Salmeterol

Salmeterol
Clinical data

Trade names	Serevent
AHFS/Drugs.com	Monograph
Pregnancy category	C
Routes of administration	Inhalation (MDI, DPI)
ATC code	R03AC12 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	96%
Metabolism	Hepatic (CYP3A4)
Biological 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^Y
PubChem CID	5152
IUPHAR/BPS	559
DrugBank	DB00938^Y
ChemSpider	7987886^Y
UNII	2I4BC502BT
KEGG	D05792^N
ChEBI	CHEBI:9011^N
ChEMBL	CHEMBL1263^N
ECHA InfoCard	100.122.879
Chemical and physical data
Formula	C₂₅H₃₇NO₄
Molar mass	415.57
3D model (Jmol)	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^Y Key:GIIZNNXWQWCKIB-RUZDIDTESA-N^Y
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Salmeterol is a long-acting β₂ adrenergic receptor agonist (LABA) used in the maintenance and prevention of asthma symptoms and maintenance 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 is marketed as Serevent in the US. It is available as a dry powder inhaler 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 still available as an MDI in the UK as of 2013.

Salmeterol is used in moderate-to-severe persistent asthma following previous treatment with a short-acting β₂ adrenoreceptor agonist (SABA) such as salbutamol (albuterol). LABAs should not be used as a monotherapy, instead, they should be used concurrently with an inhaled corticosteroid, such as beclometasone dipropionate or fluticasone propionate in the treatment of asthma to minimize serious reactions such as asthma-related deaths. In chronic obstructive pulmonary disease (COPD), LABAs may be used as monotherapy or in combination with corticosteroids. In exercise-induced bronchospasm monotherapy may be indicated in patients without persistent asthma. LABAs should not be used to treat acute symptoms.

The primary noticeable difference of salmeterol from salbutamol, and other short-acting β₂ adrenoreceptor agonists (SABAs), is its duration of action. Salmeterol lasts approximately 12 hours in comparison with the salbutamol, which last about 4–6 hours.

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