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Details

Stereochemistry RACEMIC
Molecular Formula C11H17NO3
Molecular Weight 211.258
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METAPROTERENOL

SMILES

CC(C)NCC(c1cc(cc(c1)O)O)O

InChI

InChIKey=LMOINURANNBYCM-UHFFFAOYSA-N
InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3

HIDE SMILES / InChI
Metaproterenol, also known as Orciprenaline, is a brochodilator that is FDA approved for the treatment of bronchial asthma and for reversible bronchospasm which may occur in association with bronchitis and emphysema. Metaproterenol Sulfate is a potent beta-adrenergic stimulator with a rapid onset of action. It is postulated that beta-adrenergic stimulants produce many of their pharmacological effects by activation of adenyl cyclase, the enzyme which catalyzes the conversion of adrenosine triphosphate to cyclic adenosine monosphosphate. Metaproterenol is a moderately selective beta(2)-adrenergic agonist that stimulates receptors of the smooth muscle in the lungs, uterus, and vasculature supplying skeletal muscle, with minimal or no effect on alpha-adrenergic receptors.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Metaproterenol

Approved Use

Metaproterenol Sulfate Inhalation Solution is indicated as a bronchodilator for bronchial asthma and for reversible bronchospasm which may occur in association with bronchitis and emphysema.

Launch Date

112924800000
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.1 h
single, oral
METAPROTERENOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mL 3 times / day multiple, oral
Dose: 10 mL, 3 times / day
Route: oral
Route: multiple
Dose: 10 mL, 3 times / day
Sources:
unhealthy, adults
Other AEs: Tachycardia, Headache...
Other AEs:
Tachycardia (6.1%)
Headache (1.1%)
Nervousness (4.8%)
Nausea (1.3%)
Tremor (1.6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Headache 1.1%
10 mL 3 times / day multiple, oral
Dose: 10 mL, 3 times / day
Route: oral
Route: multiple
Dose: 10 mL, 3 times / day
Sources:
unhealthy, adults
Nausea 1.3%
10 mL 3 times / day multiple, oral
Dose: 10 mL, 3 times / day
Route: oral
Route: multiple
Dose: 10 mL, 3 times / day
Sources:
unhealthy, adults
Tremor 1.6%
10 mL 3 times / day multiple, oral
Dose: 10 mL, 3 times / day
Route: oral
Route: multiple
Dose: 10 mL, 3 times / day
Sources:
unhealthy, adults
Nervousness 4.8%
10 mL 3 times / day multiple, oral
Dose: 10 mL, 3 times / day
Route: oral
Route: multiple
Dose: 10 mL, 3 times / day
Sources:
unhealthy, adults
Tachycardia 6.1%
10 mL 3 times / day multiple, oral
Dose: 10 mL, 3 times / day
Route: oral
Route: multiple
Dose: 10 mL, 3 times / day
Sources:
unhealthy, adults
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [Km 780.5 uM]
PubMed

PubMed

TitleDatePubMed
Intravenous isoprenaline and orciprenaline as a guide to the drug treatment of Stokes-Adams attacks.
1968 Feb 17
Myocardial necrosis in the rat: a comparison between isoprenaline, orciprenaline, salbutamol and terbutaline.
1973
Comparison of fenoterol and orciprenaline with regard to broncho-dilating action and beta 2-selectivity.
1980
Objective and subjective tremor responses to oral beta 2 agents on first exposure. A comparison of metaproterenol and terbutaline.
1982 Oct
Combination low-dose metaproterenol-theophylline therapy in asthma.
1983
Bronchodilator and side effects of different modes of administration of metaproterenol: inhaled, oral, and in combination.
1986 Mar
Bronchodilator effects of oral metaproterenol sulfate in preschool children with asthma.
1987 Jan
Hypokalemia induced by inhaled bronchodilators.
1988 Oct
Bradycardia due to biperiden.
1989 Jan
Case of psychosis due to prednisone-clarithromycin interaction.
1998 Sep
Chronic beta-adrenoreceptor stimulation in vivo decreased Bcl-2 and increased Bax expression but did not activate apoptotic pathways in mouse heart.
2004 Mar
Pleiotropic beta-agonist-promoted receptor conformations and signals independent of intrinsic activity.
2007 Feb
Synthesis, pharmacological and in silico evaluation of 1-(4-di-hydroxy-3,5-dioxa-4-borabicyclo[4.4.0]deca-7,9,11-trien-9-yl)-2-(tert-butylamino)ethanol, a compound designed to act as a beta2 adrenoceptor agonist.
2009 Jul
Biomarker panel of cardiac and skeletal muscle troponins, fatty acid binding protein 3 and myosin light chain 3 for the accurate diagnosis of cardiotoxicity and musculoskeletal toxicity in rats.
2012 Dec 16
Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies.
2013 Oct
Patents

Patents

Sample Use Guides

Metaproterenol Sulfate Inhalation Solution is for administration with the aid of an intermittent positive pressure breathing apparatus (IPPB) or air driven nebulizer. The usual adult dose is one vial per nebulization treatment. Each vial of 0.4% is equivalent to 0.2 mL Metaproterenol Sulfate Inhalation Solution 5% diluted 2.5 mL with Normal Saline. Each vial of 0.6% is equivalent to 0.3 mL Metaproterenol Sulfate Inhalation Solution 5% diluted to 2.5 mL with Normal Saline.
Route of Administration: Respiratory
In Vitro Use Guide
Metaproterenol (10(-4), 10(-5) and 10(-6)M) significantly inhibited the in vitro development of memory CTL activity of young mice.
Name Type Language
METAPROTERENOL
MI   VANDF  
Common Name English
ORCIPRENALINE
INN   WHO-DD  
INN  
Official Name English
METAPROTERENOL [MI]
Common Name English
ORCIPRENALINE [INN]
Common Name English
ORCIPRENALINE [WHO-DD]
Common Name English
METAPROTERENOL [VANDF]
Common Name English
NSC-757089
Code English
(RS)-1-(3,5-DIHYDROXYPHENYL)-2-ISOPROPYLAMINOETHANOL
Systematic Name English
Classification Tree Code System Code
WHO-VATC QR03AB03
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
NDF-RT N0000009922
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
WHO-ATC R03AB03
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
WHO-ATC R03CB03
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
WHO-VATC QR03CB53
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
NCI_THESAURUS C319
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
NDF-RT N0000175779
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
LIVERTOX 608
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
WHO-VATC QR03CB03
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
WHO-ATC R03CB53
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
Code System Code Type Description
PUBCHEM
4086
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
LACTMED
Metaproterenol
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
FDA UNII
53QOG569E0
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
DRUG CENTRAL
1720
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL2109143
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
WIKIPEDIA
ORCIPRENALINE
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
NCI_THESAURUS
C61834
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
EPA CompTox
586-06-1
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
RXCUI
7688
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY RxNorm
EVMPD
SUB03532MIG
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
ALTERNATIVE
ECHA (EC/EINECS)
209-569-1
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
CAS
586-06-1
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
INN
1586
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
MESH
D009921
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
IUPHAR
7250
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
DRUG BANK
DB00816
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
EVMPD
SUB09457MIG
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY
MERCK INDEX
M7272
Created by admin on Fri Jun 25 21:51:42 UTC 2021 , Edited by admin on Fri Jun 25 21:51:42 UTC 2021
PRIMARY Merck Index