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Identification
Name Procaterol
Accession Number DB01366
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Pro-Air
Brand mixtures Not Available
Categories
  • Sympathomimetics
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
CAS number 72332-33-3
Weight Average: 290.3575
Monoisotopic: 290.16304258
Chemical Formula C16H22N2O3
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Hydroxyquinolines
  • Quinolinones
  • Fluoroquinolones and Quinolones
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Pyridines and Derivatives
  • Benzene and Derivatives
  • Hydroxyquinolines
  • Amino Alcohols
  • Phenethylamines
  • Pyridines
  • Heterocyclic compounds
  • Aromatic compounds
  • Quinolinones
  • (Iso)quinolines and Derivatives
  • Alcohols and Polyols
  • Phenyl Esters
  • Amphetamines
  • Fluoroquinolones and Quinolones
Pharmacology
Indication For the treatment of asthma and chronic obstructive pulmonary disease (COPD).
Pharmacodynamics Procaterol 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 action Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.
Absorption Because of the small therapeutic dose, systemic levels of salmeterol are low or undetectable after inhalation of recommended doses.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms 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
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices
Unit description Cost Unit
ProAir HFA 108 (90 Base)mcg/act Aerosol 8.5 gm Inhaler 45.99 USD inhaler
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 3.29e-01 g/l ALOGPS
logP 1.28 ALOGPS
logP 0.88 ChemAxon Molconvert
logS -3 ALOGPS
pKa 13.85 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 81.59 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 84.58 ChemAxon Molconvert
polarizability 31.69 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 688561 Link_out
PubChem Substance 46507907 Link_out
ChemSpider 599984 Link_out
Therapeutic Targets Database DAP000944 Link_out
PharmGKB PA10168 Link_out
ATC Codes
  • R03CC08
  • R03AC16
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Amitriptyline The tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of procaterol.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of procaterol.
Atenolol Antagonism
Bisoprolol Antagonism
Carvedilol Antagonism
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of procaterol.
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of procaterol.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of procaterol.
Esmolol Antagonism
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of procaterol.
Isocarboxazid Increased arterial pressure
Labetalol Antagonism
Linezolid Possible increase of arterial pressure
Methyldopa Increased arterial pressure
Metoprolol Antagonism
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect of procaterol.
Nadolol Antagonism
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of procaterol.
Phenelzine Increased arterial pressure
Pindolol Antagonism
Propranolol Antagonism
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Timolol Antagonism
Food Interactions Not Available
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Drug created on July 06, 2007 14:23 / Updated on February 14, 2012 11:47