LEVALBUTEROL TARTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C13H21NO3.C4H6O6
Molecular Weight	628.7083
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(C)(C)NC[C@H](O)C1=CC(CO)=C(O)C=C1.CC(C)(C)NC[C@H](O)C2=CC(CO)=C(O)C=C2

InChI

InChIKey=VNVNZKCCDVFGAP-FPDJQMMJSA-N

InChI=1S/2C13H21NO3.C4H6O6/c2*1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15;5-1(3(7)8)2(6)4(9)10/h2*4-6,12,14-17H,7-8H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t2*12-;1-,2-/m001/s1

HIDE SMILES / InChI

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C13H21NO3
Molecular Weight	239.3107
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

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

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...

Showing 1 to 2 of 2 entries

Previous1Next

AEs

Show entries

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

Showing 1 to 5 of 16 entries

Previous1 2 3 4Next

Sourcing

Sourcing

Show entries

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

Showing 1 to 5 of 20 entries

Previous1 2 3 4Next

PubMed

Show entries

Title	Date	PubMed
(S)-albuterol increases the production of histamine and IL-4 in mast cells.	2001 Apr	11340331
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
A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism.	2001 Jul	11447392
Definition of a solvent system for spherical crystallization of salbutamol sulfate by quasi-emulsion solvent diffusion (QESD) method.	2001 Oct	11745720

Showing 1 to 5 of 26 entries

Previous1 2 3 4 5 6Next

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
Record UNII	ADS4I3E22M
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

LEVOSALBUTAMOL TARTRATE

Preferred Name

English

LEVALBUTEROL TARTRATE

Official Name

English

Levosalbutamol tartrate [WHO-DD]

Common Name

English

LEVALBUTEROL TARTRATE [ORANGE BOOK]

Common Name

English

LEVOSALBUTAMOL TARTRATE [MART.]

Common Name

English

Showing 1 to 5 of 8 entries

Previous1 2Next

Show entries

Classification Tree

Code System

Code

Adrenergic Agonist

NCI_THESAURUS

C48149

Anti-asthmatic Agent

NCI_THESAURUS

C319

Showing 1 to 2 of 2 entries

Previous1Next

Show entries

Code System

Code

Type

Description

RXCUI

487066

PRIMARY

RxNorm

ChEMBL

CHEMBL1002

PRIMARY

USAN

QQ-74

PRIMARY

NCI_THESAURUS

C66003

PRIMARY

CAS

661464-94-4

PRIMARY

Showing 1 to 5 of 12 entries

Previous1 2 3Next

Show entries

Related Record

Type

Details


					W4888I119H

Tartaric Acid

PARENT -> SALT/SOLVATE


					EDN2NBH5SS

LEVALBUTEROL

PARENT -> SALT/SOLVATE

Showing 1 to 2 of 2 entries

Previous1Next

Show entries

Related Record

Type

Details


					ZLD7GSP3RV

N-nitroso-levalbuterol

IMPURITY -> PARENT

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

Show entries

Related Record

Type

Details


					EDN2NBH5SS

LEVALBUTEROL

ACTIVE MOIETY

Showing 1 to 1 of 1 entries

Previous1Next

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound