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
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
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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Metaproterenol SulfateSyrup10 mg/5mLOralQualitest1992-07-222016-11-16Us
Metaproterenol SulfateTablet10 mg/1OralPar Pharmaceutical1988-06-28Not applicableUs
Metaproterenol SulfateSyrup10 mg/5mLOralSilarx Pharmaceuticals, Inc.2009-09-08Not applicableUs
Metaproterenol SulfateTablet20 mg/1OralPar Pharmaceutical1988-06-28Not applicableUs
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.

Structured Indications
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
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Orciprenaline.Experimental
AcebutololAcebutolol may decrease the bronchodilatory activities of Orciprenaline.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Orciprenaline.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Orciprenaline.Approved, Withdrawn
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Orciprenaline.Illicit, Withdrawn
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Orciprenaline.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Orciprenaline.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Orciprenaline.Approved, Illicit
AtenololAtenolol may decrease the bronchodilatory activities of Orciprenaline.Approved
AtomoxetineAtomoxetine may increase the hypertensive activities of Orciprenaline.Approved
AtosibanThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Atosiban.Approved, Investigational
BendroflumethiazideOrciprenaline may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Orciprenaline.Withdrawn
BenzphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysineOrciprenaline may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Orciprenaline can be decreased when used in combination with Betahistine.Approved
BetaxololBetaxolol may decrease the bronchodilatory activities of Orciprenaline.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Orciprenaline.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Orciprenaline.Approved
BrofaromineThe risk or severity of adverse effects can be increased when Brofaromine is combined with Orciprenaline.Experimental
BromocriptineBromocriptine may increase the hypertensive activities of Orciprenaline.Approved, Investigational
BucindololThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Bucindolol.Investigational
BumetanideOrciprenaline may increase the hypokalemic activities of Bumetanide.Approved
BunazosinBunazosin may decrease the vasoconstricting activities of Orciprenaline.Investigational
BupranololBupranolol may decrease the bronchodilatory activities of Orciprenaline.Approved
CabergolineCabergoline may increase the hypertensive activities of Orciprenaline.Approved
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Orciprenaline.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Orciprenaline.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Orciprenaline.Approved, Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Orciprenaline.Approved, Investigational
ChlorothiazideOrciprenaline may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorphentermineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Chlorphentermine.Illicit, Withdrawn
ChlorthalidoneOrciprenaline may increase the hypokalemic activities of Chlorthalidone.Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Clenbuterol.Approved, Investigational, Vet Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Orciprenaline.Approved, Vet Approved
CloranololCloranolol may decrease the bronchodilatory activities of Orciprenaline.Experimental
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Orciprenaline.Approved
CyclopenthiazideOrciprenaline may increase the hypokalemic activities of Cyclopenthiazide.Experimental
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Orciprenaline.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Orciprenaline.Approved
DibenzepinThe risk or severity of adverse effects can be increased when Dibenzepin is combined with Orciprenaline.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Orciprenaline.Approved
DobutamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dobutamine.Approved
DopamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dopamine.Approved
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Orciprenaline.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Orciprenaline.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Orciprenaline.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Orciprenaline.Approved, Illicit
DuloxetineDuloxetine may increase the tachycardic activities of Orciprenaline.Approved
EpanololThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Epanolol.Experimental
EphedrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Ephedrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Orciprenaline.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Orciprenaline.Approved
ErgonovineErgonovine may increase the hypertensive activities of Orciprenaline.Approved
ErgotamineErgotamine may increase the hypertensive activities of Orciprenaline.Approved
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Orciprenaline.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Orciprenaline.Approved
Etacrynic acidOrciprenaline may increase the hypokalemic activities of Etacrynic acid.Approved
EtilefrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Etilefrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Fenoterol.Approved, Investigational
FenozoloneThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Fenozolone.Experimental
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Orciprenaline.Approved, Investigational, Vet Approved
FurosemideOrciprenaline may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Orciprenaline.Experimental
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Orciprenaline.Experimental
HydrochlorothiazideOrciprenaline may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideOrciprenaline may increase the hypokalemic activities of Hydroflumethiazide.Approved, Investigational
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Hydroxyamphetamine.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Orciprenaline.Approved
IndapamideOrciprenaline may increase the hypokalemic activities of Indapamide.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Orciprenaline.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Orciprenaline.Approved, Investigational
IprindoleThe risk or severity of adverse effects can be increased when Iprindole is combined with Orciprenaline.Experimental
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Orciprenaline.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Orciprenaline.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Orciprenaline.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Isoprenaline.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Isoxsuprine.Approved, Withdrawn
