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Details

Stereochemistry RACEMIC
Molecular Formula C19H24N2O4
Molecular Weight 344.4049
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FORMOTEROL

SMILES

COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1

InChI

InChIKey=BPZSYCZIITTYBL-YJYMSZOUSA-N
InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1

HIDE SMILES / InChI

Description

Formoterol is a long-acting selective beta2-adrenergic receptor agonist (beta2-agonist). Inhaled formoterol fumarate acts locally in the lung as a bronchodilator. In vitro studies have shown that formoterol has more than 200-fold greater agonist activity at beta2-receptors than at beta1- receptors. Although beta2-receptors are the predominant adrenergic receptors in bronchial smooth muscle and beta1-receptors are the predominant receptors in the heart, there are also beta2-receptors in the human heart comprising 10%-50% of the total beta-adrenergic receptors. The precise function of these receptors has not been established, but they raise the possibility that even highly selective beta2- agonists may have cardiac effects. The pharmacologic effects of beta2-adrenoceptor agonist drugs, including formoterol, are at least in part attributable to stimulation of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3', 5'-adenosine monophosphate (cyclic AMP). Increased cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibits the release of pro-inflammatory mast-cell mediators such as histamine and leukotrienes. Formoterol also inhibits histamine-induced plasma albumin extravasation in anesthetized guinea pigs and inhibits allergen-induced eosinophil influx in dogs with airway hyper-responsiveness. The relevance of these in vitro and animal findings to humans is unknown. Formoterol is used for use as long-term maintenance treatment of asthma in patients 6 years of age and older with reversible obstructive airways disease, including patients with symptoms of nocturnal asthma, who are using optimal corticosteroid treatment and experiencing regular or frequent breakthrough symptoms requiring use of a short-acting bronchodilator. Not indicated for asthma that can be successfully managed with occasional use of an inhaled, short-acting beta2-adrenergic agonist. Also used for the prevention of exercise-induced bronchospasm, as well as long-term treatment of bronchospasm associated with COPD. Marketed as Foradil Aerolizer.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.2 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FORADIL AEROLIZER
Primary
FORADIL AEROLIZER
PubMed

PubMed

TitleDatePubMed
Formoterol. An update of its pharmacological properties and therapeutic efficacy in the management of asthma.
1998 Feb
A 3-month comparison of formoterol with terbutaline via turbuhaler. A placebo-controlled study.
1998 Sep
The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors.
2010 Jul
Effects of beclomethasone/formoterol fixed combination on lung hyperinflation and dyspnea in COPD patients.
2011
The β2-subtype of adrenoceptors mediates inhibition of pro-fibrotic events in human lung fibroblasts.
2011 Aug
Rapid nongenomic actions of inhaled corticosteroids on long-acting β(2)-agonist transport in the airway.
2011 Dec
Asthma control in patients receiving inhaled corticosteroid and long-acting beta2-agonist fixed combinations. A real-life study comparing dry powder inhalers and a pressurized metered dose inhaler extrafine formulation.
2011 Jul 15
Effects on small airway obstruction of long-term treatments with beclomethasone/formoterol hydrofluoroalkane (metered-dose inhaler) versus fluticasone/salmeterol (dry-powder inhaler) in asthma: a preliminary study.
2011 Nov-Dec
Budesonide/formoterol maintenance and reliever therapy in Asian patients (aged ≥16 years) with asthma: a sub-analysis of the COSMOS study.
2012 Jul 1
Real-life effectiveness of extrafine beclometasone dipropionate/formoterol in adults with persistent asthma according to smoking status.
2012 Jun
Potentiated interaction between ineffective doses of budesonide and formoterol to control the inhaled cadmium-induced up-regulation of metalloproteinases and acute pulmonary inflammation in rats.
2014
Patents

Patents

Sample Use Guides

In Vivo Use Guide
For oral inhalation only. DO NOT swallow Foradil capsule. Foradil capsule should be always used with Aerolizer inhaler ONLY. Treatment of asthma in patients ≥5 years: Inhalation of one capsule every 12 hours in addition to concomitant treatment with a long-term control medication such as an inhaled corticosteroid. EIB: Inhalation of one capsule at least 15 minutes before exercise Additional doses should not be used for 12 hours. Maintenance treatment of bronchoconstriction in patients with COPD: Inhalation of one capsule every 12 hours.
Route of Administration: oral inhalation
In Vitro Use Guide
Formoterol (0.3nM) attenuated isoprenaline-induced bronchodilatation in human precision-cut lung slices containing small airways model.
Name Type Language
FORMOTEROL
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
OXIS
Brand Name English
FORMOTEROL [HSDB]
Common Name English
FORMOTEROL [MI]
Common Name English
FORMOTEROL [WHO-DD]
Common Name English
EFORMOTEROL
Common Name English
FORMOTEROL [INN]
Common Name English
FORMOTEROL [VANDF]
Common Name English
FORMAMIDE, N-(2-HYDROXY-5-(1-HYDROXY-2-((2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)PHENYL)-
Systematic Name English
Classification Tree Code System Code
WHO-VATC QR03AK08
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
NDF-RT N0000175779
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-VATC QR03AK09
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-ATC R03AK08
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-ATC R03AK09
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
NDF-RT N0000009922
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-VATC QR03AC13
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-VATC QR03AK07
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-ATC R03AK11
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-ATC R03AC13
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-VATC QR03AK11
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-ATC R03AL05
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
LIVERTOX 435
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
WHO-ATC R03AK07
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
Code System Code Type Description
RXCUI
25255
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY RxNorm
PUBCHEM
3083544
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY SWITZERF
MERCK INDEX
M5542
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY Merck Index
DRUG BANK
DB00983
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
IUPHAR
3465
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
ChEMBL
CHEMBL1256786
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
INN
4935
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
NCI_THESAURUS
C65754
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
LactMed
73573-87-2
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
HSDB
73573-87-2
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
CAS
73573-87-2
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
EVMPD
SUB07788MIG
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
WIKIPEDIA
FORMOTEROL
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY
EPA CompTox
73573-87-2
Created by admin on Tue Mar 06 11:22:11 UTC 2018 , Edited by admin on Tue Mar 06 11:22:11 UTC 2018
PRIMARY