Salmeterol

  • IUPAC: (RS ) -1 - (4- hydroxy-3- hydroxymethylphenyl ) -2 - [6 - (4- phenylbutoxy ) - hexylamino ] -ethanol
  • Rac-1 -(4- hydroxy-3- hydroxymethyl -phenyl) -2 - [6 - (4- phenylbutoxy ) - hexylamino ] -ethanol
  • (±) -1 - (4- hydroxy-3- hydroxymethylphenyl ) -2 - [6 - (4- phenylbutoxy ) - hexylamino ] -ethanol
  • DL -1 -(4- hydroxy-3- hydroxymethylphenyl ) -2 - [6 - (4- phenylbutoxy ) - hexylamino ] -ethanol
  • C25H37NO4 ( salmeterol )
  • C25H37NO4 · C11H8O3 ( salmeterol 1-hydroxy- 2-naphthoate )
  • 89365-50-4 ( salmeterol )
  • 94749-08-3 ( salmeterol 1-hydroxy- 2-naphthoate )
  • R03AC12
  • R03AK06

β2 -agonists

  • 415.57 g · mol -1 ( salmeterol )
  • 603.75 g.mol -1 ( salmeterol 1-hydroxy- 2-naphthoate )
  • 75.5 to 76.5 ° C ( salmeterol )
  • 137-138 ° C ( salmeterol 1-hydroxy- 2-naphthoate )

Slightly soluble in methanol, bad in ethanol, chloroform and isopropanol, slightly soluble in water

> 1000 mg · kg -1 ( LD50, Rat, oral, xinafoate )

Template: Infobox chemical / molecular formula search available

Salmeterol is a drug from the group of β2 -agonists. It expands the bronchi, and is used for treatment of bronchial asthma and COPD used.

Salmeterol is inhaled as a suspension or powder and administered by metered dose inhaler or dry powder inhaler.

Pharmacology

Salmeterol is as formoterol, a long-acting β2 -sympathomimetic. As such it enables the β2 -adrenoceptors of the bronchial muscles, resulting in a widening of the bronchi. It is not suitable because of its slow action occurrence for acute treatment. The use of long-acting β2 -agonists without concomitant inhaled corticosteroids in the treatment of bronchial asthma is associated with increased mortality.

Stereoisomerism

Salmeterol is chiral, ie contains a stereocenter. Thus, there are two enantiomers, the ( R) form and the ( S) form. Is used medicinally salmeterol as a racemate ( 1:1 mixture of enantiomers) in the form of the salt of 1-hydroxy- 2-naphthoic acid ( = salmeterol xinafoate ), the pharmaceutical quality in the European Pharmacopoeia is characterized.

Production

A synthesis of Salmeterol, starting from 4-phenyl -1-butanol is described in the literature.

Trade names

Aeromax (D), Serevent (A, CH, D)

With fluticasone (as fluticasone 17-propionate ): Atmadisc (D), Rolenium (D), Seretide (D, CH, A), Viani (D, A)

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System DrugBank Active ingredient Digital Object Identifier Drugs (journal)
86141
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