5-hydroxypropafenone (BioDeep_00000054408)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


1-{5-hydroxy-2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one

化学式: C21H27NO4 (357.19399820000007)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 66.67%

分子结构信息

SMILES: CCCNCC(COC1=C(C=C(C=C1)O)C(=O)CCC2=CC=CC=C2)O
InChI: InChI=1S/C21H27NO4/c1-2-12-22-14-18(24)15-26-21-11-9-17(23)13-19(21)20(25)10-8-16-6-4-3-5-7-16/h3-7,9,11,13,18,22-24H,2,8,10,12,14-15H2,1H3

描述信息

5-hydroxypropafenone is a metabolite of propafenone. Propafenone is a class of anti-arrhythmic medication, which treats illnesses associated with rapid heart beats such as atrial and ventricular arrhythmias. (Wikipedia)
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D018674 - Adrenergic Antagonists
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents

同义名列表

2 个代谢物同义名

1-{5-hydroxy-2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one; 5-hydroxypropafenone



数据库引用编号

5 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

  • Kosuke Doki, Yuki Shirayama, Yukio Sekiguchi, Kazutaka Aonuma, Yukinao Kohda, Masaki Ieda, Masato Homma. Effect of CYP2D6 genetic polymorphism on peak propafenone concentration: no significant effect of CYP2D6*10. Pharmacogenomics. 2020 12; 21(18):1279-1288. doi: 10.2217/pgs-2020-0105. [PMID: 33203295]
  • Harilal Patel, Ashok Ghoghari, Chandrakant Bhatt, Shaival Shah, Anilkumar Jha, Nirmal Desai, Nuggehally R Srinivas. A sensitive quantitative assay for the determination of propafenone and two metabolites, 5-hydroxypropafenone and N-depropylpropafenone, in human K2EDTA plasma using LC-MS/MS with ESI operated in positive mode. Biomedical chromatography : BMC. 2017 Oct; 31(10):. doi: 10.1002/bmc.3967. [PMID: 28261841]
  • Zhiyan Chi, Ruijuan Liu, Y Li, Keli Wang, Chang Shu, L Ding. A Sensitive and Rapid LC-MS-MS Method for Simultaneous Determination of Propafenone and Its Active Metabolite 5-Hydroxypropafenone in Human Plasma and Its Application in a Pharmacokinetic Study. Journal of chromatographic science. 2017 Oct; 55(9):911-917. doi: 10.1093/chromsci/bmx049. [PMID: 28985274]
  • Mohammad-Reza Rouini, Minoo Afshar. Effect of CYP2D6 polymorphisms on the pharmacokinetics of propafenone and its two main metabolites. Therapie. 2017 Jun; 72(3):373-382. doi: 10.1016/j.therap.2016.10.005. [PMID: 28087064]
  • Hanna Ovaska, Andrew Ludman, Edgar P Spencer, David M Wood, Alison L Jones, Paul I Dargan. Propafenone poisoning--a case report with plasma propafenone concentrations. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2010 Mar; 6(1):37-40. doi: 10.1007/s13181-010-0037-2. [PMID: 20373066]
  • Minoo Afshar, Wolfgang Thormann. Validated capillary electrophoresis assay for the simultaneous enantioselective determination of propafenone and its major metabolites in biological samples. Electrophoresis. 2006 Apr; 27(8):1517-25. doi: 10.1002/elps.200500663. [PMID: 16532516]
  • Iouri Bachmakov, Sabine Rekersbrink, Ute Hofmann, Michel Eichelbaum, Martin F Fromm. Characterisation of (R/S)-propafenone and its metabolites as substrates and inhibitors of P-glycoprotein. Naunyn-Schmiedeberg's archives of pharmacology. 2005 Mar; 371(3):195-201. doi: 10.1007/s00210-005-1025-y. [PMID: 15900513]
  • M S Chow, C M White, C P Lau, C Fan, M O Tang. Evaluation of CYP2D6 oxidation of dextromethorphan and propafenone in a Chinese population with atrial fibrillation. Journal of clinical pharmacology. 2001 Jan; 41(1):92-6. doi: 10.1177/00912700122009737. [PMID: 11144999]
  • X Chen, D Zhong, H Blume. Stereoselective pharmacokinetics of propafenone and its major metabolites in healthy Chinese volunteers. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2000 Mar; 10(1):11-6. doi: 10.1016/s0928-0987(99)00083-4. [PMID: 10699379]
