Orciprenaline: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 408782146

| IUPAC_name = (''RS'')-5-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,3-diol

| image = Orciprenaline.svg

| width =

| chirality = [[Racemic mixture]]

| USAN = Metaproterenol

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

| Drugs.com = {{drugs.com|monograph|metaproterenol-sulfate}}

| MedlinePlus = a682084

| pregnancy_AU = A

| legal_AU = S4

| pregnancy_US = C

| legal_US = Rx-only

| routes_of_administration = Inhalation ([[Metered-dose inhaler|MDI]]) and [[Tablet (pharmacy)|tablets]]

<!--Pharmacokinetic data-->| bioavailability = 3% if inhaled, 40% if taken orally

| protein_bound =

| metabolism = [[Gastrointestinal tract|Gastrointestinal]] and [[liver|hepatic]]

<!--Identifiers-->| IUPHAR_ligand = 7250

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 586-06-1

| ATC_prefix = R03

| ATC_suffix = AB03

| ATC_supplemental = {{ATC|R03|CB03}}<br>{{ATC|R03|CB53}}

| PubChem = 4086

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB00816

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

| ChemSpiderID = 3944

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

| UNII = 53QOG569E0

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08300

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 82719

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

| ChEMBL = 776

<!--Chemical data-->| C = 11

| H = 17

| N = 1

| O = 3

| smiles = Oc1cc(cc(O)c1)C(O)CNC(C)C

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

| StdInChI = 1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3

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

| StdInChIKey = LMOINURANNBYCM-UHFFFAOYSA-N

| solubility = 9.7

'''Orciprenaline''', also known as '''metaproterenol''', is a [[bronchodilator]] used in the treatment of [[asthma]].<ref>{{cite journal |title = DrugBank 3.0: a comprehensive resource for omics research on drugs |vauthors=Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS |journal = Nucleic Acids Res. |year = 2011 |volume = 39 |issue = Database issue |pages = D1035-41 | pmid =21059682 |doi=10.1093/nar/gkq1126 |pmc=3013709}}</ref><ref>{{cite journal |title = DrugBank: a knowledgebase for drugs, drug actions and drug targets|author1-link=David S. Wishart |vauthors=Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M |journal = Nucleic Acids Res |year = 2008 |volume = 36 |issue = Database issue |pages = D901-6 |pmid = 18048412 |doi=10.1093/nar/gkm958 |pmc=2238889}}</ref> Orciprenaline is a moderately selective [[Beta2-adrenergic agonist|β₂ adrenergic receptor agonist]] that stimulates receptors of the [[smooth muscle]] in the lungs, uterus, and vasculature supplying [[skeletal muscle]], with minimal or no effect on α adrenergic receptors. The pharmacologic effects of β adrenergic [[agonist]] drugs, such as orciprenaline, are at least in part attributable to stimulation through β adrenergic receptors of intracellular [[adenylyl cyclase]], the enzyme which catalyzes the conversion of [[Adenosine triphosphate|ATP]] to [[Cyclic adenosine monophosphate|cAMP]]. Increased cAMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of [[immediate hypersensitivity]] from many cells, especially from [[mast cell]]s.

__TOC__

== Possible side effects ==

* tremor

* nervousness

* dizziness

* weakness

* headache

* nausea

* [[tachycardia]]

;Rare side effects that could be life-threatening

* increased difficulty breathing

* rapid or increased heart rate

* irregular heartbeat

* chest pain or discomfort

== Brand names ==

* Alupent

* Metaprel

* Orcibest

== References ==

{{reflist}}

{{Asthma_and_copd rx}}

{{Adrenergics}}

{{Phenethylamines}}

[[Category:Chemical substances for emergency medicine]]

[[Category:Phenylethanolamines]]

[[Category:Bronchodilators]]

{{respiratory-system-drug-stub}}