Procaterol is an intermediate-acting[citation needed]β2 adrenoreceptor agonist used for the treatment of
asthma. It has never been filed for
FDA evaluation in the
United States, where it is not marketed. The drug is readily
oxidized in the presence of moisture and air, making it unsuitable for therapeutic use by inhalation.[1] Pharmaceutical company
Parke-Davis/
Warner-Lambert researched a stabilizer to prevent oxidation, but an effective one was never developed.[1]
It was patented in 1974 and came into medical use in 1980.[2]
Synthesis
Like pirbuterol, procaterol exhibits similar broncholytic properties as
salbutamol (albuterol), but it has somewhat of a more prolonged action. It is recommended for use as an inhaled drug for treating asthma.
8-Hydroxycarbostyril 1 is acylated with 2-bromobutyric acid chloride 2 at the fifth position of the quinoline system, which gives the compound 3. This undergoes action of isopropylamine, forming an aminoketone, the carbonyl group of which is reduced by sodium borohydride, giving procaterol 4.
Names
It is also known as procaterol hydrochloride (
USAN).
Procaterol is available under a number of trade names (Onsukil, Masacin, Procadil and others), the most common seems to be Meptin ((
KR), (
CN), (
ID), (
MY), (
PH), (
SG), (
TH), (
HK)).[7]
References
^
abUS 4616022, Ghebre-sellassie I, Nesbitt Jr RU, "Procaterol stabilization", published 1984, issued 1986, assigned to Warner Lambert Co LLC
^Yoshizaki S, Tanimura K, Tamada S, Yabuuchi Y, Nakagawa K (September 1976). "Sympathomimetic amines having a carbostyril nucleus". Journal of Medicinal Chemistry. 19 (9): 1138–1142.
doi:
10.1021/jm00231a011.
PMID10441.
^Yoshizaki S, Manabe Y, Tamada S, Nakagawa K, Tei S (August 1977). "Isomers of erythro-5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril, a new bronchodilator". Journal of Medicinal Chemistry. 20 (8): 1103–1104.
doi:
10.1021/jm00218a024.
PMID894683.