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Formoterol

Formoterol Structure
CAS No.
73573-87-2
Chemical Name:
Formoterol
Synonyms
FORMOTEROL TARTRATE;Oxis;FORMOTEROL;Formoteral;Eformoterol;FormoterolBase;1-nitrotridec-1-ene;Formoterol Standard;FORMOTEROL TARTARATE;Formoterol USP/EP/BP
CBNumber:
CB7722411
Molecular Formula:
C19H24N2O4
Molecular Weight:
344.4
MOL File:
73573-87-2.mol
Modify Date:
2024/3/19 15:37:50

Formoterol Properties

Boiling point 603.2±55.0 °C(Predicted)
Density 1.233±0.06 g/cm3(Predicted)
solubility DMSO: 20 mg/mL, soluble
form solid
pka 8.95±0.50(Predicted)
color off-white
Stability Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference 73573-87-2(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Warning
Hazard statements  H362-H361
Precautionary statements  P201-P260-P263-P264-P270-P308+P313-P201-P202-P281-P308+P313-P405-P501
WGK Germany  3

Formoterol Chemical Properties,Uses,Production

Chemical Properties

solid

Uses

Labeled Formoterol, intended for use as an internal standard for the quantification of Formoterol by GC- or LC-mass spectrometry.

Definition

ChEBI: A phenylethanoloamine having 4-hydroxy and 3-formamido substituents on the phenyl ring and an N-(4-methoxyphenyl)propan-2-yl substituent.

General Description

Formoterol (Foradil) isalso a lipophilic (log P= 1.6) and long-acting β2-agonist. Ithas 3'-formylamino ( β-directing) and 4 OH groups on onephenyl ring and a lipophilic -directing N-isopropyl-pmethoxyphenylgroup on the nitrogen atom. Its long DOA(12 hours), which is comparable to that of salmeterol, hasbeen suggested to result from its association with the membranelipid bilayer, from which it gradually diffuses to provideprolonged stimulation of β2 receptors and its resistanceto MAO and COMT. Formoterol has a much faster onset ofaction than does salmeterol as result of its lower lipophilicity.Both of these long-acting drugs are used by inhalationand are recommended for maintenance treatment of asthma,usually in conjunction with an inhaled corticosteroid.

Mechanism of action

Formoterol has 3′-formylamino and 4′-hydroxy ring R3 substitution pattern but also an alkoxyphenylethyl lipophilic group R1 on the nitrogen, similar to ritodrine. Although it is less lipophilic (log P = 1.6) than salmeterol, it has a 12-hour duration of action similar to that for salmeterol. It is administered as an inhaled dry powder, because it is unstable to heat and moisture. It is a mixture of (R,R)-(–)- and (S,S)-(+)-stereoisomers, with the (R,R)-isomer having approximately 1,000-fold more affinity for the β2-receptor than the (S,S)-isomer. Because of its high potency and low dose, however, there is no clinical advantage for using (R,R)-formoterol as bronchodilator compared to the racemate. Unlike salmeterol, formoterol has a faster onset of action as a result of its lower lipophilicity. It is also more potent; a 12-μg dose of formoterol has been demonstrated to be equivalent to a 50-μg dose of salmeterol.

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n-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl)propan-2-ylamino]ethyl]phenyl]formamide FORMOTEROL TARTARATE FormoterolBase Formoterol Fumarate 43229-80-7 / Base Eformoterol Formamide, N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, rel- Formamide, N-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, (R*,R*)- Formamide, N-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, (R*,R*)-(+-)- Oxis N-[2-Hydroxy-5-[1(R)-hydroxy-2-[[2-(4-methoxyphenyl)-1(R)-methylethyl] amino]ethyl]phenyl]formamide FORMOTEROL rel-N-(2-Hydroxy-5-((R)-1-hydroxy-2-(((R)-1-(4-Methoxyphenyl)propan-2-yl)aMino)ethyl)phenyl)forMaMide N-(2-Hydroxy-5-((R)-1-hydroxy-2-(((R)-1-(4-methoxyphenyl)propan-2-yl)amino)ethyl)phenyl)formamide 1-nitrotridec-1-ene Formoterol USP/EP/BP Formoterol (10mM in DMSO) Formoteral FORMOTEROL TARTRATE Formoterol Standard 73573-87-2 C19H24N2O4 Other APIs Inhibitors (intermediates of formoterol ) API