Levobetaxolol HCl - 10mM in DMSO , Beta-1 adrenergic receptor antagonist, CAS No.116209-55-3, Beta-1 adrenergic receptor antagonist

CAS: 116209-55-3 Cat. No.: L420744 Molecular Weight: 343.89

GRADE & PURITY 10mM in DMSO

Synonyms

2-Propanol, 1-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-, hydrochloride, (S)- | 8MR4W4O06J | Levobetaxolol (hydrochloride) | Levobetaxolol hydrochloride (USAN) | (2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)p

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Levobetaxolol (AL 1577A) exhibits a higher affinity at cloned human β1 and β2 receptors with Kivalue of 0.76 nM and 32.6 nM, respectively.

Targets

β1-adrenergic receptor ; β2-adrenergic receptor 0.76 nM(Ki); 32.6 nM(Ki)

In vitro

Levobetaxolol potently antagonizes functional activities at cloned human β1 and β2 receptors, and also at guinea pig atrial β1, tracheal β2 and rat colonic β3 receptors with IC50s of 33.2 nM, 2970 nM and 709 nM, respectively. Levobetaxolol (Ki = 16.4 nM) is more potent than dextrobetaxolol (Ki = 2.97 μM) at inhibiting isoproterenol-induced cAMP production in human non-pigmented ciliary epithelial cells. Levobetaxolol (topically applied) has been shown to reach the back of the eye in sufficient quantities to protect retinal ganglion cells from various types of insults. Levobetaxolol displaces [³H]-nitrendipine for L-type voltage-dependent calcium channel receptor with IC50 of 29.5 μM in rat cortex. Levobetaxolol reduces NMDA-stimulated 45Ca²⁺ influx by 47.3%. Levobetaxolol (topically applied) reduces the b-wave amplitude caused by ischaemia/reperfusion.

In vivo

Levobetaxolol (150 mg/eye) is more potent than dextrobetaxolol, reducing intraocular pressure by 25.9% in conscious ocular hypertensive cynomolgus monkeys. Levobetaxolol (20 mg/kg) significant protects retinal function and results in significantly thicker the RPE and outer nuclear layer in a photic-induced retinopathy rat model. Levobetaxolol (20 mg/kg) results in a 10-fold up-regulation of bFGF and a two-fold up-regulation of CNTF mRNA levels, trophic factors that have been shown to inhibit retinal degeneration in a number of species.

Specifications

Synonyms

2-Propanol, 1-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-, hydrochloride, (S)- | 8MR4W4O06J | Levobetaxolol (hydrochloride) | Levobetaxolol hydrochloride (USAN) | (2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)p

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Levobetaxolol (AL 1577A) exhibits a higher affinity at cloned human β1 and β2 receptors with K_i value of 0.76 nM and 32.6 nM, respectively.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ANTAGONIST

Mechanism of action

Beta-1 adrenergic receptor antagonist

Names and Identifiers

• Canonical Smiles: CC(C)NCC(COC1=CC=C(C=C1)CCOCC2CC2)O.Cl
• IUPAC Name: (2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol;hydrochloride
• InChIKey: CHDPSNLJFOQTRK-LMOVPXPDSA-N
• INCHI: 1S/C18H29NO3.ClH/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16;/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3;1H/t17-;/m0./s1
• Isomeric SMILES: CC(C)NC[C@@H](COC1=CC=C(C=C1)CCOCC2CC2)O.Cl
• Molecular Weight: 343.89
• Reaxy-Rn: 5182512
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5182512&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenols
      • Subclass Tyrosols and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenols
• Subclass: Tyrosols and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Tyrosols and derivatives
• Alternative Parents: Phenoxy compounds Phenol ethers Alkyl aryl ethers Secondary alcohols 1,2-aminoalcohols Dialkylamines Dialkyl ethers Organopnictogen compounds Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Tyrosol derivative - Phenoxy compound - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - 1,2-aminoalcohol - Secondary alcohol - Dialkyl ether - Secondary aliphatic amine - Secondary amine - Ether - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrochloride - Hydrocarbon derivative - Organopnictogen compound - Amine - Organic oxygen compound - Alcohol - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as tyrosols and derivatives. These are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.
• External Descriptors: betaxolol hydrochloride

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 343.900 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 343.191 Da
• Monoisotopic Mass: 343.191 Da
• Topological Polar Surface Area: 50.700 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 286.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3