Reproterol: Difference between revisions

{{Short description|Chemical compound}}

| Verifiedfields = changed

| verifiedrevid = 448131419

| IUPAC_name = (''RS'')-7-(3-<nowiki/>{[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino}propyl)-1,3-dimethyl-3,7-dihydro-1''H''-purine-2,6-dione

| image = (RS)-Reproterol Structural Formula V1.svg

| width = 250

| pregnancy_US = <!-- A / B / C / D / X -->

| legal_DE = Rx only

| legal_status =

| routes_of_administration = Inhalation ([[Metered-dose inhaler|MDI]]), [[Intravenous therapy|IV]]

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

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1095607

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 23898

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C18H23N5O5/c1-21-16-15(17(27)22(2)18(21)28)23(10-20-16)5-3-4-19-9-14(26)11-6-12(24)8-13(25)7-11/h6-8,10,14,19,24-26H,3-5,9H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = WVLAAKXASPCBGT-UHFFFAOYSA-N

'''Reproterol''' is a short-acting<ref>{{cite journal | vauthors = Küpper T, Goebbels K, Kennes LN, Netzer NC | title = Cromoglycate, reproterol, or both--what's best for exercise-induced asthma? | journal = Sleep & Breathing = Schlaf & Atmung | volume = 16 | issue = 4 | pages = 1229–35 | date = December 2012 | pmid = 22198635 | doi = 10.1007/s11325-011-0638-2 | s2cid = 10032756 }}</ref> [[Beta2-adrenergic agonist|β₂ adrenoreceptor agonist]] used in the treatment of [[asthma]].<ref name="pmid10364735">{{cite journal | vauthors = Virchow JC | title = Reproterol: beta-2-agonist, theophylline, or both? | journal = Respiration; International Review of Thoracic Diseases | volume = 66 | issue = 3 | pages = 210–1 | date = 1999 | pmid = 10364735 | doi = 10.1159/000029379 | s2cid = 203732706 }}</ref>

<!-- Society and culture -->

It was patented in 1965 and came into medical use in 1977.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=54X |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA54X |language=en}}</ref>

== Stereochemistry ==

Reproterol contains a stereocenter and is [[chirality (chemistry) | chiral]]. There are thus two [[enantiomers]], the (''R'')-form and the (''S'')-form. The commercial preparations contain the drug as a [[racemate]], an equal mixture of the two enantiomers.<ref name="Rote Liste">{{cite book | title = Rote Liste 2017 – Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte) | publisher = Rote Liste Service GmbH | location = Frankfurt/Main | date = 2017 | volume = 57 | isbn = 978-3-946057-10-9 | page = 196 }}</ref>

{| class="wikitable" style="text-align:center"

|- class="hintergrundfarbe6"

! colspan="2"| Enantiomers of reproterol

|-

| [[File:(R)-Reproterol Structural Formula V1.svg|250 px]]<br />(''R'')-Reproterol<br><small> CAS number: 210710-33-1</small>

| [[File:(S)-Reproterol Structural Formula V1.svg|250 px]]<br />(''S'')-Reproterol<br><small> CAS number: 210710-34-2</small>

|}

== References ==

{{reflist}}

{{Adrenergic agonists}}

[[Category:Phenylethanolamines]]