Reproterol

Chemical compound

R03AC15 (WHO)

Legal statusLegal status

DE: § 48 AMG/§ 1 MPAV (Prescription only)

Identifiers

IUPAC name

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

CAS Number

54063-54-6^Y

PubChem CID

25654

ChemSpider

23898^N

UNII

11941YC6RN

KEGG

D08474^Y

ChEMBL

ChEMBL1095607^N

CompTox Dashboard (EPA)

DTXSID8023553

ECHA InfoCard100.053.579

Chemical and physical dataFormulaC₁₈H₂₃N₅O₅Molar mass389.412 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

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

InChI

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

^NY (what is this?) (verify)

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

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

^ 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.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 54X. ISBN 9783527607495.
^ 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.

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol
Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol
Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol
Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast
Arachidonate 5-lipoxygenase inhibitors	Zileuton
Thromboxane receptor antagonists	Ramatroban Seratrodast
Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast