Procaterol

Procaterol

Systematic (IUPAC) name
(±)-(1R,2S)-rel-8-Hydroxy-5-[1-hydroxy-2-(isopropylamino)butyl]-quinolin-2(1H)-one
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral, inhalation
Identifiers
CAS Number	59828-07-8 Y
ATC code	R03AC16 (WHO) R03CC08
PubChem	CID: 4916
ChemSpider	599984 N
UNII	X7I3EMM5K0 Y
KEGG	D08424 Y
Chemical data
Formula	C16H22N2O3
Molecular mass	290.357 g/mol
SMILES CC(C)NC(CC)C(O)c2ccc(O)c1NC(=O)C=Cc12
NY (what is this?)  (verify)

Procaterol, applied as procaterol hydrochloride (USAN), is an intermediate-acting β₂-adrenergic receptor 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 oxidised in the presence of moisture and air, making it unsuitable for therapeutic use by inhalation. Pharmaceutical company Parke-Davis/Warner-Lambert researched a stabilizer to prevent oxidation, but an effective one was never developed.

Synthesis

Like pirbuterol, procaterol exhibits similar broncholytic properties as albuteral, but it has somewhat of a more prolonged action. It is recommended for use as an inhaled drug for treating bronchial asthma.

Procaterol synthesis:

8-Hydroxycarbostyril is acylated with 2-bromobutyric acid chloride 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.

Synonyms of this drug are onsukil, masacin, procadil, meptin, and others.