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Orciprenaline.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Orciprenaline.Approved
LinezolidLinezolid may increase the hypertensive activities of Orciprenaline.Approved, Investigational
LofepramineThe risk or severity of adverse effects can be increased when Lofepramine is combined with Orciprenaline.Experimental
LoxapineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Loxapine.Approved
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Orciprenaline.Withdrawn
MefenorexThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Mefenorex.Experimental
MephentermineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Mephentermine.Approved
MepindololMepindolol may decrease the bronchodilatory activities of Orciprenaline.Experimental
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Orciprenaline.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Methamphetamine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Orciprenaline.Approved, Investigational
MethyclothiazideOrciprenaline may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Orciprenaline.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive activities of Orciprenaline.Approved
MetolazoneOrciprenaline may increase the hypokalemic activities of Metolazone.Approved
MetoprololMetoprolol may decrease the bronchodilatory activities of Orciprenaline.Approved, Investigational
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Orciprenaline.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Orciprenaline.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Orciprenaline.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Orciprenaline.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Orciprenaline.Approved
NabiloneNabilone may increase the tachycardic activities of Orciprenaline.Approved, Investigational
NebivololNebivolol may decrease the bronchodilatory activities of Orciprenaline.Approved, Investigational
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Orciprenaline.Withdrawn
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Orciprenaline.Approved
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Orciprenaline.Approved
NylidrinThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Nylidrin.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Orciprenaline.Withdrawn
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Orciprenaline.Investigational
OxprenololOxprenolol may decrease the bronchodilatory activities of Orciprenaline.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Oxymetazoline.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Orciprenaline.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Orciprenaline.Approved, Investigational
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Orciprenaline.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Orciprenaline.Withdrawn
PhenmetrazineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Phenmetrazine.Approved, Illicit
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Orciprenaline.Withdrawn
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Orciprenaline.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Orciprenaline.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Orciprenaline.Approved, Vet Approved, Withdrawn
PiretanideOrciprenaline may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Orciprenaline.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Orciprenaline.Withdrawn
PolythiazideOrciprenaline may increase the hypokalemic activities of Polythiazide.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Orciprenaline.Approved
PrenalterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Prenalterol.Experimental
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Orciprenaline.Approved
ProcaterolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Procaterol.Approved, Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Orciprenaline.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Pseudoephedrine.Approved
QuinethazoneOrciprenaline may increase the hypokalemic activities of Quinethazone.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Racepinephrine.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Orciprenaline.Approved
RitodrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Ritodrine.Approved, Investigational
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Orciprenaline.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Orciprenaline.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Orciprenaline.Approved
SotalolSotalol may decrease the bronchodilatory activities of Orciprenaline.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Orciprenaline.Approved
SynephrineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Synephrine.Experimental
TamsulosinTamsulosin may decrease the vasoconstricting activities of Orciprenaline.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Orciprenaline.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Orciprenaline.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Terbutaline.Approved
TertatololTertatolol may decrease the bronchodilatory activities of Orciprenaline.Experimental
TetryzolineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Tetryzoline.Approved
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Orciprenaline.Approved, Investigational
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Orciprenaline.Approved
TorasemideOrciprenaline may increase the hypokalemic activities of Torasemide.Approved
TramazolineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Tramazoline.Investigational
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Orciprenaline.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Orciprenaline.Approved
TretoquinolThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Tretoquinol.Experimental
TrichlormethiazideOrciprenaline may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Orciprenaline.Experimental
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Orciprenaline.Approved
TyramineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Tyramine.Investigational, Nutraceutical
UrapidilUrapidil may decrease the vasoconstricting activities of Orciprenaline.Investigational
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Orciprenaline.Approved
VenlafaxineVenlafaxine may increase the tachycardic activities of Orciprenaline.Approved
Food Interactions
  • Avoid high doses of caffeine.
  • Take without regard to meals.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB14954
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, combinationsR03AB03 — OrciprenalineR03CB03 — 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
Dosage forms
FormRouteStrength
AerosolOral; Respiratory (inhalation).75 mg
LiquidOral; Respiratory (inhalation)50 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.
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 December 10, 2017 17:18