Procaterol

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Procaterol
Clinical data
Trade namesMeptin, others
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral (tablets, syrup), inhalation (DPI)
ATC code
Identifiers
  • (±)-(1R,2S)-rel-8-Hydroxy-5-[1-hydroxy-2-(isopropylamino)butyl]-quinolin-2(1H)-one
JSmol)
ChiralityRacemic mixture
  • CC(C)NC(CC)C(O)c2ccc(O)c1NC(=O)C=Cc12
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Procaterol is an intermediate-acting[

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.

Procaterol synthesis:[3][4][5][6]

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

  1. ^ a b US 4616022, Ghebre-sellassie I, Nesbitt Jr RU, "Procaterol stabilization", published 1984, issued 1986, assigned to Warner Lambert Co LLC 
  2. ISBN 9783527607495
    .
  3. ^ US 4026897, Nakagawa K, Yoshizaki S, "5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives", issued 31 May 1977, assigned to Otsuka Pharmaceutical Co Ltd 
  4. doi:10.1248/cpb.28.3441
    .
  5. PMID 10441
    .
  6. PMID 894683
    .
  7. ^ "International Drugs: Procaterol". Drugs.com. Retrieved 7 March 2016.
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