Page last updated: 2024-11-10

arformoterol

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Description

arformoterol : 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). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID3083544
CHEMBL ID1363
CHEBI ID408174
SCHEMBL ID4247
MeSH IDM0398106

Synonyms (66)

Synonym
formamide, n-(2-hydroxy-5-((1r)-1-hydroxy-2-(((1r)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)-
formamide, n-(2-hydroxy-5-(1-hydroxy-2-((2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)-, (r-(r*,r*))-
unii-f91h02ebwt
f91h02ebwt ,
arformoterol [inn]
cid_9912089
bdbm50151720
n-(2-hydroxy-5-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide
n-(2-hydroxy-5-((r)-1-hydroxy-2-((r)-1-(4-methoxyphenyl)propan-2-ylamino)ethyl)phenyl)formamide
atimos
ym-08316
perforomist
foradil
n-{2-hydroxy-5-[(1r)-1-hydroxy-2-({(1r)-1-methyl-2-[4-(methyloxy)phenyl]ethyl}amino)ethyl]phenyl}formamide
eformoterol
oxis
hsdb 7287
formoterol, ((r*,r*)-(+-))-isomer
(+-)-2'-hydroxy-5'-((rs)-1-hydroxy-2-(((rs)-p-methoxy-alpha-methylphenethyl)amino)ethyl)formanilide
formoterol [usan:inn:ban]
67346-49-0
D07463
arformoterol (inn)
(r,r)-formoterol
(-)-formoterol
arformoterol
DB01274
formoterol r,r-form
CHEMBL1363 ,
chebi:408174 ,
n-{2-hydroxy-5-[(1r)-1-hydroxy-2-{[(2r)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide
n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide
innovair
fluir
formoterolum
(+-)-formoterol
5zz84gcw8b ,
racemic formoterol
unii-5zz84gcw8b
AKOS015969668
CS-1413
arformoterol [vandf]
formamide, n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-
n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide
arformoterol [who-dd]
(-)-n-(2-hydroxy-5-((1r)-1-hydroxy-2-(((1r)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)formamide hydrogen (2r,3r)-2,3-dihydroxybutanedioate
formoterol r,r-form [mi]
formoterol [who-dd]
formoterol [hsdb]
formoterol [mi]
formoterol [vandf]
rel-n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide
formamide, n-(2-hydroxy-5-(1-hydroxy-2-((2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)-
formoterol [inn]
HY-B0010A
BPZSYCZIITTYBL-YJYMSZOUSA-N
SCHEMBL4247
gtpl7479
mfcd05662345
H98 ,
DTXSID40110071
Q4789167
D87655
EN300-174504
n-(2-hydroxy-5-((1r)-1-hydroxy-2-(((2r)-1-(4-methoxyphenyl)propan-2-yl)amino)ethyl)phenyl)formamide
arformoterolum
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
bronchodilator agentAn agent that causes an increase in the expansion of a bronchus or bronchial tubes.
anti-asthmatic drugA drug used to treat asthma.
beta-adrenergic agonistAn agent that selectively binds to and activates beta-adrenergic receptors.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamideA phenylethanoloamine having 4-hydroxy and 3-formamido substituents on the phenyl ring and an N-(4-methoxyphenyl)propan-2-yl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-2 adrenergic receptorHomo sapiens (human)EC50 (µMol)0.00150.00000.311110.0000AID1060997; AID1760529
Beta-1 adrenergic receptorHomo sapiens (human)EC50 (µMol)0.10900.00010.49146.0000AID1760528
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
diet induced thermogenesisBeta-2 adrenergic receptorHomo sapiens (human)
regulation of sodium ion transportBeta-2 adrenergic receptorHomo sapiens (human)
transcription by RNA polymerase IIBeta-2 adrenergic receptorHomo sapiens (human)
receptor-mediated endocytosisBeta-2 adrenergic receptorHomo sapiens (human)
smooth muscle contractionBeta-2 adrenergic receptorHomo sapiens (human)
cell surface receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
activation of transmembrane receptor protein tyrosine kinase activityBeta-2 adrenergic receptorHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
endosome to lysosome transportBeta-2 adrenergic receptorHomo sapiens (human)
response to coldBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of protein kinase A signalingBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of bone mineralizationBeta-2 adrenergic receptorHomo sapiens (human)
heat generationBeta-2 adrenergic receptorHomo sapiens (human)
negative regulation of multicellular organism growthBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeBeta-2 adrenergic receptorHomo sapiens (human)
bone resorptionBeta-2 adrenergic receptorHomo sapiens (human)
negative regulation of G protein-coupled receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIBeta-2 adrenergic receptorHomo sapiens (human)
negative regulation of smooth muscle contractionBeta-2 adrenergic receptorHomo sapiens (human)
brown fat cell differentiationBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of mini excitatory postsynaptic potentialBeta-2 adrenergic receptorHomo sapiens (human)
adrenergic receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of protein serine/threonine kinase activityBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of cold-induced thermogenesisBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of autophagosome maturationBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of lipophagyBeta-2 adrenergic receptorHomo sapiens (human)
cellular response to amyloid-betaBeta-2 adrenergic receptorHomo sapiens (human)
response to psychosocial stressBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of cAMP-dependent protein kinase activityBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of AMPA receptor activityBeta-2 adrenergic receptorHomo sapiens (human)
norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressureBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of heart rate by epinephrine-norepinephrineBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of the force of heart contraction by epinephrine-norepinephrineBeta-1 adrenergic receptorHomo sapiens (human)
diet induced thermogenesisBeta-1 adrenergic receptorHomo sapiens (human)
response to coldBeta-1 adrenergic receptorHomo sapiens (human)
heat generationBeta-1 adrenergic receptorHomo sapiens (human)
