Page last updated: 2024-09-24

alpha-hydroxymetoprolol

Description

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]

Cross-References

ID SourceID
PubMed CID114962
CHEMBL ID3544701
CHEBI ID165230
SCHEMBL ID21792781
MeSH IDM0094101

Synonyms (28)

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

Drug Classes (1)

ClassDescription
aromatic etherAny 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]

Pathways (1)

alpha-hydroxymetoprolol is involved in 1 pathway(s), involving a total of 4 unique proteins and 4 unique compounds

PathwayProteinsCompounds
Metoprolol Pathway, Pharmacokinetics44

Research

Studies (59)

TimeframeStudies, This Drug (%)All Drugs %
pre-199026 (44.07)18.7374
1990's9 (15.25)18.2507
2000's12 (20.34)29.6817
2010's8 (13.56)24.3611
2020's4 (6.78)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (10.17%)5.53%
Reviews0 (0.00%)6.00%
Case Studies2 (3.39%)4.05%
Observational0 (0.00%)0.25%
Other51 (86.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
Impact of CYP2D6 genotype on adverse effects during treatment with metoprolol: a prospective clinical study.
Clinical pharmacology and therapeutics, Volume: 78, Issue: 4
2005
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (10)

ArticleYear
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, Volume: 45, Issue: 3
2015
Simultaneous determination of metoprolol and its metabolites, α-hydroxymetoprolol and O-desmethylmetoprolol, in human plasma by liquid chromatography with tandem mass spectrometry: Application to the pharmacokinetics of metoprolol associated with CYP2D6 g
Journal of separation science, Volume: 37, Issue: 11
2014
Influence of CYP2D6*10 on the pharmacokinetics of metoprolol in healthy Korean volunteers.
Journal of clinical pharmacy and therapeutics, Volume: 33, Issue: 5
2008
Influence of input rate on the stereospecific and nonstereospecific first pass metabolism and pharmacokinetics of metoprolol extended release formulations.
Chirality, May-05, Volume: 14, Issue: 4
2002
Effects and pharmacokinetics of high dose metoprolol on chest pain in patients with suspected or definite acute myocardial infarction.
European journal of clinical pharmacology, Volume: 53, Issue: 1
1997
The effect of age on the pharmacokinetics of metoprolol and its metabolites.
British journal of clinical pharmacology, Volume: 11, Issue: 3
1981
Pharmacokinetics of metoprolol and its metabolite alpha-OH-metoprolol in healthy, non-smoking, elderly individuals.
European journal of clinical pharmacology, Volume: 24, Issue: 2
1983
Pharmacokinetics of metoprolol in healthy, elderly, non-smoking individuals after a single dose and two weeks of treatment.
European journal of clinical pharmacology, Volume: 27, Issue: 2
1984
The effect of impaired renal function on the pharmacokinetics of metoprolol after single administration of a 14/190 metoprolol OROS system.
American heart journal, Volume: 120, Issue: 2
1990
Variation of pharmacokinetics after oral administration of slow-release metoprolol tablets and pharmacogenetic considerations.
Arzneimittel-Forschung, Volume: 42, Issue: 6
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (3)

ArticleYear
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, Volume: 16, Issue: 6
1998
Pregnancy-induced increase in metoprolol metabolism.
Clinical pharmacology and therapeutics, Volume: 37, Issue: 6
1985
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, Volume: 19 Suppl 2
1985
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (8)

ArticleYear
Simultaneous time-course measurements of metoprolol and α-hydroxyl metoprolol in fingermarks after oral administration by liquid chromatography tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, Nov-01, Volume: 1156
2020
The relevance of CYP2D6 genetic polymorphism on chronic metoprolol therapy in cardiovascular patients.
Journal of clinical pharmacy and therapeutics, Volume: 31, Issue: 1
2006
Impact of CYP2D6 genotype on adverse effects during treatment with metoprolol: a prospective clinical study.
Clinical pharmacology and therapeutics, Volume: 78, Issue: 4
2005
The effect of age on the pharmacokinetics of metoprolol and its metabolites.
British journal of clinical pharmacology, Volume: 11, Issue: 3
1981
Pregnancy-induced increase in metoprolol metabolism.
Clinical pharmacology and therapeutics, Volume: 37, Issue: 6
1985
The relationship between serum concentrations and central nervous system actions of metoprolol.
Journal of neurology, neurosurgery, and psychiatry, Volume: 48, Issue: 2
1985
Analysis of alpha-hydroxy metabolites of metoprolol in human urine after phosgene/trimethylsilyl derivatization.
Biomedical & environmental mass spectrometry, Volume: 14, Issue: 10
1987
Metoprolol alpha-hydroxylation polymorphism in the San Bushmen of southern Africa.
Human toxicology, Volume: 8, Issue: 1
1989
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (1)

ArticleYear
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, Volume: 29, Issue: 9
2015
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]