UNII:C19D0413EL (BioDeep_00000447748)
代谢物信息卡片
α-Hydroxymetoprolol
化学式: C15H25NO4 (283.178349)
中文名称: α-羟基美托洛尔(非对映异构体混合物)
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)NCC(COC1=CC=C(C=C1)C(COC)O)O
InChI: InChI=1S/C15H25NO4/c1-11(2)16-8-13(17)9-20-14-6-4-12(5-7-14)15(18)10-19-3/h4-7,11,13,15-18H,8-10H2,1-3H3
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:165230
- PubChem: 114962
- Metlin: METLIN1253
- ChEMBL: CHEMBL3544701
- CAS: 56392-16-6
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
- Maxime Meloche, Martin Jutras, Isabelle St-Jean, Simon de Denus, Grégoire Leclair. Isocyanate derivatization coupled with phospholipid removal microelution-solid phase extraction for the simultaneous quantification of (S)-metoprolol and (S)-α-hydroxymetoprolol in human plasma with LC-MS/MS.
Journal of pharmaceutical and biomedical analysis.
2021 Sep; 204(?):114263. doi:
10.1016/j.jpba.2021.114263. [PMID: 34274593] - Marion Leclercq, Marion Soichot, Brigitte Delhotal-Landes, Emmanuel Bourgogne, Hervé Gourlain, Bruno Mégarbane, Laurence Labat. False positive amphetamines and 3,4-methylenedioxymethamphetamine immunoassays in the presence of metoprolol-two cases reported in clinical toxicology.
Journal of analytical toxicology.
2020 Mar; 44(2):200-205. doi:
10.1093/jat/bkz051. [PMID: 31384953] - Zhi Rao, Yan-rong Ma, Hong-yan Qin, Ya-feng Wang, Yu-hui Wei, Yan Zhou, Guo-qiang Zhang, Xing-dong Wang, Xin-an Wu. Development of a LC-MS/MS method for simultaneous determination of metoprolol and its metabolites, α-hydroxymetoprolol and O-desmethylmetoprolol, in rat plasma: application to the herb-drug interaction study of metoprolol and breviscapine.
Biomedical chromatography : BMC.
2015 Sep; 29(9):1453-60. doi:
10.1002/bmc.3445. [PMID: 25753317] - Doo-Yeoun Cho, Soo Hyeon Bae, Joeng Kee Lee, Jung Bae Park, Yang-Weon Kim, Sukhyang Lee, Euichaul Oh, Bom-Taeck Kim, Soo Kyung Bae. Effect of the potent CYP2D6 inhibitor sarpogrelate on the pharmacokinetics and pharmacodynamics of metoprolol in healthy male Korean volunteers.
Xenobiotica; the fate of foreign compounds in biological systems.
2015 Mar; 45(3):256-63. doi:
10.3109/00498254.2014.967824. [PMID: 25268386] - Daniel Valente Neves, Vera Lucia Lanchote, Luiz de Souza, Miyeko Hayashida, Maria Sueli Nogueira, Natália Valadares de Moraes, Evandro José Cesarino. Metoprolol oxidation polymorphism in Brazilian elderly cardiac patients.
The Journal of pharmacy and pharmacology.
2013 Sep; 65(9):1347-53. doi:
10.1111/jphp.12109. [PMID: 23927473] - Natalícia De Jesus Antunes, Ricardo Carvalho Cavalli, Maria Paula Marques, Vera Lucia Lanchote. Stereoselective determination of metoprolol and its metabolite α-hydroxymetoprolol in plasma by LC-MS/MS: application to pharmacokinetics during pregnancy.
Chirality.
2013 Jan; 25(1):1-7. doi:
10.1002/chir.22102. [PMID: 23097090] - Hui-Wen Gu, Hai-Long Wu, Ya-Juan Liu, Xiao-Li Yin, Zhi-Yi Su, Shan-Shan Li, Ru-Qin Yu. Simultaneous determination of metoprolol and α-hydroxymetoprolol in human plasma using excitation-emission matrix fluorescence coupled with second-order calibration methods.
Bioanalysis.
2012 Dec; 4(23):2781-93. doi:
10.4155/bio.12.265. [PMID: 23216119] - Irena Baranowska, Andrzej Wilczek. Simultaneous RP-HPLC determination of sotalol, metoprolol, alpha-hydroxymetoprolol, paracetamol and its glucuronide and sulfate metabolites in human urine.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
2009 Jun; 25(6):769-72. doi:
10.2116/analsci.25.769. [PMID: 19531885] - S K Jin, H J Chung, M W Chung, J-I Kim, J-H Kang, S W Woo, S Bang, S H Lee, H J Lee, J Roh. Influence of CYP2D6*10 on the pharmacokinetics of metoprolol in healthy Korean volunteers.
