Levalbuterol

Names

[ Name ]:
Levalbuterol

[Synonym ]:
(-)-Albuterol
(R)-albuterol
R-Albuterol
Levosalbutamol
(a1R)-a1-[[(1,1-Dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol
(l)-albuterol
(R)-a1-((tert-Butylamino)methyl)-4-hydroxy-m-xylene-a,a'-diol
1,3-Benzenedimethanol, α-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-, (αR)-
(-)-a1-(((1,1-Dimethylethyl)amino)methyl)-4-hydroxy-1,3-benzenedimethanol
(R)-salbutamol
4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
2-(Hydroxymethyl)-4-{(1R)-1-hydroxy-2-[(2-methyl-2-propanyl)amino]ethyl}phenol
R-Salbutamol
UNII-EDN2NBH5SS
(-)-Salbutamol
Levalbuterol
Albuterol
MFCD00869868
1,3-Benzenedimethanol, α1-(((1,1-dimethylethyl)amino)methyl)-4-hydroxy-, (α1R)-
Salbutamol

Biological Activity

[Description]:

Levalbuterol ((R)-Albuterol; (R)-Salbutamol) is a short-acting β2-adrenergic receptor agonist and the active (R)-enantiomer of Salbutamol. Levalbuterol is a more potent bronchodilator than Salbutamol and has the potential for the treatment of COPD[1].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

Research Areas >> Inflammation/Immunology

[In Vitro]

Levalbuterol (10 μM; 24 hours) induces 11β-HSD1 mRNA expression, however, it does not influence 11β-HSD2expression in airway epithelial cells[1]. Levalbuterol (10 μM; 24 hours) significantly reduces both LPS- and TNF-α-induced NF-κB activity while increasing GRE activation in an 11β-HSD1 dependent manner in a transformed mouse airway epithelial cell line[1]. RT-PCR[1] Cell Line: Murine Club (MTCC) cells Concentration: 10 μM Incubation Time: 24 hours Result: Increased 11β-HSD1 mRNA expression selectively.

[In Vivo]

Levalbuterol (subcutaneous injection; 1 mg/kg; 14 days) significantly decreases pulmonary inflammation in OVA mice, demonstrated a decrease in eosinophilia and IgE[3]. Animal Model: C57BL/6 female mice with a pulmonary allergic model[3] Dosage: 1 mg/kg Administration: Subcutaneous injection; 1 mg/kg; 14 days Result: Decreased pulmonary inflammation after OVA sensitization.

[References]

[1]. Randall MJ, et al. Anti-inflammatory effects of levalbuterol-induced 11β-hydroxysteroid dehydrogenase type 1 activity in airway epithelial cells.Front Endocrinol (Lausanne). 2015 Jan 12;5:236.

[2]. Ferrada MA, et al. (R)-albuterol decreases immune responses: role of activated T cells.Respir Res. 2008 Jan 14;9:3.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
433.5±40.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₃H₂₁NO₃

[ Molecular Weight ]:
239.311

[ Flash Point ]:
159.5±17.9 °C

[ Exact Mass ]:
239.152145

[ PSA ]:
72.72000

[ LogP ]:
0.01

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.566

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CZ6426700

CHEMICAL NAME :: 1,3-Benzenedimethanol, alpha(sup 1)-(((1,1-dimethylethyl)amino)methyl)-4-hydroxy-, (-)-

CAS REGISTRY NUMBER :: 34391-04-3

LAST UPDATED :: 199606

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C13-H21-N-O3

MOLECULAR WEIGHT :: 239.35

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 225 mg/kg/90D-I

TOXIC EFFECTS :: Endocrine - hypoglycemia Endocrine - changes in spleen weight

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 30,106,1996

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ HS Code ]:
2922509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922509090

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%