Procaterol

Procaterol
Clinical data
Trade names	Meptin, others
Other names	CI-888; CI888; OPC-2009; OPC2009
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Oral (tablets, syrup), inhalation (DPITooltip dry-powder inhaler)
Drug class	β2-Adrenergic receptor agonist; Bronchodilator; Antiasthmatic
ATC code	R03AC16 (WHO) R03CC08 (WHO);
Pharmacokinetic data
Metabolism	Hepatic (extensive)
Elimination half-life	3.8–4.3 hours
Duration of action	4–12 hours
Excretion	Urine: 70% (20% unchanged); Feces: 24% (21% unchanged)
Identifiers
	IUPAC name (±)-(1R,2S)-rel-8-Hydroxy-5-[1-hydroxy-2-(isopropylamino)butyl]-quinolin-2(1H)-on e;
CAS Number	72332-33-3 ; HCl: 59828-07-8 ;
PubChem CID	4916;
DrugBank	DB01366 ;
ChemSpider	599984 ;
UNII	X7I3EMM5K0; HCl: 4VD1BRT7T8 ;
KEGG	D08424 ;
ChEBI	CHEBI:135209;
ChEMBL	ChEMBL160519;
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;
	InChI InChI=1S/C16H22N2O3/c1-4-12(17-9(2)3)16(21)11-5-7-13(19)15-10(11)6-8-14(20)18-15/h5-9,12,16-17,19,21H,4H2,1-3H3,(H,18,20); Key:FKNXQNWAXFXVNW-UHFFFAOYSA-N;
	(what is this?) (verify)

Procaterol (INNTooltip International Nonproprietary Name), sold under the brand name Meptin among others, is a β₂-adrenergic receptor agonist which is used in the treatment of asthma.^[5]^[6]^[7] It has been used extensively in Japan and is available in many countries, but is not marketed in the United States or the United Kingdom.^[6]^[8]^[3] The drug is orally active and can also be used by inhalation.^[1]^[4]

Procaterol was patented in 1974 and came into medical use in 1980.^[9] It is similar to salbutamol (albuterol), but has a somewhat more prolonged action. The drug is readily oxidized in the presence of moisture and air, and requires stabilizers for use by inhalation.^[10]

Side effects

Side effects of procaterol include tremors and nervousness among others.^[11]

Chemistry

Procaterol is a substituted phenylisobutylamine (α-ethylphenethylamine), β-hydroxyamphetamine, and cyclized phenethylamine. It has an unusual chemical structure compared to many other β-adrenergic receptor agonists.^[4]^[11]

Synthesis

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.^[12]^[13]^[14]^[15]

Analogues

Analogues of procaterol include isoprenaline (isoproterenol), isoetarine (isoetharine), isoetarine, and salbutamol, among others.

Society and culture

Names

It is also known as procaterol hydrochloride (USAN). Procaterol is available under a number of trade names (Onsukil, Masacin, Procadil and others).^[16]

References

1 2 3 4 5 Eldon MA, Battle MM, Coon MJ, Nordblom GD, Sedman AJ, Colburn WA (April 1993). "Clinical pharmacokinetics and relative bioavailability of oral procaterol". Pharmaceutical Research. 10 (4): 603–605. doi:10.1023/a:1018966506819. PMID 8483846.
↑ Kobayashi H, Masuda M, Kashiyama E, Koga N, Yasuda Y, Shibutani T, et al. (November 2010). "Pharmacokinetic study of the oral administration of procaterol hydrochloride hydrate 50 µg in healthy adult Japanese men". International Journal of Clinical Pharmacology and Therapeutics. 48 (11): 744–750. doi:10.5414/cpp48744. PMID 20979933.
1 2 Gern JE, Lemanske RF (1993). "β-Adrenergic Agonist Therapy". Immunology and Allergy Clinics of North America. 13 (4): 839–860. doi:10.1016/S0889-8561(22)00663-4.
1 2 3 Kemp JP (1983). "Adrenergic bronchodilators, old and new". The Journal of Asthma. 20 (6): 445–453. doi:10.3109/02770908309077387. PMID 6243013.
↑ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3. Retrieved 26 July 2026.
1 2 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. ISBN 978-3-88763-075-1. Retrieved 26 July 2026.
↑ Morton DI, Morton IK, Hall JM, Hall DJ (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-0-7514-0499-9. Retrieved 26 July 2026.
↑ "Procaterol". Drugs.com. Retrieved 27 July 2026.
↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 978-3-527-60749-5.
↑ US 4616022, Ghebre-sellassie I, Nesbitt JR, "Procaterol stabilization", published 1984, issued 1986, assigned to Warner Lambert Co LLC
1 2 Siegel SC, Katz RM, Rachelefsky GS, Brandon ML, Borgen LA (June 1985). "A placebo-controlled trial of procaterol: a new long-acting oral beta 2-agonist in bronchial asthma". The Journal of Allergy and Clinical Immunology. 75 (6): 698–705. doi:10.1016/0091-6749(85)90096-x. PMID 2861219.
1 2 US 4026897, Nakagawa K, Yoshizaki S, "5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives", published 1977-05-31, issued 31 May 1977, assigned to Otsuka Pharmaceutical Co Ltd
1 2 Yoshizaki 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.
1 2 Yoshizaki 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.
1 2 Yoshizaki 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.
↑ "International Drugs: Procaterol". Drugs.com. Retrieved 7 March 2016.

