Reproterol

Reproterol is a short-acting[1] β2 adrenoreceptor agonist used in the treatment of asthma.[2]

Reproterol
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Inhalation (MDI), IV
ATC code
Legal status
Legal status
  • DE: § 48 AMG/§ 1 MPAV (Prescription only)
Identifiers
  • (RS)-7-(3-{[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino}propyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.579
Chemical and physical data
FormulaC18H23N5O5
Molar mass389.412 g·mol−1
3D model (JSmol)
  • CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CCCNCC(C3=CC(=CC(=C3)O)O)O
  • InChI=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 ☒N
  • Key:WVLAAKXASPCBGT-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

It was patented in 1965 and came into medical use in 1977.[3]

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.[4]

Enantiomers of reproterol

(R)-Reproterol
CAS number: 210710-33-1
(S)-Reproterol
CAS number: 210710-34-2

References
  1. Küpper T, Goebbels K, Kennes LN, Netzer NC (December 2012). "Cromoglycate, reproterol, or both--what's best for exercise-induced asthma?". Sleep & Breathing = Schlaf & Atmung. 16 (4): 1229–35. doi:10.1007/s11325-011-0638-2. PMID 22198635. S2CID 10032756.
  2. Virchow JC (1999). "Reproterol: beta-2-agonist, theophylline, or both?". Respiration; International Review of Thoracic Diseases. 66 (3): 210–1. doi:10.1159/000029379. PMID 10364735. S2CID 203732706.
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 54X. ISBN 9783527607495.
  4. Rote Liste 2017 – Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte). Vol. 57. Frankfurt/Main: Rote Liste Service GmbH. 2017. p. 196. ISBN 978-3-946057-10-9.
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