Journal of clinical pharmacy and therapeutics.
2008 Oct; 33(5):567-73. doi:
10.1111/j.1365-2710.2008.00945.x. [PMID: 18834373] - Ksenia Goryachkina, Aleksandra Burbello, Svetlana Boldueva, Svetlana Babak, Ulf Bergman, Leif Bertilsson. Inhibition of metoprolol metabolism and potentiation of its effects by paroxetine in routinely treated patients with acute myocardial infarction (AMI).
European journal of clinical pharmacology.
2008 Mar; 64(3):275-82. doi:
10.1007/s00228-007-0404-3. [PMID: 18043911] - R Ismail, L K Teh. The relevance of CYP2D6 genetic polymorphism on chronic metoprolol therapy in cardiovascular patients.
Journal of clinical pharmacy and therapeutics.
2006 Feb; 31(1):99-109. doi:
10.1111/j.1365-2710.2006.00699.x. [PMID: 16476126] - Richard Fux, Klaus Mörike, Anne M T Pröhmer, Ursula Delabar, Matthias Schwab, Elke Schaeffeler, Gernot Lorenz, Christoph H Gleiter, Michel Eichelbaum, Kari T Kivistö. Impact of CYP2D6 genotype on adverse effects during treatment with metoprolol: a prospective clinical study.
Clinical pharmacology and therapeutics.
2005 Oct; 78(4):378-87. doi:
10.1016/j.clpt.2005.07.004. [PMID: 16198657] - Vanessa Bergamin Boralli, Eduardo Barbosa Coelho, Paula Macedo Cerqueira, Vera Lucia Lanchote. Stereoselective analysis of metoprolol and its metabolites in rat plasma with application to oxidative metabolism.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2005 Sep; 823(2):195-202. doi:
10.1016/j.jchromb.2005.06.038. [PMID: 16029965] - Paula Macedo Cerqueira, Evandro José Cesarino, Carlo Bertucci, Pierina Sueli Bonato, Vera Lucia Lanchote. Stereoselective metabolism of metoprolol: enantioselectivity of alpha-hydroxymetoprolol in plasma and urine.
Chirality.
2003 Jun; 15(6):542-9. doi:
10.1002/chir.10244. [PMID: 12774293] - Thomas Rau, Roland Heide, Klaus Bergmann, Henrike Wuttke, Ulrike Werner, Nico Feifel, Thomas Eschenhagen. Effect of the CYP2D6 genotype on metoprolol metabolism persists during long-term treatment.
Pharmacogenetics.
2002 Aug; 12(6):465-72. doi:
10.1097/00008571-200208000-00007. [PMID: 12172215] - Bipin Mistry, James L Leslie, Natalie D Eddington. Influence of input rate on the stereospecific and nonstereospecific first pass metabolism and pharmacokinetics of metoprolol extended release formulations.
Chirality.
2002 May; 14(4):297-304. doi:
10.1002/chir.10045. [PMID: 11968069] - B Mistry, J L Leslie, N D Eddington. Enantiomeric separation of metoprolol and alpha-hydroxymetoprolol by liquid chromatography and fluorescence detection using a chiral stationary phase.
Journal of chromatography. B, Biomedical sciences and applications.
2001 Jul; 758(2):153-61. doi:
10.1016/s0378-4347(01)00166-9. [PMID: 11486824] - L Labbé, C Sirois, S Pilote, M Arseneault, N M Robitaille, J Turgeon, B A Hamelin. Effect of gender, sex hormones, time variables and physiological urinary pH on apparent CYP2D6 activity as assessed by metabolic ratios of marker substrates.
Pharmacogenetics.
2000 Jul; 10(5):425-38. doi:
10.1097/00008571-200007000-00006. [PMID: 10898112] - B Mistry, J Leslie, N E Eddington. A sensitive assay of metoprolol and its major metabolite alpha-hydroxy metoprolol in human plasma and determination of dextromethorphan and its metabolite dextrorphan in urine with high performance liquid chromatography and fluorometric detection.
Journal of pharmaceutical and biomedical analysis.
1998 Feb; 16(6):1041-9. doi:
10.1016/s0731-7085(97)00115-5. [PMID: 9547708] - B Everts, B W Karlson, J Herlitz, N J Abdon, T Hedner. Effects and pharmacokinetics of high dose metoprolol on chest pain in patients with suspected or definite acute myocardial infarction.
European journal of clinical pharmacology.
1997; 53(1):23-31. doi:
10.1007/s002280050332. [PMID: 9349926] - H G Xie, H H Zhou. Assay of metoprolol and alpha-hydroxymetoprolol in human urine by reversed-phase liquid chromatography with direct-injection.
