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Details

Stereochemistry RACEMIC
Molecular Formula 2C11H17NO3.H2O4S
Molecular Weight 520.5956
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of (+/-)-3,5-DIHYDROXY-.ALPHA.-((ISOPROPYLAMINO)METHYL)BENZYL ALCOHOL SULFATE (2:1)

SMILES

CC(C)NCC(c1cc(cc(c1)O)O)O.CC(C)NCC(c1cc(cc(c1)O)O)O.OS(=O)(=O)O

InChI

InChIKey=MKFFGUZYVNDHIH-UHFFFAOYSA-N
InChI=1S/2C11H17NO3.H2O4S/c2*1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8;1-5(2,3)4/h2*3-5,7,11-15H,6H2,1-2H3;(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula C11H17NO3
Molecular Weight 211.258
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula H2O4S
Molecular Weight 98.0796
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1.12924803E11
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
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. 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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:55:43 UTC 2021
Edited
by admin
on Fri Jun 25 20:55:43 UTC 2021
Record UNII
GJ20H50YF0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(+/-)-3,5-DIHYDROXY-.ALPHA.-((ISOPROPYLAMINO)METHYL)BENZYL ALCOHOL SULFATE (2:1)
Systematic Name English
METAPROTERENOL SULFATE [USP]
Common Name English
METAPROTERENOL SULFATE [USP MONOGRAPH]
Common Name English
ORCIPRENALINE SULFATE [MART.]
Common Name English
TH-152
Code English
(+/-)-3,5-DIHYDROXY-.ALPHA.-((ISOPROPYLAMINO)METHYL)BENZYL ALCOHOL SULPHATE (2:1)
Systematic Name English
METAPROTERENOL SULFATE [ORANGE BOOK]
Common Name English
ORCIPRENALINE SULFATE [EP MONOGRAPH]
Common Name English
1,3-BENZENEDIOL, 5-(1-HYDROXY-2-(1-METHYLETHYL)AMINO)ETHYL-, (+/-)-, SULPHATE (2:1) (SALT)
Common Name English
ORCIPRENALINE SULFATE
EP   MART.   WHO-DD  
Common Name English
METAPROTERENOL SULFATE [USP-RS]
Common Name English
ORCIPRENALINE SULPHATE
Common Name English
1,3-BENZENEDIOL, 5-(1-HYDROXY-2-(1-METHYLETHYL)AMINO)ETHYL-, (+/-)-, SULFATE (2:1) (SALT)
Common Name English
ALUPENT
Brand Name English
METAPROTERENOL SULFATE [VANDF]
Common Name English
METAPROTERENOL SULPHATE
Common Name English
METAPROTERENOL SULFATE [USAN]
Common Name English
PROMETA
Brand Name English
ORCIPRENALINE SULFATE [JAN]
Common Name English
METAPROTERENOL SULFATE [MI]
Common Name English
ORCIPRENALINE SULFATE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C319
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL776
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
MERCK INDEX
M7272
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY Merck Index
CAS
5874-97-5
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
DRUG BANK
DBSALT000295
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
RXCUI
6804
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
227-539-6
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
USP_CATALOG
1395500
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY USP-RS
FDA UNII
GJ20H50YF0
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
PUBCHEM
441333
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
EVMPD
SUB03533MIG
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
NCI_THESAURUS
C47605
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
EPA CompTox
5874-97-5
Created by admin on Fri Jun 25 20:55:43 UTC 2021 , Edited by admin on Fri Jun 25 20:55:43 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY