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Identification
NameOrciprenaline
Accession NumberDB00816  (APRD00210)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
Metaproterenol
Orciprenalina
Orciprenaline
Orciprenalinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alupent Aeraerosol.75 mginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1970-12-312000-01-19Canada
Alupent Liq 50mg/mlliquid50 mginhalation; oralBoehringer 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
Nu-orciprenalinesyrup2 mgoralNu Pharm IncNot applicableNot applicableCanada
Orciprensyrup10 mgoralTechnilab Pharma Inc.1997-05-272005-08-05Canada
Orciprenalinesyrup2 mgoralAa Pharma Inc1997-11-21Not applicableCanada
Ratio-orciprenaline Syrup 2mg/mlsyrup2 mgoralRatiopharm Inc Division Of Teva Canada Limited1997-01-062006-08-04Canada
Tanta Orciprenaline Syrup - Syr 2mg/mlsyrup2 mgoralTanta Pharmaceuticals Inc1997-04-102009-09-15Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Metaproterenol Sulfatesyrup10 mg/5mLoralQualitest Pharmaceuticals, Inc,1992-07-22Not applicableUs
Metaproterenol Sulfatesyrup10 mg/5mLoralSilarx Pharmaceuticals, Inc2009-09-08Not applicableUs
Metaproterenol Sulfatetablet20 mg/1oralPar Pharmaceutical Inc1988-06-28Not applicableUs
Metaproterenol Sulfatetablet10 mg/1oralPar Pharmaceutical Inc1988-06-28Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AlupentNot Available
MetaprelNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Orciprenaline Sulfate
Thumb
  • InChI Key: MKFFGUZYVNDHIH-UHFFFAOYNA-N
  • Monoisotopic Mass: 520.209066072
  • Average Mass: 520.594
DBSALT000295
Categories
UNII53QOG569E0
CAS number586-06-1
WeightAverage: 211.2576
Monoisotopic: 211.120843415
Chemical FormulaC11H17NO3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentResorcinols
Alternative Parents
Substituents
  • Resorcinol
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.
PharmacodynamicsOrciprenaline (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 actionOrciprenaline 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.
Related Articles
Absorption3% (oral bioavailability of 40%)
Volume of distributionNot Available
Protein bindingNot 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.

SubstrateEnzymesProduct
Orciprenaline
Not Available
Orciprenaline-3-O-sulfateDetails
Route of eliminationNot Available
Half life6 hours
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Aerosolinhalation; oral.75 mg
Liquidinhalation; oral50 mg
Syruporal10 mg
Tabletoral20 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point100 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesR03AB03R03CB03R03CB53
AHFS Codes
  • 12:12.08.12
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (54.2 KB)
Interactions
Drug Interactions
Drug
AcebutololAcebutolol may decrease the activities of Orciprenaline.
AcetaminophenThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Acetaminophen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Acetylsalicylic acid.
AminophyllineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Aminophylline.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Orciprenaline.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Orciprenaline.
AmphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Articaine.
AtenololAtenolol may decrease the activities of Orciprenaline.
AtomoxetineAtomoxetine may increase the hypertensive activities of Orciprenaline.
BendroflumethiazideBendroflumethiazide may decrease the activities of Orciprenaline.
BenzphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Benzphetamine.
BetahistineThe therapeutic efficacy of Orciprenaline can be decreased when used in combination with Betahistine.
BetaxololBetaxolol may decrease the activities of Orciprenaline.
BisoprololBisoprolol may decrease the activities of Orciprenaline.
BumetanideOrciprenaline may increase the hypokalemic activities of Bumetanide.
ButalbitalThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Caffeine.
CarteololCarteolol may decrease the activities of Orciprenaline.
CarvedilolCarvedilol may decrease the activities of Orciprenaline.
ChlorothiazideOrciprenaline may increase the hypokalemic activities of Chlorothiazide.
ChlorthalidoneOrciprenaline may increase the hypokalemic activities of Chlorthalidone.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Orciprenaline.
CocaineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Cocaine.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Orciprenaline.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dopamine.
DoxapramThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Doxapram.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Orciprenaline.
DronabinolDronabinol may increase the tachycardic activities of Orciprenaline.
DyphyllineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Epinephrine.
EsmololEsmolol may decrease the activities of Orciprenaline.
Etacrynic acidOrciprenaline may increase the hypokalemic activities of Ethacrynic acid.
FenoterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Fenoterol.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Formoterol.
FurosemideOrciprenaline may increase the hypokalemic activities of Furosemide.
HydrochlorothiazideOrciprenaline may increase the hypokalemic activities of Hydrochlorothiazide.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Orciprenaline.
IndacaterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Indacaterol.
IndapamideOrciprenaline may increase the hypokalemic activities of Indapamide.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Orciprenaline.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Ipratropium bromide.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Orciprenaline.
IsomethepteneThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Isometheptene.
LabetalolLabetalol may decrease the activities of Orciprenaline.
LevobunololLevobunolol may decrease the activities of Orciprenaline.
LevonordefrinThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Orciprenaline.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Lisdexamfetamine.
MepivacaineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Mepivacaine.
MethamphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Methamphetamine.
MethyclothiazideOrciprenaline may increase the hypokalemic activities of Methyclothiazide.
MethylphenidateThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Methylphenidate.
MetipranololMetipranolol may decrease the activities of Orciprenaline.
MetolazoneOrciprenaline may increase the hypokalemic activities of Metolazone.
MetoprololMetoprolol may decrease the activities of Orciprenaline.
MidodrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Midodrine.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Orciprenaline.
ModafinilThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Modafinil.
NabiloneNabilone may increase the tachycardic activities of Orciprenaline.
NadololNadolol may decrease the activities of Orciprenaline.
NaphazolineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Naphazoline.
NebivololNebivolol may decrease the activities of Orciprenaline.
NorepinephrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Norepinephrine.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Orciprenaline.
OlodaterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Olodaterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Oxymetazoline.
PenbutololPenbutolol may decrease the activities of Orciprenaline.
PhendimetrazineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Orciprenaline.
PheniramineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Pheniramine.
PhentermineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Phenylephrine.
PindololPindolol may decrease the activities of Orciprenaline.
PirbuterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Pirbuterol.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Orciprenaline.
PropranololPropranolol may decrease the activities of Orciprenaline.
PropylhexedrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Propylhexedrine.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Orciprenaline.
PseudoephedrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Racepinephrine.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Orciprenaline.
SalbutamolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Salmeterol.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Orciprenaline.
SotalolSotalol may decrease the activities of Orciprenaline.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Orciprenaline.
TerbutalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Terbutaline.
TheophyllineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Theophylline.
TimololTimolol may decrease the activities of Orciprenaline.
TorasemideOrciprenaline may increase the hypokalemic activities of Torasemide.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Orciprenaline.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Orciprenaline.
TriprolidineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Vilanterol.
Food Interactions
  • Avoid high doses of caffeine.
  • Take without regard to meals.

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 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12