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MedKoo Cat#: 599234 | Name: Metoprolol
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Description:

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

Metoprolol is a β1 selective aryloxypropanolamine andrenergic antagonist. Used in the treatment of a variety of cardiovascular disorder.

Chemical Structure

Metoprolol
Metoprolol
CAS#51384-51-1 (free base)

Theoretical Analysis

MedKoo Cat#: 599234

Name: Metoprolol

CAS#: 51384-51-1 (free base)

Chemical Formula: C15H25NO3

Exact Mass: 267.1834

Molecular Weight: 267.37

Elemental Analysis: C, 67.38; H, 9.43; N, 5.24; O, 17.95

Price and Availability

Size Price Availability Quantity
1g USD 250.00
2g USD 450.00
5g USD 650.00
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Related CAS #
51384-51-1 (free base) 56392-17-7 (tartrate) 56392-18-8 (HCl) 80274-67-5 (fumarate) 98418-47-4 (succinate)
Synonym
Metoprolol; Loresor; Preblok; Metohexal; Selo-Zok;
IUPAC/Chemical Name
1-(isopropylamino)-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol
InChi Key
IUBSYMUCCVWXPE-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3
SMILES Code
OC(COC1=CC=C(CCOC)C=C1)CNC(C)C
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
Certificate of Analysis
View CoA: current batch, Lot#O20W05C05
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Metoprolol is an orally active, selective β1-adrenoceptor antagonist.
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/
Solvent mg/mL mM comments
Solubility
DMSO 76.5 286.12
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 267.37 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.
1: Karlson BW, Dellborg M, Gullestad L, Aberg J, Sugg J, Herlitz J. A pharmacokinetic and pharmacodynamic comparison of immediate-release metoprolol and extended-release metoprolol CR/XL in patients with suspected acute myocardial infarction: a randomized, open-label study. Cardiology. 2014;127(2):73-82. doi: 10.1159/000355003. Epub 2013 Nov 14. PubMed PMID: 24247812. 2: Mateos A, García-Lunar I, García-Ruiz JM, Pizarro G, Fernández-Jiménez R, Huertas P, García-Álvarez A, Fernández-Friera L, Bravo J, Flores-Arias J, Barreiro MV, Chayán-Zas L, Corral E, Fuster V, Sánchez-Brunete V, Ibáñez B; METOCARD-CNIC Investigators. Efficacy and safety of out-of-hospital intravenous metoprolol administration in anterior ST-segment elevation acute myocardial infarction: insights from the METOCARD-CNIC trial. Ann Emerg Med. 2015 Mar;65(3):318-24. doi: 10.1016/j.annemergmed.2014.07.010. Epub 2014 Aug 14. PubMed PMID: 25129820. 3: Antunes Nde J, Cavalli RC, Marques MP, Moisés EC, Lanchote VL. Influence of gestational diabetes on the stereoselective pharmacokinetics and placental distribution of metoprolol and its metabolites in parturients. Br J Clin Pharmacol. 2015 Apr;79(4):605-16. doi: 10.1111/bcp.12523. PubMed PMID: 25291152; PubMed Central PMCID: PMC4386945. 4: Cho DY, Bae SH, Lee JK, Park JB, Kim YW, Lee S, Oh E, Kim BT, Bae SK. Effect of the potent CYP2D6 inhibitor sarpogrelate on the pharmacokinetics and pharmacodynamics of metoprolol in healthy male Korean volunteers. Xenobiotica. 2015 Mar;45(3):256-63. doi: 10.3109/00498254.2014.967824. Epub 2014 Sep 30. PubMed PMID: 25268386. 5: Patel RS, Sharma KH, Kamath NA, Patel NH, Thakkar AM. Cost-effectiveness analysis of nebivolol and metoprolol in essential hypertension: a pharmacoeconomic comparison of antihypertensive efficacy of beta blockers. Indian J Pharmacol. 2014 Sep-Oct;46(5):485-9. doi: 10.4103/0253-7613.140577. PubMed PMID: 25298575; PubMed Central PMCID: PMC4175882. 6: Inoue S, Shimizu M, Arita K, Akimoto K. The effect of AST-120 on the single-dose pharmacokinetics of metoprolol extended-release tablets in healthy subjects. Drug Metabol Drug Interact. 