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 (tablets, syrup), inhalation (DPI)
Identifiers
CAS Number	59828-07-8
ATC code	R03AC16 (WHO) R03CC08 (WHO)
PubChem	CID 4916
ChemSpider	599984
UNII	X7I3EMM5K0
KEGG	D08424
Chemical data
Formula	C16H22N2O3
Molar mass	290.357 g/mol
Chirality	Racemic mixture
SMILES CC(C)NC(CC)C(O)c2ccc(O)c1NC(=O)C=Cc12
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Procaterol, applied as procaterol hydrochloride (USAN), is an intermediate-acting 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]

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.

Procaterol synthesis:^[2][3][4][5]

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.

Trade names

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)).^[6]

References

1. US, "Procaterol stabilization", published 1984, issued 1986 
2. K. Nakagawa, S. Yoshizaki, U.S. Patent 4,026,897 (1977).
3. S. Yoshizaki, M. Osaki, K. Nakagawa, Y. Yamura, Chem. Pharm. Bull., 28, 3441 (1980).
4. Yoshizaki, Shiro; Tanimura, Kaoru; Tamada, Shigeharu; Yabuuchi, Youichi; Nakagawa, Kazuyuki (1976). "Sympathomimetic amines having a carbostyril nucleus". Journal of Medicinal Chemistry 19 (9): 1138. doi:10.1021/jm00231a011. PMID 10441.
5. Yoshizaki, Shiro; Manabe, Yoshiaki; Tamada, Shigeharu; Nakagawa, Kazuyuki; Tei, Seiso (1977). "Isomers of erythro-5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril, a new bronchodilator". Journal of Medicinal Chemistry 20 (8): 1103. doi:10.1021/jm00218a024. PMID 894683.
6. "International Drugs: Procaterol". Drugs.com. Retrieved 7 March 2016.