Reproterol

IUPAC: (RS)-7-(3-{[2-(3,5-Dihydroxyphenyl)-2-hydroxyethyl]amino}propyl)-1,3-dimethyl-3,7-dihydro-1H-purin-2,6-dion

  • C18H23N5O5 ( reproterol )
  • C18H23N5O5 · HCl ( reproterol · monohydrochloride )
  • 54063-54-6 ( reproterol )
  • 13055-82-8 ( reproterol · monohydrochloride )

R03CC14; R03AK05

β2 -agonists

  • 389.41 g · mol -1 ( reproterol )
  • 425.87 g · mol -1 ( reproterol · monohydrochloride )

249-250 ° C ( reproterol · monohydrochloride )

145 mg · kg -1 ( LD50, mouse, i.v.)

Template: Infobox chemical / molecular formula search available

Reproterol is a drug from the group of β2 -agonists, and is used as a racemate. As metered dose inhaler or solution for injection, it expands the bronchi, and is used for the treatment of bronchial asthma.

Pharmacology

Areas of application

Reproterol is used in combination with cromolyn sodium for the prevention and treatment of dyspnea in asthma in patients who also require a bronchodilator therapy in addition to anti-inflammatory therapy based.

Mechanism of Action

Reproterol, whose half-life is 1.5 hours leads as an agonist at the sympathetic β2 ​​-adrenoceptors to relaxation ( relaxation ) of the smooth muscles of the bronchi and thus to a reduction in airway resistance.

Side effects

As was observed in β2 -agonists, can occur occasionally side effects on the cardiovascular system (tachycardia, palpitations). In addition, tremors, restlessness and feeling a rise in blood sugar can be observed.

Interactions

Other β -agonists, theophylline, and anticholinergics strengthen the cardiovascular side effects of reproterol. MAO inhibitors slow the breakdown of reproterol.

Stereoisomerism

Reproterol is chiral, ie contains a stereocenter. Thus, there are two enantiomers, the ( R) form and the ( S) form. The commercial preparations containing the drug as a racemate ( 1:1 mixture of enantiomers).

Production

A synthesis for reproterol, starting from theophylline, is described in the literature.

Other Information

Due to its mechanism of action reproterol is on the prohibited list of the World Anti-Doping Code and is therefore not allowed in doping substances in sports. Taking reproterolhaltigen drugs must be reported to the doping control.

Trade names

Bronchospasmin (D)

Aarane (D), Allergospasmin (D)

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System Active ingredient Smooth muscle tissue
679025
de