Levosalbutamol

Identification

Summary

Levosalbutamol is a beta-2 adrenergic receptor agonist used to treat COPD and asthma.

Brand Names
Xopenex
Generic Name
Levosalbutamol
DrugBank Accession Number
DB13139
Background

Levosalbutamol, or levalbuterol, is a short-acting β2 adrenergic receptor agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD). Salbutamol has been marketed as a racemic mixture, although beta2-agonist activity resides almost exclusively in the (R)-enantiomer. The enantioselective disposition of salbutamol and the possibility that (S)-salbutamol has adverse effects have led to the development of an enantiomerically pure (R)-salbutamol formulation known as levosalbutamol (levalbuterol).

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 239.3107
Monoisotopic: 239.152143543
Chemical Formula
C13H21NO3
Synonyms
  • (-)-Albuterol
  • (-)-Salbutamol
  • (R)-salbutamol
  • Levalbuterol
  • Levosalbutamol
  • R-salbutamol
External IDs
  • ASF-1096

Pharmacology

Indication

Indicated for the management of COPD (chronic obstructive pulmonary disease, also known as chronic obstructive lung disease) and asthma.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

It acts by relaxing smooth muscle in the bronchial tubes to increase air flow and relieve acute shortness of breath.

Mechanism of action

β2 adrenergic receptors on airway smooth muscle are Gs coupled and their activation by levosalbutamol leads to activation of adenylate cyclase and to an increase in the intracellular concentration of 3',5'-cyclic adenosine monophosphate (cyclic AMP). Increased cyclic AMP activates protein kinase A which itself inhibits the phosphorylation of myosin produces lower intracellular ionic calcium concentrations, inducing muscle relaxation. Increased cyclic AMP concentrations are also associated with the inhibition of the release of mediators from mast cells in the airways, potentially contributing to its benefit in asthma attacks.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Humans
Absorption

Inhalation delivers the medication directly into the airways and lungs, thereby minimizing side effects because of reduced systemic absorption of the inhaled medications.

Volume of distribution

Not Available

Protein binding

plasma protein binding is relatively low.

Metabolism

Pure (R)-salbutamol formulation known as levosalbutamol is metabolised up to 12 times faster than (S)-salbutamol by intestine.

Route of elimination

excreted into the urine.

Half-life

3.3 - 4 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Levosalbutamol which could result in a higher serum level.
AcebutololThe therapeutic efficacy of Levosalbutamol can be decreased when used in combination with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Levosalbutamol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Levosalbutamol which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Levosalbutamol which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Levosalbutamol which could result in a lower serum level and potentially a reduction in efficacy.
AcetylcysteineThe excretion of Levosalbutamol can be decreased when combined with Acetylcysteine.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Levosalbutamol which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Levosalbutamol which could result in a higher serum level.
AcrivastineAcrivastine may decrease the excretion rate of Levosalbutamol which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Levosalbutamol hydrochlorideWDQ1526QJM50293-90-8OWNWYCOLFIFTLK-YDALLXLXSA-N
Levosalbutamol sulfate71TH42O2CQ148563-16-0BNPSSFBOAGDEEL-NMFAMCKASA-N
Levosalbutamol tartrateADS4I3E22M661464-94-4VNVNZKCCDVFGAP-FPDJQMMJSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Levalbuterol HydrochlorideSolution0.31 mg/3mLRespiratory (inhalation)Actavis Pharma Company2012-08-202015-05-31US flag
Levalbuterol HydrochlorideSolution1.25 mg/3mLRespiratory (inhalation)Prasco Laboratories2015-02-27Not applicableUS flag
Levalbuterol HydrochlorideSolution1.25 mg/3mLRespiratory (inhalation)Actavis Pharma Company2012-08-202015-08-31US flag
Levalbuterol HydrochlorideSolution0.63 mg/3mLRespiratory (inhalation)Prasco Laboratories2015-02-27Not applicableUS flag
Levalbuterol HydrochlorideSolution0.63 mg/3mLRespiratory (inhalation)Actavis Pharma Company2012-08-202015-07-31US flag
Levalbuterol HydrochlorideSolution0.31 mg/3mLRespiratory (inhalation)Prasco Laboratories2015-02-27Not applicableUS flag
XopenexSolution0.31 mg/3mLRespiratory (inhalation)Akorn, Inc.2015-02-27Not applicableUS flag
XopenexSolution1.25 mg/3mLRespiratory (inhalation)Remedy Repack2016-06-092016-06-09US flag
XopenexSolution1.25 mg/3mLRespiratory (inhalation)Sunovion1999-04-012017-02-28US flag
XopenexSolution, concentrate1.25 mg/0.5mLRespiratory (inhalation)Physicians Total Care, Inc.2009-04-21Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LevalbuterolSolution, concentrate1.25 mg/0.5mLRespiratory (inhalation)Aurobindo Pharma Limited2017-01-31Not applicableUS flag
LevalbuterolSolution1.25 mg/3mLRespiratory (inhalation)Teva Pharmaceuticals USA, Inc.2013-04-29Not applicableUS flag
LevalbuterolSolution, concentrate1.25 mg/0.5mLRespiratory (inhalation)Teva Pharmaceuticals USA, Inc.2014-12-16Not applicableUS flag
LevalbuterolSolution0.63 mg/3mLRespiratory (inhalation)Burel Pharmaceuticals, Inc.2021-04-01Not applicableUS flag
LevalbuterolSolution0.31 mg/3mLRespiratory (inhalation)Aurobindo Pharma Limited2016-12-30Not applicableUS flag
LevalbuterolSolution0.31 mg/3mLRespiratory (inhalation)Mylan Pharmaceuticals Inc.2013-03-152019-08-31US flag
LevalbuterolSolution, concentrate1.25 mg/0.5mLRespiratory (inhalation)Mylan Pharmaceuticals Inc.2009-08-28Not applicableUS flag
LevalbuterolSolution1.25 mg/3mLRespiratory (inhalation)REMEDYREPACK INC.2020-05-29Not applicableUS flag
LevalbuterolSolution1.25 mg/3mLRespiratory (inhalation)Amneal Pharmaceuticals of New York Llc2016-03-22Not applicableUS flag
LevalbuterolSolution0.63 mg/3mLRespiratory (inhalation)Mylan Pharmaceuticals Inc.2018-07-23Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
İPRALEV 20 MCG/50 MCG AEROSOL İNHALASYONU,SÜSPANSİYON, 200 DOZLevosalbutamol (50 mcg) + Ipratropium bromide monohydrate (20 mcg)SuspensionRespiratory (inhalation)CELTİS İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzyl alcohols
Direct Parent
Benzyl alcohols
Alternative Parents
Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Benzyl alcohol / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
albuterol (CHEBI:8746)
Affected organisms
Not Available

Chemical Identifiers

UNII
EDN2NBH5SS
CAS number
34391-04-3
InChI Key
NDAUXUAQIAJITI-LBPRGKRZSA-N
InChI
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
IUPAC Name
4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
SMILES
CC(C)(C)NC[C@H](O)C1=CC(CO)=C(O)C=C1

References

General References
  1. Boulton DW, Fawcett JP: The pharmacokinetics of levosalbutamol: what are the clinical implications? Clin Pharmacokinet. 2001 Jan;40(1):23-40. [Article]
  2. Sciencedirect [Link]
KEGG Drug
D08124
KEGG Compound
C11770
PubChem Compound
123600
PubChem Substance
347829257
ChemSpider
110192
BindingDB
50361247
RxNav
237159
ChEBI
8746
ChEMBL
CHEMBL1002
ZINC
ZINC000000007601
PDBe Ligand
68H
Wikipedia
Levosalbutamol
PDB Entries
2y04 / 6h7m / 7dhi

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedHealth Services ResearchAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
4CompletedSupportive CareChronic Obstructive Pulmonary Disease (COPD) / Septic / Shock1
4CompletedTreatmentAsthma4
4CompletedTreatmentMucociliary Clearance1
4TerminatedTreatmentAsthma Acute1
4WithdrawnTreatmentAsthma1
3CompletedTreatmentAsthma8
3CompletedTreatmentAsthma / Bronchoconstriction1
3CompletedTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionRespiratory (inhalation)
PowderRespiratory (inhalation)
SuspensionRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
SolutionRespiratory (inhalation)1.25 mg
SuspensionRespiratory (inhalation)65.68 mcg
SolutionRespiratory (inhalation)0.31 mg/3mL
AerosolBuccal50 mcg
SolutionRespiratory (inhalation)
Aerosol; suspensionRespiratory (inhalation)
SolutionRespiratory (inhalation)0.63 mg/3mL
SolutionRespiratory (inhalation)1.25 mg/3mL
Solution, concentrateRespiratory (inhalation)1.25 mg/0.5mL
Aerosol, meteredOral45 ug/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6451289No2002-09-172021-03-21US flag
US7256310No2007-08-142024-10-08US flag
US8765153No2014-07-012023-12-08US flag
US5836299No1998-11-172015-11-17US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.15 mg/mLALOGPS
logP0.44ALOGPS
logP0.34ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)10.12ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.87 m3·mol-1ChemAxon
Polarizability26.87 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-052r-4960000000-11e534d73f624db9d896
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-0002-0900000000-1320ba6a3f38ebdb80a3
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-002f-8900000000-4735e41255f39d1d99d4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. UniProt [Link]
  2. KEGG [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. UniProt [Link]
  2. ChEMBL [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. ChEMBL [Link]
  2. UniProt [Link]

Drug created on October 27, 2016 17:42 / Updated on February 21, 2021 18:54