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Procaterol

From Wikipedia, the free encyclopedia
Pharmaceutical drug
Pharmaceutical compound
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
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
ECHA InfoCard100.069.606Edit this at Wikidata
Chemical and physical data
FormulaC16H22N2O3
Molar mass290.363 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • CC(C)NC(CC)C(O)c2ccc(O)c1NC(=O)C=Cc12
 ☒NcheckY (what is this?)  (verify)

Procaterol is aβ2 adrenoreceptor agonist used for the treatment ofasthma in many countries, but is not approved in theUnited States. The drug is readilyoxidized 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 tosalbutamol (albuterol), but has a somewhat more prolonged action. It can be taken orally or by inhalation to treat asthma.

Synthesis

[edit]

8-Hydroxycarbostyril1 is acylated with 2-bromobutyric acid chloride2 at the fifth position of the quinoline system, which gives the compound3. This undergoes action of isopropylamine, forming an aminoketone, the carbonyl group of which is reduced by sodium borohydride, giving procaterol4.[3][4][5][6]

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

Names

[edit]

It is also known as procaterol hydrochloride (USAN).

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

References

[edit]
  1. ^US 4616022, Ghebre-sellassie I, Nesbitt Jr RU, "Procaterol stabilization", published 1984, issued 1986, assigned to Warner Lambert Co LLC 
  2. ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery. John Wiley & Sons. p. 543.ISBN 9783527607495.
  3. ^abUS 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. ^abYoshizaki 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. ^abYoshizaki 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. ^abYoshizaki 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. ^"International Drugs: Procaterol".Drugs.com. Retrieved7 March 2016.
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