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

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

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 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
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
Expression of inwardly rectifying potassium channels (GIRKs) and beta-adrenergic regulation of breast cancer cell lines.
2004 Dec 16
Long-acting beta2-adrenergic formoterol and salmeterol induce the apoptosis of B-chronic lymphocytic leukaemia cells.
2004 Jan
Inhaled beta agonists.
2007 Jul
Formoterol in the management of chronic obstructive pulmonary disease.
2008
Intramuscular beta2-agonist administration enhances early regeneration and functional repair in rat skeletal muscle after myotoxic injury.
2008 Jul
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
Real-life effectiveness of extrafine beclometasone dipropionate/formoterol in adults with persistent asthma according to smoking status.
2012 Jun
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 Fri Dec 15 15:43:11 UTC 2023
Edited
by admin
on Fri Dec 15 15:43:11 UTC 2023
Record UNII
W34SHF8J2K
Record Status Validated (UNII)
Record Version
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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 Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
EMA ASSESSMENT REPORTS BRETARIS GENUAIR (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
EMA ASSESSMENT REPORTS VYLAER SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
EMA ASSESSMENT REPORTS DUORESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
EMA ASSESSMENT REPORTS BUDESONIDA (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
EMA ASSESSMENT REPORTS BIRESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
Code System Code Type Description
EVMPD
SUB02257MIG
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
MERCK INDEX
m5542
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1256786
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
EVMPD
SUB25661
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
NCI_THESAURUS
C81648
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
RS_ITEM_NUM
1286107
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
EVMPD
SUB25660
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
RXCUI
236216
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
ALTERNATIVE
PUBCHEM
45358055
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
CAS
183814-30-4
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
FDA UNII
W34SHF8J2K
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
DAILYMED
W34SHF8J2K
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
USAN
JJ-46
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID5045679
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
SMS_ID
100000090127
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
DRUG BANK
DBSALT001371
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 UTC 2023
PRIMARY
RXCUI
998038
Created by admin on Fri Dec 15 15:43:11 UTC 2023 , Edited by admin on Fri Dec 15 15:43:11 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