U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H21NO3
Molecular Weight 239.3107
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVALBUTEROL

SMILES

CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1

InChI

InChIKey=NDAUXUAQIAJITI-LBPRGKRZSA-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/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula C13H21NO3
Molecular Weight 239.3107
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
236.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
XOPENEX

Approved Use

XOPENEX (levalbuterol HCl) Inhalation Solution Concentrate 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.

Launch Date

9.2231998E11
Primary
XOPENEX

Approved Use

XOPENEX (levalbuterol HCl) Inhalation Solution Concentrate 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.

Launch Date

9.2231998E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
199 pg/mL
90 μg single, respiratory
dose: 90 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
238 pg/mL
180 μg single, respiratory
dose: 180 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.5 ng/mL
1.25 mg 4 times / 2 hours multiple, respiratory
dose: 1.25 mg
route of administration: Respiratory
experiment type: MULTIPLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.1 ng/mL
1.25 mg single, respiratory
dose: 1.25 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
163 pg/mL
90 μg single, respiratory
dose: 90 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
238 pg/mL
180 μg single, respiratory
dose: 180 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
0.303 ng/mL
0.31 mg single, respiratory
dose: 0.31 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
0.521 ng/mL
0.63 mg single, respiratory
dose: 0.63 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
695 pg × h/mL
90 μg single, respiratory
dose: 90 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
798 pg × h/mL
180 μg single, respiratory
dose: 180 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
17.4 ng × h/mL
1.25 mg 4 times / 2 hours multiple, respiratory
dose: 1.25 mg
route of administration: Respiratory
experiment type: MULTIPLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.3 ng × h/mL
1.25 mg single, respiratory
dose: 1.25 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
579 pg × h/mL
90 μg single, respiratory
dose: 90 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
828 pg × h/mL
180 μg single, respiratory
dose: 180 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
1.36 ng × h/mL
0.31 mg single, respiratory
dose: 0.31 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
2.55 ng × h/mL
0.63 mg single, respiratory
dose: 0.63 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
1.25 mg 4 times / 2 hours multiple, respiratory
dose: 1.25 mg
route of administration: Respiratory
experiment type: MULTIPLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.3 h
1.25 mg single, respiratory
dose: 1.25 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LEVALBUTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
90.55%
LEVALBUTEROL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
90 ug 1 times / day steady, respiratory
Recommended
Dose: 90 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 1 times / day
Sources:
unhealthy, 4 - 11 years
n = 76
Health Status: unhealthy
Condition: Asthma
Age Group: 4 - 11 years
Sex: M+F
Population Size: 76
Sources:
Disc. AE: Asthma...
AEs leading to
discontinuation/dose reduction:
Asthma (1 patient)
Sources:
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Disc. AE: Bronchitis, Dyspnea...
Other AEs: Apparent life threatening event, Bronchitis...
AEs leading to
discontinuation/dose reduction:
Bronchitis (45 patients)
Dyspnea (45 patients)
Lung disorder (45 patients)
Other AEs:
Apparent life threatening event (18 patients)
Bronchitis (131 patient)
Dyspnea (131 patient)
Lung disorder (131 patient)
Tachycardia (67 patients)
Palpitation (67 patients)
Chest pain (67 patients)
Arrhythmia (67 patients)
Hypertension (67 patients)
Dyspepsia (67 patients)
Nausea (67 patients)
Leg cramps (67 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Asthma 1 patient
Disc. AE
90 ug 1 times / day steady, respiratory
Recommended
Dose: 90 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 1 times / day
Sources:
unhealthy, 4 - 11 years
n = 76
Health Status: unhealthy
Condition: Asthma
Age Group: 4 - 11 years
Sex: M+F
Population Size: 76
Sources:
Bronchitis 131 patient
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Dyspnea 131 patient
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Lung disorder 131 patient
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Apparent life threatening event 18 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Bronchitis 45 patients
Disc. AE
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Dyspnea 45 patients
Disc. AE
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Lung disorder 45 patients
Disc. AE
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Arrhythmia 67 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Chest pain 67 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Dyspepsia 67 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Hypertension 67 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Leg cramps 67 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Nausea 67 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Palpitation 67 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Tachycardia 67 patients
90 ug 4 times / day steady, respiratory
Studied dose
Dose: 90 ug, 4 times / day
Route: respiratory
Route: steady
Dose: 90 ug, 4 times / day
Sources:
unhealthy, > 12 years
n = 496
Health Status: unhealthy
Condition: Asthma
Age Group: > 12 years
Sex: M+F
Population Size: 496
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
(S)-albuterol increases the production of histamine and IL-4 in mast cells.
2001 Apr
Delivery of HFA and CFC salbutamol from spacer devices used in infancy.
2001 Jul 3
Single-isomer beta-agonists.
2001 Mar
Levalbuterol and racemic albuterol: are there therapeutic differences?
2001 Nov
Evaluation of flow properties of dry powder inhalation of salbutamol sulfate with lactose carrier.
2001 Oct
A study of the crystallisation of amorphous salbutamol sulphate using water vapour sorption and near infrared spectroscopy.
2002 Apr 26
Levalbuterol has not been established to have therapeutic advantage over racemic albuterol.
2002 Aug
Bronchodilating effects of salbutamol from a novel inhaler Airmax.
2002 Jul
Effect of levalbuterol on prehospital patient parameters.
2002 Sep
Effect of aerosolized albuterol sulfate on resting energy expenditure determined by use of open-flow indirect calorimetry in horses with recurrent airway obstruction.
2003 Feb
Launois-Bensaude syndrome in a female with type 2 diabetes.
2003 Feb
Influence of physico-chemical carrier properties on the in vitro aerosol deposition from interactive mixtures.
2003 Feb 18
Preparation of dry powder inhalation by surface treatment of lactose carrier particles.
2003 Jan
Characterisation and deposition studies of engineered lactose crystals with potential for use as a carrier for aerosolised salbutamol sulfate from dry powder inhalers.
2003 Jul
The effect of mechanical processing on surface stability of pharmaceutical powders: visualization by atomic force microscopy.
2003 Mar
Single-isomer levalbuterol: a review of the acute data.
2003 Mar
Characterisation of surface modified salbutamol sulphate-alkylpolyglycoside microparticles prepared by spray drying.
2003 Mar 6
A meta-analysis of randomized controlled trials evaluating the efficacy of epinephrine for the treatment of acute viral bronchiolitis.
2003 Oct
Albuterol aerosol delivered via metered-dose inhaler to intubated pediatric models of 3 ages, with 4 spacer designs.
2003 Oct
Changes in heart rate associated with nebulized racemic albuterol and levalbuterol in intensive care patients.
2003 Oct 1
Levalbuterol is not more cost-effective than albuterol for COPD.
2003 Sep
Patents

