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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
MOL RATIO 2 MOL RATIO (average)
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
MOL RATIO 2 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

Primary TargetPharmacologyConditionPotency
0.2 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FORADIL AEROLIZER
Primary
FORADIL AEROLIZER

PubMed

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: Other
In Vitro Use Guide
Formoterol (0.3nM) attenuated isoprenaline-induced bronchodilatation in human precision-cut lung slices containing small airways model.
Substance Class Chemical
Record UNII
W34SHF8J2K
Record Status Validated (UNII)
Record Version