Formoterol

Not to be confused with Fenoterol.

Formoterol

Formoterol (top), (R,R)-(−)-formoterol (center) and (S,S)-(+)-formoterol (bottom)
Names
Trade names	Oxeze, Perforomist, others
IUPAC name (RR,SS)-N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide
Clinical data
Drug class	LABA
Main uses	Asthma, COPD
Side effects	Dry mouth, trouble sleeping, nausea, throat inflammation
Pregnancy category	AU: B3
Routes of use	Inhalation (capsules for oral inhalation, DPI, MDI)
Onset of action	Up to 3 hr for max. effect
Duration of action	12 h
External links
AHFS/Drugs.com	Monograph
Legal
License data	EU EMA: by formoterol fumarate dihydrate
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only EU: Rx-only In general: ℞ (Prescription only)
Pharmacokinetics
Protein binding	61% to 64%
Metabolism	Liver demethylation and glucuronidation (CYP2D6, CYP2C19, CYP2C9 and CYP2A6 involved)
Elimination half-life	10 h
Excretion	Kidney and fecal
Chemical and physical data
Formula	C19H24N2O4
Molar mass	344.411 g·mol−1
3D model (JSmol)	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, also known as eformoterol, is a used in the long term management of asthma and chronic obstructive pulmonary disease (COPD). It is used by breathing it into the lungs. Full effects take about 2 hours and last about 12 h.

Common side effects include dry mouth, trouble sleeping, nausea, and throat inflammation. Other side effects may include bronchospasm, anaphylaxis, and QT prolongation. In asthma, it may increase the risk of death if used without an inhaled steroid. Use in pregnancy is of unclear safety. It is a long-acting β₂ agonist (LABA).

Formoterol was patented in 1972 and came into medical use in 1998. It is available as a generic medication. In the United Kingdom it costs the NHS about £12 per month as of 2021. In the United States this amount costs about 285 USD. It is also available in combination as budesonide/formoterol and mometasone/formoterol.

Medical uses

Dosage

It is often used at a dose of 12 micrograms twice per day.

Combinations

• Combination drugs:
  • Aclidinium bromide/formoterol
  • Budesonide/formoterol
  • Mometasone furoate/formoterol
• Arformoterol ((R,R)-(−)-formoterol) — an enantiopure compound used in the management of COPD

Side effects

In November 2005, the US Food and Drug Administration (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.

Mechanism of action

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.

Society and culture

Brand names

Inhaler for a powder based in budesonide and formoterol

It is marketed in three forms: a dry-powder inhaler (DPI), a metered-dose inhaler (MDI) and an inhalation solution, under various brand names including Atock, Atimos/Atimos Modulite, Foradil/Foradile, Oxeze/Oxis, and Perforomist.

• Foradil/Foradile capsules for oral inhalation (Schering-Plough in the U.S., Novartis rest of world)
• Oxeze/Oxis Turbuhaler Dry powder inhaler (DPI) (AstraZeneca)
• Atock (Astellas)
• Atimos/Atimos Modulite Metered-dose inhaler (MDI) (Chiesi)
• Perforomist inhalation solution (Mylan N.V.)

External links

External sites:	US NLM: Formoterol
Identifiers:	ATC code: R03AC13 (WHO) CAS Number: 73573-87-2 Y PubChem CID: 3083544 IUPHAR/BPS: 3465 DrugBank: DB00983 Y ChemSpider: 2340731 Y UNII: 5ZZ84GCW8B KEGG: D07990 Y ChEBI: CHEBI:408174 ChEMBL: ChEMBL1363 Y

• "Formoterol fumarate". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 2021-04-15. Retrieved 2021-07-12.