Reproterol

Structural formula
	Mixture of stereoisomers - structural formula without stereochemistry
General
Non-proprietary name	Reproterol
other names	( RS ) -7- (3 - {[2- (3,5-dihydroxyphenyl) -2-hydroxyethyl] amino} propyl) -1,3-dimethyl-3,7-dihydro-1 H -purine-2,6 -dion ( IUPAC )
Molecular formula	C 18 H 23 N 5 O 5 (reproterol) ; C 18 H 23 N 5 O 5 HCl (reproterol monohydrochloride) ;
External identifiers / databases
EC number	258-956-1
ECHA InfoCard	100.053.579
PubChem	25654
ChemSpider	23898
DrugBank	DB12846
Wikidata	Q1292703
Drug information
ATC code	R03 CC14 ; R03 AK05
Drug class	β 2 sympathomimetics
properties
Molar mass	389.41 g · mol -1 (reproterol) ; 425.87 g · mol -1 (reproterol monohydrochloride) ;
Physical state	firmly
Melting point	249–250 ° C (reproterol monohydrochloride)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	145 mg kg −1 ( LD 50 , mouse , iv , reproterol) ; 148 mg kg −1 ( LD 50 , mouse , iv , hydrochloride) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Reproterol is a drug from the group of β ₂ sympathomimetics and is used as a racemate . Administered as a metered aerosol or injection solution, it dilates the bronchi and is used for the treatment of bronchial asthma.

pharmacology

application areas

Reproterol is used as a metered dose aerosol in combination with cromoglicinic acid to prevent and treat dyspnoea in asthma in patients who require bronchodilator therapy in addition to basic anti-inflammatory therapy. Reproterol solution for injection is given intravenously for the short-term treatment of a severe asthma attack.

Mechanism of action

Reproterol, which has a half-life of 1.5 hours, acts as an agonist on the sympathetic β ₂ -adrenoceptors to relaxation (slackening) of the smooth muscles of the bronchi and thus to a reduction in breathing resistance.

Side effects

As has been observed with β ₂ -sympathomimetics, side effects on the cardiovascular system ( tachycardia , palpitations) can occasionally occur. In addition, tremors, restlessness and a rise in blood sugar can be observed.

Interactions

Other β-sympathomimetics, theophylline and anticholinergics increase the cardiovascular side effects of reproterol. MAOIs slow down the breakdown of reproterol.

Stereoisomerism

Reproterol is chiral , so it contains a stereocenter. There are thus two enantiomers , the ( R ) form and the ( S ) form. The commercial preparations contain the drug as a racemate (1: 1 mixture of enantiomers).

Enantiomers of reproterol
CAS number: 210710-33-1	CAS number: 210710-34-2

Manufacturing

A synthesis for reproterol, starting from theophylline , is described in the literature.

Other Information

Due to its mechanism of action, Reproterol is on the prohibited list of the World Anti Doping Code and is therefore a prohibited doping agent in sport. The use of drugs containing reproterol must be reported to the doping control.

Trade names

Monopreparations

Bronchospasm (D)

Combination preparations

Aarane (D), Allergospasmin (D)

Individual evidence

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1402, ISBN 978-0-911910-00-1 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b Entry on Reproterol. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.
↑ Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10-9 , p. 196.
^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.
↑ Red List Online, as of August 2009

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1402, ISBN 978-0-911910-00-1 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[rol-3] Entry on Reproterol. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.

[Rote_Liste-4] Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10-9 , p. 196.

[A._Kleemann-5] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.

[6] Red List Online, as of August 2009