Orciprenaline

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Structural formula
Structure of orciprenaline
( R ) -form (top) and ( S ) -form (bottom), 1: 1 stereoisomeric mixture
General
Non-proprietary name Orciprenaline
other names
  • Metaproterenol
  • ( RS ) -1- (3,5-dihydroxyphenyl) -2-isopropylaminoethanol ( IUPAC )
  • Orciprenalinum ( Latin )
Molecular formula C 11 H 17 NO 3
Brief description

white to almost white, crystalline, slightly hygroscopic powder

External identifiers / databases
CAS number
  • 586-06-1
  • 5874-97-5 (sulfate 2: 1)
EC number 209-569-1
ECHA InfoCard 100.008.701
PubChem 4086
ChemSpider 3944
DrugBank DB00816
Wikidata Q416473
Drug information
ATC code
Drug class

β-sympathomimetics

properties
Molar mass 211.26 g · mol -1
Physical state

firmly

Melting point

100 ° C

solubility

Easily soluble in water and ethanol , practically insoluble in dichloromethane

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 332
P: no P-phrases
MAK

0.015 mg m −3

Toxicological data

3370 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 .

Orciprenaline is a drug , more precisely a β-sympathomimetic . It is chiral and is used as a racemate . Orciprenaline is now only approved for the treatment of acute asthma attacks . It can greatly increase the heart rate . It has a similar effect to adrenaline , but without leading to such a pronounced increase in blood pressure. Orciprenaline is used as an emergency medication for very slow heartbeats ( bradycardia ) in medicine and veterinary medicine ( off-label use ). The trade name for orciprenaline in Germany is Alupent .

Dosage form

Orciprenaline tablets used to be available, but now only intravenous administration is available. The 1 ml ampoule contains 0.5 mg orciprenaline sulfate. There is also a vial of concentrate for infusion solution. This contains 5 mg orciprenaline sulfate in 10 ml, so that this concentrate may only be given in diluted form using a syringe pump.

Pharmacokinetics

The effect occurs very quickly after intravenous administration. After initial redistribution (steady state volume of distribution approx. 60 liters), the terminal elimination half-life is 2.6 hours. This results in a dose-dependent duration of action of several hours.

effect

Orciprenalin is a sympathomimetic at the B 1 adrenoreceptor and B 2 adrenoreceptor .

Applications

Orciprenaline is now only approved for the treatment of acute asthma attacks , but is only rarely used in this context because more effective agents such as reproterol are available.

In cardiology and emergency medicine , orciprenaline is mostly used in emergencies - outside of the approval as off-label use - for bradycardiac arrhythmias in order to bridge the time until the final pacemaker therapy . It is also used as an antidote for relative and absolute overdose of beta blockers .

Contraindications

Orciprenaline should not be used or should only be used with great caution in the following diseases :

Side effects

With orciprenaline the heart rate can be greatly increased, extrasystoles are possible. Whether vasodilation with a drop in blood pressure or an increase in blood pressure due to an acceleration of the heartbeat will occur cannot be predicted in individual cases and must be monitored by measuring blood pressure. In extreme cases, ventricular fibrillation or an angina pectoris attack can occur. Furthermore, allergic reactions of the skin (itching, exanthema, redness, edema formation) are possible. Occasionally a fine tremor occurs in the muscles . Psychological effects such as restlessness have also been described. At high doses, blood sugar levels can rise; occasionally, nausea, anxiety and sleep disorders occur.

Interactions

All other sympathomimetics and betamimetic asthma drugs are enhanced in their effects and side effects by orciprenaline. If diuretics and glycosides are administered at the same time , extrasystoles and other cardiac arrhythmias may increase.

Individual evidence

  1. ↑ a b c data sheet ORCIPRENALINE SULPHATE CRS (PDF) at EDQM , accessed on July 27, 2008.
  2. ↑ a b Entry on orciprenaline in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. ↑ a b Data sheet Metaproterenol hemisulfate salt from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).
  4. ↑ Specialist information on Alupent® .
  5. ↑ Last Minute Pharmacology . 2011, p. 13, Dellas, Claudia, Elsevier.

Trade names

  • Alupent (A, D), Isuprel (A)