Reproterol

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 448131419

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

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

| width = 250

| tradename =

| Drugs.com = {{drugs.com|international|reproterol}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_DE = Rx only

| legal_status =

| routes_of_administration = Inhalation (MDI), IV

| bioavailability =

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

| CAS_number = 54063-54-6

| ATC_prefix = R03

| ATC_suffix = AC15

| ATC_supplemental =

| PubChem = 25654

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

| DrugBank =

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

| ChEMBL = 1095607

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

| UNII = 11941YC6RN

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

| KEGG = D08474

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

| ChemSpiderID = 23898

| chemical_formula =

| C=18 | H=23 | N=5 | O=5

| smiles = CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CCCNCC(C3=CC(=CC(=C3)O)O)O

| 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{{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 }} β2 adrenoreceptor agonist used in the treatment of asthma.{{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 }}

It was patented in 1965 and came into medical use in 1977.{{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}}

Stereochemistry

Reproterol contains a stereocenter and is 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.{{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 }}

class="wikitable" style="text-align:center"
class="hintergrundfarbe6"

! colspan="2"| Enantiomers of reproterol

250 px
(R)-Reproterol
CAS number: 210710-33-1

| 250 px
(S)-Reproterol
CAS number: 210710-34-2

References

{{reflist}}

{{Drugs for obstructive airway diseases}}

{{Adrenergic agonists}}

Category:Antiasthmatic drugs

Category:Beta-adrenergic agonists

Category:Xanthines

Category:Phenylethanolamines

Category:Resorcinols

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