Procaterol

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Procaterol
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Clinical data
Trade namesMeptin, others
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral (tablets, syrup), inhalation (DPI)
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Identifiers
  • (±)-(1R,2S)-rel-8-Hydroxy-5-[1-hydroxy-2-(isopropylamino)butyl]-quinolin-2(1H)-one
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Chemical and physical data
FormulaC16H22N2O3
Molar mass290.363 g·mol−1
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ChiralityRacemic mixture
  • CC(C)NC(CC)C(O)c2ccc(O)c1NC(=O)C=Cc12
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Procaterol is a β2 adrenoreceptor agonist used for the treatment of asthma in many countries, but is not approved in the United States. The drug is readily oxidized in the presence of moisture and air, and requires stabilizers for use by inhalation.[1]

It was patented in 1974 and came into medical use in 1980.[2] Procaterol is similar to salbutamol (albuterol), but has a somewhat more prolonged action. It can be taken orally or by inhalation to treat asthma.

Synthesis

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.[3][4][5][6]

File:Procaterol-synthesis.svg
Procaterol synthesis:[3][4][5][6]

Names

It is also known as procaterol hydrochloride (USAN).

Procaterol is available under a number of trade names (Onsukil, Masacin, Procadil and others).[7]

References

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  1. ^ Page Template:Citation/styles.css has no content.US 4616022, Ghebre-sellassie I, Nesbitt Jr RU, "Procaterol stabilization", published Script error: No such module "auto date formatter"., issued Script error: No such module "auto date formatter"., assigned to Warner Lambert Co LLC 
  2. ^ Page Module:Citation/CS1/styles.css has no content.Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495.
  3. ^ a b Page Template:Citation/styles.css has no content.US 4026897, Nakagawa K, Yoshizaki S, "5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives", issued Script error: No such module "auto date formatter"., assigned to Otsuka Pharmaceutical Co Ltd 
  4. ^ a b Page Module:Citation/CS1/styles.css has no content.Yoshizaki S, Osaki M, Nakagawa K, Yamura Y (November 1980). "Synthesis of 8-hydroxycarbostyril". Chemical and Pharmaceutical Bulletin. 28 (11): 3441–3443. doi:10.1248/cpb.28.3441.
  5. ^ a b Page Module:Citation/CS1/styles.css has no content.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. PMID 10441.
  6. ^ a b Page Module:Citation/CS1/styles.css has no content.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. PMID 894683.
  7. ^ Page Module:Citation/CS1/styles.css has no content."International Drugs: Procaterol". Drugs.com. Retrieved 7 March 2016.

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