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
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
| Molecular Formula | C11H17NO3 |
| Molecular Weight | 211.2576 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 4.81 µM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Metaproterenol Approved UseMetaproterenol 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 Date1973 |
Doses
| Dose | Population | Adverse 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 Health Status: unhealthy Age Group: adults Sources: |
Other AEs: Tachycardia, Headache... Other AEs: Tachycardia (6.1%) Sources: Headache (1.1%) Nervousness (4.8%) Nausea (1.3%) Tremor (1.6%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 Health Status: unhealthy Age Group: adults 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 Health Status: unhealthy Age Group: adults 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 Health Status: unhealthy Age Group: adults 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 Health Status: unhealthy Age Group: adults 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 Health Status: unhealthy Age Group: adults Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies. | 2013-10 |
|
| 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. | 2012-12-16 |
|
| 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. | 2009-07 |
|
| Pleiotropic beta-agonist-promoted receptor conformations and signals independent of intrinsic activity. | 2007-02 |
|
| Chronic beta-adrenoreceptor stimulation in vivo decreased Bcl-2 and increased Bax expression but did not activate apoptotic pathways in mouse heart. | 2004-03 |
|
| Case of psychosis due to prednisone-clarithromycin interaction. | 1998-09 |
|
| Bradycardia due to biperiden. | 1989-01 |
|
| Hypokalemia induced by inhaled bronchodilators. | 1988-10 |
|
| Bronchodilator effects of oral metaproterenol sulfate in preschool children with asthma. | 1987-01 |
|
| Bronchodilator and side effects of different modes of administration of metaproterenol: inhaled, oral, and in combination. | 1986-03 |
|
| Combination low-dose metaproterenol-theophylline therapy in asthma. | 1983 |
|
| Objective and subjective tremor responses to oral beta 2 agents on first exposure. A comparison of metaproterenol and terbutaline. | 1982-10 |
|
| Comparison of fenoterol and orciprenaline with regard to broncho-dilating action and beta 2-selectivity. | 1980 |
|
| Myocardial necrosis in the rat: a comparison between isoprenaline, orciprenaline, salbutamol and terbutaline. | 1973 |
|
| Intravenous isoprenaline and orciprenaline as a guide to the drug treatment of Stokes-Adams attacks. | 1968-02-17 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/metaproterenol.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8383747
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
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53QOG569E0
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