Oxymorphone (BioDeep_00000001508)
Secondary id: BioDeep_00000405972
human metabolite Endogenous blood metabolite Volatile Flavor Compounds
代谢物信息卡片
(1S,5R,13R,17S)-10,17-dihydroxy-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: C17H19NO4 (301.1314014)
中文名称: 氢羟吗啡酮
谱图信息:
最多检出来源 Homo sapiens(blood) 0.44%
分子结构信息
SMILES: CN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O
InChI: InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1
描述信息
An opioid analgesic with actions and uses similar to those of morphine, apart from an absence of cough suppressant activity. It is used in the treatment of moderate to severe pain, including pain in obstetrics. It may also be used as an adjunct to anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1092)
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
N - Nervous system > N02 - Analgesics > N02A - Opioids > N02AA - Natural opium alkaloids
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
17 个代谢物同义名
(1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one; Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-methyl-, (5.alpha.)-; Bristol-myers squibb brand OF oxymorphone hydrochloride; endo Brand OF oxymorphone hydrochloride; endo Brand OF oxymorphine HCL; 14-Hydroxydihydromorphinone; Oxymorphone hydrochloride; Dihydrohydroxymorphinone; Dihydroxymorphinone; Oxymorphone HCL; Oximorphonum; Oxymorphine; oxymorphone; Numorphan; EN3202; Opana; Oxymorphone
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:7865
- KEGG: C08019
- KEGGdrug: D08323
- PubChem: 5284604
- PubChem: 4639
- HMDB: HMDB0015323
- Metlin: METLIN43294
- DrugBank: DB01192
- ChEMBL: CHEMBL963
- Wikipedia: Oxymorphone
- MeSH: Oxymorphone
- chemspider: 4447650
- CAS: 76-41-5
- PMhub: MS000000673
- PubChem: 10219
- NIKKAJI: J4.174B
- RefMet: Oxymorphone
- KNApSAcK: 7865
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
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Basic & clinical pharmacology & toxicology.
2019 Nov; 125(5):430-438. doi:
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Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
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Drug and alcohol dependence.
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Nephrology (Carlton, Vic.).
2018 Oct; 23(10):921-926. doi:
10.1111/nep.13153. [PMID: 28802086] - T Sobolevsky, Y Kucherova, B Ahrens. Identification of oxymorphone as decomposition product of the permitted drug methylnaltrexone.
Drug testing and analysis.
2018 May; 10(5):892-895. doi:
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2018 Apr; 152(?):204-214. doi:
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Journal of analytical toxicology.
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Journal of analytical toxicology.
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Journal of analytical toxicology.
2016 Sep; 40(7):543-5. doi:
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2014 Nov; 38(9):653-9. doi:
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2014 Sep; 38(7):462. doi:
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2014 Sep; 38(7):463. doi:
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American journal of hematology.
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American journal of kidney diseases : the official journal of the National Kidney Foundation.
2014 Jun; 63(6):1022-6. doi:
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Pain medicine (Malden, Mass.).
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Veterinary anaesthesia and analgesia.
2013 Sep; 40(5):537-45. doi:
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Journal of clinical pharmacology.
2011 Nov; 51(11):1529-38. doi:
10.1177/0091270010388033. [PMID: 21209234] - Gobi Paramanandam, Eric Prommer, Dawn C Schwenke. Adverse effects in hospice patients with chronic kidney disease receiving hydromorphone.
Journal of palliative medicine.
2011 Sep; 14(9):1029-33. doi:
10.1089/jpm.2011.0103. [PMID: 21823925] - 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] - Amadeo Pesce, Cameron West, Robert West, Bridgit Crews, Charles Mikel, Murray Rosenthal, Perla Almazon, Sergey Latyshev. Determination of medication cutoff values in a pain patient population.
Journal of opioid management.
2011 Mar; 7(2):117-22. doi:
10.5055/jom.2011.0054. [PMID: 21561035] - Irma H Benedek, Janet Jobes, Qinfang Xiang, William D Fiske. Bioequivalence of oxymorphone extended release and crush-resistant oxymorphone extended release.
Drug design, development and therapy.
2011; 5(?):455-63. doi:
10.2147/dddt.s24372. [PMID: 22162639] - Timo Korjamo, Ari Tolonen, Veli-Pekka Ranta, Miia Turpeinen, Hannu Kokki. Metabolism of oxycodone in human hepatocytes from different age groups and prediction of hepatic plasma clearance.
Frontiers in pharmacology.
2011; 2(?):87. doi:
10.3389/fphar.2011.00087. [PMID: 22291644] - 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] - Matthew J Geraci, James Peele, Stacey L McCoy, Brad Elias. Phencyclidine false positive induced by lamotrigine (Lamictal®) on a rapid urine toxicology screen.
