Bisoprolol | CAS# 66722-44-9 | cardioselective beta-1 adrenergic blocker

MedKoo Cat#: 413010 | Name: Bisoprolol

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Description:

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

Bisoprolol is a cardioselective beta-1 adrenergic blocker. It is effective in the management of HYPERTENSION and ANGINA PECTORIS.

Chemical Structure

Bisoprolol

CAS#66722-44-9 (free base)

Theoretical Analysis

MedKoo Cat#: 413010

Name: Bisoprolol

CAS#: 66722-44-9 (free base)

Chemical Formula: C18H31NO4

Exact Mass: 325.2253

Molecular Weight: 325.45

Elemental Analysis: C, 66.43; H, 9.60; N, 4.30; O, 19.66

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 600.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Related CAS #

66722-44-9 (free base) 104344-23-2 (hemifumarate)

Synonym

Bisoprolol; CL297,939; CL-297,939; CL 297,939

IUPAC/Chemical Name

2-Propanol, 1-(4-((2-(1-methylethoxy)ethoxy)methyl)phenoxy)-3-((1-methylethyl)amino)-, (+-)-

InChi Key

VHYCDWMUTMEGQY-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H31NO4/c1-14(2)19-11-17(20)13-23-18-7-5-16(6-8-18)12-21-9-10-22-15(3)4/h5-8,14-15,17,19-20H,9-13H2,1-4H3

SMILES Code

OC(CNC(C)C)COC1=CC=C(COCCOC(C)C)C=C1

Appearance

Solid powder

Purity

>95% (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

>2 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:

Bisoprolol is a potent, selective and orally active β1-adrenergic receptor blocker.

In vitro activity:

As GH₃ cells were exposed to BIS (bisoprolol), amplitude of IK(M) was suppressed with an IC50 value of 1.21 μM. In cell-attached current, BIS decreased the open probability of M-type K⁺ (KM) channels, along with decreased mean opening time of the channel. BIS decreased IK(erg) amplitude with an IC50 value of 6.42 μM. Under current-clamp conditions, BIS depolarization increased the firing of spontaneous action potentials in GH₃ cells; addition of flupirtine, but not ractopamine, reversed BIS-induced firing rateIn hippocampal mHippoE-14 neurons, BIS inhibited IK(M) to a greater extent compared to its depressant effect on IK(erg). Reference: Int J Mol Sci. 2019 Feb; 20(3): 657. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6386942/

In vivo activity:

The areas of cerebral infarction, MPO, and MDA levels in biso (bisoprolol), vit E, and combination group were significantly reduced compared with I/R rat group. Histopathological analysis demonstrated a significant reduction in leukocyte infiltration in all treated groups with the most profound reduction in the combination group. According to the behavioral tests, administration of biso and/or vit E protected locomotive ability and improved spatial memory after cerebral I/R. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2021 Apr;394(4):685-695. https://pubmed.ncbi.nlm.nih.gov/33106920/

Preparing Stock Solutions

The following data is based on the product molecular weight 325.45 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. So EC, Foo NP, Ko SY, Wu SN. Bisoprolol, Known to Be a Selective β₁-Receptor Antagonist, Differentially but Directly Suppresses IK(M) and IK(erg) in Pituitary Cells and Hippocampal Neurons. Int J Mol Sci. 2019 Feb 2;20(3):657. doi: 10.3390/ijms20030657. PMID: 30717422; PMCID: PMC6386942. 2. Wang J, Liu J, Xie L, Cai X, Ma X, Gong J. Bisoprolol, a β1 antagonist, protects myocardial cells from ischemia-reperfusion injury via PI3K/AKT/GSK3β pathway. Fundam Clin Pharmacol. 2020 Dec;34(6):708-720. doi: 10.1111/fcp.12562. Epub 2020 May 25. PMID: 32363697. 3. Salehi C, Seiiedy M, Soraya H, Fazli F, Ghasemnejad-Berenji M. Pretreatment with bisoprolol and vitamin E alone or in combination provides neuroprotection against cerebral ischemia/reperfusion injury in rats. Naunyn Schmiedebergs Arch Pharmacol. 2021 Apr;394(4):685-695. doi: 10.1007/s00210-020-02007-9. Epub 2020 Oct 27. PMID: 33106920. 4. Zhang C, He S, Li Y, Li F, Liu Z, Liu J, Gong J. Bisoprolol protects myocardium cells against ischemia/reperfusion injury by attenuating unfolded protein response in rats. Sci Rep. 2017 Sep 19;7(1):11859. doi: 10.1038/s41598-017-12366-8. PMID: 28928480; PMCID: PMC5605660.

