Salmeterol

Structural formula
	( R ) -Salmeterol (top) and ( S ) -Salmeterol (bottom), 1: 1 mixture of stereoisomers
General
Non-proprietary name	Salmeterol
other names	( RS ) -1- (4-Hydroxy-3-hydroxymethylphenyl) -2- [6- (4-phenylbutoxy) -hexylamino] -ethanol ( IUPAC ); 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;
Molecular formula	C 25 H 37 NO 4 (salmeterol) ; C 25 H 37 NO 4 C 11 H 8 O 3 (salmeterol-1-hydroxy-2-naphthoate) ;
External identifiers / databases
ECHA InfoCard	100.122.879
PubChem	5152
DrugBank	DB00938
Wikidata	Q424333
Drug information
ATC code	R03 AC12 ; R03 AK06 ;
Drug class	β 2 sympathomimetics
properties
Molar mass	415.57 g · mol -1 (salmeterol) ; 603.75 g mol −1 (salmeterol 1-hydroxy-2-naphthoate) ;
Melting point	75.5-76.5 ° C (salmeterol) ; 137-138 ° C (salmeterol-1-hydroxy-2-naphthoate) ;
solubility	Easily soluble in methanol , poorly in ethanol , chloroform and isopropanol , hardly soluble in water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 1000 mg kg −1 ( LD 50 , rat , oral , xinafoate)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Salmeterol is a drug from the group of β ₂ sympathomimetics . It dilates the bronchi and is used to treat bronchial asthma and COPD .

Salmeterol is inhaled as a suspension or powder and administered using a metered dose aerosol or powder inhaler.

pharmacology

Salmeterol as formoterol a long-term effective β ₂ - sympathomimetic . As such, it activates the β ₂ -adrenoceptors of the bronchial muscles, resulting in the expansion of the bronchi. Because of its slow onset of action, it is not suitable for acute treatment. The use of long-acting β ₂ -sympathomimetics without simultaneous administration of inhaled corticosteroids in the therapy of bronchial asthma is associated with an increased mortality.

Stereoisomerism

Salmeterol is chiral , so it contains a stereocenter. There are thus two enantiomers , the ( R ) form and the ( S ) form. Salmeterol is used medicinally 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 of which is characterized in the European Pharmacopoeia .

Manufacturing

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

Trade names

Monopreparations

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

Combination preparations

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

literature

Lasserson TJ, Cates CJ, Ferrara G, Casali L: Combination fluticasone and salmeterol versus fixed dose combination budesonide and formoterol for chronic asthma in adults and children . In: Cochrane Database Syst Rev . No. 3, 2008, p. CD004106. doi : 10.1002 / 14651858.CD004106.pub3 . PMID 18646100 .
Brogden RN, Faulds D: Salmeterol xinafoate. A review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease . In: Drugs . 42, No. 5, November 1991, pp. 895-912. PMID 1723379 .

Individual evidence

↑ ^a ^b ^c The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1439, ISBN 978-0-911910-00-1 .
↑ ^a ^b ^c Data sheet Salmeterol xinafoate ≥ 98% (HPLC), solid from Sigma-Aldrich , accessed on December 26, 2019 ( PDF ).
↑ Salpeter SR, Buckley NS, Ormiston TM, Salpeter EE: Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths . In: Ann. Intern. Med. . 144, No. 12, June 2006, pp. 904-912. PMID 16754916 .
^ Cates CJ, Cates MJ: Regular treatment with salmeterol for chronic asthma: serious adverse events . In: Cochrane Database Syst Rev . No. 3, 2008, p. CD006363. doi : 10.1002 / 14651858.CD006363.pub2 . PMID 18646149 .
↑ Monograph 01/2008: 1765 salmeterol xinafoate. European Pharmacopoeia, Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 3893-3895, ISBN 978-3-7692-3962-1 .
^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1439, ISBN 978-0-911910-00-1 .

[Sigma-2] Data sheet Salmeterol xinafoate ≥ 98% (HPLC), solid from Sigma-Aldrich , accessed on December 26, 2019 ( PDF ).

[pmid16754916-3] Salpeter SR, Buckley NS, Ormiston TM, Salpeter EE: Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths . In: Ann. Intern. Med. . 144, No. 12, June 2006, pp. 904-912. PMID 16754916 .

[4] Cates CJ, Cates MJ: Regular treatment with salmeterol for chronic asthma: serious adverse events . In: Cochrane Database Syst Rev . No. 3, 2008, p. CD006363. doi : 10.1002 / 14651858.CD006363.pub2 . PMID 18646149 .

[EuropäischesArzneibuch-5] Monograph 01/2008: 1765 salmeterol xinafoate. European Pharmacopoeia, Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 3893-3895, ISBN 978-3-7692-3962-1 .

[A._Kleemann-6] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.