International journal of emergency medicine.
2010 Nov; 3(4):327-31. doi:
10.1007/s12245-010-0235-3. [PMID: 21373301] - Shawn P Vorce, Barry Levine, Pamela C McDonough, Marilyn R Past. An overdose death involving the insufflation of extended-release oxymorphone tablets.
Journal of analytical toxicology.
2010 Oct; 34(8):521-6. doi:
10.1093/jat/34.8.521. [PMID: 21819798] - P V Robandt, H M Bui, J M Scancella, K L Klette. Automated solid-phase extraction-liquid chromatography-tandem mass spectrometry analysis of 6-acetylmorphine in human urine specimens: application for a high-throughput urine analysis laboratory.
Journal of analytical toxicology.
2010 Oct; 34(8):470-5. doi:
10.1093/jat/34.8.470. [PMID: 21819792] - Tuija H Nieminen, Nora M Hagelberg, Teijo I Saari, Mikko Neuvonen, Pertti J Neuvonen, Kari Laine, Klaus T Olkkola. Oxycodone concentrations are greatly increased by the concomitant use of ritonavir or lopinavir/ritonavir.
European journal of clinical pharmacology.
2010 Oct; 66(10):977-85. doi:
10.1007/s00228-010-0879-1. [PMID: 20697700] - Tuija H Nieminen, Nora M Hagelberg, Teijo I Saari, Mikko Neuvonen, Pertti J Neuvonen, Kari Laine, Klaus T Olkkola. Grapefruit juice enhances the exposure to oral oxycodone.
Basic & clinical pharmacology & toxicology.
2010 Oct; 107(4):782-8. doi:
10.1111/j.1742-7843.2010.00582.x. [PMID: 20406214] - Juha Grönlund, Teijo I Saari, Nora M Hagelberg, Pertti J Neuvonen, Klaus T Olkkola, Kari Laine. Exposure to oral oxycodone is increased by concomitant inhibition of CYP2D6 and 3A4 pathways, but not by inhibition of CYP2D6 alone.
British journal of clinical pharmacology.
2010 Jul; 70(1):78-87. doi:
10.1111/j.1365-2125.2010.03653.x. [PMID: 20642550] - C F Samer, Y Daali, M Wagner, G Hopfgartner, C B Eap, M C Rebsamen, M F Rossier, D Hochstrasser, P Dayer, J A Desmeules. The effects of CYP2D6 and CYP3A activities on the pharmacokinetics of immediate release oxycodone.
British journal of pharmacology.
2010 Jun; 160(4):907-18. doi:
10.1111/j.1476-5381.2010.00673.x. [PMID: 20590587] - 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] - Pedro Boscan, Bruno H Pypendop, Kristine T Siao, Thierry Francey, Kristy Dowers, Larry Cowgill, Jan E Ilkiw. Fluid balance, glomerular filtration rate, and urine output in dogs anesthetized for an orthopedic surgical procedure.
American journal of veterinary research.
2010 May; 71(5):501-7. doi:
10.2460/ajvr.71.5.501. [PMID: 20433374] - 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] - Marie Gingras, Marie-Hélène Laberge, Michel Lefebvre. Evaluation of the usefulness of an oxycodone immunoassay in combination with a traditional opiate immunoassay for the screening of opiates in urine.
Journal of analytical toxicology.
2010 Mar; 34(2):78-83. doi:
10.1093/jat/34.2.78. [PMID: 20223099] - 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] - Tim Dahn, Josh Gunn, Scott Kriger, Andrea R Terrell. Quantitation of morphine, codeine, hydrocodone, hydromorphone, oxycodone, oxymorphone, and 6-monoacetylmorphine (6-MAM) in urine, blood, serum, or plasma using liquid chromatography with tandem mass spectrometry detection.
Methods in molecular biology (Clifton, N.J.).
2010; 603(?):411-22. doi:
10.1007/978-1-60761-459-3_40. [PMID: 20077093] - Rebecca Heltsley, Anne Zichterman, David L Black, Beverly Cawthon, Tim Robert, Frank Moser, Yale H Caplan, Edward J Cone. Urine drug testing of chronic pain patients. II. Prevalence patterns of prescription opiates and metabolites.
Journal of analytical toxicology.
2010 Jan; 34(1):32-8. doi:
10.1093/jat/34.1.32. [PMID: 20109300] - 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] - Iain M McIntyre, James L Sherrard, Craig L Nelson. Case report: Oxymorphone-involved fatalities: a report of two cases.
Journal of analytical toxicology.