In vitro protocol:

In vivo protocol:

1. Salehi C, Seiiedy M, Soraya H, Fazli F, Ghasemnejad-Berenji M. Pretreatment with bisoprolol and vitamin E alone or in combination provides neuroprotection against cerebral ischemia/reperfusion injury in rats. Naunyn Schmiedebergs Arch Pharmacol. 2021 Apr;394(4):685-695. doi: 10.1007/s00210-020-02007-9. Epub 2020 Oct 27. PMID: 33106920. 2. Zhang C, He S, Li Y, Li F, Liu Z, Liu J, Gong J. Bisoprolol protects myocardium cells against ischemia/reperfusion injury by attenuating unfolded protein response in rats. Sci Rep. 2017 Sep 19;7(1):11859. doi: 10.1038/s41598-017-12366-8. PMID: 28928480; PMCID: PMC5605660.

1: Muresan L, Cismaru G, Muresan C, Rosu R, Gusetu G, Puiu M, Mada RO, Martins RP. Beta-blockers for the treatment of arrhythmias: Bisoprolol - a systematic review. Ann Pharm Fr. 2022 Sep;80(5):617-634. doi: 10.1016/j.pharma.2022.01.007. Epub 2022 Jan 31. PMID: 35093388. 2: Bakheit AH, Ali R, Alshahrani AD, El-Azab AS. Bisoprolol: A comprehensive profile. Profiles Drug Subst Excip Relat Methodol. 2021;46:51-89. doi: 10.1016/bs.podrm.2020.07.006. Epub 2020 Sep 8. PMID: 33461700. 3: Kotecha D, Bunting KV, Gill SK, Mehta S, Stanbury M, Jones JC, Haynes S, Calvert MJ, Deeks JJ, Steeds RP, Strauss VY, Rahimi K, Camm AJ, Griffith M, Lip GYH, Townend JN, Kirchhof P; Rate Control Therapy Evaluation in Permanent Atrial Fibrillation (RATE-AF) Team. Effect of Digoxin vs Bisoprolol for Heart Rate Control in Atrial Fibrillation on Patient-Reported Quality of Life: The RATE-AF Randomized Clinical Trial. JAMA. 2020 Dec 22;324(24):2497-2508. doi: 10.1001/jama.2020.23138. PMID: 33351042; PMCID: PMC7756234. 4: Cotton S, Devereux G, Abbas H, Briggs A, Campbell K, Chaudhuri R, Choudhury G, Dawson D, De Soyza A, Fielding S, Gompertz S, Haughney J, Lang CC, Lee AJ, MacLennan G, MacNee W, McCormack K, McMeekin N, Mills NL, Morice A, Norrie J, Petrie MC, Price D, Short P, Vestbo J, Walker P, Wedzicha J, Wilson A, Lipworth BJ. Use of the oral beta blocker bisoprolol to reduce the rate of exacerbation in people with chronic obstructive pulmonary disease (COPD): a randomised controlled trial (BICS). Trials. 2022 Apr 14;23(1):307. doi: 10.1186/s13063-022-06226-8. PMID: 35422024; PMCID: PMC9009490. 5: Castaño-Amores C, Díaz-Villamarín X, Pérez-Gutiérrez AM, Antúnez-Rodríguez A, Pozo-Agundo A, Moreno-Escobar E, Sánchez-Ramos JG, Martínez-González LJ, Dávila- Fajardo CL. Pharmacogenetic polymorphisms affecting bisoprolol response. Biomed Pharmacother. 2021 Oct;142:112069. doi: 10.1016/j.biopha.2021.112069. Epub 2021 Aug 27. PMID: 34470728. 6: Gottwald-Hostalek U, Sun N, Barho C, Hildemann S. Management of Hypertension With a Fixed-Dose (Single-Pill) Combination of Bisoprolol and Amlodipine. Clin Pharmacol Drug Dev. 2017 Jan;6(1):9-18. doi: 10.1002/cpdd.309. Epub 2016 Oct 26. PMID: 27653022. 