Formoterol

Formoterol

Formoterol (top), (R,R)-(−)-formoterol (center) and (S,S)-(+)-formoterol (bottom)
Clinical data
Trade names	See below
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	Inhalation (capsules for oral inhalation, DPI, MDI)
ATC code	R03AC13 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	61–64%
Metabolism	Hepatic demethylation and glucuronidation (CYP2D6, CYP2C19, CYP2C9 and CYP2A6 involved)
Biological half-life	10 hours
Excretion	Renal and fecal
Identifiers
IUPAC name (RR,SS)-N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide
CAS Number	73573-87-2 Y
PubChem CID	3083544 3034756
IUPHAR/BPS	3465
DrugBank	DB00983 Y
ChemSpider	2340731 Y
UNII	5ZZ84GCW8B
KEGG	D07990 Y
ChEBI	CHEBI:408174 Y
ChEMBL	CHEMBL1363 Y
ECHA InfoCard	100.131.654
Chemical and physical data
Formula	C19H24N2O4
Molar mass	344.405 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES O=CNc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc2ccc(OC)cc2
InChI InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1 Y Key:BPZSYCZIITTYBL-YJYMSZOUSA-N Y

Formoterol (INN) or eformoterol (former BAN) is a long-acting β₂ agonist (LABA) used in the management of asthma and COPD. It is marketed in three forms: a dry-powder inhaler, a metered-dose inhaler and an inhalation solution, under various trade names including Atock, Atimos/Atimos Modulite, Foradil/Foradile, Oxeze/Oxis, and Perforomist. It is also marketed in the combination formulations budesonide/formoterol and mometasone/formoterol.

Formoterol has an extended duration of action (up to 12 hours) compared to short-acting β₂ agonists such as salbutamol (albuterol), which are effective for 4–6 hours. LABAs such as formoterol are used as "symptom controllers" to supplement prophylactic corticosteroid therapy. A "reliever" short-acting β₂ agonist (e.g., salbutamol) is still required, since LABAs are not recommended for the treatment of acute asthma.

Inhaled formoterol works like other β₂ agonists, causing bronchodilation by relaxing the smooth muscle in the airway so as to treat the exacerbation of asthma.

In November 2005, the US FDA released a health advisory alerting the public to findings that show the use of long-acting β₂ agonists could lead to a worsening of wheezing symptoms in some patients.

At the current time, available long-acting β₂ agonists include salmeterol, formoterol, bambuterol, and sustained-release oral salbutamol.