13392-18-2

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statement Codes:

P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501

Hazard Classes and Categories:

Acute Tox. 4 (100%)

Usage

Uses

Used in Pharmaceutical Industry:
Fenoterol is used as an anti-inflammatory agent for its bronchodilating properties, helping to manage reversible airway obstruction. It is available under various brand names such as Berotec (as hydrobromide) by Boehringer Ingelheim, Dosberotec, Duovent, Fensol, and Partusisten.

Therapeutic Function

Bronchodilator

World Health Organization (WHO)

Fenoterol, a beta 2-adrenoreceptor agonist with bronchodilator activity, was introduced in 1971 for the management of asthma. In the 1960's, the use of other sympathomimetics in pressurised aerosols had already been associated with an increase in mortality due to asthma. However, it was not clear whether patients died from the severity of the asthma attack or from its treatment.

Mechanism of action

Fenoterol is a selective stimulant of β2-adrenoreceptors. It dilates bronchi and blood vessels, has a pronounced tocolytic action, lowers contractile activity and reduces uterus tonicity. It is mainly used in premature births.

Synthesis

Fenoterol, 3,5-dihydroxy-α[[(-p-hydroxy-α-methylphenethyl)amino]methyl]- benzyl alcohol (23.3.16), is synthesized from 3,5-diacetoxyacetophenone, which is brominated to give 3,5-diacetoxybromacetophenone (23.3.12). This is reacted with 2-benzylamino-1-(4-methoxyphenyl)-propane, giving the corresponding tertiary amine 23.3.13. Hydrolysis of the acetyl group of this product and removal of the protective benzyl group by hydrogen reduction using a palladium on carbon catalyst gives a secondary amine 23.3.14. This is reacted with hydrobromic acid, which cleaves the ether bond in the benzene ring, producing phenol derivative 23.3.15. Finally, reduction of the carbonyl group with hydrogen gives the desired fenoterol (23.3.16).

InChI:InChI=1/C17H21NO4/c1-11(6-12-2-4-14(19)5-3-12)18-10-17(22)13-7-15(20)9-16(21)8-13/h2-5,7-9,11,17-22H,6,10H2,1H3

Upstream product

• 100246-85-3 bis-(3-chloro-2-hydroxy-propyl)-cyclohexyl-amine 
• 108-91-8 cyclohexylamine 
• 61272-39-7 (+/-)-1-chloro-3-cyclohexylamino-2-propanol 

Downstream Products

• 130156-24-0 (S,S)-(+)-Fenoterol 
• 130156-24-0 (R,R)-(-)-Fenoterol 

Related news

Anti-inflammatory activities of Fenoterol (cas 13392-18-2) through β-arrestin-2 and inhibition of AMPK and NF-κB activation in AICAR-induced THP-1 cells07/31/2019

The AMP-activated protein kinase (AMPK) pathway has been shown to be able to regulate inflammation in several cell lines. We reported that fenoterol, a β2-adrenergic receptor (β2-AR) agonist, inhibited lipopolysaccharide (LPS)-induced AMPK activation and inflammatory cytokine production in THP...detailed

Stereochemical and conformational study on Fenoterol (cas 13392-18-2) by ECD spectroscopy and TD-DFT calculations07/30/2019

Fenoterol and its derivatives are selective β2-adrenergic receptor (β2-AR) agonists whose stereoselective biological activities have been extensively investigated in the past decade; a complete stereochemical characterization of fenoterol derivatives is therefore crucial for a better understan...detailed

In vitro transdermal permeation of Fenoterol (cas 13392-18-2) hydrobromide07/29/2019

The aim of this study was to determine if transdermal penetration of fenoterol, a β-agonist drug, could be enhanced and controlled by formulation modification and formulation of transdermal patches. Pre-formulation studies were performed to determine the feasibility of a transdermal dosage form...detailed

Effect of betamethasone, indomethacin and Fenoterol (cas 13392-18-2) on neonatal and maternal mononuclear cells stimulated with Escherichia coli07/28/2019

Despite considerable progress in the field of perinatal care, infectious diseases, especially when caused by gram negative bacteria, remain a major reason for neonatal morbidity and mortality. Notably infants born prematurely and those with very low birth weight are at risk due to their immature...detailed

Effects of Fenoterol (cas 13392-18-2) on the skeletal system depend on the androgen level07/27/2019

BackgroundThe role of sympathetic nervous system in the osseous tissue remodeling is not clear enough.detailed

Utility of Europium ion characteristic peak for quantitation of Fenoterol (cas 13392-18-2) hydrobromide and Salmeterol xinafoate in different matrices; application to stability studies07/26/2019

A simple selective luminescent dependent approach was established for quantitation of two selective β2 agonists namely; Fenoterol hydrobromide (FEN) and Salmeterol xinafoate (SAL). This approach utilizes the capability of the cited drugs to undergo a complexation reaction with Europium ion (Eu3...detailed

Relevant academic research and scientific papers

Combined doses

The present invention discloses a method and a pharmaceutical dry powder combined dose for the prophylaxis or treatment of a respiratory disorder in a mammalian host by inhalation of a metered dry powder combined dose of finely divided dry medication powders. At least one dry powder medicament is selected from a first group of bronchodilating medicaments and at least one dry powder medicament from a second group of anti-inflammatory medicaments. A metered dry powder medicinal combined dose comprising separately metered deposits of medicinally suitable quantities of each of the selected medicaments is prepared, in which the sum of the metered deposits constitutes the metered quantities of powder of the combined dose and the medicinal combined dose is introduced into an adapted inhaler device for a generally simultaneous delivery of the medicinal combined dose during the course of a single inhalation by a user, such that the delivered medicinal combined dose is composed of a high proportion of mixed de-aggregated fine particles of the selected medicaments, whereby an desired therapeutic or treating effect to the user is achieved.

Pharmaceutical formula

The present invention concerns a pharmacological vehicle or carrier system, which makes possible administration of the active ingredient with a high absorption thereof in the blood circulation of the patient treated therewith, in particular also in the case of oral administration. The pharmacological vehicle system according to the invention comprises ultrafine particles of a reaction product of a reactive derivative of an at least dibasic inorganic acid or an alkane-carboxylic acid having 2 or 3 carboxyl groups and optionally one or two hydroxy groups, wherein one bond of the dibasic inorganic acid or one carboxy group of the alkane-carboxylic acid is bonded to a pharmacological active ingredient containing a hydroxy group, SH group and/or a primary or secondary amino group having a ractive hydrogen atom on this group, and the other bond is bonded to the free hydroxy group of a glycerolipid having at least one free hydroxy group on the glycerol. The invention further concerns these reaction products and a process for the preparation of ultrafine particles of these reaction products.