[EldonBattleCoon1993-1] 1 2 3 4 5 Eldon MA, Battle MM, Coon MJ, Nordblom GD, Sedman AJ, Colburn WA (April 1993). "Clinical pharmacokinetics and relative bioavailability of oral procaterol". Pharmaceutical Research. 10 (4): 603–605. doi:10.1023/a:1018966506819. PMID 8483846.

[KobayashiMasudaKashiyama2010-2] Kobayashi H, Masuda M, Kashiyama E, Koga N, Yasuda Y, Shibutani T, et al. (November 2010). "Pharmacokinetic study of the oral administration of procaterol hydrochloride hydrate 50 µg in healthy adult Japanese men". International Journal of Clinical Pharmacology and Therapeutics. 48 (11): 744–750. doi:10.5414/cpp48744. PMID 20979933.

[GernLemanske1993-3] 1 2 Gern JE, Lemanske RF (1993). "β-Adrenergic Agonist Therapy". Immunology and Allergy Clinics of North America. 13 (4): 839–860. doi:10.1016/S0889-8561(22)00663-4.

[Kemp1983-4] 1 2 3 Kemp JP (1983). "Adrenergic bronchodilators, old and new". The Journal of Asthma. 20 (6): 445–453. doi:10.3109/02770908309077387. PMID 6243013.

[Elks2014-5] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3. Retrieved 26 July 2026.

[IndexNominum2000-6] 1 2 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. ISBN 978-3-88763-075-1. Retrieved 26 July 2026.

[MortonMortonHall1999-7] Morton DI, Morton IK, Hall JM, Hall DJ (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-0-7514-0499-9. Retrieved 26 July 2026.

[Drugs.com-8] "Procaterol". Drugs.com. Retrieved 27 July 2026.

[Fis2006-9] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 978-3-527-60749-5.

[patent-10] US 4616022, Ghebre-sellassie I, Nesbitt JR, "Procaterol stabilization", published 1984, issued 1986, assigned to Warner Lambert Co LLC

[SiegelKatzRachelefsky1985-11] 1 2 Siegel SC, Katz RM, Rachelefsky GS, Brandon ML, Borgen LA (June 1985). "A placebo-controlled trial of procaterol: a new long-acting oral beta 2-agonist in bronchial asthma". The Journal of Allergy and Clinical Immunology. 75 (6): 698–705. doi:10.1016/0091-6749(85)90096-x. PMID 2861219.

[5_1_Hydroxy-12] 1 2 US 4026897, Nakagawa K, Yoshizaki S, "5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives", published 1977-05-31, issued 31 May 1977, assigned to Otsuka Pharmaceutical Co Ltd

[Yoshizaki_1980-13] 1 2 Yoshizaki 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.

[Yoshizaki_1976-14] 1 2 Yoshizaki 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.

[Yoshizaki_1977-15] 1 2 Yoshizaki 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.

[16] "International Drugs: Procaterol". Drugs.com. Retrieved 7 March 2016.

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