Identification

Name
Procaterol
Accession Number
DB01366
Type
Small Molecule
Groups
Approved, Investigational
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
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Procaterol hydrochloride hemihydrate8404I5HKFJ81262-93-3RZKAQAPBCFPJTK-GOPHCVLGSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pro-air Aerosol 10mcg/aemAerosol, metered10 mcgRespiratory (inhalation)Parke Davis Division, Warner Lambert Canada Inc.1989-12-311996-09-10Canada
International/Other Brands
Pro-Air
Categories
UNII
X7I3EMM5K0
CAS number
72332-33-3
Weight
Average: 290.3575
Monoisotopic: 290.16304258
Chemical Formula
C16H22N2O3
InChI Key
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[C@H](NC(C)C)[C@H](O)C1=C2C=CC(=O)NC2=C(O)C=C1

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.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when Procaterol is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Procaterol is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Procaterol is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Procaterol is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Procaterol is combined with 4-Bromo-2,5-dimethoxyamphetamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Procaterol is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Procaterol is combined with 7-Deazaguanine.
7,9-DimethylguanineThe risk or severity of adverse effects can be increased when Procaterol is combined with 7,9-Dimethylguanine.
8-azaguanineThe risk or severity of adverse effects can be increased when Procaterol is combined with 8-azaguanine.
8-chlorotheophyllineThe risk or severity of adverse effects can be increased when Procaterol is combined with 8-chlorotheophylline.
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0015453
PubChem Compound
688561
PubChem Substance
46507907
ChemSpider
599984
BindingDB
50167071
ChEMBL
CHEMBL1478530
Therapeutic Targets Database
DAP000944
PharmGKB
PA164748908
Wikipedia
Procaterol
ATC Codes
R03AC16 — ProcaterolR03CC08 — Procaterol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentModerate Acute Asthma1
4CompletedTreatmentAsthma Bronchial1
4TerminatedTreatmentPulmonary Disease, Chronic Obstructive1
Not AvailableRecruitingTreatmentCoughing1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)10 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

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 hydroquinolones. These are compounds containing a hydrogenated quinoline bearing a ketone group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinolones and derivatives
Direct Parent
Hydroquinolones
Alternative Parents
8-hydroxyquinolines / Hydroquinolines / Pyridinones / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Heteroaromatic compounds / Secondary alcohols / Lactams / 1,2-aminoalcohols / Dialkylamines
show 5 more
Substituents
Dihydroquinolone / 8-hydroxyquinoline / Dihydroquinoline / 1-hydroxy-2-unsubstituted benzenoid / Pyridinone / Aralkylamine / Pyridine / Benzenoid / Heteroaromatic compound / 1,2-aminoalcohol
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not 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 ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
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]

Drug created on July 06, 2007 14:23 / Updated on November 02, 2018 08:47