Orciprenaline

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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 .

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.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Humans
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
Medicalerrors
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Toxicity

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.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Orciprenaline can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Orciprenaline is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Orciprenaline is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Orciprenaline is combined with Acetylsalicylic acid.
AclidiniumThe risk or severity of Tachycardia can be increased when Orciprenaline is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Orciprenaline.
AlclofenacThe risk or severity of hypertension can be increased when Orciprenaline is combined with Alclofenac.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Orciprenaline.
AlfuzosinThe therapeutic efficacy of Orciprenaline can be decreased when used in combination with Alfuzosin.
Interactions
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Food Interactions
  • Limit caffeine intake.
  • Take with or without food. The absorption is unaffected by food.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Orciprenaline SulfateGJ20H50YF05874-97-5MKFFGUZYVNDHIH-UHFFFAOYSA-N
International/Other Brands
Metaprel
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlupentAerosol, metered0.650 mg/1Respiratory (inhalation)Physicians Total Care, Inc.1973-07-312007-06-30US flag
AlupentAerosol, metered0.650 mg/1Respiratory (inhalation)Boehringer Ingelheim1989-10-012008-11-17US flag
Alupent AerAerosol.75 mgRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1970-12-312000-01-19Canada flag
Alupent Liq 50mg/mlLiquid50 mg / mLRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1970-12-311997-08-14Canada flag
Alupent Syr 10mg/5.0mlSyrup10 mg / 5 mLOralBoehringer Ingelheim (Canada) Ltd Ltee1972-12-312004-07-16Canada flag
Alupent Tab 20mgTablet20 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1970-12-312001-07-30Canada flag
OrciprenSyrup10 mg / 5 mLOralTechnilab Pharma Inc.1997-05-272005-08-05Canada flag
OrciprenalineSyrup10 mg / 5 mLOralAa Pharma Inc1997-11-21Not applicableCanada flag
Tanta Orciprenaline Syrup - Syr 2mg/mlSyrup2 mg / mLOralTanta Pharmaceuticals Inc1997-04-102009-09-15Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Metaproterenol SulfateSyrup10 mg/5mLOralLannett Company, Inc.2009-09-08Not applicableUS flag
Metaproterenol SulfateSyrup10 mg/5mLOralQualitest1992-07-222014-12-31US flag
Metaproterenol SulfateSolution15 mg/2.5mLRespiratory (inhalation)Mylan Specialty2009-06-292009-06-30US flag
Metaproterenol SulfateTablet20 mg/1OralPar Pharmaceutical, Inc.1988-06-282019-09-30US flag
Metaproterenol SulfateTablet20 mg/1OralPhysicians Total Care, Inc.1988-06-282002-06-30US flag
Metaproterenol SulfateTablet10 mg/1OralPar Pharmaceutical, Inc.1988-06-282019-09-30US flag
Metaproterenol SulfateSyrup10 mg/5mLOralbryant ranch prepack2009-09-08Not applicableUS flag
Metaproterenol SulfateSolution10 mg/2.5mLRespiratory (inhalation)Mylan Specialty2009-05-302009-05-31US flag
Nu-orciprenalineSyrup2 mg / mLOralNu Pharm IncNot applicableNot applicableCanada flag
Ratio-orciprenaline Syrup 2mg/mlSyrup2 mg / mLOralRatiopharm Inc Division Of Teva Canada Limited1997-01-062006-08-04Canada flag

Categories

ATC Codes
R03AB03 — OrciprenalineR03CB03 — OrciprenalineR03CB53 — Orciprenaline, combinations
Drug Categories
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
Human Metabolome Database
HMDB0014954
KEGG Drug
D00685
KEGG Compound
C07144
PubChem Compound
4086
PubChem Substance
46504464
ChemSpider
3944
BindingDB
50295572
RxNav
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
PhaseStatusPurposeConditionsCount

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
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)0.650 mg/1
SolutionRespiratory (inhalation)
AerosolRespiratory (inhalation).75 mg
LiquidRespiratory (inhalation)50 mg / mL
SyrupOral10 mg / 5 mL
TabletOral20 mg
SolutionRespiratory (inhalation)10 mg/2.5mL
SolutionRespiratory (inhalation)15 mg/2.5mL
SyrupOral10 mg/5mL
TabletOral10 mg/1
TabletOral20 mg/1
SyrupOral2 mg / mL
Prices
Unit descriptionCostUnit
Metaproterenol sulfate powder6.14USD g
Metaproterenol 10 mg tablet1.0USD tablet
Metaproterenol 20 mg tablet0.22USD tablet
Apo-Orciprenaline 2 mg/ml Syrup0.06USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)100 °CPhysProp
water solubility9.7mg/LNot Available
logP1Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.92 mg/mLALOGPS
logP-0.32ALOGPS
logP0.21ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)9.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.4 m3·mol-1ChemAxon
Polarizability23.12 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.991
Blood Brain Barrier-0.951
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.5665
P-glycoprotein inhibitor INon-inhibitor0.9348
P-glycoprotein inhibitor IINon-inhibitor0.9756
Renal organic cation transporterNon-inhibitor0.8917
CYP450 2C9 substrateNon-substrate0.775
CYP450 2D6 substrateNon-substrate0.7495
CYP450 3A4 substrateNon-substrate0.704
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9371
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.919
CYP450 3A4 inhibitorNon-inhibitor0.8943
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9496
Ames testNon AMES toxic0.9226
CarcinogenicityNon-carcinogens0.8864
BiodegradationNot ready biodegradable0.8428
Rat acute toxicity1.8283 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9169
hERG inhibition (predictor II)Non-inhibitor0.9269
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific 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 ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. 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]
  2. Gelmont DM, Balmes JR, Yee A: Hypokalemia induced by inhaled bronchodilators. Chest. 1988 Oct;94(4):763-6. [Article]
  3. Fitch KD: The use of anti-asthmatic drugs. Do they affect sports performance? Sports Med. 1986 Mar-Apr;3(2):136-50. [Article]
  4. 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]
  5. 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]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 24, 2021 14:57