Salmeterol

Salmeterol
Clinical data
Trade names	Serevent, Aeromax, Qitai, Seretide, others
AHFS/Drugs.com	Monograph
License data	EU EMA: by INN; US DailyMed: Salmeterol;
Pregnancy; category	AU: B3;
Routes of; administration	Respiratory inhalation (Metered-dose inhaler (MDI), Dry-powder inhaler (DPI))
ATC code	R03AC12 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	96%
Metabolism	Liver (CYP3A4)
Elimination half-life	5.5 hours
Identifiers
	IUPAC name (RS)-2-(hydroxymethyl)-4-{1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl}phenol;
CAS Number	89365-50-4 ;
PubChem CID	5152;
IUPHAR/BPS	559;
DrugBank	DB00938 ;
ChemSpider	7987886 ;
UNII	2I4BC502BT;
KEGG	D05792 ;
ChEBI	CHEBI:9011 ;
ChEMBL	ChEMBL1263 ;
PDB ligand	K5Y (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID6023571 ;
ECHA InfoCard	100.122.879
Chemical and physical data
Formula	C25H37NO4
Molar mass	415.574 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES OCc1cc(ccc1O)[C@H](O)CNCCCCCCOCCCCc2ccccc2;
	InChI InChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2/t25-/m1/s1 ; Key:GIIZNNXWQWCKIB-RUZDIDTESA-N ;
	(what is this?) (verify)

Salmeterol is a long-acting β₂ adrenergic receptor agonist (LABA) used in the treatment and prevention of asthma symptoms and control of chronic obstructive pulmonary disease (COPD) symptoms.^[2] Symptoms of bronchospasm include shortness of breath, wheezing, coughing and chest tightness. It is also used to prevent breathing difficulties during exercise (exercise-induced bronchoconstriction).^[3]

It was patented in 1983 and came into medical use in 1990.^[4] It is marketed as Serevent in the US.^[5] It is available as a dry-powder inhaler (DPI) that releases a powdered form of the drug. It was previously available as a metered-dose inhaler (MDI) but was discontinued in the US in 2002.^[2]^[6] It is available as an MDI in other countries as of 2020.^[7]

^ Cite error: The named reference Serevent FDA label was invoked but never defined (see the help page).
^ ^a ^b "global initiative for chronic obstructive disease" (PDF). goldcopd.org. Archived from the original (PDF) on 24 September 2015. Retrieved 30 October 2014.
^ "National Asthma Education and Prevention Program". Archived from the original on January 23, 2009. Retrieved 30 October 2014.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495.
^ "Salmeterol inhalation index". Retrieved 30 October 2014.
^ "Benefit Risk Assessment of Salmeterol for the Treatment of Asthma in Adults and Children" (PDF). fda.gov. Archived from the original (PDF) on 26 January 2018.
^ "Serevent Dosieraeros 25 mcg FCKW-frei". compendium.ch (in German). Archived from the original on 2021-07-24. Retrieved 2020-03-25.

[Serevent_FDA_label-1] Cite error: The named reference Serevent FDA label was invoked but never defined (see the help page).

[GOLD-2] "global initiative for chronic obstructive disease" (PDF). goldcopd.org. Archived from the original (PDF) on 24 September 2015. Retrieved 30 October 2014.

[NIH-3] "National Asthma Education and Prevention Program". Archived from the original on January 23, 2009. Retrieved 30 October 2014.

[Fis2006-4] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495.

[medicinet-5] "Salmeterol inhalation index". Retrieved 30 October 2014.

[FDA-6] "Benefit Risk Assessment of Salmeterol for the Treatment of Asthma in Adults and Children" (PDF). fda.gov. Archived from the original (PDF) on 26 January 2018.

[7] "Serevent Dosieraeros 25 mcg FCKW-frei". compendium.ch (in German). Archived from the original on 2021-07-24. Retrieved 2020-03-25.

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