Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Pirbuterol: Difference between pages

{{Short description|Chemical compound}}

{{other uses|Maxair (disambiguation)}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464207791

| IUPAC_name = (''RS'')-6-[2-(''tert''-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol

| image = Pirbuterol.svg

| width = 240

| chirality = [[Racemic mixture]]

<!--Clinical data-->| tradename = Maxair

| Drugs.com = {{drugs.com|CDI|pirbuterol}}

| MedlinePlus = a601096

| legal_AU = S4

| legal_US = Rx-only

| routes_of_administration = Inhalational ([[Metered-dose inhaler|MDI]])

<!--Identifiers-->| IUPHAR_ligand = 7272

| CAS_number_Ref = {{cascite|correct|CAS}}

| index2_label = HCl

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 38029-10-6

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = J6793T658K

| CAS_number = 38677-81-5

| ATC_prefix = R03

| ATC_suffix = AC08

| ATC_supplemental = {{ATC|R03|CC07}}

| PubChem = 4845

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01291

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4679

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = OG645J8RVW

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D08387

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1094966

<!--Chemical data-->| C = 12

| H = 20

| N = 2

| O = 3

| SMILES = Oc1ccc(nc1CO)C(O)CNC(C)(C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C12H20N2O3/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8/h4-5,11,13,15-17H,6-7H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VQDBNKDJNJQRDG-UHFFFAOYSA-N

<!-- Definition and medical uses -->

'''Pirbuterol''' (trade name '''Maxair''') is a short-acting [[Beta2-adrenergic agonist|β₂ adrenoreceptor agonist]] with [[Bronchodilator|bronchodilating]] action used in the treatment of [[asthma]], available (as pirbuterol acetate) as a breath-activated [[metered-dose inhaler]].

<!-- Society and culture -->

It was patented in 1971 and came into medical use in 1983.<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>

==Medical use==

Pirbuterol is used in asthma for reversal of acute [[bronchospasm]], and also as a maintenance medication to prevent future attacks. It should be used in patients 12 years of age and older with or without concurrent [[theophylline]] and/or inhaled [[corticosteroid]].<ref name="PI">{{cite web|title=Maxair Autohaler (pirbuterol acetate inhalation aerosol) For Oral Inhalation Only. U.S. Full Prescribing Information|url=http://solutions.3m.com/3MContentRetrievalAPI/BlobServlet?lmd=1137774415000&locale=en_US&univid=1114282316409&fallback=true&assetType=MMM_Image&blobAttribute=ImageFile&placeId=39903&version=current|publisher=3M Pharmaceuticals. Northridge, CA 91324|access-date=7 March 2016|archive-url=https://web.archive.org/web/20180920082834/http://solutions.3m.com/3MContentRetrievalAPI/BlobServlet?lmd=1137774415000&locale=en_US&univid=1114282316409&fallback=true&assetType=MMM_Image&blobAttribute=ImageFile&placeId=39903&version=current|archive-date=20 September 2018|url-status=dead}}</ref><ref name="BianchiClavenna2010">{{cite journal | vauthors = Bianchi M, Clavenna A, Bonati M | s2cid = 21834280 | title = Inter-country variations in anti-asthmatic drug prescriptions for children. Systematic review of studies published during the 2000-2009 period | journal = European Journal of Clinical Pharmacology | volume = 66 | issue = 9 | pages = 929–36 | date = September 2010 | pmid = 20533030 | doi = 10.1007/s00228-010-0845-y | url = https://hal.archives-ouvertes.fr/hal-00599220/file/PEER_stage2_10.1007%252Fs00228-010-0845-y.pdf }}</ref>

==Mode of action==

{{Further|Beta2-adrenergic agonist}}

==Pharmacokinetics==

After inhalation of doses up to 800 [[Microgram|''μ''g]] (twice the maximum recommended dose) systemic blood levels of pirbuterol are below the limit of assay sensitivity (2–5&nbsp;ng/ml). A mean of 51% of the dose is recovered in urine as pirbuterol plus its sulfate conjugate following administration by aerosol. Pirbuterol is not metabolized by [[Catechol-O-methyl transferase|catechol-''O''-methyltransferase]]. The plasma half-life measured after oral administration is about two hours.<ref name="PI" />

==Adverse effects==

{{Further|Beta2-adrenergic agonist}}

== References ==

{{Reflist}}

== External links ==

* [http://www.rxlist.com/cgi/generic/pirbu.htm RxList: Maxair (Pirbuterol)]

{{Adrenergic agonists}}

{{Asthma_and_copd_rx}}

{{Phenethylamines}}

[[Category:Phenylethanolamines]]

[[Category:Beta2-adrenergic agonists]]

[[Category:Pyridines]]

{{respiratory-system-drug-stub}}