negative regulation of multicellular organism growthBeta-1 adrenergic receptorHomo sapiens (human)
fear responseBeta-1 adrenergic receptorHomo sapiens (human)
regulation of circadian sleep/wake cycle, sleepBeta-1 adrenergic receptorHomo sapiens (human)
brown fat cell differentiationBeta-1 adrenergic receptorHomo sapiens (human)
regulation of postsynaptic membrane potentialBeta-1 adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of cold-induced thermogenesisBeta-1 adrenergic receptorHomo sapiens (human)
norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressureBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeBeta-1 adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
amyloid-beta bindingBeta-2 adrenergic receptorHomo sapiens (human)
beta2-adrenergic receptor activityBeta-2 adrenergic receptorHomo sapiens (human)
protein bindingBeta-2 adrenergic receptorHomo sapiens (human)
adenylate cyclase bindingBeta-2 adrenergic receptorHomo sapiens (human)
potassium channel regulator activityBeta-2 adrenergic receptorHomo sapiens (human)
identical protein bindingBeta-2 adrenergic receptorHomo sapiens (human)
protein homodimerization activityBeta-2 adrenergic receptorHomo sapiens (human)
protein-containing complex bindingBeta-2 adrenergic receptorHomo sapiens (human)
norepinephrine bindingBeta-2 adrenergic receptorHomo sapiens (human)
beta-adrenergic receptor activityBeta-1 adrenergic receptorHomo sapiens (human)
beta1-adrenergic receptor activityBeta-1 adrenergic receptorHomo sapiens (human)
protein bindingBeta-1 adrenergic receptorHomo sapiens (human)
PDZ domain bindingBeta-1 adrenergic receptorHomo sapiens (human)
alpha-2A adrenergic receptor bindingBeta-1 adrenergic receptorHomo sapiens (human)
protein heterodimerization activityBeta-1 adrenergic receptorHomo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of postsynaptic membrane potentialBeta-1 adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
nucleusBeta-2 adrenergic receptorHomo sapiens (human)
lysosomeBeta-2 adrenergic receptorHomo sapiens (human)
endosomeBeta-2 adrenergic receptorHomo sapiens (human)
early endosomeBeta-2 adrenergic receptorHomo sapiens (human)
Golgi apparatusBeta-2 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-2 adrenergic receptorHomo sapiens (human)
endosome membraneBeta-2 adrenergic receptorHomo sapiens (human)
membraneBeta-2 adrenergic receptorHomo sapiens (human)
apical plasma membraneBeta-2 adrenergic receptorHomo sapiens (human)
clathrin-coated endocytic vesicle membraneBeta-2 adrenergic receptorHomo sapiens (human)
neuronal dense core vesicleBeta-2 adrenergic receptorHomo sapiens (human)
receptor complexBeta-2 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-2 adrenergic receptorHomo sapiens (human)
early endosomeBeta-1 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-1 adrenergic receptorHomo sapiens (human)
Schaffer collateral - CA1 synapseBeta-1 adrenergic receptorHomo sapiens (human)
neuronal dense core vesicleBeta-1 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-1 adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1346250Human beta2-adrenoceptor (Adrenoceptors)2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
Long-chain formoterol analogues: an investigation into the effect of increasing amino-substituent chain length on the beta2-adrenoceptor activity.
AID1346260Human beta1-adrenoceptor (Adrenoceptors)2010Bioorganic & medicinal chemistry letters, Sep-01, Volume: 20, Issue:17
A physical properties based approach for the exploration of a 4-hydroxybenzothiazolone series of beta2-adrenoceptor agonists as inhaled long-acting bronchodilators.
AID1589638Antiviral activity against Enterovirus D68 US/KY/14-18953 infected in human RD cells assessed as inhibition of virus-induced cytopathic effect incubated for 5 mins under shaking condition and measured after 3 days by neutral red dye-based photometric meth2019Journal of medicinal chemistry, 04-25, Volume: 62, Issue:8
Discovery of Quinoline Analogues as Potent Antivirals against Enterovirus D68 (EV-D68).
AID1760529Agonist activity at human beta2 adrenoceptor expressed in CHO cells assessed as increase in intracellular cAMP level incubated for 1 hr by alphascreen technology2020Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24
Recent Advances in β
AID1060997Agonist activity at beta2-adrenergic receptor (unknown origin)2014Bioorganic & medicinal chemistry letters, Jan-01, Volume: 24, Issue:1
Design, synthesis and evaluation of dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors.
AID1060999Agonist activity at guinea pig trachea beta2-adrenergic receptor assessed as relaxation of histamine-induced tracheal ring contraction2014Bioorganic & medicinal chemistry letters, Jan-01, Volume: 24, Issue:1
Design, synthesis and evaluation of dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors.
AID1589639Cytotoxicity against human RD cells after 3 days by neutral red dye-based photometric method2019Journal of medicinal chemistry, 04-25, Volume: 62, Issue:8
Discovery of Quinoline Analogues as Potent Antivirals against Enterovirus D68 (EV-D68).
AID1760528Agonist activity at human beta1 adrenoceptor expressed in CHO cells assessed as increase in intracellular cAMP level incubated for 1 hr by alphascreen technology2020Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24
Recent Advances in β
AID1589640Selectivity index, ratio of CC50 for human RD cells to EC50 for Enterovirus D68 US/KY/14-18953 infected in human RD cells2019Journal of medicinal chemistry, 04-25, Volume: 62, Issue:8
Discovery of Quinoline Analogues as Potent Antivirals against Enterovirus D68 (EV-D68).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 64.29

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index64.29 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.63 (4.65)
Search Engine Demand Index103.11 (26.88)
Search Engine Supply Index2.03 (0.95)

This Compound (64.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]