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Details

Stereochemistry RACEMIC
Molecular Formula 2C19H24N2O4.C4H4O4.2H2O
Molecular Weight 840.9124
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FORMOTEROL FUMARATE

SMILES

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

InChI

InChIKey=RATSWNOMCHFQGJ-TUYNVFRMSA-N
InChI=1S/2C19H24N2O4.C4H4O4.2H2O/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);2*1H2/b;;2-1+;;/t2*13-,19+;;;/m00.../s1

HIDE SMILES / InChI

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

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 H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Effects of adding a leukotriene antagonist or a long-acting beta(2)-agonist in asthmatic patients with the glycine-16 beta(2)-adrenoceptor genotype.
2000 Aug 1
beta(2)-adrenoceptor agonist suppresses renal tumour necrosis factor and enhances interleukin-6 gene expression induced by endotoxin.
2000 Dec
Formoterol: a review of its use in chronic obstructive pulmonary disease.
2002
Comparison of second controller medications in addition to inhaled corticosteroid in patients with moderate asthma.
2002 May
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
Long-acting beta2-adrenergic formoterol and salmeterol induce the apoptosis of B-chronic lymphocytic leukaemia cells.
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
Comparative safety of long-acting inhaled bronchodilators: a cohort study using the UK THIN primary care database.
2007
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
Formoterol in the management of chronic obstructive pulmonary disease.
2008
Anti-proliferative and anti-remodelling effect of beclomethasone dipropionate, formoterol and salbutamol alone or in combination in primary human bronchial fibroblasts.
2008 Apr
Intramuscular beta2-agonist administration enhances early regeneration and functional repair in rat skeletal muscle after myotoxic injury.
2008 Jul
Long duration of airway but not systemic effects of inhaled formoterol in asthmatic patients.
2008 Mar
Arrhythmias in patients with chronic obstructive pulmonary disease (COPD): occurrence frequency and the effect of treatment with the inhaled long-acting beta2-agonists arformoterol and salmeterol.
2008 Nov
Budesonide prevents cytokine-induced decrease of the relaxant responses to formoterol and terbutaline, but not to salmeterol, in mouse trachea.
2010 Apr
The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors.
2010 Jul
Effects of formoterol and ipratropium bromide on repeated cadmium inhalation-induced pulmonary inflammation and emphysema in rats.
2010 Nov 25
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

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 23:12:02 UTC 2023
Edited
by admin
on Wed Jul 05 23:12:02 UTC 2023
Record UNII
W34SHF8J2K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FORMOTEROL FUMARATE
ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
CGP 25827A
Code English
FORMOTEROL FUMARATE [USP MONOGRAPH]
Common Name English
BEVESPI AEROSPHERE COMPONENT FORMOTEROL FUMARATE
Common Name English
FORADIL
Brand Name English
FORMOTEROL FUMARATE DIHYDRATE [EP IMPURITY]
Common Name English
FORMOTEROL FUMARATE DIHYDRATE [VANDF]
Common Name English
PERFORMIST
Brand Name English
FORMOTEROL FUMARATE [VANDF]
Common Name English
FORMOTEROL FUMARATE COMPONENT OF BREZTRI
Brand Name English
(±)-2'-HYDROXY-5'-((R*)-1-HYDROXY-2-(((R*)-P-METHOXY-.ALPHA.-METHYLPHENETHYL)AMINO)ETHYL)FORMANILIDE FUMARATE (2:1) (SALT), DIHYDRATE
Common Name English
Formoterol fumarate dihydrate [WHO-DD]
Common Name English
SYMBICORT COMPONENT FORMOTEROL FUMARATE DIHYDRATE
Brand Name English
FORMOTEROL FUMARATE DIHYDRATE
EP   MI   ORANGE BOOK   VANDF  
Common Name English
FORMOTEROL FUMARATE HYDRATE
JAN  
Common Name English
FORASEQ
Brand Name English
CGP-25827A
Code English
FORMOTEROL FUMARATE [USP-RS]
Common Name English
FORMOTEROL FUMARATE COMPONENT OF DULERA
Common Name English
FORMOTEROL FUMARATE [ORANGE BOOK]
Common Name English
FORMOTEROL FUMARATE COMPONENT OF BEVESPI AEROSPHERE
Common Name English
FORMOTEROL FUMARATE DIHYDRATE [EP MONOGRAPH]
Common Name English
ATOCK
Brand Name English
BD-40A
Code English
YM-08316
Code English
FORMOTEROL FUMARATE [USAN]
Common Name English
DULERA COMPONENT FORMOTEROL FUMARATE
Common Name English
BD 40A
Code English
FORMOTEROL FUMARATE DIHYDRATE [MI]
Common Name English
BREZTRI COMPONENT FORMOTEROL FUMARATE
Brand Name English
FORMOTEROL FUMARATE HYDRATE [JAN]
Common Name English
FORMOTEROL FUMARATE COMPONENT OF DUAKLIR PRESSAIR
Common Name English
FORMOTEROL FUMARATE DIHYDRATE [ORANGE BOOK]
Common Name English
(R*,R*)-(±)-N-(2-HYDROXY-5-(1-HYDROXY-2-((2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)PHENYL)FORMAMIDE, (E)-2-BUTENDIOATE(2:1), DIHYDRATE
Common Name English
OXEZE
Brand Name English
DUAKLIR PRESSAIR COMPONENT FORMOTEROL FUMARATE
Common Name English
TRIMBOW COMPONENT FORMOTEROL FUMARATE DIHYDRATE
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS DUAKLIR GENUAIR (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
EMA ASSESSMENT REPORTS BRETARIS GENUAIR (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
NCI_THESAURUS C48149
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
EMA ASSESSMENT REPORTS VYLAER SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
EMA ASSESSMENT REPORTS DUORESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
NCI_THESAURUS C319
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
EMA ASSESSMENT REPORTS BUDESONIDA (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
EMA ASSESSMENT REPORTS BIRESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
Code System Code Type Description
EVMPD
SUB02257MIG
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
MERCK INDEX
M5542
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1256786
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
EVMPD
SUB25661
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
NCI_THESAURUS
C81648
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
RS_ITEM_NUM
1286107
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
EVMPD
SUB25660
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
RXCUI
236216
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
ALTERNATIVE
PUBCHEM
45358055
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
CAS
183814-30-4
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
FDA UNII
W34SHF8J2K
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
DAILYMED
W34SHF8J2K
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
USAN
JJ-46
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID5045679
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
SMS_ID
100000090127
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
DRUG BANK
DBSALT001371
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
RXCUI
998038
Created by admin on Wed Jul 05 23:12:02 UTC 2023 , Edited by admin on Wed Jul 05 23:12:02 UTC 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.75
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
The reporting threshold is▲ (IRA 1-Jan-2020) 0.05%
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY