Ketobemidone (BioDeep_00000008874)

 

Secondary id: BioDeep_00000858672

human metabolite


代谢物信息卡片


{1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone}

化学式: C15H21NO2 (247.1572)
中文名称: 凯托米酮
谱图信息: 最多检出来源 Mus musculus(not specific) 4.83%

分子结构信息

SMILES: CCC(=O)C1(c2cccc(O)c2)CCN(C)CC1
InChI: InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3

描述信息

Ketobemidone (Cliradon, Ketogan, Ketodur, Cymidon, Ketorax, &c.) is a powerful opioid analgesic. Its effectiveness against pain is in the same range as morphine, and it also has some NMDA-antagonist properties imparted by its metabolite norketobemidone. This makes it useful for some types of pain that dont respond well to other opioids. The most commonly cited equalisation ratio for analgesic doses is 25 mg of ketobemidone hydrobromide to 60 mg of morphine hydrochloride or sulfate and circa 8 mg of ketobemidone by injection. Ketobemidone is 1-methyl-4-(3-hydroxyphenyl)-4-propionylpiperidine. It is usually available as the hydrochloride, which is a white powder. It is synthesized by alkylating (3-methoxyphenyl)acetonitrile with bis(2-chloroethyl)methylamine, followed by reaction with ethylmagnesiumbromide, and finally O-demethylation with hydrobromic acid.
D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
N - Nervous system > N02 - Analgesics > N02A - Opioids > N02AB - Phenylpiperidine derivatives
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
Same as: D08100

同义名列表

21 个代谢物同义名

{1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone}; 1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one; Ethyl {[4-(m-hydroxyphenyl)-1-methyl]-4-piperidyl} ketone; 1-(4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl)-1-propanone; 1-[4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone; Ethyl (4-(m-hydroxyphenyl)-1-methyl)-4-piperidyl ketone; 4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl ethyl ketone; Ketone, ethyl 4-(m-hydroxyphenyl)-1-methylpiperidyl; 4-(m-Hydroxyphenyl)-1-methyl-4-propionylpiperidine; Ketobemidone hydrochloride; a 21 Lundbeck; Cetobemidone; Ketobemidone; Cetobemidon; Cliradone; Cliradon; Ketogan; Ketodur; Cymidon; Ketorax; Ketobemidone



