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

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

Molecular Formula	C13H21NO3
Molecular Weight	239.3107
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 203	Agonist 2,678		236.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241	Primary		Approved 8,429	XOPENEX
Chronic obstructive pulmonary disease 174	Primary		Approved 8,429	XOPENEX

C_max

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

AUC

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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4 h	1.25 mg 4 times / 2 hours multiple, respiratory		LEVALBUTEROL plasma	Homo sapiens
3.3 h	1.25 mg single, 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 n = 76	Disc. AE: Asthma...
90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years n = 496	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 n = 76
Bronchitis	131 patient	90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years n = 496
Dyspnea	131 patient	90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years n = 496
Lung disorder	131 patient	90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years n = 496
Apparent life threatening event	18 patients	90 ug 4 times / day steady, respiratory Studied dose	unhealthy, > 12 years n = 496

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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
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
Factors affecting the efficiency of aerosol therapy with pressurised metered-dose inhalers through plastic spacers.	2001 Jan 12	11205181
A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism.	2001 Jul	11447392
Use of solid corrugated particles to enhance powder aerosol performance.	2001 Nov	11758765

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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

Substance Class	Chemical
Record UNII	QF8SVZ843E
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

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

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Classification Tree

Code System

Code

Asthma

LIVERTOX

NBK548685

Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics

WHO-ATC

R03AK13

Selective beta-2-adrenoreceptor agonists

WHO-VATC

QR03CC02

Selective beta-2-adrenoreceptor agonists

WHO-ATC

R03AC02

Anti-asthmatic Agent

NCI_THESAURUS

C319

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Code System

Code

Type

Description

WHO INTERNATIONAL PHARMACOPEIA

ALBUTEROL

PRIMARY

Description: A white or almost white, crystalline powder; odourless. Solubility: Soluble in 70 parts of water; soluble in ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Antiasthmatic drug. Storage: Salbutamol should be kept in a well-closed container, protected from light. Definition: Salbutamol contains not less than 98.0% and not more than 101.0% of C13H21NO3, calculated with reference to the dried substance.

EVMPD

SUB10422MIG

PRIMARY

PUBCHEM

2083

PRIMARY

SMS_ID

100000091629

PRIMARY

DRUG CENTRAL

105

PRIMARY

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Related Record

Type

Details


					E39FUD9DLJ

SULFOTRANSFERASE 1A3

METABOLIC ENZYME -> SUBSTRATE

Amount:


					021SEF3731

ALBUTEROL SULFATE

SALT/SOLVATE -> PARENT

Amount:


					289U58VGDE

ALBUTEROL ADIPATE DIETHANOLATE

SALT/SOLVATE -> PARENT

Amount:


					QF8SVZ843E

ALBUTEROL

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (TITRATION)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [98 to 101] WEIGHT PERCENT (limits)


					P12862PDAK

ALBUTEROL HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Amount:

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Related Record

Type

Details


					2CX9CN85QM

ALBUTEROL-4-SULFATE, (+/-)-

METABOLITE -> PARENT

Interaction Type:

IN-VIVO

Qualification:

URINE


					EO86K90G5U

ALBUTEROL-4-SULFATE, (S)-

METABOLITE INACTIVE -> PARENT

Comments:

catalysed almost exclusively by sulphotransferase (SULT) 1A3

Amount:


					38DWL97D64

LEVALBUTEROL-4-O-SULPHATE

METABOLITE -> PARENT

Comments:

catalysed almost exclusively by sulphotransferase (SULT) 1A3

Interaction Type:

MAJOR

Qualification:

PLASMA

Amount:

Showing 1 to 3 of 3 entries

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Related Record

Type

Details


					97BD6L3N4P

(2-(Benzyloxy)phenyl)methanol

IMPURITY -> PARENT


					DBE2T7A8M8

1-(4-(Benzyloxy)phenyl)-2-bromoethanone

IMPURITY -> PARENT


					4RM5R3DQXG

T-BUTYLNORSYNEPHRINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<0.3] PERCENT PEAK AREA (limits)


					2092ANO5GJ

4-BENZYL ALBUTEROL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<0.3] PERCENT PEAK AREA (limits)


					FJF9ZQJ4US

Methyl 3-acetyl-6-(benzyloxy)-2-hydroxybenzoate

IMPURITY -> PARENT

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Related Record

Type

Details


					QF8SVZ843E

ALBUTEROL

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	3.4 Liters/Kilogram (average)

ORAL BIOAVAILABILITY	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT ADMINISTERED [<20] % (average) NEBULIZED INHALATION	ORAL, EXTENDED-RELEASE TABLET PHARMACOKINETIC MOLE PERCENT OF AMOUNT ADMINISTERED 100 % (average) RELATIVE TO IMMEDIATE-RELEASE TABLET

Tmax	PHARMACOKINETIC	[2 to 6] hours (average) ORAL	HYDROFLUOROALKANE (HFA) INHALER PHARMACOKINETIC [0.42 to 3.05] hours (average) CHLOROFLUOROCARBON INHALER PHARMACOKINETIC 0.17 hours (average) NEBULIZER PHARMACOKINETIC 0.5 hours (average) DRY POWDER METERED DOSE INHALER PHARMACOKINETIC 2.48 hours (average)

Biological Half-life	PHARMACOKINETIC	[2.7 to 5] hours (average)

Volume of Distribution	PHARMACOKINETIC	156 LITERS [118 to 194] (average)

MAXIMUM TOLERATED DOSE	TOXICITY	8 mg/day (average) ORAL SYRUP AND TABLET	EXTENDED-RELEASE TABLET PHARMACOKINETIC 16 mg (average) EVERY 12 HOURS

Biological Half-life	PHARMACOKINETIC	9.3 hours (average) ORAL, EXTENDED-RELEASE TABLET	ORAL, INHALATION PHARMACOKINETIC [4.6 to 6] hours (average) ORAL, TABLET AND SYRUP PHARMACOKINETIC [5 to 7.2] hours (average)

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