procaterol

{{Short description|Pharmaceutical drug}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 443406123

| IUPAC_name = (±)-(1R,2S)-rel-8-Hydroxy-5-[1-hydroxy-2-(isopropylamino)butyl]-quinolin-2(1H)-one

| image = Procaterol.svg

| width = 200

| chirality = Racemic mixture

| tradename = Meptin, others

| Drugs.com = {{drugs.com|CONS|procaterol}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_status =

| routes_of_administration = Oral (tablets, syrup), inhalation (DPI)

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| 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

| C=16 | H=22 | N=2 | O=3

| smiles = CC(C)NC(CC)C(O)c2ccc(O)c1NC(=O)C=Cc12

}}

Procaterol is a β2 adrenoreceptor agonist used for the treatment of asthma in many countries, but is not approved in the United States. The drug is readily oxidized in the presence of moisture and air, and requires stabilizers for use by inhalation.{{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 }}

It was patented in 1974 and came into medical use in 1980.{{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}} Procaterol is similar to salbutamol (albuterol), but has a somewhat more prolonged action. It can be taken orally or by inhalation to treat asthma.

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.

File:Procaterol-synthesis.svg

Names

It is also known as procaterol hydrochloride (USAN).

Procaterol is available under a number of trade names (Onsukil, Masacin, Procadil and others).{{cite web|title=International Drugs: Procaterol|url=https://www.drugs.com/international/procaterol.html|website=Drugs.com.|access-date=7 March 2016}}

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References

{{reflist}}

{{Adrenergic agonists}}

{{Asthma and copd rx}}

Category:2-Quinolones

Category:Beta-Hydroxyamphetamines

Category:Beta2-adrenergic agonists

Category:Quinolinols

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