Zhongguo yao li xue bao = Acta pharmacologica Sinica.
1995 Jan; 16(1):32-5. doi:
NULL. [PMID: 7771192] - D R Sohn, M Kusaka, S G Shin, I J Jang, K Chiba, T Ishizaki. Utility of a one-point (3-hour postdose) plasma metabolic ratio as a phenotyping test using metoprolol in two east Asian populations.
Therapeutic drug monitoring.
1992 Jun; 14(3):184-9. doi:
10.1097/00007691-199206000-00002. [PMID: 1412602] - H Shimizu, H Noguchi, K Uno. Variation of pharmacokinetics after oral administration of slow-release metoprolol tablets and pharmacogenetic considerations.
Arzneimittel-Forschung.
1992 Jun; 42(6):802-6. doi:
NULL. [PMID: 1418033] - K Balmér, A Persson, P O Lagerström, B A Persson, G Schill. Liquid chromatographic separation of the enantiomers of metoprolol and its alpha-hydroxy metabolite on Chiralcel OD for determination in plasma and urine.
Journal of chromatography.
1991 Aug; 553(1-2):391-7. doi:
10.1016/s0021-9673(01)88509-5. [PMID: 1787165] - P Lloyd, V A John, M Signy, S E Smith. The effect of impaired renal function on the pharmacokinetics of metoprolol after single administration of a 14/190 metoprolol OROS system.
American heart journal.
1990 Aug; 120(2):478-82. doi:
10.1016/0002-8703(90)90108-a. [PMID: 2382632] - D R Rutledge, C Garrick. Determination of metoprolol and its alpha-hydroxide metabolite in serum by reversed-phase high-performance liquid chromatography.
Journal of chromatographic science.
1989 Sep; 27(9):561-5. doi:
10.1093/chromsci/27.9.561. [PMID: 2808643] - J Moncrieff, D Simpson. Determination of metoprolol and its alpha-hydroxy metabolite in urine by direct-injection reversed-phase high-performance liquid chromatography with fluorimetric detection.
Journal of chromatography.
1989 Mar; 488(2):498-502. doi:
10.1016/s0378-4347(00)82976-x. [PMID: 2745638] - D K Sommers, J Moncrieff, J Avenant. Metoprolol alpha-hydroxylation polymorphism in the San Bushmen of southern Africa.
Human toxicology.
1989 Jan; 8(1):39-43. doi:
10.1177/096032718900800107. [PMID: 2714809] - D Schuster, M W Modi, D Lalka, F M Gengo. Reversed-phase high-performance liquid chromatographic assay to quantitate diastereomeric derivatives of metoprolol enantiomers in plasma.
Journal of chromatography.
1988 Dec; 433(?):318-25. doi:
10.1016/s0378-4347(00)80615-5. [PMID: 3235562] - S Lindeberg, B Holm, P Lundborg, C G Regårdh, B Sandström. The effect of hydralazine on steady-state plasma concentrations of metoprolol in pregnant hypertensive women.
European journal of clinical pharmacology.
1988; 35(2):131-5. doi:
10.1007/bf00609241. [PMID: 3191932] - Y Horai, T Ishizaki, M Kusaka, G Tsujimoto, K Hashimoto. Simultaneous determination of metoprolol and alpha-hydroxymetoprolol in human plasma and urine by liquid chromatography with a preliminary observation on metoprolol oxidation in Japanese subjects.
Therapeutic drug monitoring.
1988; 10(4):428-33. doi:
10.1097/00007691-198804000-00009. [PMID: 3201527] - K J Hoffmann, O Gyllenhaal, J Vessman. Analysis of alpha-hydroxy metabolites of metoprolol in human urine after phosgene/trimethylsilyl derivatization.
Biomedical & environmental mass spectrometry.
1987 Oct; 14(10):543-8. doi:
10.1002/bms.1200141003. [PMID: 2962654] - M Ervik, K Kylberg-Hanssen, L Johansson. Determination of metoprolol in plasma and urine using high-resolution gas chromatography and electron-capture detection.
Journal of chromatography.
1986 Aug; 381(1):168-74. doi:
10.1016/s0378-4347(00)83577-x. [PMID: 3771715] - S Högstedt, B Lindberg, D R Peng, C G Regårdh, A Rane. Pregnancy-induced increase in metoprolol metabolism.
Clinical pharmacology and therapeutics.
1985 Jun; 37(6):688-92. doi:
10.1038/clpt.1985.114. [PMID: 4006368] - F M Gengo, J C Ermer, C Carey, G C Kalonaros, W B McHugh. The relationship between serum concentrations and central nervous system actions of metoprolol.
