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| 500mg | ||
| 1g | ||
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Orciprenaline (Metaproterenol) is a potent bronchodilator agent acting as a direct-acting sympathomimetic and a β2-adrenergic receptor (β2AR) agonist (IC50 = 68 nM) with anti-inflammatory activity. It can be used in the treatment of asthma.
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| ln Vitro |
In high glucose-induced THP-1 cells and bone marrow macrophages, metaproterenol (10 μM; 74 hours) administration increases β-arrestin2 and its association with IκBα[1]. In high glucose-induced THP-1 cells and bone marrow macrophages, treatment with metaproterenol (10 μM; 74 hours) results in the downregulation of NF-κB[1].
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| ln Vivo |
Metaproterenol treatment for a duration of 12 weeks attenuates pro-inflammatory and pro-fibrotic reactions in the kidneys and heart, as well as monocyte activation in Zucker diabetic fatty rats. Therefore, metaproterenol may provide protection against cardiovascular and renal problems associated with diabetes[1].
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| Cell Assay |
Western Blot Analysis[1]
Cell Types: THP-1 cells and bone marrow macrophages Tested Concentrations: 10 μM Incubation Duration: 74 hrs (hours) Experimental Results: Enhanced β-arrestin2 and its interaction with IκBα. RT-PCR[1] Cell Types: THP-1 cells and bone marrow macrophages Tested Concentrations: 10 μM Incubation Duration: 74 hrs (hours) Experimental Results: Led to downregulation of NF-κB. |
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
3% (oral bioavailability of 40%) Metabolism / Metabolites Hepatic and gastric. The major metabolite, orciprenaline-3-0-sulfate, is produced in the gastrointestinal tract. Orciprenaline is not metabolized by catechol-0-methyltransferase nor have glucuronide conjugates been isolated to date. Biological Half-Life 6 hours |
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation Metaproterenol (orciprenaline) is no longer marketed in the US. Although no published data exist on the use of metaproterenol by mouth or inhaler during lactation, data from the related drug, terbutaline, indicate that very little is expected to be excreted into breastmilk. The authors of several reviews and an expert panel agree that use of inhaled bronchodilators is acceptable during breastfeeding because of the low bioavailability and maternal serum levels after use. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
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| Additional Infomation |
Metaproterenol is a member of phenylethanolamines.
Metaproterenol is a beta2-Adrenergic Agonist. The mechanism of action of metaproterenol is as an Adrenergic beta2-Agonist. A beta-2 adrenergic agonist used in the treatment of ASTHMA and BRONCHIAL SPASM. Drug Indication For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema. Mechanism of Action Orciprenaline stimulates the β2-adrenergic receptor expressed in the lungs, uterus, and vasculature supplying skeletal muscles by acting as a moderately selective agonist. It exerts minimal or no effect on alpha-adrenergic receptors. Intracellularly, the actions of orciprenaline are mediated by cAMP, the production of which is augmented by beta stimulation. The drug is believed to work by activating adenylate cyclase, the enzyme responsible for producing the cellular mediator cAMP. Pharmacodynamics Orciprenaline (also known as metaproterenol), a synthetic amine, is structurally and pharmacologically similar to isoproterenol. Orciprenaline is used exclusively as a bronchodilator. The pharmacological effects of beta adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased cAMP levels lead to relaxation of bronchial smooth muscles and inhibition of the release of inalammatory mediators from mast cells that are involved in promoting immediate hypersensitivity . |
| Molecular Formula |
C11H17NO3
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| Molecular Weight |
211.26
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| Exact Mass |
211.12
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| CAS # |
586-06-1
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| Related CAS # |
Metaproterenol hemisulfate;5874-97-5
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| PubChem CID |
4086
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
417.5±40.0 °C at 760 mmHg
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| Flash Point |
179.7±17.9 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.579
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| LogP |
0.13
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
15
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| Complexity |
177
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)NCC(C1=CC(=CC(=C1)O)O)O
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| InChi Key |
LMOINURANNBYCM-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.7335 mL | 23.6675 mL | 47.3350 mL | |
| 5 mM | 0.9467 mL | 4.7335 mL | 9.4670 mL | |
| 10 mM | 0.4734 mL | 2.3668 mL | 4.7335 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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