2009 Nov; 33(9):615-9. doi:
10.1093/jat/33.9.615. [PMID: 20040137] - Markus Fridén, Susanne Winiwarter, Gunilla Jerndal, Ola Bengtsson, Hong Wan, Ulf Bredberg, Margareta Hammarlund-Udenaes, Madeleine Antonsson. Structure-brain exposure relationships in rat and human using a novel data set of unbound drug concentrations in brain interstitial and cerebrospinal fluids.
Journal of medicinal chemistry.
2009 Oct; 52(20):6233-43. doi:
10.1021/jm901036q. [PMID: 19764786] - 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] - Lisa Krugner-Higby, Butch KuKanich, Brynn Schmidt, Timothy D Heath, Carolyn Brown, Lesley J Smith. Pharmacokinetics and behavioral effects of an extended-release, liposome-encapsulated preparation of oxymorphone in rhesus macaques.
The Journal of pharmacology and experimental therapeutics.
2009 Jul; 330(1):135-41. doi:
10.1124/jpet.108.150052. [PMID: 19351868] - Tuija H Nieminen, Nora M Hagelberg, Teijo I Saari, Antti Pertovaara, Mikko Neuvonen, Kari Laine, Pertti J Neuvonen, Klaus T Olkkola. Rifampin greatly reduces the plasma concentrations of intravenous and oral oxycodone.
Anesthesiology.
2009 Jun; 110(6):1371-8. doi:
10.1097/aln.0b013e31819faa54. [PMID: 19417618] - Stine T Zwisler, Thomas P Enggaard, Lene Noehr-Jensen, Rasmus S Pedersen, Soeren Mikkelsen, Flemming Nielsen, Kim Brosen, Soeren H Sindrup. The hypoalgesic effect of oxycodone in human experimental pain models in relation to the CYP2D6 oxidation polymorphism.
Basic & clinical pharmacology & toxicology.
2009 Apr; 104(4):335-44. doi:
10.1111/j.1742-7843.2009.00378.x. [PMID: 19281600] - Diana Garside, Robert L Hargrove, Ruth E Winecker. Concentration of oxymorphone in postmortem fluids and tissue.
Journal of analytical toxicology.
2009 Apr; 33(3):121-8. doi:
10.1093/jat/33.3.121. [PMID: 19371460] - Nora M Hagelberg, Tuija H Nieminen, Teijo I Saari, Mikko Neuvonen, Pertti J Neuvonen, Kari Laine, Klaus T Olkkola. Voriconazole drastically increases exposure to oral oxycodone.
European journal of clinical pharmacology.
2009 Mar; 65(3):263-71. doi:
10.1007/s00228-008-0568-5. [PMID: 18836708] - Christelle Boileau, Johanne Martel-Pelletier, Judith Caron, Philippe Msika, Georges B Guillou, Caroline Baudouin, Jean-Pierre Pelletier. Protective effects of total fraction of avocado/soybean unsaponifiables on the structural changes in experimental dog osteoarthritis: inhibition of nitric oxide synthase and matrix metalloproteinase-13.
Arthritis research & therapy.
2009; 11(2):R41. doi:
10.1186/ar2649. [PMID: 19291317] - Paul Sloan. Review of oral oxymorphone in the management of pain.
Therapeutics and clinical risk management.
2008 Aug; 4(4):777-87. doi:
10.2147/tcrm.s1784. [PMID: 19209260] - 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] - Veronica Santos, Karin Jannet Vera López, Luciana Moraes Santos, Mauricio Yonamine, Maria José Carvalho Carmona, Silvia Regina Cavani Jorge Santos. Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.
Clinics (Sao Paulo, Brazil).
2008 Jun; 63(3):307-14. doi:
10.1590/s1807-59322008000300004. [PMID: 18568238] - Pamela C McDonough, Barry Levine, Shawn Vorce, Rebecca A Jufer, David Fowler. The detection of hydromorphone in urine specimens with high morphine concentrations.
Journal of forensic sciences.
2008 May; 53(3):752-4. doi:
10.1111/j.1556-4029.2008.00730.x. [PMID: 18471228] - Edward J Cone, Yale H Caplan, Frank Moser, Tim Robert, David Black. Evidence that morphine is metabolized to hydromorphone but not to oxymorphone.
Journal of analytical toxicology.
2008 May; 32(4):319-23. doi:
10.1093/jat/32.4.319. [PMID: 18430301] - 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] - Steven C Curry, David J Watts, Kenneth D Katz, Dale Bikin, Bonny L Bukaveckas. The effect of single-dose tramadol on oxycodone clearance.
The Journal of emergency medicine.
2007 Nov; 33(4):407-11. doi:
10.1016/j.jemermed.2007.03.042. [PMID: 17976797]