Formoterol

Title: Formoterol
CAS Registry Number: 73573-87-2
CAS Name: rel-N-[2-Hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide
Additional Names: 3-formylamino-4-hydroxy-a-[N-[1-methyl-2-(p-methoxyphenyl)ethyl]aminomethyl]benzyl alcohol; (±)-2¢-hydroxy-5¢-[(RS)-1-hydroxy-2-[[(RS)-p-methoxy-a-methylphenethyl]amino]ethyl]formanilide
Molecular Formula: C19H24N2O4
Molecular Weight: 344.40
Percent Composition: C 66.26%, H 7.02%, N 8.13%, O 18.58%
Literature References: Selective b2-adrenergic receptor agonist. Mixture of R,R (-) and S,S (+) enantiomers. Prepn: M. Murakami et al., DE 2305092; eidem, US 3994974 (1973, 1976 both to Yamanouchi); K. Murase et al., Chem. Pharm. Bull. 25, 1368 (1977). Absolute configuration and activity of isomers: eidem, ibid. 26, 1123 (1978). Toxicity studies: T. Yoshida et al., Pharmacometrics 26, 811 (1983). HPLC determn in plasma: J. Campestrini et al., J. Chromatogr. B 704, 221 (1997). Review of pharmacology: G. P. Anderson, Life Sci. 52, 2145-2160 (1993); and clinical efficacy: R. A. Bartow, R. N. Brogden, Drugs 55, 303-322 (1998).
Derivative Type: Fumarate dihydrate
CAS Registry Number: 43229-80-7
Manufacturers' Codes: BD-40A
Trademarks: Atock (Yamanouchi); Foradil (Novartis); Oxeze (AstraZeneca)
Molecular Formula: (C19H24N2O4)2.C4H4O4.2H2O
Molecular Weight: 840.91
Percent Composition: C 59.99%, H 6.71%, N 6.66%, O 26.64%
Properties: Crystals from 95% isopropyl alcohol, mp 138-140°. pKa1 7.9; pKa2 9.2. Log P (octanol/water): 0.4 (pH 7.4). Freely sol in glacial acetic acid; sol in methanol; sparingly sol in ethanol, isopropanol; slightly sol in water. Practically insol in acetone, ethyl acetate, diethyl ether. LD50 in male, female, rats, mice (mg/kg): 3130, 5580, 6700, 8310 orally; 98, 100, 72, 71 i.v.; 1000, 1100, 640, 670 s.c.; 170, 210, 240, 210 i.p. (Yoshida).
Melting point: mp 138-140°
pKa: pKa1 7.9; pKa2 9.2
Log P: Log P (octanol/water): 0.4 (pH 7.4)
Toxicity data: LD50 in male, female, rats, mice (mg/kg): 3130, 5580, 6700, 8310 orally; 98, 100, 72, 71 i.v.; 1000, 1100, 640, 670 s.c.; 170, 210, 240, 210 i.p. (Yoshida)
Derivative Type: R,R-Form
CAS Registry Number: 67346-49-0
Additional Names: Arformoterol
Derivative Type: R,R-Form L-tartrate
CAS Registry Number: 200815-49-2
Additional Names: Arformoterol tartrate
Molecular Formula: C19H24N2O4.C4H6O6
Molecular Weight: 494.49
Percent Composition: C 55.86%, H 6.12%, N 5.67%, O 32.36%
Literature References: Prepn: Y. Gao et al., WO 9821175; eidem, US 6040344 (1998, 2000 both to Sepracor). Pharmacology: D. A. Handley et al., Pulm. Pharmacol. Ther. 15, 135 (2002).
Properties: Off-white powder, mp 184°.
Melting point: mp 184°
Therap-Cat: Antiasthmatic.
Keywords: ?Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives.
Formothion Formyl Fluoride Fortimicins Foscarnet Sodium Fosetyl Al

Formoterol
Systematic (IUPAC) name
rac-(R,R)-N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide
Clinical data
Trade names Foradil/Foradile (Schering-Plough in the U.S., Novartis rest of world), Oxeze/Oxis, Symbicort (AstraZeneca), Atock (Astellas), Atimos/Atimos Modulite (Chiesi), and Perforomist (Dey)
AHFS/Drugs.com monograph
Pregnancy cat. B3 (AU) C (US)
Legal status POM (UK) -only (US)
Routes Oral, Inhalation
Pharmacokinetic data
Protein binding 61–64%
Metabolism Hepatic demethylation and glucuronidation (CYP2D6, CYP2C19, CYP2C9 and CYP2A6 involved)
Half-life 10 hours
Excretion Renal and fecal
Identifiers
CAS number 73573-87-2 YesY
ATC code R03AC13
PubChem CID 3083544
IUPHAR ligand 3465
DrugBank DB00983
ChemSpider 2340731 YesY
UNII 5ZZ84GCW8B YesY
KEGG D07990 YesY
ChEBI CHEBI:408174 YesY
ChEMBL CHEMBL1363 YesY
Chemical data
Formula C19H24N2O4 
Mol. mass 344.405 g/mol
 YesY (what is this?)  (verify)

Formoterol (INN) or eformoterol (former BAN) is a long-acting β2 agonist used in the management of asthma and chronic obstructive pulmonary disease (COPD). It is marketed in four forms: a dry-powder inhaler, a metered-dose inhaler, an oral tablet, and an inhalation solution, under various trade names including Foradil/Foradile (Schering-Plough in the U.S., Novartis rest of world), Oxeze/Oxis, and (with Budenoside) Symbicort (AstraZeneca), Atock (Astellas), Atimos (Modulite) (Chiesi), and Perforomist (Dey).

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