Formoterol fumarate Chemical Properties

Melting point:

138-140°C

storage temp. 

Room temperature

solubility 

Slightly soluble in water, soluble in methanol, slightly soluble in 2-propanol, practically insoluble in acetonitrile.

pka

pKa1 7.9; pKa2 9.2(at 25℃)

form 

Solid

color 

White to off-white

λmax

284nm(lit.)

Merck 

14,4245

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

Safety Information

RIDADR 

3249

RTECS 

LQ2988000

HazardClass 

6.1(b)

PackingGroup 

II

Toxicity

LD50 in male, female, rats, mice (mg/kg): 3130, 5580, 6700, 8310 orally; 98, 100, 72, 71 i.v.; 1000, 1100, 640, 670 s.c.; 170, 210, 240, 210 i.p. (Yoshida)

Formoterol fumarate Usage And Synthesis

Description

Formoterol fumarate is a β2-selective adrenergic agonist useful in the treatment of bronchial asthma. It s potency and duration of action a r e reported to exceed those of salbutamol, as is its ability to inhibit allergic and non-allergic histamine release.

Chemical Properties

Crystalline Solid

Originator

Yarnanouchi (Japan)

Uses

Formoterol fumarate is a potent β2-AR agonist.

Uses

antiasthmatic;?2-agonist

Uses

long-acting β 2-agonist, anti-asthmatic

Uses

A selective 2-adrenergic receptor agonist. Used as an antiasthmatic

Definition

ChEBI: (S,S)-formoterol fumarate is a fumarate salt prepared from (S,S)-formoterol by reaction of one molecule of fumaric acid for every two molecules of (S,S)-formoterol. It contains a (S,S)-formoterol(1+). It is an enantiomer of an arformoterol fumarate.

brand name

Foradil (Novartis);ATOCK.

Mechanism of action

This is believed to result from formoterol's greater water solubility, allowing it to get to the receptor sites faster, whereas its moderate lipophilicity keeps it in the lungs longer. It is indicated for the long-term maintenance treatment of asthma and for patients with symptoms of nocturnal asthma who require regular treatment with inhaled, short-acting, β2-agonists. It is not indicated for patients whose asthma can be managed by occasional use of inhaled, short-acting, β2-agonists. Formoterol is available only as a powder in a capsule for administration via the aerosolizer. Patients should be cautioned not to take the capsules orally and to keep them in a safe place to avoid accidental oral administration.

Clinical Use

Formoterol has a β-directing N-isopropyl-p-methoxyphenyl group and a unique m-formamide and p-hydroxyphenyl ring, which provides selectivity for β2-receptors. It is resistant to MAO and COMT, making it a long-acting agonist. Formoterol has a more rapid onset as compared to salmeterol while maintaining the same long duration of action.

storage

Store at RT

References

1) Anderson et al. (1993), Formoterol: pharmacology, molecular basis of agonism and mechanism of long duration of a highly potent and selective beta 2-adrenoceptor agonist bronchodilator; Life Sciences, 52 2145 2) Teng et al. (2005), Structure-activity relationship study of novel necroptosis inhibitors; Bioorg. Med. Chem. Lett., 15 5039 3) Noguchi et al. (2015), Effect of beta2-adrenergic agonist on eosinophil adhesion, superoxide anion generation, and degranulation; Allergol. Int., 64 S46 4)Busquets et al. (2004), Anticachectic effects of formoterol: a drug for potential treatment of muscle wasting; Cancer Res., 64 6725 5) O’Neill et al. (2020), Pharmacological targeting of ?2-adrenoceptors is neuroprotective in the LPS inflammatory rat model of Parkinson’s disease; Br. J. Pharmacol., 177 282

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