Procaterol

Clinical data
Trade names	Meptin, others
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral (tablets, syrup), inhalation (DPI)
ATC code	R03AC16 (WHO) R03CC08 (WHO)
Identifiers
IUPAC name (±)-(1R,2S)-rel-8-Hydroxy-5-[1-hydroxy-2-(isopropylamino)butyl]-quinolin-2(1H)-one
CAS Number	72332-33-3 Y HCl: 59828-07-8 Y
PubChem CID	4916
ChemSpider	599984 N
UNII	X7I3EMM5K0 HCl: 4VD1BRT7T8 Y
KEGG	D08424 Y
CompTox Dashboard (EPA)	DTXSID5045673
ECHA InfoCard	100.069.606
Chemical and physical data
Formula	C16H22N2O3
Molar mass	290.363 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CC(C)NC(CC)C(O)c2ccc(O)c1NC(=O)C=Cc12
NY (what is this?)  (verify)

Procaterol is an intermediate-acting^{[citation needed]} β₂ adrenoreceptor 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 oxidized in the presence of moisture and air, making it unsuitable for therapeutic use by inhalation.^[1] Pharmaceutical company Parke-Davis/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.

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]