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 ;
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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. 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).

It was patented in 1983 and came into medical use in 1990. It is marketed as Serevent in the US. 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. It is available as an MDI in other countries as of 2020.