View source for Chemistry:Procaterol

{{Short description|Pharmaceutical drug}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 443406123
| IUPAC_name = (±)-(1''R'',2''S'')-''rel''-8-Hydroxy-5-[1-hydroxy-2-(isopropylamino)butyl]-quinolin-2(1''H'')-one
| image = Procaterol.svg
| width = 200
| chirality = [[Chemistry:Racemic mixture|Racemic mixture]]

<!--Clinical data-->
| tradename = Meptin, others
| Drugs.com = {{drugs.com|CONS|procaterol}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_status =
| routes_of_administration = Oral ([[Medicine:Tablet (pharmacy)|tablets]], [[Chemistry:Syrup|syrup]]), inhalation ([[Medicine:Dry-powder inhaler|DPI]])

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 72332-33-3
| index2_label = HCl
| CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 	59828-07-8
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 4VD1BRT7T8
| ATC_prefix = R03
| ATC_suffix = AC16
| ATC_supplemental =  {{ATC|R03|CC08}}
| PubChem = 4916
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 599984
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X7I3EMM5K0
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08424

<!--Chemical data-->
| C=16 | H=22 | N=2 | O=3
| smiles = CC(C)NC(CC)C(O)c2ccc(O)c1NC(=O)C=Cc12
}}

'''Procaterol''' is an intermediate-acting{{cn|date=March 2016}} [[Chemistry:Beta2-adrenergic agonist|β<sub>2</sub> adrenoreceptor agonist]] used for the treatment of [[Medicine:Asthma|asthma]]. It has never been filed for [[Organization:Food and Drug Administration|FDA]] evaluation in the {{wipe|United States}}, where it is not marketed. The drug is readily [[Chemistry:Redox|oxidized]] in the presence of moisture and air, making it unsuitable for therapeutic use by inhalation.<ref name="patent">{{cite patent | inventor = Ghebre-sellassie I, Nesbitt Jr RU | assign1 = Warner Lambert Co LLC | publication-date = 1984 | issue-date = 1986 | title = Procaterol stabilization | country-code = US | number = 4616022 }}</ref> Pharmaceutical company Parke-Davis/Warner-Lambert researched a stabilizer to prevent oxidation, but an effective one was never developed.<ref name="patent" />

<!-- Society and culture -->
It was patented in 1974 and came into medical use in 1980.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=543 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA543 |language=en}}</ref>

==Synthesis==
Like pirbuterol, procaterol exhibits similar broncholytic properties as [[Chemistry:Salbutamol|salbutamol]] (albuterol), but it has somewhat of a more prolonged action. It is recommended for use as an inhaled drug for treating asthma.

[[File:Procaterol-synthesis.svg|thumb|left|700px|Procaterol synthesis:<ref>{{cite patent | inventor = Nakagawa K, Yoshizaki S | title = 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxycarbostyril derivatives | assign1 = Otsuka Pharmaceutical Co Ltd | country = US | number = 4026897 | gdate = 31 May 1977 }}</ref><ref>{{cite journal | vauthors = Yoshizaki S, Osaki M, Nakagawa K, Yamura Y | title = Synthesis of 8-hydroxycarbostyril | journal = Chemical and Pharmaceutical Bulletin | date = November 1980 | volume = 28 | issue = 11 | pages = 3441–3443 | doi = 10.1248/cpb.28.3441 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Yoshizaki S, Tanimura K, Tamada S, Yabuuchi Y, Nakagawa K | title = Sympathomimetic amines having a carbostyril nucleus | journal = Journal of Medicinal Chemistry | volume = 19 | issue = 9 | pages = 1138–1142 | date = September 1976 | pmid = 10441 | doi = 10.1021/jm00231a011 }}</ref><ref>{{cite journal | vauthors = Yoshizaki S, Manabe Y, Tamada S, Nakagawa K, Tei S | title = Isomers of erythro-5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril, a new bronchodilator | journal = Journal of Medicinal Chemistry | volume = 20 | issue = 8 | pages = 1103–1104 | date = August 1977 | pmid = 894683 | doi = 10.1021/jm00218a024 }}</ref>]]

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 (<small>({{wipe|South Korea}})</small>, <small>({{wipe|China}})</small>, <small>(ID)</small>, <small>(MY)</small>, <small>({{wipe|Philippines}})</small>, <small>([[Place:Singapore|SG]])</small>, <small>(TH)</small>, <small>([[Place:Hong Kong|HK]])</small>).<ref>{{cite web|title=International Drugs: Procaterol|url=https://www.drugs.com/international/procaterol.html|website=Drugs.com.|access-date=7 March 2016}}</ref>
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== References ==
{{reflist}}

{{Adrenergic agonists}}
{{Asthma and copd rx}}

[[Category:Phenylethanolamines]]
[[Category:Beta2-adrenergic agonists]]
[[Category:Quinolinols]]


{{Sourceattribution|Procaterol}}