ALBUTEROL

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H21NO3
Molecular Weight	239.3107
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1

InChI

InChIKey=NDAUXUAQIAJITI-UHFFFAOYSA-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

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020837s036lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/15293593 | https://www.ncbi.nlm.nih.gov/pubmed/10452786

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
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020837s036lbl.pdf	Agonist 2752		236.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15293593 http://adisinsight.springer.com/drugs/800005434	Primary		Approved 8583	XOPENEX Approved Use XOPENEX (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 Date 1999
Chronic obstructive pulmonary disease 175 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15293593 http://adisinsight.springer.com/drugs/800005434	Primary		Approved 8583	XOPENEX Approved Use XOPENEX (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 Date 1999

C_max

Value	Dose	Analyte	Population
1.1 ng/mL DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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
4.5 ng/mL DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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
0.303 ng/mL DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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 DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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
199 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021730s039lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021730s039lbl.pdf	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
163 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021730s039lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021730s039lbl.pdf	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

AUC

Value	Dose	Analyte	Population
3.3 ng × h/mL DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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
17.4 ng × h/mL DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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
1.36 ng × h/mL DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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 DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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
695 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021730s039lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021730s039lbl.pdf	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
579 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021730s039lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021730s039lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.3 h DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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
4 h DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f3ce78d9-e923-400e-b3cd-3e6124ac7f6d&type=display	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
90.55% REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021730s000_PharmR.pdf			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: https://pubmed.ncbi.nlm.nih.gov/16846555/	unhealthy, 4 - 11 years Health Status: unhealthy Age Group: 4 - 11 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16846555/	Disc. AE: Asthma... AEs leading to discontinuation/dose reduction: Asthma (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/16846555/
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: https://pubmed.ncbi.nlm.nih.gov/18219836/	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18219836/	Disc. AE: Bronchitis, Dyspnea... Other AEs: Apparent life threatening event, Bronchitis... AEs leading to discontinuation/dose reduction: Bronchitis (45 patients) Dyspnea (45 patients) Lung disorder (45 patients) Other AEs: Apparent life threatening event (18 patients) 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) Sources: https://pubmed.ncbi.nlm.nih.gov/18219836/

AEs

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1685	http://www.3bsc.com/index/pro_info.php?id=56215
Aurora Fine Chemicals LLC	A24.079.424	http://online.aurorafinechemicals.com/info?ID=A24.079.424
Aurora Fine Chemicals LLC	K16.552.699	http://online.aurorafinechemicals.com/info?ID=K16.552.699
BioChemPartner	BCP28425	http://www.biochempartner.com/34391-04-3-BCP28425
BioSynth	J-019582	https://www.biosynth.com/en/products/all-products/products/J-019582.html
Chem Scene	CS-0013639	http://www.chemscene.com/34391-04-3.html
ChemMol	49408687	http://www.chemmol.com/chemmol/49408687.html
Chemspace	CSSB00000055422	https://chem-space.com/CSSB00000055422
Clearsynth	CS-O-10263	http://www.clearsynth.com/en/CSO10263.html
eNovation Chemicals	D145873	https://www.enovationchem.com/ProductDetails.asp?ProductID=D145873
Hairui	HR126344	http://www.hairuichem.com/en/product/34391-04-3.html
Hairui	HR136879	http://www.hairuichem.com/en/product/51022-70-9.html
iChemical	EBD2321897	http://www.ichemical.com/products/34391-04-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01343705	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343705
MedChem Express	HY-B1675	https://www.medchemexpress.com/levalbuterol.html
Parchem	29245	http://www.parchem.com/chemical-supplier-distributor/Levalbuterol-019245.aspx
Parchem	29262	http://www.parchem.com/chemical-supplier-distributor/Levosalbutamol-Levalbuterol--019262.aspx
Smolecule	S591464	https://www.smolecule.com/products/s591464
Synblock Inc	SB19749	http://www.synblock.com/product/34391-04-3.html
THE BioTek	bt-312097	https://www.thebiotek.com/product/others/bt-312097

