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
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
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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/14725487
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20406080 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | BROVANA Approved UseBROVANA 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 Date2006 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
---|---|---|
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
Edited
Wed Apr 02 09:16:20 GMT 2025
by
admin
on
Wed Apr 02 09:16:20 GMT 2025
|
Record UNII |
F91H02EBWT
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
|
|||