Patents

Sample Use Guides

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
Curator's Comment: Levalbuterol inhibits cell growth by activating the cAMP/PKA pathway and inhibiting PI-3 kinase, NF-kappaB and Rb protein expression
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:45:21 UTC 2023
Edited
by admin
on Fri Dec 15 15:45:21 UTC 2023
Record UNII
EDN2NBH5SS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVALBUTEROL
VANDF  
Common Name English
Levosalbutamol [WHO-DD]
Common Name English
LEVALBUTEROL [VANDF]
Common Name English
ALBUTEROL (R)-FORM [MI]
Common Name English
ASF-1096
Code English
LEVOSALBUTAMOL
INN   MART.   WHO-DD  
INN  
Official Name English
R-SALBUTAMOL
Common Name English
levosalbutamol [INN]
Common Name English
(R)-.ALPHA.(SUP 1)-((TERT-BUTYLAMINO)METHYL)-4-HYDROXY-M-XYLENE-.ALPHA.,.ALPHA.'-DIOL
Common Name English
LEVOSALBUTAMOL [MART.]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175779
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
NDF-RT N0000009922
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
Code System Code Type Description
FDA UNII
EDN2NBH5SS
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
EVMPD
SUB08491MIG
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
DRUG CENTRAL
1575
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
DAILYMED
EDN2NBH5SS
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL1002
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID80187964
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
PUBCHEM
123600
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
MERCK INDEX
m1480
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
LEVOSALBUTAMOL
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
INN
7681
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
DRUG BANK
DB13139
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
CHEBI
8746
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
RXCUI
237159
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY RxNorm
SMS_ID
100000082284
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
NCI_THESAURUS
C74196
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
LACTMED
Levalbuterol
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
CAS
34391-04-3
Created by admin on Fri Dec 15 15:45:21 UTC 2023 , Edited by admin on Fri Dec 15 15:45:21 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ACTIVE ENANTIOMER
TARGET -> AGONIST
SHORT-ACTING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE INACTIVE -> PARENT
catalysed almost exclusively by sulphotransferase (SULT) 1A3
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC