Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C13H21NO3.C4H6O6 |
Molecular Weight | 628.7083 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1.CC(C)(C)NC[C@H](O)C2=CC=C(O)C(CO)=C2
InChI
InChIKey=VNVNZKCCDVFGAP-FPDJQMMJSA-N
InChI=1S/2C13H21NO3.C4H6O6/c2*1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15;5-1(3(7)8)2(6)4(9)10/h2*4-6,12,14-17H,7-8H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t2*12-;1-,2-/m001/s1
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 Date1999 |
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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 Date1999 |
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 |
---|---|---|
Comparison of the effectiveness of inhaler devices in asthma and chronic obstructive airways disease: a systematic review of the literature. | 2001 |
|
Levalbuterol and racemic albuterol: are there therapeutic differences? | 2001 Nov |
|
Comparison of innovator and generic salbutamol inhalers: a double-blind randomized study of efficacy and tolerance. | 2002 |
|
[Pharmacodynamics of inhalation broncholytic agents introduced in a single dose by nebulizer in patients with severe exacerbation of bronchial asthma]. | 2002 |
|
Pressurised metered-dose inhalers versus all other hand-held inhalers devices to deliver bronchodilators for chronic obstructive pulmonary disease. | 2002 |
|
Comparative efficacy of levalbuterol and racemic albuterol in the treatment of asthma. | 2002 Aug |
|
Levalbuterol hydrochloride. | 2002 Feb |
|
Bronchodilating effects of salbutamol from a novel inhaler Airmax. | 2002 Jul |
|
Effects of albuterol enantiomers on ciliary beat frequency in ovine tracheal epithelial cells. | 2002 Jun |
|
[Clinical effect and mechanism of nitroglycerin patch on arresting preterm labor]. | 2002 Mar |
|
Xopenex. New asthma relief for kids. | 2002 May |
|
Release of salbutamol sulphate and ketoprofen enantiomers from matrices containing HPMC and cellulose derivatives. | 2002 Nov |
|
Application of the chiral acyl anion equivalent, trans-1,3-dithiane 1,3-dioxide, to an asymmetric synthesis of (R)-salbutamol. | 2002 Nov 29 |
|
A facile method of delivery of liposomes by nebulization. | 2002 Nov 7 |
|
The effect of heliox-driven bronchodilator aerosol therapy on pulmonary function tests in patients with asthma. | 2002 Oct |
|
The influence of relative humidity on particulate interactions in carrier-based dry powder inhaler formulations. | 2002 Oct 10 |
|
Effect of levalbuterol on prehospital patient parameters. | 2002 Sep |
|
Influence of excipients, drugs, and osmotic agent in the inner core on the time-controlled disintegration of compression-coated ethylcellulose tablets. | 2002 Sep |
|
Novolizer: a multidose dry powder inhaler. | 2003 |
|
Investigation of processing parameters of spray freezing into liquid to prepare polyethylene glycol polymeric particles for drug delivery. | 2003 |
|
Salbutamol sulfate suppositories: influence of formulation on physical parameters and stability. | 2003 |
|
Investigation into the effect of humidity on drug-drug interactions using the atomic force microscope. | 2003 Apr |
|
Comparison of racemic albuterol and levalbuterol for treatment of acute asthma. | 2003 Dec |
|
Mirror images: is levalbuterol the fairest of them all? | 2003 Dec |
|
Prospective observational cohort safety study to monitor the introduction of a non-CFC formulation of salbutamol with HFA134a in England. | 2003 Feb |
|
Influence of physico-chemical carrier properties on the in vitro aerosol deposition from interactive mixtures. | 2003 Feb 18 |
|
Metabolism of salbutamol differs between asthmatic patients and healthy volunteers. | 2003 Jan |
|
Preparation of dry powder inhalation by surface treatment of lactose carrier particles. | 2003 Jan |
|
Three useful bromimetric methods for the determination of salbutamol sulfate. | 2003 Jul |
|
Albuterol improves response to levodopa and increases skeletal muscle mass in patients with fluctuating Parkinson disease. | 2003 Jul-Aug |
|
Levalbuterol: pharmacologic properties and use in the treatment of pediatric and adult asthma. | 2003 Jun |
|
Levalbuterol toxicity: no reason to be jittery. | 2003 Jun |
|
(R,S)-salbutamol plasma concentrations in severe asthma. | 2003 Jun |
|
Planar gamma scintigraphy--points to consider when quantifying pulmonary dry powder aerosol deposition. | 2003 Jun 4 |
|
Characterization of particle-interactions by atomic force microscopy: effect of contact area. | 2003 Mar |
|
Managing outpatient asthma exacerbations. | 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 |
|
Immobilization of fine particles on lactose carrier by precision coating and its effect on the performance of dry powder formulations. | 2003 May |
|
The influence of carrier and drug morphology on drug delivery from dry powder formulations. | 2003 May 12 |
|
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 |
|
Investigation of the physical properties of spray-dried stabilised lysozyme particles. | 2003 Sep |
|
Management of the acute exacerbation of asthma. | 2003 Sep |
|
Levalbuterol is not more cost-effective than albuterol for COPD. | 2003 Sep |
|
Levalbuterol vs racemic albuterol: science or drug company propaganda? | 2003 Sep |
|
An evaluation of nebulized levalbuterol in stable COPD. | 2003 Sep |
|
Urgent adenotonsillectomy: an analysis of risk factors associated with postoperative respiratory morbidity. | 2003 Sep |
|
Effects of carriers and storage of formulation on the lung deposition of a hydrophobic and hydrophilic drug from a DPI. | 2003 Sep 16 |
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
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C48149
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NCI_THESAURUS |
C319
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487066
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CHEMBL1002
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QQ-74
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD