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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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
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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

[edit | edit source]

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]

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

Names

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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. ^ US 4616022, Ghebre-sellassie I, Nesbitt Jr RU, "Procaterol stabilization", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Warner Lambert Co LLC 
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ a b US 4026897, Nakagawa K, Yoshizaki S, "5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives", issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Otsuka Pharmaceutical Co Ltd 
  4. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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