LEVALBUTEROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H21NO3
Molecular Weight	239.3107
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1

InChI

InChIKey=NDAUXUAQIAJITI-LBPRGKRZSA-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/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C13H21NO3
Molecular Weight	239.3107
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 203 Target ID: CHEMBL210 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020837s036lbl.pdf	Agonist 2678		236.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15293593 http://adisinsight.springer.com/drugs/800005434	Primary		Approved 8429	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 174 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15293593 http://adisinsight.springer.com/drugs/800005434	Primary		Approved 8429	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
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

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 n = 76 Health Status: unhealthy Condition: Asthma Age Group: 4 - 11 years Sex: M+F Population Size: 76 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 n = 496 Health Status: unhealthy Condition: Asthma Age Group: > 12 years Sex: M+F Population Size: 496 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
Hairui	HR126344	http://www.hairuichem.com/en/product/34391-04-3.html
Hairui	HR136879	http://www.hairuichem.com/en/product/51022-70-9.html
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
eNovation Chemicals	D145873	https://www.enovationchem.com/ProductDetails.asp?ProductID=D145873
iChemical	EBD2321897	http://www.ichemical.com/products/34391-04-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Differential inhibition of human liver and duodenum sulphotransferase activities by quercetin, a flavonoid present in vegetables, fruit and wine.	2001 Dec	11780759
Low-dose levalbuterol in children with asthma: safety and efficacy in comparison with placebo and racemic albuterol.	2001 Dec	11742271
The pharmacokinetics of levosalbutamol: what are the clinical implications?	2001 Jan	11236808
Randomized comparison of a dry powder inhaler and metered dose inhaler with spacer in management of children with asthma.	2001 Jan	11175930
Human adult and foetal liver sulphotransferases: inhibition by mefenamic acid and salicylic acid.	2001 Mar	11465392
Single-isomer beta-agonists.	2001 Mar	11253864
Long-acting beta2-agonist monotherapy vs continued therapy with inhaled corticosteroids in patients with persistent asthma: a randomized controlled trial.	2001 May 23-30	11368732
Formulation and evaluation of controlled-release transdermal patches of theophylline-salbutamol sulfate.	2001 Nov	11794808
The therapeutic ratio of R-albuterol is comparable with that of RS-albuterol in asthmatic patients.	2001 Nov	11692096
Comparison of innovator and generic salbutamol inhalers: a double-blind randomized study of efficacy and tolerance.	2002	12837043
The effect of alkylpolyglycoside surfactants on the crystallization of spray-dried salbutamol sulphate: a GravimetricNear-Infrared Spectroscopy Study.	2002	12423065
[Pharmacodynamics of inhalation broncholytic agents introduced in a single dose by nebulizer in patients with severe exacerbation of bronchial asthma].	2002	11980113
Comparative efficacy of levalbuterol and racemic albuterol in the treatment of asthma.	2002 Aug	12170276
A novel approach to the pulmonary delivery of liposomes in dry powder form to eliminate the deleterious effects of milling.	2002 Feb	11835207
Bronchodilating effects of salbutamol from a novel inhaler Airmax.	2002 Jul	12194632
[Clinical effect and mechanism of nitroglycerin patch on arresting preterm labor].	2002 Mar	11953077
Adhesion of powders for inhalation: an evaluation of drug detachment from surfaces following deposition from aerosol streams.	2002 Mar	11934240
Modulation of T-cell function by (R)- and (S)-isomers of albuterol: anti-inflammatory influences of (R)-isomers are negated in the presence of the (S)-isomer.	2002 Mar	11897990
A facile method of delivery of liposomes by nebulization.	2002 Nov 7	12399169
The influence of relative humidity on particulate interactions in carrier-based dry powder inhaler formulations.	2002 Oct 10	12270608
Effect of levalbuterol on prehospital patient parameters.	2002 Sep	12216049
Influence of excipients, drugs, and osmotic agent in the inner core on the time-controlled disintegration of compression-coated ethylcellulose tablets.	2002 Sep	12210050
Investigation of processing parameters of spray freezing into liquid to prepare polyethylene glycol polymeric particles for drug delivery.	2003	12916894
Investigation into the effect of humidity on drug-drug interactions using the atomic force microscope.	2003 Apr	12661066
Comparison of racemic albuterol and levalbuterol for treatment of acute asthma.	2003 Dec	14657817
Mirror images: is levalbuterol the fairest of them all?	2003 Dec	14657810
Influence of physico-chemical carrier properties on the in vitro aerosol deposition from interactive mixtures.	2003 Feb 18	12550784
Levalbuterol compared to racemic albuterol: efficacy and outcomes in patients hospitalized with COPD or asthma.	2003 Jan	12527613
Preparation of dry powder inhalation by surface treatment of lactose carrier particles.	2003 Jan	12520118
Planar gamma scintigraphy--points to consider when quantifying pulmonary dry powder aerosol deposition.	2003 Jan 30	12527173
Characterisation and deposition studies of engineered lactose crystals with potential for use as a carrier for aerosolised salbutamol sulfate from dry powder inhalers.	2003 Jul	12885385
Levalbuterol is as effective as racemic albuterol in lowering serum potassium.	2003 Jul	12865102
Albuterol improves response to levodopa and increases skeletal muscle mass in patients with fluctuating Parkinson disease.	2003 Jul-Aug	12897642
Levalbuterol toxicity: no reason to be jittery.	2003 Jun	12797506
Planar gamma scintigraphy--points to consider when quantifying pulmonary dry powder aerosol deposition.	2003 Jun 4	12753769
Characterization of particle-interactions by atomic force microscopy: effect of contact area.	2003 Mar	12669976
The effect of mechanical processing on surface stability of pharmaceutical powders: visualization by atomic force microscopy.	2003 Mar	12587123
Characterisation of surface modified salbutamol sulphate-alkylpolyglycoside microparticles prepared by spray drying.	2003 Mar 6	12593937
The influence of carrier and drug morphology on drug delivery from dry powder formulations.	2003 May 12	12711183
Albuterol aerosol delivered via metered-dose inhaler to intubated pediatric models of 3 ages, with 4 spacer designs.	2003 Oct	14525631
Effects of carriers and storage of formulation on the lung deposition of a hydrophobic and hydrophilic drug from a DPI.	2003 Sep 16	12954190

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:45:21 GMT 2023` Edited by `admin` on `Fri Dec 15 15:45:21 GMT 2023`
Record UNII	EDN2NBH5SS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVALBUTEROL

Common Name

English

Levosalbutamol [WHO-DD]

Common Name

English

LEVALBUTEROL [VANDF]

Common Name

English

ALBUTEROL (R)-FORM [MI]

Common Name

English

ASF-1096

Code

English

LEVOSALBUTAMOL

Official Name

English

R-SALBUTAMOL

Common Name

English

levosalbutamol [INN]

Common Name

English

(R)-.ALPHA.(SUP 1)-((TERT-BUTYLAMINO)METHYL)-4-HYDROXY-M-XYLENE-.ALPHA.,.ALPHA.'-DIOL

Common Name

English

LEVOSALBUTAMOL [MART.]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175779