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Identification
NameProcaterol
Accession NumberDB01366
TypeSmall Molecule
GroupsApproved
DescriptionA long-acting beta-2-adrenergic receptor agonist. It is a potent bronchodilator that may be administered orally or by aerosol inhalation. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pro-air Aerosol 10mcg/aemmetered-dose aerosol10 mcginhalationParke Davis Division, Warner Lambert Canada Inc.1989-12-311996-09-10Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Pro-AirNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Procaterol hydrochloride hemihydrate
ThumbNot applicableDBSALT001184
Categories
UNIIX7I3EMM5K0
CAS number72332-33-3
WeightAverage: 290.3575
Monoisotopic: 290.16304258
Chemical FormulaC16H22N2O3
InChI KeyInChIKey=FKNXQNWAXFXVNW-BLLLJJGKSA-N
InChI
InChI=1S/C16H22N2O3/c1-4-12(17-9(2)3)16(21)11-5-7-13(19)15-10(11)6-8-14(20)18-15/h5-9,12,16-17,19,21H,4H2,1-3H3,(H,18,20)/t12-,16+/m0/s1
IUPAC Name
8-hydroxy-5-[(1R,2S)-1-hydroxy-2-[(propan-2-yl)amino]butyl]-1,2-dihydroquinolin-2-one
SMILES
CC[[email protected]](NC(C)C)[[email protected]](O)C1=C2C=CC(=O)NC2=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyquinolines. These are compounds containing a quinoline moiety bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassHydroxyquinolines
Direct ParentHydroxyquinolines
Alternative Parents
Substituents
  • 8-hydroxyquinoline
  • Hydroxyquinoline
  • Dihydroquinolone
  • Dihydroquinoline
  • Aralkylamine
  • Pyridinone
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactam
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of asthma and chronic obstructive pulmonary disease (COPD).
PharmacodynamicsProcaterol is a long-acting beta-2-adrenergic receptor agonist. It is a potent bronchodilator that may be administered orally or by aerosol inhalation.
Mechanism of actionBeta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.
Related Articles
AbsorptionBecause of the small therapeutic dose, systemic levels of salmeterol are low or undetectable after inhalation of recommended doses.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor.
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+0.9964
Blood Brain Barrier+0.5966
Caco-2 permeable-0.6522
P-glycoprotein substrateSubstrate0.7018
P-glycoprotein inhibitor INon-inhibitor0.8943
P-glycoprotein inhibitor IINon-inhibitor0.9204
Renal organic cation transporterNon-inhibitor0.9311
CYP450 2C9 substrateNon-substrate0.8105
CYP450 2D6 substrateNon-substrate0.6879
CYP450 3A4 substrateSubstrate0.5942
CYP450 1A2 substrateNon-inhibitor0.538
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.8986
CYP450 2C19 inhibitorInhibitor0.8774
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6783
Ames testNon AMES toxic0.8558
CarcinogenicityNon-carcinogens0.9066
BiodegradationNot ready biodegradable0.9889
Rat acute toxicity2.4772 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9921
hERG inhibition (predictor II)Non-inhibitor0.6841
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Metered-dose aerosolinhalation10 mcg
Prices
Unit descriptionCostUnit
ProAir HFA 108 (90 Base)mcg/act Aerosol 8.5 gm Inhaler45.99USD inhaler
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.329 mg/mLALOGPS
logP1.28ALOGPS
logP0.88ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.52ChemAxon
pKa (Strongest Basic)9.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area81.59 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity84.58 m3·mol-1ChemAxon
Polarizability31.69 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Mitsuji Akazawa, Teruo Hama, Yukio Kimura, Yoshinobu Yasuda, “Procaterol-containing preparation for application to the skin.” U.S. Patent US5480649, issued February, 1989.

US5480649
General ReferencesNot Available
External Links
ATC CodesR03AC16R03CC08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
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 Procaterol.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Procaterol.
AlprenololAlprenolol may decrease the bronchodilatory activities of Procaterol.
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Procaterol.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Procaterol.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Procaterol.
AtenololAtenolol may decrease the bronchodilatory activities of Procaterol.
AtomoxetineAtomoxetine may increase the hypertensive activities of Procaterol.
AtosibanThe risk or severity of adverse effects can be increased when Procaterol is combined with Atosiban.
BendroflumethiazideProcaterol may increase the hypokalemic activities of Bendroflumethiazide.
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Procaterol.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Procaterol.
BetahistineThe therapeutic efficacy of Procaterol can be decreased when used in combination with Betahistine.
BetaxololBetaxolol may decrease the bronchodilatory activities of Procaterol.
BisoprololBisoprolol may decrease the bronchodilatory activities of Procaterol.
BopindololBopindolol may decrease the bronchodilatory activities of Procaterol.
BumetanideProcaterol may increase the hypokalemic activities of Bumetanide.
BupranololBupranolol may decrease the bronchodilatory activities of Procaterol.
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Procaterol.
CarteololCarteolol may decrease the bronchodilatory activities of Procaterol.
CeliprololThe risk or severity of adverse effects can be increased when Procaterol is combined with Celiprolol.
ChlorothiazideProcaterol may increase the hypokalemic activities of Chlorothiazide.
ChlorphentermineThe risk or severity of adverse effects can be increased when Procaterol is combined with Chlorphentermine.
ChlorthalidoneProcaterol may increase the hypokalemic activities of Chlorthalidone.
ClenbuterolThe risk or severity of adverse effects can be increased when Procaterol is combined with Clenbuterol.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Procaterol.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Procaterol.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Procaterol.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Procaterol.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Procaterol.
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Procaterol.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Procaterol.
DoxofyllineThe risk or severity of adverse effects can be increased when Procaterol is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Procaterol.
EphedrineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Procaterol.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Procaterol.
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Procaterol.
EsmololEsmolol may decrease the bronchodilatory activities of Procaterol.
Etacrynic acidProcaterol may increase the hypokalemic activities of Etacrynic acid.
EtilefrineThe risk or severity of adverse effects can be increased when Procaterol is combined with Etilefrine.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Procaterol.
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Procaterol.
FurosemideProcaterol may increase the hypokalemic activities of Furosemide.
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Procaterol.
HydrochlorothiazideProcaterol may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazideProcaterol may increase the hypokalemic activities of Hydroflumethiazide.
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Procaterol is combined with Hydroxyamphetamine hydrobromide.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Procaterol.
IndapamideProcaterol may increase the hypokalemic activities of Indapamide.
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Procaterol.
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Procaterol.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Procaterol.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Procaterol.
IsoxsuprineThe risk or severity of adverse effects can be increased when Procaterol is combined with Isoxsuprine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Procaterol.
LinezolidLinezolid may increase the hypertensive activities of Procaterol.
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Procaterol.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Procaterol.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Procaterol.
MethamphetamineThe risk or severity of adverse effects can be increased when Procaterol is combined with Methamphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Procaterol.
MethyclothiazideProcaterol may increase the hypokalemic activities of Methyclothiazide.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Procaterol.
MetolazoneProcaterol may increase the hypokalemic activities of Metolazone.
MetoprololMetoprolol may decrease the bronchodilatory activities of Procaterol.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Procaterol.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Procaterol.
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Procaterol.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Procaterol.
NabiloneNabilone may increase the tachycardic activities of Procaterol.
NadololNadolol may decrease the bronchodilatory activities of Procaterol.
NebivololNebivolol may decrease the bronchodilatory activities of Procaterol.
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Procaterol.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Procaterol.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Procaterol.
NylidrinThe risk or severity of adverse effects can be increased when Procaterol is combined with Nylidrin.
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Procaterol.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Procaterol.
OxprenololOxprenolol may decrease the bronchodilatory activities of Procaterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Procaterol.
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Procaterol.
PenbutololPenbutolol may decrease the bronchodilatory activities of Procaterol.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Procaterol.
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Procaterol.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Procaterol.
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Procaterol.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Procaterol.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Procaterol.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Procaterol.
PindololPindolol may decrease the bronchodilatory activities of Procaterol.
PiretanideProcaterol may increase the hypokalemic activities of Piretanide.
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Procaterol.
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Procaterol.
PolythiazideProcaterol may increase the hypokalemic activities of Polythiazide.
PropranololPropranolol may decrease the bronchodilatory activities of Procaterol.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Procaterol.
PseudoephedrineThe risk or severity of adverse effects can be increased when Procaterol is combined with Pseudoephedrine.
QuinethazoneProcaterol may increase the hypokalemic activities of Quinethazone.
RacepinephrineThe risk or severity of adverse effects can be increased when Procaterol is combined with Racepinephrine.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Procaterol.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Procaterol.
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Procaterol.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Procaterol.
SotalolSotalol may decrease the bronchodilatory activities of Procaterol.
SynephrineThe risk or severity of adverse effects can be increased when Procaterol is combined with Synephrine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Procaterol.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Procaterol.
TetryzolineThe risk or severity of adverse effects can be increased when Procaterol is combined with Tetryzoline.
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Procaterol.
TimololTimolol may decrease the bronchodilatory activities of Procaterol.
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Procaterol.
TorasemideProcaterol may increase the hypokalemic activities of Torasemide.
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Procaterol.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Procaterol.
TrichlormethiazideProcaterol may increase the hypokalemic activities of Trichlormethiazide.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Procaterol.
TyramineThe risk or severity of adverse effects can be increased when Procaterol is combined with Tyramine.
Food InteractionsNot Available

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. Kobayashi M, Kishimoto N, Ohnishi H, Tada S, Ueda N, Kamei T, Fujita J, Taguchi H: [beta 2-adrenoceptor polymorphism and effect of inhaled beta 2-stimulant (procaterol) on airway resistance measured by body plethysmography in healthy volunteers]. Nihon Kokyuki Gakkai Zasshi. 2002 Aug;40(8):637-43. [PubMed:12428391 ]
  2. Yamasaki Y, Kishimoto N, Ohnishi H, Fujita J, Kobayashi M, Kamei T, Tada S, Ueda N: [Beta 2-adrenoceptor polymorphism and effects of inhaled beta 2-stimulant (procaterol) and an anti-cholinergic drug (oxitropium) on the airway resistance]. Nihon Kokyuki Gakkai Zasshi. 2004 Mar;42(3):239-46. [PubMed:15069780 ]
  3. Noguchi K, Ojiri Y, Chibana T, Moromizato H, Sakanashi M: Cardiac effects of beta-2 adrenoceptor stimulation with intracoronary procaterol in the absence and presence of regional myocardial ischemia in dogs. J Pharmacol Exp Ther. 1991 Nov;259(2):732-7. [PubMed:1682484 ]
  4. Aizawa H, Inoue H, Ikeda T, Hirose T, Ito Y: Effects of procaterol, a beta-2-adrenoceptor stimulant, on neuroeffector transmission in human bronchial tissue. Respiration. 1991;58(3-4):163-6. [PubMed:1684063 ]
  5. Brodde OE, Daul A, Michel-Reher M, Boomsma F, Man in 't Veld AJ, Schlieper P, Michel MC: Agonist-induced desensitization of beta-adrenoceptor function in humans. Subtype-selective reduction in beta 1- or beta 2-adrenoceptor-mediated physiological effects by xamoterol or procaterol. Circulation. 1990 Mar;81(3):914-21. [PubMed:1968366 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on July 06, 2007 14:23 / Updated on August 17, 2016 12:23