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

SMILES

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

Description

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	Agonist 2,752		236.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244	Primary		Approved 8,583	XOPENEX
Chronic obstructive pulmonary disease 175	Primary		Approved 8,583	XOPENEX

C_max

Value	Dose	Analyte	Population
1.1 ng/mL	1.25 mg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
4.5 ng/mL	1.25 mg 4 times / 2 hours multiple, respiratory	LEVALBUTEROL plasma	Homo sapiens
0.303 ng/mL	0.31 mg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
0.521 ng/mL	0.63 mg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
199 pg/mL	90 μg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
238 pg/mL	180 μg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
163 pg/mL	90 μg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
238 pg/mL	180 μg single, respiratory	LEVALBUTEROL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
3.3 ng × h/mL	1.25 mg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
17.4 ng × h/mL	1.25 mg 4 times / 2 hours multiple, respiratory	LEVALBUTEROL plasma	Homo sapiens
1.36 ng × h/mL	0.31 mg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
2.55 ng × h/mL	0.63 mg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
695 pg × h/mL	90 μg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
798 pg × h/mL	180 μg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
579 pg × h/mL	90 μg single, respiratory	LEVALBUTEROL plasma	Homo sapiens
828 pg × h/mL	180 μg single, respiratory	LEVALBUTEROL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.3 h	1.25 mg single, respiratory		LEVALBUTEROL plasma	Homo sapiens
4 h	1.25 mg 4 times / 2 hours multiple, respiratory		LEVALBUTEROL plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
90.55%			LEVALBUTEROL plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
90 ug 1 times / day steady, respiratory Recommended	unhealthy, 4 - 11 years	Disc. AE: Asthma...
90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years	Disc. AE: Bronchitis, Dyspnea... Other AEs: Apparent life threatening event, Bronchitis...

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AEs

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AE	Significance	Dose	Population
Asthma	1 patient Disc. AE	90 ug 1 times / day steady, respiratory Recommended	unhealthy, 4 - 11 years
Bronchitis	131 patient	90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years
Dyspnea	131 patient	90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years
Lung disorder	131 patient	90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years
Apparent life threatening event	18 patients	90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Comparison of the effectiveness of inhaler devices in asthma and chronic obstructive airways disease: a systematic review of the literature.	2001	11701099
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
The use of lactose recrystallised from carbopol gels as a carrier for aerosolised salbutamol sulphate.	2001 Jan	11154904

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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

Show entries

Name

Type

Language

LEVALBUTEROL

Common Name

English

LEVOSALBUTAMOL

Preferred Name