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ALB, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP3A4, ERC1, ITPR3
Peripheral membrane protein 2 CYP2B6, ERC1
Endoplasmic reticulum membrane 10 CYP1A2, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP3A4, CYP3A5, ITPR3, UGT2B7
Nucleus 1 ALB
cytosol 1 ALB
dendrite 1 OPRM1
centrosome 2 ALB, ERC1
nucleoplasm 1 ITPR3
Cell membrane 4 GRID1, OPRD1, OPRM1, TNF
Cell projection, axon 1 OPRM1
Multi-pass membrane protein 4 GRID1, ITPR3, OPRD1, OPRM1
Golgi apparatus membrane 1 ERC1
Synapse 2 ERC1, OPRM1
cell surface 2 C3, TNF
glutamatergic synapse 1 GRID1
Golgi apparatus 2 ALB, OPRM1
Golgi membrane 1 ERC1
neuronal cell body 2 ITPR3, TNF
presynaptic membrane 2 ERC1, OPRD1
Presynapse 1 ERC1
endosome 1 OPRM1
plasma membrane 9 C3, CYP2C19, CYP2C8, CYP2C9, GRID1, ITPR3, OPRD1, OPRM1, TNF
synaptic vesicle membrane 1 OPRD1
Membrane 8 CYP2D6, CYP3A4, CYP3A5, ERC1, ITPR3, OPRD1, OPRM1, UGT2B7
axon 1 OPRM1
brush border 1 ITPR3
extracellular exosome 3 ALB, C3, GRID1
endoplasmic reticulum 4 ALB, CYP2D6, ITPR3, OPRM1
extracellular space 5 ALB, C3, CRP, CXCL8, TNF
mitochondrion 1 CYP2D6
protein-containing complex 2 ALB, C3
intracellular membrane-bounded organelle 8 CYP1A2, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP3A4, CYP3A5
Microsome membrane 6 CYP1A2, CYP2B6, CYP2C9, CYP2D6, CYP3A4, CYP3A5
Secreted 4 ALB, C3, CRP, CXCL8
extracellular region 5 ALB, C3, CRP, CXCL8, TNF
Single-pass membrane protein 2 CYP2D6, UGT2B7
anchoring junction 2 ALB, ERC1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 ERC1
external side of plasma membrane 1 TNF
perikaryon 1 OPRM1
nucleolus 2 ITPR3, PNMA2
apical part of cell 1 ITPR3
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 GRID1
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 ERC1
GABA-ergic synapse 1 GRID1
sarcoplasmic reticulum 1 ITPR3
nuclear outer membrane 1 ITPR3
Postsynaptic cell membrane 1 GRID1
receptor complex 1 ITPR3
neuron projection 2 OPRD1, OPRM1
ciliary basal body 2 ALB, ERC1
phagocytic cup 1 TNF
cytoskeleton 1 ERC1
Cell projection, podosome 1 ERC1
podosome 1 ERC1
centriole 1 ALB
Nucleus, nucleolus 1 PNMA2
spindle pole 1 ALB
blood microparticle 2 ALB, C3
Endomembrane system 1 ERC1
Cell projection, dendrite 1 OPRM1
Presynaptic cell membrane 1 ERC1
secretory granule lumen 1 C3
secretory granule membrane 1 ITPR3
endoplasmic reticulum lumen 2 ALB, C3
platelet alpha granule lumen 1 ALB
axon terminus 1 OPRD1
azurophil granule lumen 1 C3
postsynaptic density membrane 2 GRID1, OPRD1
neuronal dense core vesicle 1 OPRD1
IkappaB kinase complex 1 ERC1
platelet dense tubular network membrane 1 ITPR3
cytoskeleton of presynaptic active zone 1 ERC1
dendrite membrane 1 OPRD1
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR3
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
transport vesicle membrane 1 ITPR3
cytoplasmic side of endoplasmic reticulum membrane 1 ITPR3
[Isoform 12]: Cytoplasm 1 OPRM1
spine apparatus 1 OPRD1
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • 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]
  • Ingela Sundström, Joris Arts, Douglas Westerlund, Per E Andrén. In vivo investigation of brain and systemic ketobemidone metabolism. The Analyst. 2010 Feb; 135(2):405-13. doi: 10.1039/b917940b. [PMID: 20098777]
  • Andrea Perniola, Anil Gupta, Kristina Crafoord, Bijan Darvish, Anders Magnuson, Kjell Axelsson. Intraabdominal local anaesthetics for postoperative pain relief following abdominal hysterectomy: a randomized, double-blind, dose-finding study. European journal of anaesthesiology. 2009 May; 26(5):421-9. doi: 10.1097/eja.0b013e3283261b53. [PMID: 19521298]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Alvaro J Santos-Neto, Jonas Bergquist, Fernando M Lanças, Per J R Sjöberg. Simultaneous analysis of five antidepressant drugs using direct injection of biofluids in a capillary restricted-access media-liquid chromatography-tandem mass spectrometry system. Journal of chromatography. A. 2008 May; 1189(1-2):514-22. doi: 10.1016/j.chroma.2008.02.107. [PMID: 18355831]
  • H B Klinke, K Linnet. Performance of four mixed-mode solid-phase extraction columns applied to basic drugs in urine. Scandinavian journal of clinical and laboratory investigation. 2007; 67(7):778-82. doi: 10.1080/00365510701449362. [PMID: 17963158]
  • Anil Gupta, Andrea Perniola, Kjell Axelsson, Sven E Thörn, Kristina Crafoord, Narinder Rawal. Postoperative pain after abdominal hysterectomy: a double-blind comparison between placebo and local anesthetic infused intraperitoneally. Anesthesia and analgesia. 2004 Oct; 99(4):1173-1179. doi: 10.1213/01.ane.0000130260.24433.a2. [PMID: 15385371]
  • Matilda Lampinen, Ulf Bondesson, Elisabeth Fredriksson, Mikael Hedeland. Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Jun; 789(2):347-54. doi: 10.1016/s1570-0232(03)00138-7. [PMID: 12742125]
  • Ayman Al-Shurbaji, Leif Tokics. The pharmacokinetics of ketobemidone in critically ill patients. British journal of clinical pharmacology. 2002 Dec; 54(6):583-6. doi: 10.1046/j.1365-2125.2002.t01-2-01689.x. [PMID: 12492604]
