Chemistry:Procaterol

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Procaterol (INN), sold under the brand name Meptin among others, is a β2-adrenergic receptor agonist which is used in the treatment of asthma.[1][2][3] 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.[2][4][5] The drug is orally active and can also be used by inhalation.[6][7]

Procaterol was patented in 1974 and came into medical use in 1980.[8] 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.[9]

Side effects

Side effects of procaterol include tremors and nervousness among others.[10]

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.[7][10]

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.[11][12][13][14]

Procaterol synthesis:[11][12][13][14]

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).[15]

See also

  • Substituted phenylisobutylamine
  • Substituted β-hydroxyamphetamine

References

  1. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1021. Retrieved 26 July 2026. 
  2. ↑ 2.0 2.1 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA878. Retrieved 26 July 2026. 
  3. ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 31 October 1999. ISBN 978-0-7514-0499-9. https://books.google.com/books?id=mqaOMOtk61IC&pg=PA232. Retrieved 26 July 2026. 
  4. ↑ "Procaterol". https://www.drugs.com/international/procaterol.html. 
  5. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named GernLemanske1993
  6. ↑ "Clinical pharmacokinetics and relative bioavailability of oral procaterol". Pharmaceutical Research 10 (4): 603–605. April 1993. doi:10.1023/a:1018966506819. PMID 8483846. 
  7. ↑ 7.0 7.1 Cite error: Invalid <ref> tag; no text was provided for refs named Kemp1983
  8. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 543. ISBN 978-3-527-60749-5. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA543. 
  9. ↑ Ghebre-sellassie I, Nesbitt JR, "Procaterol stabilization", US patent 4616022, published 1984, issued 1986, assigned to Warner Lambert Co LLC
  10. ↑ 10.0 10.1 "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. June 1985. doi:10.1016/0091-6749(85)90096-x. PMID 2861219. 
  11. ↑ 11.0 11.1 Nakagawa K, Yoshizaki S, "5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives", US patent 4026897, published 1977-05-31, issued 31 May 1977, assigned to Otsuka Pharmaceutical Co Ltd
  12. ↑ 12.0 12.1 "Synthesis of 8-hydroxycarbostyril". Chemical and Pharmaceutical Bulletin 28 (11): 3441–3443. November 1980. doi:10.1248/cpb.28.3441. 
  13. ↑ 13.0 13.1 "Sympathomimetic amines having a carbostyril nucleus". Journal of Medicinal Chemistry 19 (9): 1138–1142. September 1976. doi:10.1021/jm00231a011. PMID 10441. 
  14. ↑ 14.0 14.1 "Isomers of erythro-5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril, a new bronchodilator". Journal of Medicinal Chemistry 20 (8): 1103–1104. August 1977. doi:10.1021/jm00218a024. PMID 894683. 
  15. ↑ "International Drugs: Procaterol". https://www.drugs.com/international/procaterol.html. 



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