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
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.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir 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 The risk or severity of hypertension can be increased when Aceclofenac is combined with Levosalbutamol. Acemetacin The risk or severity of hypertension can be increased when Levosalbutamol is combined with Acemetacin. Acetaminophen Acetaminophen 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 The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Levosalbutamol. 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. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Levalbuterol Hydrochloride Solution 0.31 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 1.25 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 Levalbuterol Hydrochloride Solution 0.63 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 Xopenex Solution 1.25 mg/3mL Respiratory (inhalation) Remedy Repack 2016-06-09 2016-06-09 US Xopenex Solution 0.63 mg/3mL Respiratory (inhalation) Sunovion 1999-04-01 2016-09-30 US Xopenex Solution 0.63 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 - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Levalbuterol Solution 1.25 mg/3mL Respiratory (inhalation) Teva Pharmaceuticals USA, Inc. 2013-04-29 Not applicable US Levalbuterol Solution 0.63 mg/3mL Respiratory (inhalation) A-S Medication Solutions 2013-04-29 2017-12-21 US Levalbuterol Solution 0.63 mg/3mL Respiratory (inhalation) Proficient Rx LP 2013-04-29 Not applicable US Levalbuterol Solution 0.63 mg/3mL Respiratory (inhalation) Preferred Pharmaceuticals, Inc. 2016-10-24 Not applicable US Levalbuterol Solution, concentrate 1.25 mg/0.5mL Respiratory (inhalation) Teva Pharmaceuticals USA, Inc. 2014-12-16 Not applicable US Levalbuterol Solution 1.25 mg/3mL Respiratory (inhalation) Mylan Pharmaceuticals Inc. 2013-03-15 2019-08-31 US Levalbuterol Solution 0.31 mg/3mL Respiratory (inhalation) Burel Pharmaceuticals, Inc. 2021-04-01 Not applicable US Levalbuterol Solution 1.25 mg/3mL Respiratory (inhalation) Amneal Pharmaceuticals of New York Llc 2016-03-22 Not applicable US Levalbuterol Solution 0.63 mg/3mL Respiratory (inhalation) Aurobindo Pharma Limited 2016-12-30 Not applicable US Levalbuterol Solution 0.31 mg/3mL Respiratory (inhalation) Ritedose Pharmaceuticals, LLC 2016-03-22 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image İPRALEV 20 MCG/50 MCG AEROSOL İNHALASYONU,SÜSPANSİYON, 200 DOZ Levosalbutamol (50 mcg) + Ipratropium bromide monohydrate (20 mcg) Suspension Respiratory (inhalation) CELTİS İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
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 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)
- 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
- 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) / Septic / Shock 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) Powder Respiratory (inhalation) Suspension Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) Solution Respiratory (inhalation) 1.25 mg Suspension Respiratory (inhalation) 65.68 mcg Solution Respiratory (inhalation) 0.31 mg/3mL Aerosol Buccal 50 mcg Solution Respiratory (inhalation) Aerosol; suspension Respiratory (inhalation) 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 US6451289 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
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
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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
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- No
- 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 17:42 / Updated on October 07, 2021 12:09