Synonym
Atenolol acid, H117-04, H 117/04, Metoprolol acid, SL 77-010
IUPAC/Chemical Name
Benzeneacetic acid, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-
InChi Key
PUQIRTNPJRFRCZ-UHFFFAOYSA-N
InChi Code
1S/C14H21NO4/c1-10(2)15-8-12(16)9-19-13-5-3-11(4-6-13)7-14(17)18/h3-6,10,12,15-16H,7-9H2,1-2H3,(H,17,18)
SMILES Code
c1(ccc(CC(O)=O)cc1)OC[C@@H](CNC(C)C)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Metoprolol acid is a pharmacologically inactive urinary metoprolol metabolite.
In vitro activity:
Using LC-MS/MS, this study investigated the effects of six commonly used beta-blockers on brain sterol biosynthesis in vitro using cell lines. Two beta-blockers, metoprolol (MTP) and nebivolol, showed extreme elevations of the highly oxidizable cholesterol precursor 7-dehydrocholesterol (7-DHC) in vitro across multiple cell lines.
Reference: Biomolecules. 2022 Aug 31;12(9):1211. https://pubmed.ncbi.nlm.nih.gov/36139049/
In vivo activity:
The aim of the present study was to evaluate the effect of metoprolol on development of atherosclerosis in ApoE(-/-) mice and investigate its effect on the release of proinflammatory cytokines. Male ApoE(-/-) mice were treated with metoprolol (2.5 mg/kg/h) or saline for 11 weeks via osmotic minipumps. Metoprolol significantly reduced atherosclerotic plaque area in thoracic aorta (P < 0.05 versus Control).This study found that a moderate dose of metoprolol significantly reduced atherosclerotic plaque area in thoracic aorta of ApoE(-/-) mice.
Reference: Biomed Res Int. 2014;2014:548783. https://pubmed.ncbi.nlm.nih.gov/25105129/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
267.33
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Allen LB, Mirnics K. Metoprolol Inhibits Developmental Brain Sterol Biosynthesis in Mice. Biomolecules. 2022 Aug 31;12(9):1211. doi: 10.3390/biom12091211. PMID: 36139049; PMCID: PMC9496459.
2. Četojević-Simin DD, Armaković SJ, Šojić DV, Abramović BF. Toxicity assessment of metoprolol and its photodegradation mixtures obtained by using different type of TiO2 catalysts in the mammalian cell lines. Sci Total Environ. 2013 Oct 1;463-464:968-74. doi: 10.1016/j.scitotenv.2013.06.083. Epub 2013 Jul 17. PMID: 23872187.
3. Ulleryd MA, Bernberg E, Yang LJ, Bergström GM, Johansson ME. Metoprolol reduces proinflammatory cytokines and atherosclerosis in ApoE-/- mice. Biomed Res Int. 2014;2014:548783. doi: 10.1155/2014/548783. Epub 2014 Jul 8. PMID: 25105129; PMCID: PMC4109227.
4. Wang D, Chen Y, Jiang J, Zhou A, Pan L, Chen Q, Qian Y, Chu M, Chen C. Carvedilol has stronger anti-inflammation and anti-virus effects than metoprolol in murine model with coxsackievirus B3-induced viral myocarditis. Gene. 2014 Sep 1;547(2):195-201. doi: 10.1016/j.gene.2014.06.003. Epub 2014 Jun 4. PMID: 24905653.
In vitro protocol:
1. Allen LB, Mirnics K. Metoprolol Inhibits Developmental Brain Sterol Biosynthesis in Mice. Biomolecules. 2022 Aug 31;12(9):1211. doi: 10.3390/biom12091211. PMID: 36139049; PMCID: PMC9496459.
2. Četojević-Simin DD, Armaković SJ, Šojić DV, Abramović BF. Toxicity assessment of metoprolol and its photodegradation mixtures obtained by using different type of TiO2 catalysts in the mammalian cell lines. Sci Total Environ. 2013 Oct 1;463-464:968-74. doi: 10.1016/j.scitotenv.2013.06.083. Epub 2013 Jul 17. PMID: 23872187.
In vivo protocol:
1. Ulleryd MA, Bernberg E, Yang LJ, Bergström GM, Johansson ME. Metoprolol reduces proinflammatory cytokines and atherosclerosis in ApoE-/- mice. Biomed Res Int. 2014;2014:548783. doi: 10.1155/2014/548783. Epub 2014 Jul 8. PMID: 25105129; PMCID: PMC4109227.
2. Wang D, Chen Y, Jiang J, Zhou A, Pan L, Chen Q, Qian Y, Chu M, Chen C. Carvedilol has stronger anti-inflammation and anti-virus effects than metoprolol in murine model with coxsackievirus B3-induced viral myocarditis. Gene. 2014 Sep 1;547(2):195-201. doi: 10.1016/j.gene.2014.06.003. Epub 2014 Jun 4. PMID: 24905653.
1: Borkar RM, Bhandi MM, Dubey AP, Ganga Reddy V, Komirishetty P, Nandekar PP, Sangamwar AT, Kamal A, Banerjee SK, Srinivas R. An evaluation of the CYP2D6 and CYP3A4 inhibition potential of metoprolol metabolites and their contribution to drug-drug and drug-herb interaction by LC-ESI/MS/MS. Biomed Chromatogr. 2016 Oct;30(10):1556-72. doi: 10.1002/bmc.3721. Epub 2016 Apr 19. PubMed PMID: 27006091.
2: Ryu RJ, Eyal S, Easterling TR, Caritis SN, Venkataraman R, Hankins G, Rytting E, Thummel K, Kelly EJ, Risler L, Phillips B, Honaker MT, Shen DD, Hebert MF. Pharmacokinetics of metoprolol during pregnancy and lactation. J Clin Pharmacol. 2016 May;56(5):581-9. doi: 10.1002/jcph.631. Epub 2015 Dec 4. PubMed PMID: 26461463; PubMed Central PMCID: PMC5564514.
3: Quarterman CP, Kendall MJ, Jack DB. The effect of age on the pharmacokinetics of metoprolol and its metabolites. Br J Clin Pharmacol. 1981 Mar;11(3):287-94. PubMed PMID: 7213530; PubMed Central PMCID: PMC1401609.