  • L R Pires de Abreu, V L Lanchote, C Bertucci, E J Cesarino, P S Bonato. Simultaneous determination of propafenone and 5-hydroxypropafenone enantiomers in plasma by chromatography on an amylose derived chiral stationary phase. Journal of pharmaceutical and biomedical analysis. 1999 Jun; 20(1-2):209-16. doi: 10.1016/s0731-7085(99)00022-9. [PMID: 10704025]
  • P Kubalec, E Brandsteterová. Determination of propafenone and its main metabolite 5-hydroxypropafenone in human serum with direct injection into a column-switching chromatographic system. Journal of chromatography. B, Biomedical sciences and applications. 1999 Apr; 726(1-2):211-8. doi: 10.1016/s0378-4347(99)00056-0. [PMID: 10348188]
  • X Chen, D Zhong, H Jiang, J Gu. [Characterization of some glucuronide conjugates by electrospray ion trap mass spectrometry]. Yao xue xue bao = Acta pharmaceutica Sinica. 1998 Nov; 33(11):849-54. doi: . [PMID: 12016947]
  • S Ito, R Gow, Z Verjee, E Giesbrecht, H Dodo, R Freedom, G R Tonn, J E Axelson, E Zalzstein, H C Rosenberg, G Koren. Intravenous and oral propafenone for treatment of tachycardia in infants and children: pharmacokinetics and clinical response. Journal of clinical pharmacology. 1998 Jun; 38(6):496-501. doi: 10.1002/j.1552-4604.1998.tb05786.x. [PMID: 9650538]
  • K Fonck, C Haenebalcke, A Hemeryck, F Belpaire, L Jordaens, P Calle, W Buylaert. ECG changes and plasma concentrations of propafenone and its metabolites in a case of severe poisoning. Journal of toxicology. Clinical toxicology. 1998; 36(3):247-51. doi: 10.3109/15563659809028948. [PMID: 9656983]
  • C Woodland, Z Verjee, E Giesbrecht, G Koren, S Ito. The digoxin-propafenone interaction: characterization of a mechanism using renal tubular cell monolayers. The Journal of pharmacology and experimental therapeutics. 1997 Oct; 283(1):39-45. doi: NULL. [PMID: 9336306]
  • M Boucher, C Chassaing, J D Hamel, J M Poirier. Cardiac electrophysiological effects of propafenone and its 5-hydroxylated metabolite in the conscious dog. European journal of pharmacology. 1996 Nov; 315(2):171-7. doi: 10.1016/s0014-2999(96)00624-3. [PMID: 8960881]
  • R Böhm, R Ellrich, R Koytchev. Quantitation of R- and S-propafenone and of the main metabolite in plasma. Die Pharmazie. 1995 Aug; 50(8):542-5. doi: NULL. [PMID: 7568317]
  • R Kern. Internally standardized simultaneous assay of propafenone and 5-hydroxypropafenone enantiomers in human plasma by means of high performance liquid chromatography. Methods and findings in experimental and clinical pharmacology. 1994 Apr; 16(3):203-10. doi: NULL. [PMID: 7913980]
  • H Y Aboul-Enein, S A Bakr. Direct enantiomeric high performance liquid chromatographic separation of propafenone and its major metabolite in serum on a cellulose tris-3,5-dimethylphenyl carbamate chiral stationary phase. Biomedical chromatography : BMC. 1993 Jan; 7(1):38-40. doi: 10.1002/bmc.1130070110. [PMID: 8094305]
  • G R Tonn, C R Kerr, J E Axelson. In vitro protein binding of propafenone and 5-hydroxypropafenone in serum, in solutions of isolated serum proteins, and to red blood cells. Journal of pharmaceutical sciences. 1992 Nov; 81(11):1098-103. doi: 10.1002/jps.2600811112. [PMID: 1447713]
  • P K Kunicki, D Paczkowski, D Sitkiewicz. High-performance liquid chromatographic method for the simultaneous determination of propafenone and 5-hydroxypropafenone in human serum. Polish journal of pharmacology and pharmacy. 1992 Mar; 44(2):161-71. doi: NULL. [PMID: 1409116]
  • R Latini, M Belloni, R Bernasconi, E Cappiello, P Giani, M Landolina, D Leopaldi, J M Castel. Identification of propafenone metaboliser phenotype from plasma and urine excretion data. European journal of clinical pharmacology. 1992; 42(1):111-4. doi: 10.1007/bf00314930. [PMID: 1541308]
  • W L Zhang, Y N Tang. [Simultaneous determination of propafenone and its active metabolite in serum by high performance liquid chromatography]. Yao xue xue bao = Acta pharmaceutica Sinica. 1992; 27(7):552-5. doi: NULL. [PMID: 1442090]
  • M Libardoni, D Piovan, E Busato, R Padrini. Transfer of propafenone and 5-OH-propafenone to foetal plasma and maternal milk. British journal of clinical pharmacology. 1991 Oct; 32(4):527-8. doi: 10.1111/j.1365-2125.1991.tb03945.x. [PMID: 1958453]
  • M S Leloux, R A Maes. Identification and determination of propafenone and its principal metabolites in human urine using capillary gas chromatography/mass spectrometry. Biological mass spectrometry. 1991 Jun; 20(6):382-8. doi: 10.1002/bms.1200200609. [PMID: 1888783]
  • G Steurer, H Weber, H Schmidinger, H Plass, B Frey, H Pürerfellner, P Probst. Plasma propafenone concentration in the evaluation of anti-arrhythmic efficacy. European heart journal. 1991 Apr; 12(4):526-32. doi: 10.1093/oxfordjournals.eurheartj.a059934. [PMID: 2065687]
  • A Capucci, G Boriani, B Marchesini, E Strocchi, L Tomasi, M Balducelli, L Frabetti, E Ambrosioni, B Magnani. Minimal effective concentration values of propafenone and 5-hydroxy-propafenone in acute and chronic therapy. Cardiovascular drugs and therapy. 1990 Feb; 4(1):281-7. doi: 10.1007/bf01857646. [PMID: 2285622]
  • S Vozeh, W Haefeli, H R Ha, J Vlcek, F Follath. Nonlinear kinetics of propafenone metabolites in healthy man. European journal of clinical pharmacology. 1990; 38(5):509-13. doi: 10.1007/bf02336693. [PMID: 2379537]
  • R G Zoble, E B Kirsten, J Brewington. Pharmacokinetic and pharmacodynamic evaluation of propafenone in patients with ventricular arrhythmia. Propafenone Research Group. Clinical pharmacology and therapeutics. 1989 May; 45(5):535-41. doi: 10.1038/clpt.1989.69. [PMID: 2721109]
  • C Funck-Brentano, H K Kroemer, H Pavlou, R L Woosley, D M Roden. Genetically-determined interaction between propafenone and low dose quinidine: role of active metabolites in modulating net drug effect. British journal of clinical pharmacology. 1989 Apr; 27(4):435-44. doi: 10.1111/j.1365-2125.1989.tb05391.x. [PMID: 2719900]
  • G Malfatto, A Zaza, M Forster, B Sodowick, P Danilo, M R Rosen. Electrophysiologic, inotropic and antiarrhythmic effects of propafenone, 5-hydroxypropafenone and N-depropylpropafenone. The Journal of pharmacology and experimental therapeutics. 1988 Aug; 246(2):419-26. doi: NULL. [PMID: 3404440]
  • E Brode, U Kripp, W Breckwoldt. HPLC determination of 5-hydroxypropafenone in plasma with electrochemical detection. Methods and findings in experimental and clinical pharmacology. 1988 May; 10(5):319-29. doi: NULL. [PMID: 3398648]
  • K A Thompson, D H Iansmith, L A Siddoway, R L Woosley, D M Roden. Potent electrophysiologic effects of the major metabolites of propafenone in canine Purkinje fibers. The Journal of pharmacology and experimental therapeutics. 1988 Mar; 244(3):950-5. doi: NULL. [PMID: 3252042]
  • P Giani, M Landolina, V Giudici, C Bianchini, G Ferrario, S Marchi, E Riva, R Latini. Pharmacokinetics and pharmacodynamics of propafenone during acute and chronic administration. European journal of clinical pharmacology. 1988; 34(2):187-94. doi: 10.1007/bf00614557. [PMID: 3383990]
  • L A Siddoway, K A Thompson, C B McAllister, T Wang, G R Wilkinson, D M Roden, R L Woosley. Polymorphism of propafenone metabolism and disposition in man: clinical and pharmacokinetic consequences. Circulation. 1987 Apr; 75(4):785-91. doi: 10.1161/01.cir.75.4.785. [PMID: 3829342]
  • R E Kates, Y G Yee, R A Winkle. Metabolite cumulation during chronic propafenone dosing in arrhythmia. Clinical pharmacology and therapeutics. 1985 Jun; 37(6):610-4. doi: 10.1038/clpt.1985.97. [PMID: 4006362]
  • E Brode, U Kripp, M Hollmann. Simultaneous determination of propafenone and 5-hydroxypropafenone in plasma by means of high pressure liquid chromatography. Arzneimittel-Forschung. 1984; 34(11):1455-60. doi: NULL. [PMID: 6151841]