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Identification
- Summary
Orciprenaline is a beta-2 adrenergic agonist used to treat bronchospasm, asthma, and COPD.
- Generic Name
- Orciprenaline
- DrugBank Accession Number
- DB00816
- Background
A beta-adrenergic agonist used in the treatment of asthma and bronchospasms. [PubChem]
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Orciprenaline (DB00816)
- Weight
- Average: 211.2576
Monoisotopic: 211.120843415 - Chemical Formula
- C11H17NO3
- Synonyms
- Metaproterenol
- Orciprenalina
- Orciprenaline
- Orciprenalinum
Pharmacology
- Indication
For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Asthma •••••••••••• Treatment of Bronchospasm •••••••••••• Management of Chronic bronchitis •••••••••••• Management of Pulmonary emphysema •••••••••••• - Contraindications & Blackbox Warnings
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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 .
- 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.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans - Absorption
3% (oral bioavailability of 40%)
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
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.
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- Route of elimination
Not Available
- Half-life
6 hours
- Clearance
Not Available
- Adverse Effects
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Symptoms of overdose include angina, hypertension or hypotension, arrhythmias, nervousness, headache, tremor, dry mouth, palpitation, nausea, dizziness, fatigue, malaise and insomnia. LD50=42 mg/kg (orally in rat).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Orciprenaline can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Orciprenaline is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Orciprenaline is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Orciprenaline is combined with Acetylsalicylic acid. Aclidinium The risk or severity of Tachycardia can be increased when Orciprenaline is combined with Aclidinium. - Food Interactions
- Limit caffeine intake.
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Orciprenaline Sulfate GJ20H50YF0 5874-97-5 MKFFGUZYVNDHIH-UHFFFAOYSA-N - International/Other Brands
- Metaprel
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alupent Aerosol, metered 0.650 mg/1 Respiratory (inhalation) Physicians Total Care, Inc. 1973-07-31 2007-06-30 US 
Alupent Aerosol, metered 0.650 mg/1 Respiratory (inhalation) Boehringer Ingelheim 1989-10-01 2008-11-17 US Alupent Aer Aerosol .75 mg Respiratory (inhalation) Boehringer Ingelheim (Canada) Ltd Ltee 1970-12-31 2000-01-19 Canada 
Alupent Liq 50mg/ml Liquid 50 mg / mL Respiratory (inhalation) Boehringer Ingelheim (Canada) Ltd Ltee 1970-12-31 1997-08-14 Canada Alupent Syr 10mg/5.0ml Syrup 10 mg / 5 mL Oral Boehringer Ingelheim (Canada) Ltd Ltee 1972-12-31 2004-07-16 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Metaproterenol Sulfate Syrup 10 mg/5mL Oral Qualitest 1992-07-22 2014-12-31 US Metaproterenol Sulfate Solution 15 mg/2.5mL Respiratory (inhalation) Mylan Specialty 2009-06-29 2009-06-30 US Metaproterenol Sulfate Tablet 10 mg/1 Oral Par Pharmaceutical, Inc. 1988-06-28 2019-09-30 US Metaproterenol Sulfate Tablet 20 mg/1 Oral Physicians Total Care, Inc. 1988-06-28 2002-06-30 US Metaproterenol Sulfate Syrup 10 mg/5mL Oral bryant ranch prepack 2009-09-08 Not applicable US
Categories
- ATC Codes
- R03AB03 — Orciprenaline
- R03AB — Non-selective beta-adrenoreceptor agonists
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03CB — Non-selective beta-adrenoreceptor agonists
- R03C — ADRENERGICS FOR SYSTEMIC USE
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics for Systemic Use
- Adrenergics, Inhalants
- Agents producing tachycardia
- Agents that produce hypertension
- Agents to Treat Airway Disease
- Alcohols
- Amines
- Amino Alcohols
- Anti-Asthmatic Agents
- Autonomic Agents
- Benzene Derivatives
- Bronchodilator Agents
- Catecholamines
- Catechols
- Drugs for Obstructive Airway Diseases
- Ethanolamines
- Neurotransmitter Agents
- Non-selective Beta-adrenergic Agonists
- Peripheral Nervous System Agents
- Phenols
- Reproductive Control Agents
- Respiratory System Agents
- Selective Beta 2-adrenergic Agonists
- Sympathomimetics
- Tocolytic Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Benzenediols
- Direct Parent
- Resorcinols
- Alternative Parents
- Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenylethanolamines (CHEBI:6792)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 53QOG569E0
- CAS number
- 586-06-1
- InChI Key
- LMOINURANNBYCM-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol
- SMILES
- CC(C)NCC(O)C1=CC(O)=CC(O)=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014954
- KEGG Drug
- D00685
- KEGG Compound
- C07144
- PubChem Compound
- 4086
- PubChem Substance
- 46504464
- ChemSpider
- 3944
- BindingDB
- 50295572
- 7688
- ChEBI
- 83329
- ChEMBL
- CHEMBL776
- Therapeutic Targets Database
- DNC000927
- PharmGKB
- PA450390
- RxList
- RxList Drug Page
- Wikipedia
- Orciprenaline
- MSDS
- Download (54.2 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Boehringer ingelheim pharmaceuticals inc
- Astrazeneca lp
- Dey lp
- Nephron pharmaceuticals corp
- Novex pharma
- Wockhardt eu operations (swiss) ag
- Muro pharmaceutical inc
- Boehringer ingelheim
- Morton grove pharmaceuticals inc
- Silarx pharmaceuticals inc
- Teva pharmaceuticals usa inc
- Teva pharmaceuticals usa
- American therapeutics inc
- Par pharmaceutical inc
- Usl pharma inc
- Watson laboratories inc
- Packagers
- Apotex Inc.
- Bryant Ranch Prepack
- Dey Pharma LP
- Dispensing Solutions
- Kaiser Foundation Hospital
- Major Pharmaceuticals
- Murfreesboro Pharmaceutical Nursing Supply
- Novartis AG
- Novex Pharma
- Par Pharmaceuticals
- PD-Rx Pharmaceuticals Inc.
- Pharmedix
- Physicians Total Care Inc.
- Prescript Pharmaceuticals
- Qualitest
- Silarx Pharmaceuticals
- Spectrum Pharmaceuticals
- Veratex Corp.
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Aerosol, metered Respiratory (inhalation) 0.650 mg/1 Solution Parenteral 0.5 mg Solution Respiratory (inhalation) Aerosol Respiratory (inhalation) .75 mg Liquid Respiratory (inhalation) 50 mg / mL Syrup Oral 10 mg / 5 mL Tablet Oral 20 mg Solution Respiratory (inhalation) 10 mg/2.5mL Solution Respiratory (inhalation) 15 mg/2.5mL Syrup Oral 10 mg/5mL Tablet Oral 10 mg/1 Tablet Oral 20 mg/1 Solution Parenteral 0.500 mg Syrup Oral 2 mg / mL - Prices
Unit description Cost Unit Metaproterenol sulfate powder 6.14USD g Metaproterenol 10 mg tablet 1.0USD tablet Metaproterenol 20 mg tablet 0.22USD tablet Apo-Orciprenaline 2 mg/ml Syrup 0.06USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 100 °C PhysProp water solubility 9.7mg/L Not Available logP 1 Not Available - Predicted Properties
Property Value Source Water Solubility 6.92 mg/mL ALOGPS logP -0.32 ALOGPS logP 0.21 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 8.84 Chemaxon pKa (Strongest Basic) 9.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 72.72 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 58.4 m3·mol-1 Chemaxon Polarizability 23.12 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.991 Blood Brain Barrier - 0.951 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.5665 P-glycoprotein inhibitor I Non-inhibitor 0.9348 P-glycoprotein inhibitor II Non-inhibitor 0.9756 Renal organic cation transporter Non-inhibitor 0.8917 CYP450 2C9 substrate Non-substrate 0.775 CYP450 2D6 substrate Non-substrate 0.7495 CYP450 3A4 substrate Non-substrate 0.704 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9371 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.919 CYP450 3A4 inhibitor Non-inhibitor 0.8943 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9496 Ames test Non AMES toxic 0.9226 Carcinogenicity Non-carcinogens 0.8864 Biodegradation Not ready biodegradable 0.8428 Rat acute toxicity 1.8283 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9169 hERG inhibition (predictor II) Non-inhibitor 0.9269
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0079-9600000000-b4e8dd229c64b2af4dce Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0ik9-2790000000-e04fefd40637410c62f8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0090000000-752b00e2483ea48eb3c4 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0zfr-6900000000-5c4b7077d6fd5d4df63c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4u-6910000000-4cb300244f687364c8fe Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-9300000000-83272e32fb7e124c18ba Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a5i-7900000000-c7667d38c9c66029b8ae Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 159.2603484 predictedDarkChem Lite v0.1.0 [M-H]- 146.03009 predictedDeepCCS 1.0 (2019) [M+H]+ 159.7259484 predictedDarkChem Lite v0.1.0 [M+H]+ 148.38809 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.1080484 predictedDarkChem Lite v0.1.0 [M+Na]+ 155.11993 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
- Specific Function
- adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Kimura M, Ogihara M: Stimulation by transforming growth factor-alpha of DNA synthesis and proliferation of adult rat hepatocytes in primary cultures: modulation by alpha- and beta-adrenoceptor agonists. J Pharmacol Exp Ther. 1999 Oct;291(1):171-80. [Article]
- Gelmont DM, Balmes JR, Yee A: Hypokalemia induced by inhaled bronchodilators. Chest. 1988 Oct;94(4):763-6. [Article]
- Fitch KD: The use of anti-asthmatic drugs. Do they affect sports performance? Sports Med. 1986 Mar-Apr;3(2):136-50. [Article]
- Singh H, Linas S: Beta 2-adrenergic function in cultured rat proximal tubule epithelial cells. Am J Physiol. 1996 Jul;271(1 Pt 2):F71-7. [Article]
- Hu DN, Woodward DF, McCormick SA: Influence of autonomic neurotransmitters on human uveal melanocytes in vitro. Exp Eye Res. 2000 Sep;71(3):217-24. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 03, 2024 04:54