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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00983Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020831s028lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00983
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
Sources: https://www.drugs.com/ppa/formoterol.html | https://www.ncbi.nlm.nih.gov/pubmed/19538157
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL210 Sources: http://www.drugbank.ca/drugs/DB00983 |
0.2 nM [EC50] | ||
Target ID: CHEMBL3390822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23573194 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | FORADIL AEROLIZER Approved UseFORADIL 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 Date2001 |
|||
Primary | FORADIL AEROLIZER Approved UseFORADIL 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 Date2001 |
PubMed
Title | Date | PubMed |
---|---|---|
Formoterol. A review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. | 1991 Jul |
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Formoterol. An update of its pharmacological properties and therapeutic efficacy in the management of asthma. | 1998 Feb |
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A 3-month comparison of formoterol with terbutaline via turbuhaler. A placebo-controlled study. | 1998 Sep |
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Formoterol and salmeterol in partially reversible chronic obstructive pulmonary disease: A crossover, placebo-controlled comparison of onset and duration of action. | 1999 |
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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 |
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Comparison of second controller medications in addition to inhaled corticosteroid in patients with moderate asthma. | 2002 May |
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Beta2-Adrenergic agonists suppress rat autoimmune myocarditis: potential role of beta2-adrenergic stimulants as new therapeutic agents for myocarditis. | 2006 Aug 29 |
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Pleiotropic beta-agonist-promoted receptor conformations and signals independent of intrinsic activity. | 2007 Feb |
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Formoterol and beclomethasone dipropionate interact positively in antagonising bronchoconstriction and inflammation in the lung. | 2007 May |
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Anti-proliferative and anti-remodelling effect of beclomethasone dipropionate, formoterol and salbutamol alone or in combination in primary human bronchial fibroblasts. | 2008 Apr |
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Intramuscular beta2-agonist administration enhances early regeneration and functional repair in rat skeletal muscle after myotoxic injury. | 2008 Jul |
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Budesonide/formoterol maintenance and reliever therapy in Asian patients (aged ≥16 years) with asthma: a sub-analysis of the COSMOS study. | 2012 Jul 1 |
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Real-life effectiveness of extrafine beclometasone dipropionate/formoterol in adults with persistent asthma according to smoking status. | 2012 Jun |
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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
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21306583
Formoterol (0.3nM) attenuated isoprenaline-induced bronchodilatation in human precision-cut lung slices containing small airways model.
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EMA ASSESSMENT REPORTS |
DUAKLIR GENUAIR (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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BRETARIS GENUAIR (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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C48149
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VYLAER SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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DUORESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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C319
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BUDESONIDA (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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BIRESP SPIROMAX (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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ACTIVE MOIETY
SUBSTANCE RECORD