CHEBI:408174 - arformoterol

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ChEBI Name arformoterol
ChEBI ID CHEBI:408174
Definition An N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamide in which both of the stereocentres have R configuration. The active enantiomer of formoterol, it is administered by inhalation (generally as the tartrate salt) as a direct-acting sympathomimetic and bronchodilator for the treatment of chronic obstructive pulmonary disease (any progressive respiratory disease that makes it harder to breathe over time, such as chronic bronchitis and emphysema).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H24N2O4
Net Charge 0
Average Mass 344.40490
Monoisotopic Mass 344.174
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
InChIKey BPZSYCZIITTYBL-YJYMSZOUSA-N
SMILES [H]C(=O)Nc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc1ccc(OC)cc1
Roles Classification
Biological Role(s): beta-adrenergic agonist
An agent that selectively binds to and activates beta-adrenergic receptors.
Application(s): bronchodilator agent
An agent that causes an increase in the expansion of a bronchus or bronchial tubes.
anti-asthmatic drug
A drug used to treat asthma.
beta-adrenergic agonist
An agent that selectively binds to and activates beta-adrenergic receptors.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing arformoterol (CHEBI:408174) has role β-adrenergic agonist (CHEBI:35522)
arformoterol (CHEBI:408174) has role anti-asthmatic drug (CHEBI:49167)
arformoterol (CHEBI:408174) has role bronchodilator agent (CHEBI:35523)
arformoterol (CHEBI:408174) is a N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamide (CHEBI:63082)
arformoterol (CHEBI:408174) is conjugate base of arformoterol(1+) (CHEBI:63107)
arformoterol (CHEBI:408174) is enantiomer of (S,S)-formoterol (CHEBI:63081)
Incoming formoterol (CHEBI:5147) has part arformoterol (CHEBI:408174)
arformoterol(1+) (CHEBI:63107) is conjugate acid of arformoterol (CHEBI:408174)
(S,S)-formoterol (CHEBI:63081) is enantiomer of arformoterol (CHEBI:408174)
IUPAC Name
N-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide
INN Source
arformoterol KEGG DRUG
Synonyms Sources
(−)-formoterol ChemIDplus
(R,R)-formoterol DrugBank
Database Links Databases
4943 DrugCentral
D07463 KEGG DRUG
DB01274 DrugBank
US2011014246 Patent
View more database links
Registry Numbers Types Sources
67346-49-0 CAS Registry Number KEGG DRUG
67346-49-0 CAS Registry Number DrugBank
67346-49-0 CAS Registry Number ChemIDplus
7861827 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
15324892 PubMed citation ChEMBL
18990965 PubMed citation Europe PMC
20214460 PubMed citation Europe PMC
20406080 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-01-10 The (R,R)-enantiomer of formoterol, arformoterol is a β2-adrenergic agonist, and is about 1000 times more potent than the (S,S)-enantiomer. It is a bronchodilator, used for the long term symptomatic treatment of reversible bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema.