Metoprolol acid
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 573541

CAS#: 56392-14-4

Description: Metoprolol acid is a pharmacologically inactive urinary metoprolol metabolite.

Chemical Structure

img
Metoprolol acid
CAS# 56392-14-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 573541
Name: Metoprolol acid
CAS#: 56392-14-4
Chemical Formula: C14H21NO4
Exact Mass: 267.15
Molecular Weight: 267.325
Elemental Analysis: C, 62.90; H, 7.92; N, 5.24; O, 23.94

Price and Availability

Size Price Availability Quantity
100mg USD 550 2 weeks
250mg USD 1050 2 Weeks
Bulk inquiry

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

Appearance: Solid powder

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

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
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.

Recalculate based on batch purity %
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.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.