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MedKoo Cat#: 319892 | Name: Levonebivolol

Description:

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

Levonebivolol, also known as R 67145, is an enantiomer of Nebivolol which is a β1 receptor blocker with nitric oxide-potentiating vasodilatory effect used in treatment of hypertension and, in Europe, also for left ventricular failure. It is highly cardioselective under certain circumstances.

Chemical Structure

Levonebivolol
CAS#118457-16-2

Theoretical Analysis

MedKoo Cat#: 319892

Name: Levonebivolol

CAS#: 118457-16-2

Chemical Formula: C22H25F2NO4

Exact Mass: 405.1752

Molecular Weight: 405.44

Elemental Analysis: C, 65.17; H, 6.22; F, 9.37; N, 3.45; O, 15.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
R67145; R-67145; R 67145; Levonebivolol
IUPAC/Chemical Name
(S)-1-((R)-6-fluorochroman-2-yl)-2-(((S)-2-((S)-6-fluorochroman-2-yl)-2-hydroxyethyl)amino)ethan-1-ol
InChi Key
KOHIRBRYDXPAMZ-YHDSQAASSA-N
InChi Code
InChI=1S/C22H25F2NO4/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2/t17-,18-,21-,22+/m0/s1
SMILES Code
O[C@@H](CNC[C@@H]([C@H]1CCC2=CC(F)=CC=C2O1)O)[C@@H]3CCC4=CC(F)=CC=C4O3
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, not in water
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:
Nebivolol (R 065824) is an orally active beta receptor blocker and has the high beta(1)-receptor affinity.
In vitro activity:
Nebivolol inhibited accelerated haCSMC proliferation even in the presence of growth factors such as TGFbeta(1) and PDGF-BB. Nebivolol concentration-dependently induced a moderate apoptosis (10(-5) mol/l: 23%) and a decrease of haCSMCs in the S-phase by 66%. HaECs showed comparable results. Reference: Cardiovasc Res. 2001 Feb 1;49(2):430-9. https://pubmed.ncbi.nlm.nih.gov/11164853/
In vivo activity:
Nebivolol treatment partially recovered glomerular filtration rate, improved renal injury, normalized blood pressure and attenuated renal vasoconstriction in Wistar rats. Reference: Front Med (Lausanne). 2022 Aug 4;9:953749. https://pubmed.ncbi.nlm.nih.gov/35991671/

Preparing Stock Solutions

The following data is based on the product molecular weight 405.44 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. Bueno-Pereira TO, Nunes PR, Matheus MB, Vieira da Rocha AL, Sandrim VC. Nebivolol Increases Nitric Oxide Synthase via β3 Adrenergic Receptor in Endothelial Cells Following Exposure to Plasma from Preeclamptic Patients. Cells. 2022 Mar 4;11(5):883. doi: 10.3390/cells11050883. PMID: 35269505; PMCID: PMC8909669. 2. Brehm BR, Wolf SC, Bertsch D, Klaussner M, Wesselborg S, Schüler S, Schulze-Osthoff K. Effects of nebivolol on proliferation and apoptosis of human coronary artery smooth muscle and endothelial cells. Cardiovasc Res. 2001 Feb 1;49(2):430-9. doi: 10.1016/s0008-6363(00)00253-4. PMID: 11164853. 3. Nascimento MM, Bernardo DRD, de Bragança AC, Massola Shimizu MH, Seguro AC, Volpini RA, Canale D. Treatment with β-blocker nebivolol ameliorates oxidative stress and endothelial dysfunction in tenofovir-induced nephrotoxicity in rats. Front Med (Lausanne). 2022 Aug 4;9:953749. doi: 10.3389/fmed.2022.953749. PMID: 35991671; PMCID: PMC9386005. 4. Naeem AG, El-Naga RN, Michel HE. Nebivolol elicits a neuroprotective effect in the cuprizone model of multiple sclerosis in mice: emphasis on M1/M2 polarization and inhibition of NLRP3 inflammasome activation. Inflammopharmacology. 2022 Dec;30(6):2197-2209. doi: 10.1007/s10787-022-01045-4. Epub 2022 Aug 10. PMID: 35948811; PMCID: PMC9700639.
In vitro protocol:
1. Bueno-Pereira TO, Nunes PR, Matheus MB, Vieira da Rocha AL, Sandrim VC. Nebivolol Increases Nitric Oxide Synthase via β3 Adrenergic Receptor in Endothelial Cells Following Exposure to Plasma from Preeclamptic Patients. Cells. 2022 Mar 4;11(5):883. doi: 10.3390/cells11050883. PMID: 35269505; PMCID: PMC8909669. 2. Brehm BR, Wolf SC, Bertsch D, Klaussner M, Wesselborg S, Schüler S, Schulze-Osthoff K. Effects of nebivolol on proliferation and apoptosis of human coronary artery smooth muscle and endothelial cells. Cardiovasc Res. 2001 Feb 1;49(2):430-9. doi: 10.1016/s0008-6363(00)00253-4. PMID: 11164853.
In vivo protocol:
1. Nascimento MM, Bernardo DRD, de Bragança AC, Massola Shimizu MH, Seguro AC, Volpini RA, Canale D. Treatment with β-blocker nebivolol ameliorates oxidative stress and endothelial dysfunction in tenofovir-induced nephrotoxicity in rats. Front Med (Lausanne). 2022 Aug 4;9:953749. doi: 10.3389/fmed.2022.953749. PMID: 35991671; PMCID: PMC9386005. 2. Naeem AG, El-Naga RN, Michel HE. Nebivolol elicits a neuroprotective effect in the cuprizone model of multiple sclerosis in mice: emphasis on M1/M2 polarization and inhibition of NLRP3 inflammasome activation. Inflammopharmacology. 2022 Dec;30(6):2197-2209. doi: 10.1007/s10787-022-01045-4. Epub 2022 Aug 10. PMID: 35948811; PMCID: PMC9700639.