7: AlHabeeb W, Mrabeti S, Abdelsalam AAI. Therapeutic Properties of Highly Selective β-blockers With or Without Additional Vasodilator Properties: Focus on Bisoprolol and Nebivolol in Patients With Cardiovascular Disease. Cardiovasc Drugs Ther. 2022 Oct;36(5):959-971. doi: 10.1007/s10557-021-07205-y. Epub 2021 Jun 9. PMID: 34106365; PMCID: PMC9519665. 8: Wang Y. The Efficacy and Safety of Bisoprolol in the Treatment of Myocardial Infarction with Cardiac Insufficiency. Comput Math Methods Med. 2022 Aug 25;2022:3098726. doi: 10.1155/2022/3098726. PMID: 36060658; PMCID: PMC9436541. 9: Minushkina LO. [Bisoprolol: opportunities in the treatment of hypertension]. Kardiologiia. 2012;52(6):80-5. Russian. PMID: 22839675. 10: Toyoda S, Haruyama A, Inami S, Arikawa T, Saito F, Watanabe R, Sakuma M, Abe S, Nakajima T, Tanaka A, Node K, Inoue T. Effects of carvedilol vs bisoprolol on inflammation and oxidative stress in patients with chronic heart failure. J Cardiol. 2020 Feb;75(2):140-147. doi: 10.1016/j.jjcc.2019.07.011. Epub 2019 Aug 21. PMID: 31444140. 11: Johns TE, Lopez LM. Bisoprolol: is this just another beta-blocker for hypertension or angina? Ann Pharmacother. 1995 Apr;29(4):403-14. doi: 10.1177/106002809502900412. PMID: 7633020. 12: Tsutsui H, Momomura SI, Masuyama T, Saito Y, Komuro I, Murohara T, Kinugawa S; CIBIS-J Investigators. Tolerability, Efficacy, and Safety of Bisoprolol vs. Carvedilol in Japanese Patients With Heart Failure and Reduced Ejection Fraction　- The CIBIS-J Trial. Circ J. 2019 May 24;83(6):1269-1277. doi: 10.1253/circj.CJ-18-1199. Epub 2019 Apr 6. PMID: 30956267. 13: Rosenberg J, Gustafsson F. Bisoprolol for congestive heart failure. Expert Opin Pharmacother. 2008 Feb;9(2):293-300. doi: 10.1517/14656566.9.2.293. PMID: 18201151. 14: McGavin JK, Keating GM. Bisoprolol: a review of its use in chronic heart failure. Drugs. 2002;62(18):2677-96. doi: 10.2165/00003495-200262180-00017. PMID: 12466013. 15: de Groote P, Ennezat PV, Mouquet F. Bisoprolol in the treatment of chronic heart failure. Vasc Health Risk Manag. 2007;3(4):431-9. PMID: 17969374; PMCID: PMC2291328. 16: Nehaj F, Sokol J, Ivankova J, Mokan M, Mokan M. Effect of Bisoprolol on the Level of Dabigatran. Am J Ther. 2020 Mar/Apr;27(2):e159-e164. doi: 10.1097/MJT.0000000000000786. PMID: 30074534. 17: Hostalek-Gottwald U, Gaciong Z. A growing evidence base for the fixed-dose combination of bisoprolol and amlodipine to manage hypertension. Curr Med Res Opin. 2022 Jul;38(7):1047-1053. doi: 10.1080/03007995.2022.2072087. Epub 2022 May 13. PMID: 35510372. 18: Kuriyama S. Bisoprolol-induced nightmares. J Hum Hypertens. 1994 Sep;8(9):730. PMID: 7807505. 19: Gach O, Falque B, Canivet A, Krzesinski F, Krzesinski JM, Lancellotti P. Le médicament du mois BIPRESSIL® : Première association fixe bisoprolol et perindopril arginine [Bipressil® : first single-pill combination of bisoprolol and perindopril arginine]. Rev Med Liege. 2017 May;72(5):260-265. French. PMID: 28520326. 20: Chopra HK. Bisoprolol and heart failure: new frontiers. Indian Heart J. 2010 Jan-Feb;62(1):7-12. PMID: 21180027.