alpha-hydroxymetoprolol: pharmacologically active urinary metoprolol metabolite 5 to 10X less potent than metoprolol; cpd is alpha-hydroxymetoprolol; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 114962 |
| CHEMBL ID | 3544701 |
| CHEBI ID | 165230 |
| SCHEMBL ID | 21792781 |
| MeSH ID | M0094101 |
| Synonym |
|---|
| 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-alpha-(methoxymethyl)benzenemethanol |
| alpha-hydroxymetoprolol |
| h 119/66 |
| benzenemethanol, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-alpha-(methoxymethyl)- |
| h119-66 |
| 56392-16-6 |
| CHEBI:165230 |
| 1-[4-(1-hydroxy-2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol |
| FT-0669857 |
| a-hydroxy metoprolol |
| c19d0413el , |
| h 119-66 |
| unii-c19d0413el |
| benzenemethanol, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-.alpha.-(methoxymethyl)- |
| .alpha.-hydroxymetoprolol |
| 1-isopropylamino-3-(4-(1-hydroxy-2-methoxyethyl)phenoxy)-2-propanol |
| alpha-hydroxy metoprolol |
| 1-[4-(1-hydroxy-2-methoxy-ethyl)phenoxy]-3-(isopropylamino)propan-2-ol |
| CHEMBL3544701 |
| alpha-hydroxymetoprolol, analytical standard |
| 1-(4-(1-hydroxy-2-methoxyethyl)phenoxy)-3-(isopropylamino)propan-2-ol |
| 1-[4-(1-hydroxy-2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol |
| SCHEMBL21792781 |
| Q27275053 |
| alpha -hydroxy metoprolol(mixture of diastereomers) |
| 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-alpha-(methoxymethyl)-benzenemethan-ol |
| DTXSID201024019 |
| F91020 |
The area under the plasma concentration-time curve (AUC(0-->infinity), the maximum plasma concentration (C(max) and the elimination half-life (T(1/2) were compared. The pharmacokinetic parameters of metoprolol and its metabolite, alpha-hydroxymetoprolOL, and the metabolic ratio for the three groups were estimated and compared.
| Excerpt | Reference | Relevance |
|---|---|---|
| " The results suggested that breviscapine have negligible effect on pharmacokinetics of MET in rats; the information may be beneficial for the application of breviscapine in combination with MET in clinical therapy." | ( 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. Ma, YR; Qin, HY; Rao, Z; Wang, XD; Wang, YF; Wei, YH; Wu, XA; Zhang, GQ; Zhou, Y, 2015) | 0.42 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The influence of nutrients and digestive secretions on the intestinal absorption and bioavailability of the beta-adrenoceptor antagonist, metoprolol, was investigated in an isolated segment of jejunum using an intestinal perfusion technique." | ( Investigation of drug absorption from the gastrointestinal tract of man. IV. Influence of food and digestive secretions on metoprolol jejunal absorption. Bernier, JJ; Bovet, M; Duval, M; Evard, D; Godbillon, J; Hirtz, J; Schoeller, JP; Vidon, N, 1985) | 0.27 |
| "A reverse-phase High Performance Liquid Chromatographic (HPLC) method was developed for the analysis of metoprolol in the large number of human plasma samples obtained in in vitro-in vivo correlations (IVIVC) and bioavailability studies of extended release formulations of metoprolol tartrate." | ( 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. Eddington, NE; Leslie, J; Mistry, B, 1998) | 0.3 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " The amounts of metoprolol and alpha-hydroxy metoprolol excreted in 0-8 h urine collection, after dosing with 100 mg metoprolol, were measured and the metabolic ratio (% dose excreted as metoprolol/% dose excreted as alpha-hydroxy metoprolol) calculated." | ( Metoprolol alpha-hydroxylation polymorphism in the San Bushmen of southern Africa. Avenant, J; Moncrieff, J; Sommers, DK, 1989) | 0.28 |
| " Oral dosing of metoprolol produced no significant changes in reaction time." | ( The relationship between serum concentrations and central nervous system actions of metoprolol. Carey, C; Ermer, JC; Gengo, FM; Kalonaros, GC; McHugh, WB, 1985) | 0.27 |
| " As a result, after oral dosing the peak plasma concentrations during pregnancy were only 12% to 55% those after delivery, and the plasma AUCs were reduced to the same extent." | ( Pregnancy-induced increase in metoprolol metabolism. Högstedt, S; Lindberg, B; Peng, DR; Rane, A; Regårdh, CG, 1985) | 0.27 |
| " Concentrations of the pharmacologically active metabolite, H119/66, remain unaltered during chronic dosing of metoprolol." | ( The effect of age on the pharmacokinetics of metoprolol and its metabolites. Jack, DB; Kendall, MJ; Quarterman, CP, 1981) | 0.26 |
| " The dosage of metoprolol was determined on an individual basis and could be freely adjusted on clinical grounds." | ( Impact of CYP2D6 genotype on adverse effects during treatment with metoprolol: a prospective clinical study. Delabar, U; Eichelbaum, M; Fux, R; Gleiter, CH; Kivistö, KT; Lorenz, G; Mörike, K; Pröhmer, AM; Schaeffeler, E; Schwab, M, 2005) | 0.33 |
| "Our data suggest that pharmacogenetic measures could be used to design a more individualized metoprolol dosage regimen for patients." | ( The relevance of CYP2D6 genetic polymorphism on chronic metoprolol therapy in cardiovascular patients. Ismail, R; Teh, LK, 2006) | 0.33 |
| " The dosage of BETALOC® was administered to subjects following single and multiple doses and its active ingredient metoprolol and its main metabolite α-hydroxyl metoprolol were selected as the analytes." | ( Simultaneous time-course measurements of metoprolol and α-hydroxyl metoprolol in fingermarks after oral administration by liquid chromatography tandem mass spectrometry. Zhang, WJ, 2020) | 0.56 |
| Class | Description |
|---|---|
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Pathway | Proteins | Compounds |
|---|---|---|
| Metoprolol Pathway, Pharmacokinetics | 4 | 4 |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 26 (44.07) | 18.7374 |
| 1990's | 9 (15.25) | 18.2507 |
| 2000's | 12 (20.34) | 29.6817 |
| 2010's | 8 (13.56) | 24.3611 |
| 2020's | 4 (6.78) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (10.26) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 6 (10.17%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 2 (3.39%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 51 (86.44%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||