamination and toxicology. 2015 Aug; 95(2):139-44. doi: 10.1007/s00128-015-1574-9. [PMID: 26067702]
  • Michael E Mullins, Karl Hock, Mitchell G Scott. Does therapeutic use of tapentadol cause false-positive urine screens for methadone or opiates?. Clinical toxicology (Philadelphia, Pa.). 2015 Jun; 53(5):493-4. doi: 10.3109/15563650.2015.1020114. [PMID: 25951899]
  • Mona Darwish, Ronghua Yang, William Tracewell, Philmore Robertson, Mary Bond. Dose proportionality of a hydrocodone extended-release tablet formulated with abuse-deterrence technology. Clinical drug investigation. 2015 May; 35(5):291-7. doi: 10.1007/s40261-015-0280-z. [PMID: 25813216]
  • Mona Darwish, Ronghua Yang, William Tracewell, Philmore Robertson, Mary Bond. Single- and multiple-dose pharmacokinetics of a hydrocodone bitartrate extended-release tablet formulated with abuse-deterrence technology in healthy, naltrexone-blocked volunteers. Clinical therapeutics. 2015 Feb; 37(2):390-401. doi: 10.1016/j.clinthera.2014.11.014. [PMID: 25542074]
  • Mona Darwish, Mary Bond, William Tracewell, Philmore Robertson, Ronghua Yang. Pharmacokinetics of hydrocodone extended-release tablets formulated with different levels of coating to achieve abuse deterrence compared with a hydrocodone immediate-release/acetaminophen tablet in healthy subjects. Clinical drug investigation. 2015 Jan; 35(1):13-22. doi: 10.1007/s40261-014-0244-8. [PMID: 25391549]
  • Roger L Bertholf, Laura M Johannsen, Gary M Reisfield. Sensitivity of an opiate immunoassay for detecting hydrocodone and hydromorphone in urine from a clinical population: analysis of subthreshold results. Journal of analytical toxicology. 2015 Jan; 39(1):24-8. doi: 10.1093/jat/bku109. [PMID: 25288720]
  • Stephen J Farr, Cynthia Y Robinson, Christopher M Rubino. Effects of food and alcohol on the pharmacokinetics of an oral, extended-release formulation of hydrocodone in healthy volunteers. Clinical pharmacology : advances and applications. 2015; 7(?):1-9. doi: 10.2147/cpaa.s70831. [PMID: 25653563]
  • Peter L Platteborze, Donald J Kippenberger, Thomas M Martin. Unauthorized drug use in the US Army based on medical review officer evaluations. Journal of analytical toxicology. 2014 Nov; 38(9):653-9. doi: 10.1093/jat/bku079. [PMID: 25002456]
  • Kate Thodey, Stephanie Galanie, Christina D Smolke. A microbial biomanufacturing platform for natural and semisynthetic opioids. Nature chemical biology. 2014 Oct; 10(10):837-44. doi: 10.1038/nchembio.1613. [PMID: 25151135]
  • Neveen H Barakat, Rabia S Atayee, Brookie M Best, Joseph D Ma. Urinary hydrocodone and metabolite distributions in pain patients. Journal of analytical toxicology. 2014 Sep; 38(7):404-9. doi: 10.1093/jat/bku051. [PMID: 24836897]
  • Jennifer M Cao, Joseph D Ma, Candis M Morello, Rabia S Atayee, Brookie M Best. Observations on hydrocodone and its metabolites in oral fluid specimens of the pain population: comparison with urine. Journal of opioid management. 2014 May; 10(3):177-86. doi: 10.5055/jom.2014.0206. [PMID: 24944068]
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  • David A Yee, Rabia S Atayee, Brookie M Best, Joseph D Ma. Observations on the urine metabolic profile of codeine in pain patients. Journal of analytical toxicology. 2014 Mar; 38(2):86-91. doi: 10.1093/jat/bkt101. [PMID: 24396053]
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  • M Elaine Stauble, Andrew W Moore, Loralie J Langman, Mark V Boswell, Richard Baumgartner, Suzanne McGee, Jonathan Metry, Saeed A Jortani. Hydrocodone in postoperative personalized pain management: pro-drug or drug?. Clinica chimica acta; international journal of clinical chemistry. 2014 Feb; 429(?):26-9. doi: 10.1016/j.cca.2013.11.015. [PMID: 24269714]
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