You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameProcaterol
Accession NumberDB01366
TypeSmall Molecule
GroupsApproved
Description

A long-acting beta-2-adrenergic receptor agonist. It is a potent bronchodilator that may be administered orally or by aerosol inhalation. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
SID11113915Not AvailableNot Available
SID26752069Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
Pro-AirNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number72332-33-3
WeightAverage: 290.3575
Monoisotopic: 290.16304258
Chemical FormulaC16H22N2O3
InChI KeyFKNXQNWAXFXVNW-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[C@H](NC(C)C)[C@H](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.
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 substrateInhibitor0.8949
CYP450 2D6 substrateNon-inhibitor0.8986
CYP450 2C19 substrateInhibitor0.8774
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
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
SpectraNot 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 ReferenceNot Available
External Links
ATC CodesR03AC16R03CC08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

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
  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
  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
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments
comments powered by Disqus
Drug created on July 06, 2007 14:23 / Updated on September 16, 2013 17:14