Journal of neurology, neurosurgery, and psychiatry.
1985 Feb; 48(2):101-6. doi:
10.1136/jnnp.48.2.101. [PMID: 3981166] - D Evard, N Vidon, J Godbillon, M Bovet, M Duval, J P Schoeller, J J Bernier, J Hirtz. Investigation of drug absorption from the gastrointestinal tract of man. IV. Influence of food and digestive secretions on metoprolol jejunal absorption.
British journal of clinical pharmacology.
1985; 19 Suppl 2(?):119S-125S. doi:
10.1111/j.1365-2125.1985.tb02752.x. [PMID: 4005113] - J B Lecaillon, P Massias, J P Schoeller, F Abadie. Influence of food on the absorption of metoprolol administered as an Oros drug delivery system to man.
British journal of clinical pharmacology.
1985; 19 Suppl 2(?):245S-249S. doi:
10.1111/j.1365-2125.1985.tb02770.x. [PMID: 4005130] - J Godbillon, D Evard, N Vidon, M Duval, J P Schoeller, J J Bernier, J Hirtz. Investigation of drug absorption from the gastrointestinal tract of man. III. Metoprolol in the colon.
British journal of clinical pharmacology.
1985; 19 Suppl 2(?):113S-118S. doi:
10.1111/j.1365-2125.1985.tb02751.x. [PMID: 4005112] - F M Gengo, J A Ulatowski, W B McHugh. Metoprolol and alpha-hydroxymetoprolol concentrations and reduction in essential tremor.
Clinical pharmacology and therapeutics.
1984 Sep; 36(3):320-5. doi:
10.1038/clpt.1984.182. [PMID: 6467791] - J Godbillon, M Duval. Determination of two metoprolol metabolites in human urine by high-performance liquid chromatography.
Journal of chromatography.
1984 Jul; 309(1):198-202. doi:
10.1016/0378-4347(84)80025-0. [PMID: 6480768] - F M Gengo, M A Ziemniak, W R Kinkel, W B McHugh. High-performance liquid chromatographic determination of metoprolol and alpha-hydroxymetoprolol concentrations in human serum, urine, and cerebrospinal fluid.
Journal of pharmaceutical sciences.
1984 Jul; 73(7):961-3. doi:
10.1002/jps.2600730725. [PMID: 6470961] - J B Lecaillon, J Godbillon, F Abadie, G Gosset. Determination of metoprolol and its alpha-hydroxylated metabolite in human plasma by high-performance liquid chromatography.
Journal of chromatography.
1984 Feb; 305(2):411-7. doi:
10.1016/s0378-4347(00)83355-1. [PMID: 6707168] - M Larsson, S Landahl, P Lundborg, C G Regårdh. Pharmacokinetics of metoprolol in healthy, elderly, non-smoking individuals after a single dose and two weeks of treatment.
European journal of clinical pharmacology.
1984; 27(2):217-22. doi:
10.1007/bf00544048. [PMID: 6499900] - D B Jack, M Wilkins, C P Quarterman. Lack of evidence for polymorphism in metoprolol metabolism.
British journal of clinical pharmacology.
1983 Aug; 16(2):188-90. doi:
10.1111/j.1365-2125.1983.tb04984.x. [PMID: 6615692] - M S Lennard, J H Silas. Rapid determination of metoprolol and alpha-hydroxymetoprolol in human plasma and urine by high-performance liquid chromatography.
Journal of chromatography.
1983 Jan; 272(1):205-9. doi:
10.1016/s0378-4347(00)86120-4. [PMID: 6841542] - C G Regårdh, S Landahl, M Larsson, P Lundborg, B Steen, K J Hoffmann, P O Lagerström. Pharmacokinetics of metoprolol and its metabolite alpha-OH-metoprolol in healthy, non-smoking, elderly individuals.
European journal of clinical pharmacology.
1983; 24(2):221-6. doi:
10.1007/bf00613821. [PMID: 6840171] - D B Pautler, W J Jusko. Determination of metoprolol and alpha-hydroxymetoprolol in plasma by high-performance liquid chromatography.
Journal of chromatography.
1982 Mar; 228(?):215-22. doi:
10.1016/s0378-4347(00)80434-x. [PMID: 7076745] - C P Quarterman, M J Kendall, D B Jack. The effect of age on the pharmacokinetics of metoprolol and its metabolites.
British journal of clinical pharmacology.
1981 Mar; 11(3):287-94. doi:
10.1111/j.1365-2125.1981.tb00536.x. [PMID: 7213530] - . .
.
. doi:
. [PMID: 24648255]