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Details

Stereochemistry RACEMIC
Molecular Formula C12H20N2O3.C2H4O2
Molecular Weight 300.3508
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRBUTEROL ACETATE

SMILES

CC(O)=O.CC(C)(C)NCC(O)C1=NC(CO)=C(O)C=C1

InChI

InChIKey=QSXMZJGGEWYVCN-UHFFFAOYSA-N
InChI=1S/C12H20N2O3.C2H4O2/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8;1-2(3)4/h4-5,11,13,15-17H,6-7H2,1-3H3;1H3,(H,3,4)

HIDE SMILES / InChI

Molecular Formula C12H20N2O3
Molecular Weight 240.2988
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Fri Dec 15 15:25:35 UTC 2023
Edited
by admin
on Fri Dec 15 15:25:35 UTC 2023
Record UNII
1EH73XKR9N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRBUTEROL ACETATE
MART.   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
SPIROLAIR
Brand Name English
CP-24314-14
Code English
MAXAIR
Brand Name English
PIRBUTEROL ACETATE [USAN]
Common Name English
2,6-PYRIDINEDIMETHANOL, .ALPHA.6-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-3-HYDROXY-, MONOACETATE (SALT)
Common Name English
PIRBUTEROL ACETATE [MART.]
Common Name English
2,6-PYRIDINEDIMETHANOL, .ALPHA.6-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-3-HYDROXY-, ACETATE (1:1)
Common Name English
CP-24,314-14
Code English
PIRBUTEROL MONOACETATE
MI  
Common Name English
α6-[(tert-Butylamino)methyl]-3-hydroxy-2,6-pyridinedimethanol monoacetate (salt)
Common Name English
PIRBUTEROL MONOACETATE [MI]
Common Name English
PIRBUTEROL ACETATE [ORANGE BOOK]
Common Name English
PIRBUTEROL ACETATE [VANDF]
Common Name English
Pirbuterol acetate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
Code System Code Type Description
CAS
65652-44-0
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
FDA UNII
1EH73XKR9N
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
ChEMBL
CHEMBL1094966
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
PUBCHEM
171674
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
RXCUI
221142
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C47675
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID40984214
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
MERCK INDEX
m8872
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY Merck Index
DRUG BANK
DBSALT000799
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
SMS_ID
100000092607
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
265-862-4
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
EVMPD
SUB03867MIG
Created by admin on Fri Dec 15 15:25:35 UTC 2023 , Edited by admin on Fri Dec 15 15:25:35 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY