Fenoterol

Structural formula
	1: 1 mixture of ( RR ) enantiomer (top) and ( SS ) enantiomer (bottom)
General
Non-proprietary name	Fenoterol
other names	( RR , SS ) - (±) -1- (3,5-Dihydroxyphenyl) -2 - [- 2- (4-hydroxyphenyl) -1-methylethylamino] ethanol; ( RR , SS ) - (±) -1- (3,5-dihydroxyphenyl) -2 - [- 2- (4-hydroxyphenyl) -2-propylamino] ethanol;
Molecular formula	C 17 H 21 NO 4
Brief description	white to almost white, crystalline powder (HBr)
External identifiers / databases
EC number	680-817-2
ECHA InfoCard	100.205.960
PubChem	3343
ChemSpider	3226
DrugBank	DB01288
Wikidata	Q420188
Drug information
ATC code	R03 AC04 , G02 CA03
Drug class	β 2 sympathomimetics
properties
Molar mass	303.35 g · mol -1
Melting point	Hydrobromide: 222-223 ° C ; Hydrochloride: 182 ° C;
solubility	soluble in water and ethanol (hydrobromide)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	1600 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fenoterol is a drug from the group of β ₂ sympathomimetics .

Fenoterol is as spray inhalation administered and causes in the lungs by binding as an agonist to the β ₂ -adrenergic receptors of bronchial a widening of the bronchi ( bronchodilation ). There is also an intravenous preparation (trade name: Partusisten iv ©) for tocolysis .

Since it is one of the short-acting bronchodilators, it is used as a reliever medication for bronchial asthma or COPD . The effect lasts three to five hours and starts a few seconds after inhalation .

Fenoterol continues to have a tocolytic effect , i.e. H. inhibiting labor . Side effects such as reflex tachycardia , angina pectoris and the blood sugar-lowering effect of antidiabetic drugs can be reduced.

Since 2013, the indication for tocolysis has been deleted for inhaled and oral fenoterol preparations due to an observation of a worsening of the fetal outcome and restricted to a maximum dose of 48 hours for intravenous administration.

Stereoisomerism

The four stereoisomers of 1- (3,5-dihydroxyphenyl) -2 - [- 2- (4-hydroxyphenyl) -2-propylamino] ethanol

Fenoterol contains two stereocenters . Hence there are four stereoisomers. The ( RR , SS ) racemate is used as a medicinal substance , since it is 9 to 20 times more effective than the ( RS , SR ) enantiomer pair.

Trade names

Monopreparations
Berotec (D, A, CH), Partusisten (D)
Combination preparations
Berodual (D, A, CH), Berodualin (A)

literature

RC Heel, RN Brogden, TM Speight, GS Avery: Fenoterol: a review of its pharmacological properties and therapeutic efficacy in asthma . In: Drugs . 15, No. 1, January 1978, pp. 3-32. PMID 342228 .
G Hochhaus, H Möllmann: Pharmacokinetic / pharmacodynamic characteristics of the beta-2-agonists terbutaline, salbutamol and fenoterol . In: Int J Clin Pharmacol Ther Toxicol . 30, No. 9, September 1992, pp. 342-362. PMID 1358833 .
E. Mutschler: drug effects . 7th edition. WVG Stuttgart, 1996, ISBN 3-8047-1377-7

Web links

Short-acting beta agonists for obstetric indications - including partusists (fenoterol): important restrictions on use . (PDF; 838 kB) Rote Hand Brief, September 30, 2013, Medicines Commission of the German Medical Association

Individual evidence

↑ ^a ^b ^c Datasheet Fenoterol Hydrobromide CRS (PDF) at EDQM , accessed on July 30, 2008.
↑ ^a ^b The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 680.
↑ ^a ^b Datasheet Fenoterol hydrobromide from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).
↑ Short-acting beta agonists for obstetric indications - including Partusisten® (fenoterol): Important restrictions on use. (PDF) In: akdae.de. September 30, 2013, accessed January 9, 2016 .
↑ JP Beale, NC Stephenson: X-ray analysis of Th 1165 and salbutamol . In: Journal of Pharmacy and Pharmacology , 24, 1972, pp. 277-280.

[Ph._Eur.-1] Datasheet Fenoterol Hydrobromide CRS (PDF) at EDQM , accessed on July 30, 2008.

[MerckIndex-2] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 680.

[Sigma-3] Datasheet Fenoterol hydrobromide from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).

[4] Short-acting beta agonists for obstetric indications - including Partusisten® (fenoterol): Important restrictions on use. (PDF) In: akdae.de. September 30, 2013, accessed January 9, 2016 .

[Beale_und_Stephenson-5] JP Beale, NC Stephenson: X-ray analysis of Th 1165 and salbutamol . In: Journal of Pharmacy and Pharmacology , 24, 1972, pp. 277-280.