Levosalbutamol
Identification
- Name
- Levosalbutamol
- Accession Number
- DB13139
- Description
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
Structure for Levosalbutamol (DB13139)
- 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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans - 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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.
Drug Interaction Unlock Additional DataAbacavir Abacavir may decrease the excretion rate of Levosalbutamol which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Levosalbutamol which could result in a higher serum level. Acebutolol The therapeutic efficacy of Levosalbutamol can be decreased when used in combination with Acebutolol. Aceclofenac Aceclofenac may decrease the excretion rate of Levosalbutamol which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Levosalbutamol which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Levosalbutamol which could result in a lower serum level and potentially a reduction in efficacy. Acetylcysteine The excretion of Levosalbutamol can be decreased when combined with Acetylcysteine. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Levosalbutamol which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Levosalbutamol which could result in a higher serum level. Acrivastine Acrivastine may decrease the excretion rate of Levosalbutamol which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Levosalbutamol hydrochloride WDQ1526QJM 50293-90-8 OWNWYCOLFIFTLK-YDALLXLXSA-N Levosalbutamol sulfate 71TH42O2CQ 148563-16-0 BNPSSFBOAGDEEL-NMFAMCKASA-N Levosalbutamol tartrate ADS4I3E22M 661464-94-4 VNVNZKCCDVFGAP-FPDJQMMJSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataLevalbuterol Hydrochloride Solution 0.31 mg/3mL Respiratory (inhalation) Prasco Laboratories 2015-02-27 Not applicable US 
Levalbuterol Hydrochloride Solution 0.63 mg/3mL Respiratory (inhalation) Actavis Pharma Company 2012-08-20 2015-07-31 US Levalbuterol Hydrochloride Solution 1.25 mg/3mL Respiratory (inhalation) Prasco Laboratories 2015-02-27 Not applicable US Levalbuterol Hydrochloride Solution 0.31 mg/3mL Respiratory (inhalation) Actavis Pharma Company 2012-08-20 2015-05-31 US Levalbuterol Hydrochloride Solution 0.63 mg/3mL Respiratory (inhalation) Prasco Laboratories 2015-02-27 Not applicable US Levalbuterol Hydrochloride Solution 1.25 mg/3mL Respiratory (inhalation) Actavis Pharma Company 2012-08-20 2015-08-31 US Xopenex Solution 0.31 mg/3mL Respiratory (inhalation) Akorn, Inc. 2015-02-27 Not applicable US Xopenex Solution 1.25 mg/3mL Respiratory (inhalation) Physicians Total Care, Inc. 2005-10-20 Not applicable US Xopenex Solution 1.25 mg/3mL Respiratory (inhalation) Sunovion 1999-04-01 2017-02-28 US Xopenex Solution, concentrate 1.25 mg/0.5mL Respiratory (inhalation) Sunovion 2004-08-01 2017-03-31 US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataLevalbuterol Solution 0.31 mg/3mL Respiratory (inhalation) Teva Pharmaceuticals USA, Inc. 2013-04-29 Not applicable US Levalbuterol Solution 0.63 mg/3mL Respiratory (inhalation) Mylan Pharmaceuticals Inc. 2018-07-23 Not applicable US Levalbuterol Solution, concentrate 1.25 mg/0.5mL Respiratory (inhalation) Aurobindo Pharma Limited 2017-01-31 Not applicable US Levalbuterol Solution 1.25 mg/3mL Respiratory (inhalation) Mylan Pharmaceuticals Inc. 2013-03-15 2019-08-31 US Levalbuterol Solution 0.63 mg/3mL Respiratory (inhalation) Ritedose Pharmaceuticals, LLC 2016-03-22 Not applicable US Levalbuterol Solution 0.31 mg/3mL Respiratory (inhalation) Aurobindo Pharma Limited 2016-12-30 Not applicable US Levalbuterol Solution 0.63 mg/3mL Respiratory (inhalation) A-S Medication Solutions 2013-04-29 2017-12-21 US Levalbuterol Solution, concentrate 1.25 mg/0.5mL Respiratory (inhalation) Mylan Pharmaceuticals Inc. 2009-08-28 Not applicable US Levalbuterol Solution 0.63 mg/3mL Respiratory (inhalation) Amneal Pharmaceuticals of New York Llc 2016-03-22 Not applicable US Levalbuterol Solution 1.25 mg/3mL Respiratory (inhalation) Teva Pharmaceuticals USA, Inc. 2013-04-29 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories
