U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula 2C19H24N2O4.C4H4O4
Molecular Weight 804.8819
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FORMOTEROL FUMARATE ANHYDROUS

SMILES

OC(=O)\C=C\C(O)=O.COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC=C(O)C(NC=O)=C2)C=C1.COC3=CC=C(C[C@@H](C)NC[C@H](O)C4=CC=C(O)C(NC=O)=C4)C=C3

InChI

InChIKey=OBRNDARFFFHCGE-QDSVTUBZSA-N
InChI=1S/2C19H24N2O4.C4H4O4/c2*1-13(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;5-3(6)1-2-4(7)8/h2*3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22);1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*13-,19+;/m11./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C19H24N2O4
Molecular Weight 344.4049
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020831s028lbl.pdf

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

Curator's Comment: can partially cross the blood-brain barrier https://med.stanford.edu/news/all-news/2013/07/drug-improves-cognitive-function-in-mouse-model-of-down-syndrome-study-says.html

Originator

Curator's Comment: Novartis

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.2 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FORADIL AEROLIZER

Approved Use

FORADIL AEROLIZER is a LABA indicated for: Treatment of asthma in patients ≥5 years as an add-on to a long-term asthma control medication such as an inhaled corticosteroid. Prevention of exercise-induced bronchospasm (EIB) in patients ≥5 years. Maintenance treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD).

Launch Date

9.8219518E11
Primary
FORADIL AEROLIZER

Approved Use

FORADIL AEROLIZER is a LABA indicated for: Treatment of asthma in patients ≥5 years as an add-on to a long-term asthma control medication such as an inhaled corticosteroid. Prevention of exercise-induced bronchospasm (EIB) in patients ≥5 years. Maintenance treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD).

Launch Date

9.8219518E11
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Formoterol. A review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease.
1991 Jul
Formoterol compared with beclomethasone and placebo on allergen-induced asthmatic responses.
1992 Nov
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
Formoterol and salmeterol in partially reversible chronic obstructive pulmonary disease: A crossover, placebo-controlled comparison of onset and duration of action.
1999
Effect of beta(2)-adrenoceptor activation and angiotensin II on tumour necrosis factor and interleukin 6 gene transcription in the rat renal resident macrophage cells.
1999 Oct
Expression of inwardly rectifying potassium channels (GIRKs) and beta-adrenergic regulation of breast cancer cell lines.
2004 Dec 16
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.
2004 Feb
Characterization of agonist stimulation of cAMP-dependent protein kinase and G protein-coupled receptor kinase phosphorylation of the beta2-adrenergic receptor using phosphoserine-specific antibodies.
2004 Jan
Biochemical interaction between effects of beclomethasone dipropionate and salbutamol or formoterol in sputum cells from mild to moderate asthmatics.
2005 Mar
Beta2-Adrenergic agonists suppress rat autoimmune myocarditis: potential role of beta2-adrenergic stimulants as new therapeutic agents for myocarditis.
2006 Aug 29
Pleiotropic beta-agonist-promoted receptor conformations and signals independent of intrinsic activity.
2007 Feb
Inhaled beta agonists.
2007 Jul
Formoterol and beclomethasone dipropionate interact positively in antagonising bronchoconstriction and inflammation in the lung.
2007 May
The effect of corticosteroids on the disposal of long-acting beta2-agonists by airway smooth muscle cells.
2007 Nov
Anti-proliferative and anti-remodelling effect of beclomethasone dipropionate, formoterol and salbutamol alone or in combination in primary human bronchial fibroblasts.
2008 Apr
Long duration of airway but not systemic effects of inhaled formoterol in asthmatic patients.
2008 Mar
Budesonide prevents cytokine-induced decrease of the relaxant responses to formoterol and terbutaline, but not to salmeterol, in mouse trachea.
2010 Apr
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
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

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: Other
Formoterol (0.3nM) attenuated isoprenaline-induced bronchodilatation in human precision-cut lung slices containing small airways model.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:26:36 UTC 2023
Edited
by admin
on Wed Jul 05 23:26:36 UTC 2023
Record UNII
P3T5QA5J9N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FORMOTEROL FUMARATE ANHYDROUS
Common Name English
FORMOTEROL HEMIFUMARATE
Common Name English
FOMOTEROL FUMARATE
Common Name English
FORMOTEROL FUMARATE [MI]
Common Name English
(±)-2'-HYDROXY-5'-((R*)-1-HYDROXY-2-(((R*)-P-METHOXY-.ALPHA.-METHYLPHENETHYL)AMINO)ETHYL)FORMANILIDE FUMARATE (2:1) (SALT)
Common Name English
FORMOTEROL FUMARATE (SUPERCEDED) [USAN]
Common Name English
NSC-299587
Code English
Formoterol fumarate [WHO-DD]
Common Name English
Code System Code Type Description
NSC
299587
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
PUBCHEM
53477580
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
EVMPD
SUB124541
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
DAILYMED
P3T5QA5J9N
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
NCI_THESAURUS
C47540
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
SMS_ID
100000090495
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
CAS
43229-80-7
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
FDA UNII
P3T5QA5J9N
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
CAS
87833-61-2
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
SUPERSEDED
EPA CompTox
DTXSID5044239
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
CHEBI
31633
Created by admin on Wed Jul 05 23:26:36 UTC 2023 , Edited by admin on Wed Jul 05 23:26:36 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SUBSTANCE->BASIS OF STRENGTH
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY