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Details

Stereochemistry RACEMIC
Molecular Formula C13H21NO3
Molecular Weight 239.3107
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALBUTEROL

SMILES

CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1

InChI

InChIKey=NDAUXUAQIAJITI-UHFFFAOYSA-N
InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C13H21NO3
Molecular Weight 239.3107
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Levalbuterol is the (R)-enantiomer of the drug substance racemic albuterol (salbutamol). Binding studies have demonstrated that (R)-albuterol binds to the beta2-adrenergic receptor with a high affinity, whereas (S)-albuterol binds with 100-fold less affinity than (R)-albuterol. Other evaluations have suggested that (R)-albuterol possesses the bronchodilatory, bronchoprotective, and ciliary-stimulatory properties of racemic albuterol, while (S)-albuterol does not contribute beneficially to the therapeutic effects of the racemate and was originally assumed to be inert. Xopenex (levalbuterol HCl) Inhalation Solution is indicated for the treatment or prevention of bronchospasm in adults, adolescents, and children 6 years of age and older with reversible obstructive airway disease.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
236.0 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
XOPENEX
Primary
XOPENEX

Cmax

ValueDoseCo-administeredAnalytePopulation
199 pg/mL
90 μg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
238 pg/mL
180 μg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
4.5 ng/mL
1.25 mg 4 times / 2 hours multiple, respiratory
LEVALBUTEROL plasma
Homo sapiens
1.1 ng/mL
1.25 mg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
163 pg/mL
90 μg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
238 pg/mL
180 μg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
0.303 ng/mL
0.31 mg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
0.521 ng/mL
0.63 mg single, respiratory
LEVALBUTEROL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
695 pg × h/mL
90 μg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
798 pg × h/mL
180 μg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
17.4 ng × h/mL
1.25 mg 4 times / 2 hours multiple, respiratory
LEVALBUTEROL plasma
Homo sapiens
3.3 ng × h/mL
1.25 mg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
579 pg × h/mL
90 μg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
828 pg × h/mL
180 μg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
1.36 ng × h/mL
0.31 mg single, respiratory
LEVALBUTEROL plasma
Homo sapiens
2.55 ng × h/mL
0.63 mg single, respiratory
LEVALBUTEROL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
1.25 mg 4 times / 2 hours multiple, respiratory
LEVALBUTEROL plasma
Homo sapiens
3.3 h
1.25 mg single, respiratory
LEVALBUTEROL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
90.55%
LEVALBUTEROL plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Children 6–11 years old: The recommended dosage of Xopenex (levalbuterol HCl) Inhalation Solution for patients 6–11 years old is 0.31 mg administered three times a day, by nebulization. Routine dosing should not exceed 0.63 mg three times a day. Adults and Adolescents ≥12 years old: The recommended starting dosage of Xopenex (levalbuterol HCl) Inhalation Solution for patients 12 years of age and older is 0.63 mg administered three times a day, every 6 to 8 hours, by nebulization.
Route of Administration: Respiratory
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
QF8SVZ843E
Record Status Validated (UNII)
Record Version