2014;29(2):115-21. doi: 10.1515/dmdi-2013-0063. PubMed PMID: 24643911. 7: Hamadeh IS, Langaee TY, Dwivedi R, Garcia S, Burkley BM, Skaar TC, Chapman AB, Gums JG, Turner ST, Gong Y, Cooper-DeHoff RM, Johnson JA. Impact of CYP2D6 polymorphisms on clinical efficacy and tolerability of metoprolol tartrate. Clin Pharmacol Ther. 2014 Aug;96(2):175-81. doi: 10.1038/clpt.2014.62. Epub 2014 Mar 17. PubMed PMID: 24637943; PubMed Central PMCID: PMC4111800. 8: Molden E, Spigset O. [Interactions between metoprolol and antidepressants]. Tidsskr Nor Laegeforen. 2011 Sep 20;131(18):1777-9. doi: 10.4045/tidsskr.11.0143. Review. Norwegian. PubMed PMID: 21946596. 9: Batty JA, Hall AS, White HL, Wikstrand J, de Boer RA, van Veldhuisen DJ, van der Harst P, Waagstein F, Hjalmarson Å, Kjekshus J, Balmforth AJ; MERIT-HF Study Group. An investigation of CYP2D6 genotype and response to metoprolol CR/XL during dose titration in patients with heart failure: a MERIT-HF substudy. Clin Pharmacol Ther. 2014 Mar;95(3):321-30. doi: 10.1038/clpt.2013.193. Epub 2013 Sep 30. PubMed PMID: 24193112. 10: Zur M, Cohen N, Agbaria R, Dahan A. The biopharmaceutics of successful controlled release drug product: Segmental-dependent permeability of glipizide vs. metoprolol throughout the intestinal tract. Int J Pharm. 2015 Jul 15;489(1-2):304-10. doi: 10.1016/j.ijpharm.2015.05.002. Epub 2015 May 6. PubMed PMID: 25957705. 11: Neves DV, Lanchote VL, de Souza L, Hayashida M, Nogueira MS, de Moraes NV, Cesarino EJ. Metoprolol oxidation polymorphism in Brazilian elderly cardiac patients. J Pharm Pharmacol. 2013 Sep;65(9):1347-53. doi: 10.1111/jphp.12109. Epub 2013 Jul 21. PubMed PMID: 23927473. 12: 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. 13: Zhou Y, Xu M, Zhang Y, Guo Y, Zhang Y, He B. Effects of long-term application of metoprolol and propranolol in a rat model of smoking. Clin Exp Pharmacol Physiol. 2014 Sep;41(9):708-15. doi: 10.1111/1440-1681.12261. PubMed PMID: 24837395. 14: Kumar K, Dhawan N, Sharma H, Patwal PS, Vaidya S, Vaidya B. Bilayer mucoadhesive microparticles for the delivery of metoprolol succinate: Formulation and evaluation. Artif Cells Nanomed Biotechnol. 2015;43(5):328-33. doi: 10.3109/21691401.2014.887017. Epub 2014 Mar 3. PubMed PMID: 24579883. 15: Krauwinkel W, Dickinson J, Schaddelee M, Meijer J, Tretter R, van de Wetering J, Strabach G, van Gelderen M. The effect of mirabegron, a potent and selective β3-adrenoceptor agonist, on the pharmacokinetics of CYP2D6 substrates desipramine and metoprolol. Eur J Drug Metab Pharmacokinet. 2014 Mar;39(1):43-52. doi: 10.1007/s13318-013-0133-1. Epub 2013 Jun 1. PubMed PMID: 23728524. 16: Lee U, Lee I, Lee BK, Kang HE. Faster non-renal clearance of metoprolol in streptozotocin-induced diabetes mellitus rats. Eur J Pharm Sci. 2013 Nov 20;50(3-4):447-53. doi: 10.1016/j.ejps.2013.08.022. Epub 2013 Aug 25. PubMed PMID: 23985694. 17: Antunes Nde J, Cavalli RC, Marques MP, Lanchote VL. 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. Epub 2012 Oct 24. PubMed PMID: 23097090. 18: Bae SH, Lee JK, Cho DY, Bae SK. 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 genotypes. J Sep Sci. 2014 Jun;37(11):1256-64. doi: 10.1002/jssc.201301353. Epub 2014 Apr 19. PubMed PMID: 24648255. 19: Rao Z, Ma YR, Qin HY, Wang YF, Wei YH, Zhou Y, Zhang GQ, Wang XD, Wu XA. 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. Biomed Chromatogr. 2015 Sep;29(9):1453-60. doi: 10.1002/bmc.3445. Epub 2015 Mar 4. PubMed PMID: 25753317. 20: Shah R, Parmar S, Patel H, Pandey S, Shah D. Formulation development of metoprolol succinate and hydrochlorothiazide compression coated tablets. Curr Drug Deliv. 2013 Dec;10(6):631-44. PubMed PMID: 23017092.