PubMed

Title	Date	PubMed
Comparison of racemic albuterol and levalbuterol for treatment of acute asthma.	2003-12	14657817
Mirror images: is levalbuterol the fairest of them all?	2003-12	14657810
Effect of surface covering of lactose carrier particles on dry powder inhalation properties of salbutamol sulfate.	2003-12	14646332
Influence of mechanical activation on the physical stability of salbutamol sulphate.	2003-11	14602182
Changes in heart rate associated with nebulized racemic albuterol and levalbuterol in intensive care patients.	2003-10-01	14531242
Effect of humidity on aerosolization of micronized drugs.	2003-10	14606660
A meta-analysis of randomized controlled trials evaluating the efficacy of epinephrine for the treatment of acute viral bronchiolitis.	2003-10	14557155
Albuterol aerosol delivered via metered-dose inhaler to intubated pediatric models of 3 ages, with 4 spacer designs.	2003-10	14525631
Retrospective comparison of nebulized levalbuterol and albuterol for adverse events in patients with acute airflow obstruction.	2003-09-17	12975718
Effects of carriers and storage of formulation on the lung deposition of a hydrophobic and hydrophilic drug from a DPI.	2003-09-16	12954190
Investigation of the physical properties of spray-dried stabilised lysozyme particles.	2003-09	14604464
Management of the acute exacerbation of asthma.	2003-09	14579990
Levalbuterol is not more cost-effective than albuterol for COPD.	2003-09	12970057
Levalbuterol vs racemic albuterol: science or drug company propaganda?	2003-09	12970056
An evaluation of nebulized levalbuterol in stable COPD.	2003-09	12970007
Urgent adenotonsillectomy: an analysis of risk factors associated with postoperative respiratory morbidity.	2003-09	12960542
Albuterol improves response to levodopa and increases skeletal muscle mass in patients with fluctuating Parkinson disease.	2003-08-05	12897642
Self-hypnosis for anxiety associated with severe asthma: a case report.	2003-07-22	12875663
Characterisation and deposition studies of engineered lactose crystals with potential for use as a carrier for aerosolised salbutamol sulfate from dry powder inhalers.	2003-07	12885385
Levalbuterol is as effective as racemic albuterol in lowering serum potassium.	2003-07	12865102
Three useful bromimetric methods for the determination of salbutamol sulfate.	2003-07	12811447
Planar gamma scintigraphy--points to consider when quantifying pulmonary dry powder aerosol deposition.	2003-06-04	12753769
Levalbuterol: pharmacologic properties and use in the treatment of pediatric and adult asthma.	2003-06	12839314
Levalbuterol toxicity: no reason to be jittery.	2003-06	12797506
(R,S)-salbutamol plasma concentrations in severe asthma.	2003-06	12795782
The influence of carrier and drug morphology on drug delivery from dry powder formulations.	2003-05-12	12711183
Immobilization of fine particles on lactose carrier by precision coating and its effect on the performance of dry powder formulations.	2003-05	12712417
Investigation into the effect of humidity on drug-drug interactions using the atomic force microscope.	2003-04	12661066
A system for the production and delivery of monodisperse salbutamol aerosols to the lungs.	2003-03-26	12623200
Characterisation of surface modified salbutamol sulphate-alkylpolyglycoside microparticles prepared by spray drying.	2003-03-06	12593937
Characterization of particle-interactions by atomic force microscopy: effect of contact area.	2003-03	12669976
The effect of mechanical processing on surface stability of pharmaceutical powders: visualization by atomic force microscopy.	2003-03	12587123
Managing outpatient asthma exacerbations.	2003-03	12562559
Single-isomer levalbuterol: a review of the acute data.	2003-03	12562558
Influence of physico-chemical carrier properties on the in vitro aerosol deposition from interactive mixtures.	2003-02-18	12550784
Prospective observational cohort safety study to monitor the introduction of a non-CFC formulation of salbutamol with HFA134a in England.	2003-02	12607629
Effect of aerosolized albuterol sulfate on resting energy expenditure determined by use of open-flow indirect calorimetry in horses with recurrent airway obstruction.	2003-02	12602595
Launois-Bensaude syndrome in a female with type 2 diabetes.	2003-02	12601297
Planar gamma scintigraphy--points to consider when quantifying pulmonary dry powder aerosol deposition.	2003-01-30	12527173
Metabolism of salbutamol differs between asthmatic patients and healthy volunteers.	2003-01	12710594
Levalbuterol compared to racemic albuterol: efficacy and outcomes in patients hospitalized with COPD or asthma.	2003-01	12527613
Preparation of dry powder inhalation by surface treatment of lactose carrier particles.	2003-01	12520118
Novolizer: a multidose dry powder inhaler.	2003	14609355
Investigation of processing parameters of spray freezing into liquid to prepare polyethylene glycol polymeric particles for drug delivery.	2003	12916894
Salbutamol sulfate suppositories: influence of formulation on physical parameters and stability.	2003	12665194
Application of the chiral acyl anion equivalent, trans-1,3-dithiane 1,3-dioxide, to an asymmetric synthesis of (R)-salbutamol.	2002-11-29	12444646
In vitro evaluation of the release of albuterol sulfate from polymer gels: effect of fatty acids on drug transport across biological membranes.	2002-11	12476868
The effect of heliox-driven bronchodilator aerosol therapy on pulmonary function tests in patients with asthma.	2002-10	12442956
Comparison of innovator and generic salbutamol inhalers: a double-blind randomized study of efficacy and tolerance.	2002	12837043
Apparent ELISA detection times for albuterol after administration with the torpex equine inhaler device.	2002	12447838

Patents

Sample Use Guides

In Vivo Use Guide

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

Unknown

Name

Type

Language

SALBUTAMOL

Preferred Name

English

ALBUTEROL

Official Name

English

1,3-BENZENEDIMETHANOL, .ALPHA.(SUP 1)-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-4-HYDROXY-

Common Name

English

ALBUTEROL [ORANGE BOOK]

Common Name

English

ALBUTEROL [HSDB]

Common Name

English

SALBUTAMOL [EP IMPURITY]

Common Name

English

VENTOLINE

Common Name

English

ETINOLINE

Common Name

English

salbutamol [INN]

Common Name

English

ALBUTEROL [USAN]

Common Name

English

ALBUTEROL [USP MONOGRAPH]

Common Name

English

ALBUTEROL [USP-RS]

Common Name

English

SALBUTAMOL [EP MONOGRAPH]

Common Name

English

SALBUTAMOL [WHO-IP]

Common Name

English

SCH 13949W

Code

English

SALBUTAMOL [MART.]

Common Name

English

NSC-757417

Code

English

Salbutamol [WHO-DD]

Common Name

English

(±)-1,3-BENZENEDIMETHANOL, .ALPHA.(SUP 1)-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-4-HYDROXY-

Common Name

English

ALBUTEROL [MI]

Common Name

English

ALBUTEROL [VANDF]

Common Name

English

SCH-13949W

Code

English

SALBUTAMOLUM [WHO-IP LATIN]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548685