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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H24N2O4
Molecular Weight 344.4049
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Arformoterol

SMILES

COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC(NC=O)=C(O)C=C2)C=C1

InChI

InChIKey=BPZSYCZIITTYBL-YJYMSZOUSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H24N2O4
Molecular Weight 344.4049
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14725487

Sepracor in the US is developing arformoterol [R,R-formoterol], a single isomer form of the beta(2)-adrenoceptor agonist formoterol [eformoterol]. This isomer contains two chiral canters and is being developed as an inhaled preparation for the treatment of respiratory disorders. Sepracor believes that arformoterol has the potential to be a once-daily therapy with a rapid onset of action and a duration of effect exceeding 12 hours. Sepracor stated in July 2003 that it had completed more than 100 preclinical studies and initiated or completed 15 clinical studies for arformoterol inhalation solution for the treatment of bronchospasm in patients with COPD. The pharmacologic effects of beta2-adrenoceptor agonist drugs, including arformoterol, are at least in part attributable to stimulation of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3′,5′-adenosine monophosphate (cyclic AMP). Increased intracellular cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells. In vitro tests show that arformoterol is an inhibitor of the release of mast cell mediators, such as histamine and leukotrienes, from the human lung. Arformoterol also inhibits histamine-induced plasma albumin extravasation in anesthetized guinea pigs and inhibits allergen-induced eosinophil influx in dogs with airway hyper-responsiveness. The relevance of these in vitro and animal findings to humans is unknown.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BROVANA

Approved Use

BROVANA Inhalation Solution is a long-acting beta2-adrenergic agonist (beta2-agonist) indicated for: Long-term, twice daily (morning and evening) administration in the maintenance treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. (1.1) Important limitations of use: BROVANA Inhalation Solution is not indicated to treat acute deteriorations of chronic obstructive pulmonary disease. (1.2, 5.2) BROVANA Inhalation Solution is not indicated to treat asthma. (1.2) 1.1 Maintenance Treatment of COPD BROVANA (arformoterol tartrate) Inhalation Solution is indicated for the long-term, twice daily (morning and evening) maintenance treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. BROVANA Inhalation Solution is for use by nebulization only. 1.2 Important Limitations of Use BROVANA Inhalation Solution is not indicated to treat acute deteriorations of chronic obstructive pulmonary disease [see WARNINGS AND PRECAUTIONS (5.2)

Launch Date

2006
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.3 pg/mL
15 μg 2 times / day steady-state, respiratory
dose: 15 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
ARFORMOTEROL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
34.5 pg × h/mL
15 μg 2 times / day steady-state, respiratory
dose: 15 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
ARFORMOTEROL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
26 h
15 μg 2 times / day steady-state, respiratory
dose: 15 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
ARFORMOTEROL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
48%
15 μg 2 times / day steady-state, respiratory
dose: 15 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
ARFORMOTEROL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Long-acting beta-agonist treatment in patients with persistent asthma already receiving inhaled corticosteroids.
2001
Choices of therapy for exercise-induced asthma in children.
2001
The evolution of beta2-agonists.
2001 Aug
Safety of formoterol Turbuhaler at cumulative dose of 90 microg in patients with acute bronchial obstruction.
2001 Dec
Development of a lyophilized formulation for (R,R)-formoterol (L)-tartrate.
2001 Jan
Decreased bronchodilating effect of salbutamol in relieving methacholine induced moderate to severe bronchoconstriction during high dose treatment with long acting beta2 agonists.
2001 Jul
Adding formoterol to budesonide in moderate asthma--health economic results from the FACET study.
2001 Jun
Protection against cold air and exercise-induced bronchoconstriction while on regular treatment with Oxis.
2001 Jun
Single-isomer beta-agonists.
2001 Mar
[Treatment of bronchial asthma using a new adjustable combination treatment plan: Asthma Control Plan (ATACO)].
2001 May
Dual components of optimal asthma therapy: scientific and clinical rationale for the use of long-acting beta-agonists with inhaled corticosteroids.
2001 Sep
Inhaled formoterol dry powder versus ipratropium bromide in chronic obstructive pulmonary disease.
2001 Sep 1
Comparison of the efficacy, tolerability, and safety of formoterol dry powder and oral, slow-release theophylline in the treatment of COPD.
2002 Apr
Formoterol fumarate.
2002 Feb 15
Delivery of formoterol from a novel multi-dose inhaler Airmax.
2002 Jun
Beta-adrenoceptor agonists and asthma--100 years of development.
2002 Jun 7
New therapeutic drugs in the management of chronic obstructive pulmonary disease.
2002 Mar
Quantification of terbutaline in urine by enzyme-linked immunosorbent assay and capillary electrophoresis after oral and inhaled administrations.
2002 Mar 5
Comparison of second controller medications in addition to inhaled corticosteroid in patients with moderate asthma.
2002 May
[Asthma therapy. Long-term spasmolytic therapy with rapid effect].
2002 May 23
Patents

Sample Use Guides

15 ug administered twice a day (morning and evening) by nebulization. A total daily dose greater than 30 ug (15 ug twice daily) is not recommended. BROVANA (arformoterol tartrate) should be administered by the inhaled route via a standard jet nebulizer connected to an air compressor
Route of Administration: Respiratory
In Vitro Use Guide
Curator's Comment: In vitro tests show that arformoterol is an inhibitor of the release of mast cell mediators, such as histamine and leukotrienes, from the human lung. Arformoterol also inhibits histamine-induced plasma albumin extravasation in anesthetized guinea pigs and inhibits allergen-induced eosinophil influx in dogs with airway hyper-responsiveness.
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:16:20 GMT 2025
Edited
by admin
on Wed Apr 02 09:16:20 GMT 2025
Record UNII
F91H02EBWT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Arformoterol
INN   VANDF   WHO-DD  
INN  
Official Name English
FORMAMIDE, N-(2-HYDROXY-5-((1R)-1-HYDROXY-2-(((1R)-2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)PHENYL)-
Preferred Name English
(-)-N-(2-HYDROXY-5-((1R)-1-HYDROXY-2-(((1R)-2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)PHENYL)FORMAMIDE HYDROGEN (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE
Systematic Name English
ARFORMOTEROL [VANDF]
Common Name English
(R,R)-FORMOTEROL
Common Name English
N-[2-Hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide
Systematic Name English
(-)-Formoterol
Common Name English
Formamide, N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-
Systematic Name English
arformoterol [INN]
Common Name English
Arformoterol [WHO-DD]
Common Name English
FORMOTEROL R,R-FORM [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000009922
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
NDF-RT N0000175779
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
NCI_THESAURUS C48149
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
Code System Code Type Description
SMS_ID
100000128220
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
WIKIPEDIA
ARFORMOTEROL
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
MERCK INDEX
m5542
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C61641
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
RXCUI
304962
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY RxNorm
FDA UNII
F91H02EBWT
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
PUBCHEM
3083544
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
DAILYMED
F91H02EBWT
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
LACTMED
Arfomoterol
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
INN
8398
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
CHEBI
408174
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
EVMPD
SUB35021
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID40110071
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
MESH
C012629
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
DRUG BANK
DB01274
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
IUPHAR
7479
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
CAS
67346-49-0
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
DRUG CENTRAL
4943
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
ChEMBL
CHEMBL1363
Created by admin on Wed Apr 02 09:16:20 GMT 2025 , Edited by admin on Wed Apr 02 09:16:20 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
BINDER->LIGAND
BINDING
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC