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
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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL210 |
236.0 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | XOPENEX Approved UseXOPENEX (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 Date9.2231998E11 |
|||
Primary | XOPENEX Approved UseXOPENEX (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 Date9.2231998E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
90.55% |
LEVALBUTEROL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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) Other AEs:Dyspnea (45 patients) Lung disorder (45 patients) Apparent life threatening event (18 patients) Sources: 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
(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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16446544
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
Edited
Fri Dec 15 15:45:21 UTC 2023
by
admin
on
Fri Dec 15 15:45:21 UTC 2023
|
Record UNII |
EDN2NBH5SS
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
|
|
|||