- Drug Categories
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Agents to Treat Airway Disease
- Alcohols
- Amines
- Amino Alcohols
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 Enzyme Inhibitors
- Drugs that are Mainly Renally Excreted
- Ethanolamines
- Ethylamines
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 substrates
- Phenethylamines
- 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)
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
- Boulton DW, Fawcett JP: The pharmacokinetics of levosalbutamol: what are the clinical implications? Clin Pharmacokinet. 2001 Jan;40(1):23-40. [PubMed:11236808]
- Sciencedirect [Link]
- External Links
- KEGG Drug
- D08124
- KEGG Compound
- C11770
- PubChem Compound
- 123600
- PubChem Substance
- 347829257
- ChemSpider
- 110192
- BindingDB
- 50361247
- 237159
- ChEBI
- 8746
- ChEMBL
- CHEMBL1002
- ZINC
- ZINC000000007601
- PDBe Ligand
- 68H
- Wikipedia
- Levosalbutamol
- PDB Entries
- 2y04 / 6h7m / 7dhi
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Health Services Research Asthma / Chronic Obstructive Pulmonary Disease (COPD) 1 4 Completed Supportive Care Chronic Obstructive Pulmonary Disease (COPD) / Sepsis / Shock syndrome 1 4 Completed Treatment Asthma 4 4 Completed Treatment Mucociliary Clearance 1 4 Terminated Treatment Asthma Acute 1 4 Withdrawn Treatment Asthma 1 3 Completed Treatment Asthma 8 3 Completed Treatment Asthma / Bronchoconstriction 1 3 Completed Treatment Asthma / Chronic Obstructive Pulmonary Disease (COPD) 1 3 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Respiratory (inhalation) 500 mcg Powder Respiratory (inhalation) 100 mcg Suspension Respiratory (inhalation) 20 mcg Aerosol, metered Respiratory (inhalation) 50 mcg Solution Respiratory (inhalation) 1.25 mg Suspension Respiratory (inhalation) 65.68 mcg Solution Respiratory (inhalation) 0.31 mg/3mL Powder Respiratory (inhalation) 100 mg Aerosol Buccal 50 mcg Solution Respiratory (inhalation) 1.25 mg/0.5mL Aerosol; suspension Respiratory (inhalation) 45 mcg Solution Respiratory (inhalation) 0.63 mg/3mL Solution Respiratory (inhalation) 1.25 mg/3mL Solution, concentrate Respiratory (inhalation) 1.25 mg/0.5mL Aerosol, metered Oral 45 ug/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS6451289 No 2002-09-17 2021-03-21 US US7256310 No 2007-08-14 2024-10-08 US US8765153 No 2014-07-01 2023-12-08 US US5836299 No 1998-11-17 2015-11-17 US Additional Data Available- Filed OnFiled OnAvailable for Purchase
The date on which a patent was filed with the relevant government.
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Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.15 mg/mL ALOGPS logP 0.44 ALOGPS logP 0.34 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 10.12 ChemAxon pKa (Strongest Basic) 9.4 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 72.72 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 67.87 m3·mol-1 ChemAxon Polarizability 26.87 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available MS/MS Spectrum - Quattro_QQQ 10V, N/A LC-MS/MS splash10-052r-4960000000-11e534d73f624db9d896 MS/MS Spectrum - Quattro_QQQ 25V, N/A LC-MS/MS splash10-0002-0900000000-1320ba6a3f38ebdb80a3 MS/MS Spectrum - Quattro_QQQ 40V, N/A LC-MS/MS splash10-002f-8900000000-4735e41255f39d1d99d4 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable [1H,13C] 2D NMR Spectrum 2D NMR Not Applicable
Targets
- 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
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
- 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
Drug created on October 27, 2016 11:42 / Updated on January 23, 2021 23:03