  • Anil Gupta, Sven E Thörn, Kjell Axelsson, Lars G Larsson, Göran Agren, Björn Holmström, Narinder Rawal. Postoperative pain relief using intermittent injections of 0.5\% ropivacaine through a catheter after laparoscopic cholecystectomy. Anesthesia and analgesia. 2002 Aug; 95(2):450-6, table of contents. doi: 10.1097/00000539-200208000-00040. [PMID: 12145070]
  • Ingela Sundström, Mikael Hedeland, Ulf Bondesson, Per E Andrén. Identification of glucuronide conjugates of ketobemidone and its phase I metabolites in human urine utilizing accurate mass and tandem time-of-flight mass spectrometry. Journal of mass spectrometry : JMS. 2002 Apr; 37(4):414-20. doi: 10.1002/jms.298. [PMID: 11948848]
  • Ayman Al-Shurbaji, Juliette Säwe. The pharmacokinetics of ketobemidone are not affected by CYP2D6 or CYP2C19 phenotype. European journal of clinical pharmacology. 2002 Feb; 57(12):877-81. doi: 10.1007/s00228-001-0413-6. [PMID: 11936707]
  • I Sundström, U Bondesson, M Hedeland. Identification of phase I and phase II metabolites of ketobemidone in patient urine using liquid chromatography-electrospray tandem mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications. 2001 Nov; 763(1-2):121-31. doi: 10.1016/s0378-4347(01)00375-9. [PMID: 11710570]
  • J O Svensson, J Säwe, A AL-Shurbaji. Determination of ketobemidone and its metabolites in plasma and urine using solid-phase extraction and liquid chromatography-mass spectrometry. Therapeutic drug monitoring. 2001 Aug; 23(4):399-405. doi: 10.1097/00007691-200108000-00013. [PMID: 11477323]
  • M Hassan, J O Svensson, C Nilsson, P Hentschke, A Al-Shurbaji, J Aschan, P Ljungman, O Ringdén. Ketobemidone may alter busulfan pharmacokinetics during high-dose therapy. Therapeutic drug monitoring. 2000 Aug; 22(4):383-5. doi: 10.1097/00007691-200008000-00003. [PMID: 10942175]
  • T Breindahl, K Andreasen. Validation of urine drug-of-abuse testing methods for ketobemidone using thin-layer chromatography and liquid chromatography-electrospray mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications. 1999 Dec; 736(1-2):103-13. doi: 10.1016/s0378-4347(99)00449-1. [PMID: 10676989]
  • E Gerdin, U Bondesson, P Hartvig. Excretion of ketobemidone in human breast milk. Journal of perinatal medicine. 1996; 24(3):293-5. doi: 10.1515/jpme.1996.24.3.293. [PMID: 8827580]
  • L B Hansen, L L Christrup, H Bundgaard. Ketobemidone prodrugs for buccal delivery. Acta pharmaceutica Nordica. 1991; 3(2):77-82. doi: NULL. [PMID: 1910550]
  • M Kjaer, H Nielsen. Analgesic effect and bioavailability of oral ketogan given as tablets or mixture to patients with chronic pain of malignant origin. Acta oncologica (Stockholm, Sweden). 1988; 27(5):583-9. doi: 10.3109/02841868809093593. [PMID: 3203014]
  • U Bondesson, P Hartvig, L Abrahamsson, N O Ahnfelt. Simultaneous determination of ketobemidone and its N-demethylated metabolite in patient plasma samples by gas chromatography mass spectrometry with selected ion monitoring. Biomedical mass spectrometry. 1983 Apr; 10(4):283-6. doi: 10.1002/bms.1200100410. [PMID: 6133568]
  • A Tamsen, U Bondesson, B Dahlström, P Hartvig. Patient-controlled analgesic therapy, Part III: pharmacokinetics and analgesic plasma concentrations of ketobemidone. Clinical pharmacokinetics. 1982 May; 7(3):252-65. doi: 10.2165/00003088-198207030-00005. [PMID: 7094500]
  • N Rawal, U H Sjöstrand, B Dahlström, P A Nydahl, J Ostelius. Epidural morphine for postoperative pain relief: a comparative study with intramuscular narcotic and intercostal nerve block. Anesthesia and analgesia. 1982 Feb; 61(2):93-8. doi: . [PMID: 6119933]
  • P Anderson, S Arnér, U Bondesson, L O Boréus, P Hartvig. Single-dose kinetics and bioavailability of ketobemidone. Acta anaesthesiologica Scandinavica. Supplementum. 1982; 74(?):59-62. doi: 10.1111/j.1399-6576.1982.tb01848.x. [PMID: 6124079]
  • U Bondesson, A Tamsen, B Dahlström, P Hartvig. Multiple dose kinetics of ketobemidone in surgical patients. Acta anaesthesiologica Scandinavica. Supplementum. 1982; 74(?):63-5. doi: 10.1111/j.1399-6576.1982.tb01849.x. [PMID: 6124080]
  • U Bondesson, P Hartvig, B Danielsson. Quantitative determination of the urinary excretion of ketobemidone and four of its metabolites after intravenous and oral administration in man. Drug metabolism and disposition: the biological fate of chemicals. 1981 Jul; 9(4):376-80. doi: . [PMID: 6114838]
  • P Anderson, S Arnér, U Bondesson, L O Boréus, P Hartvig. Clinical pharmacokinetics of ketobemidone. Its bioavailability after rectal administration. European journal of clinical pharmacology. 1981 Feb; 19(3):217-23. doi: 10.1007/bf00561953. [PMID: 7215421]
  • U Bondesson, S Arnér, P Anderson, L O Boréus, P Hartvig. Clinical pharmacokinetics and oral bioavailability of ketobemidone. European journal of clinical pharmacology. 1980 Jan; 17(1):45-50. doi: 10.1007/bf00561676. [PMID: 6102913]
  • U Bondesson, P Hartvig. Mass fragmentographic method for the determination of ketobemidone in plasma. Journal of chromatography. 1979 Nov; 179(1):207-12. doi: 10.1016/s0021-9673(00)80679-2. [PMID: 536454]