Arformoterol

Base Information

Chemical Name:Arformoterol
CAS No.:67346-49-0
Deprecated CAS:208102-40-3,289657-27-8,299964-45-7,126587-85-7,49861-99-6,183814-29-1,289657-27-8,299964-45-7
Molecular Formula:C₁₉H₂₄N₂O₄
Molecular Weight:344.411
Hs Code.:
European Community (EC) Number:615-991-0
UNII:5ZZ84GCW8B,F91H02EBWT
DSSTox Substance ID:DTXSID40110071
Nikkaji Number:J245.605B
Wikipedia:Formoterol,Arformoterol
Wikidata:Q4789167
NCI Thesaurus Code:C47540,C61641,C65240,C65754
RXCUI:25255,236216,304962,668284
Pharos Ligand ID:8VK3JF52T893,8VKJ7WK1RNCS
Metabolomics Workbench ID:43475
ChEMBL ID:CHEMBL1363
Mol file:67346-49-0.mol

Synonyms:3-formylamino-4-hydroxy-alpha-(N-1-methyl-2-p-methoxyphenethylaminomethyl)benzyl alcohol.hemifumarate;arformoterol;BD 40A;eformoterol;Foradil;formoterol;formoterol fumarate;formoterol fumarate, ((R*,R*)-(+-))-isomer;formoterol, ((R*,R*)-(+-))-isomer;Oxis

Suppliers and Price of Arformoterol

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

American Custom Chemicals Corporation
ARFORMOTEROL 95.00%
10MG
$ 224.70

Total 21 raw suppliers

Chemical Property of Arformoterol

Chemical Property:

Boiling Point:603.2°Cat760mmHg
Flash Point:318.6°C
PSA：90.82000
Density:1.233g/cm³
LogP:3.32310
XLogP3:1.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:8
Exact Mass:344.17360725
Heavy Atom Count:25
Complexity:388

Purity/Quality:

97% ^*data from raw suppliers

ARFORMOTEROL 95.00% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(CC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)NC=O)O
Isomeric SMILES:C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=CC(=C(C=C2)O)NC=O)O
Recent ClinicalTrials:A Pilot Study to Determine the Most Effective Dose of Arformoterol for Treating Acute Asthmatic Patients
Recent EU Clinical Trials:Utility of inhaled extrafine triple therapy with glycopyrronium bromide, formoterol fumarate dihydrate and beclometasone dipropionate to improve expiratory flow limitation in severe COPD exacerbations. An double-blind randomized controlled trial.
Recent NIPH Clinical Trials:A Randomized, Double-Blind, Double Dummy, Parallel Group, Multicenter Variable Length Study to Assess the Efficacy and Safety of PT010 Relative to PT009 and Symbicort in Adult and Adolescent Participants With Inadequately Controlled Asthma
Description Arformoterol, a selective long-acting b2-agonist, was launched as an inhalation solution for treatment of bronchoconstriction associated with COPD. It is the active (R,R)-enantiomer of the previously marketed b2-agonist formoterol, which is registered as a racemic mixture. Similar to other b2-agonists, the mechanism of action of formoterol and arformoterol involves activation of adenyl cyclase, leading to increased production of cyclic adenosine monophosphate (cAMP) via ATP. Increased levels of intracellular cAMP result in relaxation of the bronchial smooth muscle, and also prevent mast cells from releasing inflammatory mediators. Arformoterol has high binding affinity for the human b2 receptor (Kd 2.9 nM) and approximately 39-fold selectivity over the b1 receptor (Kd 113 nM). It is W1,000 times more potent b2 ligand than the corresponding (S,S)-enantiomer (Kd 3100 nM), and twice as potent as racemic formoterol (Kd 5.2 nM). Additionally, arformoterol acts as a full or nearly full agonist of the b2 receptor, whereas the (S,S)-enantiomer acts as an inverse agonist. Therefore, the (R,R)-enantiomer may account exclusively for the activation of b2 receptors by the racemic mixture.
Uses (R,R)-Formoterol (Arformoterol) (CAS# 67346-49-0) is aused in the methods for treating chronic obstructive pulmonary disease by administration of a bronchodilator using a nebulizer.

Technology Process of Arformoterol

There total 75 articles about Arformoterol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 43229-70-5
N-[5-(2-{benzyl[2-(4-methoxyphenyl)-1-methylethyl]amino}-1-hydroxyethyl)-2-benzyloxyphenyl]formamide

: 128954-45-0,67346-49-0
formoterol

Guidance literature:

Reference yield:

: 1316100-17-0
(R,R)-N-(2-benzyloxy-5-{1-hydroxy-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethyl}-phenyl)-formamide

: 73573-87-2,67346-49-0
(R,R)-formoterol

Guidance literature:: With 5% Pd(II)/C(eggshell); hydrogen; In methanol; for 12h; under 2327.23 Torr;
DOI:10.1002/chir.20728

Reference yield:

: 188690-82-6
(R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol

: 73573-87-2,67346-49-0
(R,R)-formoterol

Guidance literature:: Multi-step reaction with 6 steps

1: K₂CO₃ / methanol / 2.5 h / 20 °C

2: dimethylsulfoxide / 87 h / 80 °C

3: neutral Al₂O₃ (activity III)

4: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating

5: 69 percent / pyridine / 6.5 h / 60 °C

6: H₂ / 10 percentPd/C / ethanol / 20 °C

With pyridine; hydrogenchloride; aluminum oxide; hydrogen; iron; potassium carbonate; 10% palladium on active carbon; In methanol; ethanol; dimethyl sulfoxide; 1: Cyclization / 2: Addition / 3: Hydrolysis / 4: Reduction / 5: Formylation / 6: Hydrogenolysis;
DOI:10.1016/S0957-4166(00)00238-X