U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C11H17NO3
Molecular Weight 211.2576
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METAPROTERENOL

SMILES

CC(C)NCC(O)C1=CC(O)=CC(O)=C1

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

1973
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
n = 1120
Health Status: unhealthy
Condition: bronchial asthma
Age Group: adults
Population Size: 1120
Sources:
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
n = 1120
Health Status: unhealthy
Condition: bronchial asthma
Age Group: adults
Population Size: 1120
Sources:
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
n = 1120
Health Status: unhealthy
Condition: bronchial asthma
Age Group: adults
Population Size: 1120
Sources:
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
n = 1120
Health Status: unhealthy
Condition: bronchial asthma
Age Group: adults
Population Size: 1120
Sources:
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
n = 1120
Health Status: unhealthy
Condition: bronchial asthma
Age Group: adults
Population Size: 1120
Sources:
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
n = 1120
Health Status: unhealthy
Condition: bronchial asthma
Age Group: adults
Population Size: 1120
Sources:
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
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
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
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. Usually, treatment need not be repeated more often than every four hours to relieve acute attacks of bronchospasm. As part of a total treatment program in chronic bronchospastic pulmonary diseases, Metaproterenol Sulfate Inhalation Solution may be administered three or four times a day.
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 [WHO-DD]
Common Name English
orciprenaline [INN]
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 Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
NDF-RT N0000009922
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
WHO-ATC R03AB03
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
WHO-ATC R03CB03
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
WHO-VATC QR03CB53
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
NDF-RT N0000175779
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
LIVERTOX 608
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
WHO-VATC QR03CB03
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
WHO-ATC R03CB53
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
Code System Code Type Description
NSC
757089
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
PUBCHEM
4086
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PRIMARY
LACTMED
Metaproterenol
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
FDA UNII
53QOG569E0
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PRIMARY
DRUG CENTRAL
1720
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PRIMARY
ChEMBL
CHEMBL2109143
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PRIMARY
CHEBI
82719
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PRIMARY
WIKIPEDIA
ORCIPRENALINE
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
NCI_THESAURUS
C61834
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID8048529
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
RXCUI
7688
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY RxNorm
EVMPD
SUB03532MIG
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
ALTERNATIVE
ECHA (EC/EINECS)
209-569-1
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PRIMARY
CAS
586-06-1
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
INN
1586
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PRIMARY
MESH
D009921
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
IUPHAR
7250
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PRIMARY
DRUG BANK
DB00816
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
SMS_ID
100000083345
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
EVMPD
SUB09457MIG
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY
MERCK INDEX
m7272
Created by admin on Fri Dec 15 19:01:05 GMT 2023 , Edited by admin on Fri Dec 15 19:01:05 GMT 2023
PRIMARY Merck Index