Identification

Name
Orciprenaline
Accession Number
DB00816  (APRD00210)
Type
Small Molecule
Groups
Approved
Description

A beta-adrenergic agonist used in the treatment of asthma and bronchospasms. [PubChem]

Structure
Thumb
Synonyms
  • Metaproterenol
  • Orciprenalina
  • Orciprenaline
  • Orciprenalinum
Product Ingredients
IngredientUNIICASInChI Key
Orciprenaline SulfateGJ20H50YF05874-97-5MKFFGUZYVNDHIH-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlupentAerosol, metered0.650 mg/1Respiratory (inhalation)Boehringer Ingelheim1989-10-012008-11-17Us
AlupentAerosol, metered0.650 mg/1Respiratory (inhalation)Physicians Total Care, Inc.1973-07-312007-06-30Us
Alupent AerAerosol.75 mgOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1970-12-312000-01-19Canada
Alupent Liq 50mg/mlLiquid50 mgOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1970-12-311997-08-14Canada
Alupent Syr 10mg/5.0mlSyrup10 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1972-12-312004-07-16Canada
Alupent Tab 20mgTablet20 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1970-12-312001-07-30Canada
OrciprenSyrup10 mgOralTechnilab Pharma Inc.1997-05-272005-08-05Canada
OrciprenalineSyrup10 mgOralAa Pharma Inc1997-11-21Not applicableCanada
Tanta Orciprenaline Syrup - Syr 2mg/mlSyrup2 mgOralTanta Pharmaceuticals Inc1997-04-102009-09-15Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Metaproterenol SulfateSolution10 mg/2.5mLRespiratory (inhalation)Mylan Specialty2009-05-302009-05-31Us
Metaproterenol SulfateSyrup10 mg/5mLOralbryant ranch prepack2009-09-082010-09-01Us
Metaproterenol SulfateSyrup10 mg/5mLOralQualitest1992-07-222014-12-31Us
Metaproterenol SulfateSolution15 mg/2.5mLRespiratory (inhalation)Mylan Specialty2009-06-292009-06-30Us
Metaproterenol SulfateTablet20 mg/1OralPar Pharmaceutical1988-06-28Not applicableUs
Metaproterenol SulfateTablet20 mg/1OralPhysicians Total Care, Inc.1988-06-282002-06-30Us
Metaproterenol SulfateSyrup10 mg/5mLOralLannett Company, Inc.2009-09-08Not applicableUs
Metaproterenol SulfateTablet10 mg/1OralPar Pharmaceutical1988-06-28Not applicableUs
Nu-orciprenalineSyrup2 mgOralNu Pharm IncNot applicableNot applicableCanada
Ratio-orciprenaline Syrup 2mg/mlSyrup2 mgOralRatiopharm Inc Division Of Teva Canada Limited1997-01-062006-08-04Canada
International/Other Brands
Alupent / Metaprel
Categories
UNII
53QOG569E0
CAS number
586-06-1
Weight
Average: 211.2576
Monoisotopic: 211.120843415
Chemical Formula
C11H17NO3
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

Pharmacology

Indication

For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.

Associated Conditions
Pharmacodynamics

Orciprenaline (also known as metaproterenol), a synthetic amine, is structurally and pharmacologically similar to isoproterenol. Orciprenaline is used exclusively as a bronchodilator. The pharmacologic 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 c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.

Mechanism of action

Orciprenaline 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. 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
Human
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.

Route of elimination
Not Available
Half life

6 hours

Clearance
Not Available
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).

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 4-Bromo-2,5-dimethoxyamphetamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 7-Deazaguanine.
7,9-DimethylguanineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 7,9-Dimethylguanine.
8-azaguanineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 8-azaguanine.
8-chlorotheophyllineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with 8-chlorotheophylline.
Food Interactions
  • Avoid high doses of caffeine.
  • Take without regard to meals.

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
ChEBI
83329
ChEMBL
CHEMBL776
Therapeutic Targets Database
DNC000927
PharmGKB
PA450390
RxList
RxList Drug Page
Wikipedia
Orciprenaline
ATC Codes
R03CB53 — Orciprenaline, combinationsR03CB03 — OrciprenalineR03AB03 — Orciprenaline
AHFS Codes
  • 12:12.08.12 — Selective Beta 2-adrenergic Agonists
MSDS
Download (54.2 KB)

Clinical Trials

Clinical Trials
Not Available

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
AerosolOral; Respiratory (inhalation).75 mg
LiquidOral; Respiratory (inhalation)50 mg
SyrupOral10 mg
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
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

Taxonomy

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
Resorcinol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Secondary amine / Secondary aliphatic amine / Aromatic alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenylethanolamines (CHEBI:6792)

Targets

Kind
Protein
Organism
Human
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. [PubMed:10490901]
  2. Gelmont DM, Balmes JR, Yee A: Hypokalemia induced by inhaled bronchodilators. Chest. 1988 Oct;94(4):763-6. [PubMed:3168573]
  3. Fitch KD: The use of anti-asthmatic drugs. Do they affect sports performance? Sports Med. 1986 Mar-Apr;3(2):136-50. [PubMed:2870555]
  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. [PubMed:8760245]
  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. [PubMed:10973730]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2018 10:06