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Details

Stereochemistry RACEMIC
Molecular Formula C12H20N2O3
Molecular Weight 240.2993
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRBUTEROL

SMILES

CC(C)(C)NCC(c1ccc(c(CO)n1)O)O

InChI

InChIKey=VQDBNKDJNJQRDG-UHFFFAOYSA-N
InChI=1S/C12H20N2O3/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8/h4-5,11,13,15-17H,6-7H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C12H20N2O3
Molecular Weight 240.2993
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Pirbuterol (trade name Maxair) is a short-acting β2 adrenoreceptor agonist with bronchodilating action used in the treatment of asthma. The pharmacologic effects of beta-adrenergic agonist drugs, including pirbuterol, are at least in proof attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells. Pirbuterol is used in asthma for reversal of acute bronchospasm, and also as a maintenance medication to prevent future attacks. It should be used in patients 12 years of age and older with or without concurrent theophylline and/or inhaled corticosteroid. After inhalation of doses up to 800 μg (twice the maximum recommended dose) systemic blood levels of pirbuterol are below the limit of assay sensitivity (2–5 ng/ml). A mean of 51% of the dose is recovered in urine as pirbuterol plus its sulfate conjugate following administration by aerosol. Pirbuterol is not metabolized by catechol-O-methyltransferase.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAXAIR

Approved Use

Unknown

Launch Date

5.36284791E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.2 μg/L
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
9.8 μg/L
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRBUTEROL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
400 ug single, respiratory
Dose: 400 ug
Route: respiratory
Route: single
Dose: 400 ug
Sources:
unhealthy, 32 years (range: 21-56 years)
n = 14
Health Status: unhealthy
Condition: asthma
Age Group: 32 years (range: 21-56 years)
Sex: M+F
Population Size: 14
Sources:
40 mg 1 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 62 years (range 42-71 years)
n = 26
Health Status: unhealthy
Condition: chronic heart failure
Age Group: 62 years (range 42-71 years)
Sex: M+F
Population Size: 26
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Bronchospasm, prevention and treatment: Inhalation: 1 to 2 inhalations (200mcg) every 4 to 6 hours; not to exceed 12 inhalations daily. Patients should be advised to promptly consult healthcare provider or seek medical attention if no relief from acute treatment
Route of Administration: Respiratory
MDA-MB-231, SF-539, ACHN, A-549, HCT-116, SNB-19 were used for activity evaluation. Cells (1x10^5) were plated in 60mm dishes and treated with various doses of ARA-211 (Pirbuterol) or vehicle for 48 h. Apoptosis was analysed using the Cell Death Detection ELISA (Roche, Indianapolis, IN, USA) measuring cytoplasmic histoneassociated mono- and oligonucleosome DNA fragments.
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:26:50 UTC 2021
Edited
by admin
on Sat Jun 26 01:26:50 UTC 2021
Record UNII
OG645J8RVW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRBUTEROL
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
ARA-211
Code English
2,6-PYRIDINEDIMETHANOL, .ALPHA.6-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-3-HYDROXY-
Common Name English
PIRBUTEROL [MI]
Common Name English
(RS)-6-(2-(TERT-BUTYLAMINO)-1-HYDROXYETHYL)-2-(HYDROXYMETHYL)PYRIDIN-3-OL
Systematic Name English
PIRBUTEROL [INN]
Common Name English
(+/-)-PIRBUTEROL
Common Name English
PIRBUTEROL [VANDF]
Common Name English
.ALPHA.6-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-3-HYDROXY-2,6-PYRIDINEDIMETHANOL
Common Name English
PIRBUTEROL [WHO-DD]
Common Name English
PIRBUTEROL [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC R03CC07
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
WHO-VATC QR03AC08
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
NDF-RT N0000009922
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
NCI_THESAURUS C319
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
WHO-VATC QR03CC07
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
LIVERTOX PIRBUTEROL
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
WHO-ATC R03AC08
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
NDF-RT N0000175779
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
Code System Code Type Description
IUPHAR
7272
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
EPA CompTox
38677-81-5
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
RXCUI
33767
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY RxNorm
EVMPD
SUB09900MIG
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL1094966
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
DRUG CENTRAL
2199
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
PUBCHEM
4845
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
CAS
38677-81-5
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
MESH
C009118
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
WIKIPEDIA
Pirbuterol
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
MERCK INDEX
M8872
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY Merck Index
FDA UNII
OG645J8RVW
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
NCI_THESAURUS
C61893
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
LACTMED
Pirbuterol
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
DRUG BANK
DB01291
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
CAS
77145-72-3
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
SUPERSEDED
INN
3477
Created by admin on Sat Jun 26 01:26:50 UTC 2021 , Edited by admin on Sat Jun 26 01:26:50 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC