Procaterol

Identification

Summary

Procaterol is a beta-2 adrenergic receptor agonist and bronchodilator used for the treatment of asthma and chronic obstructive pulmonary disease (COPD).

Generic Name
Procaterol
DrugBank Accession Number
DB01366
Background

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

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 290.363
Monoisotopic: 290.163042576
Chemical Formula
C16H22N2O3
Synonyms
  • Procaterol
  • Procaterolo
  • Procaterolum

Pharmacology

Indication

For the treatment of asthma and chronic obstructive pulmonary disease (COPD).

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Humans
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

Adverse Effects
Adverseeffects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Procaterol is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Procaterol can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Procaterol is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Procaterol is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Procaterol.
AclidiniumThe risk or severity of Tachycardia can be increased when Procaterol is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Procaterol.
AlclofenacThe risk or severity of hypertension can be increased when Procaterol is combined with Alclofenac.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Procaterol.
AlfuzosinThe therapeutic efficacy of Procaterol can be decreased when used in combination with Alfuzosin.
Interactions
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Food Interactions
  • Take with or without food. The onset of action of procaterol may be delayed when taken with food, however, there is no impact on the efficacy or duration of action of procaterol.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Procaterol hydrochloride4VD1BRT7T862929-91-3AEQDBKHAAWUCMT-KKJWGQAZSA-N
Procaterol hydrochloride hemihydrate8404I5HKFJ81262-93-3RZKAQAPBCFPJTK-GOPHCVLGSA-N
International/Other Brands
Pro-Air
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Pro-air Aerosol 10mcg/aemAerosol, metered10 mcg / actRespiratory (inhalation)Parke Davis Division, Warner Lambert Canada Inc.1989-12-311996-09-10Canada flag

Categories

ATC Codes
R03CC08 — ProcaterolR03AC16 — Procaterol
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
X7I3EMM5K0
CAS number
72332-33-3
InChI Key
FKNXQNWAXFXVNW-WBMJQRKESA-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+/m1/s1
IUPAC Name
8-hydroxy-5-[(1S,2R)-1-hydroxy-2-[(propan-2-yl)amino]butyl]-1,2-dihydroquinolin-2-one
SMILES
CC[C@@H](NC(C)C)[C@@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2

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
Human Metabolome Database
HMDB0015453
PubChem Compound
688561
PubChem Substance
46507907
ChemSpider
599986
BindingDB
50167071
RxNav
34530
ChEBI
135209
ChEMBL
CHEMBL3249705
ZINC
ZINC000019632678
Therapeutic Targets Database
DAP000944
PharmGKB
PA164748908
Wikipedia
Procaterol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAsthma1
4TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4Unknown StatusTreatmentCough Variant Asthma1
3CompletedTreatmentAsthma2
3CompletedTreatmentModerate Acute Asthma1
2CompletedTreatmentAsthma2
1CompletedTreatmentAsthma1
1CompletedTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
Not AvailableUnknown StatusTreatmentCough1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet
Tablet50 mcg
SyrupOral25 mcg/5ml
PowderRespiratory (inhalation)
PowderRespiratory (inhalation)10 mcg/1dose
Aerosol, meteredRespiratory (inhalation)10 mcg / act
SprayRespiratory (inhalation)
AerosolRespiratory (inhalation)
SyrupOral
Tablet25 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
logP0.88ChemAxon
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
Polarizability31.25 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
Not Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created on July 06, 2007 20:23 / Updated on October 16, 2021 11:00