Bupranolol

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Structural formula
Structural formula of bupranolol
( R ) -Bupranolol (top) and ( S ) -Bupranolol (bottom), 1: 1 mixture of stereoisomers
General
Non-proprietary name Betadrenol
other names

( RS ) -1- ( tert -Butylamino) -3- (2-chloro-5-methylphenoxy) propan-2-ol

Molecular formula C 14 H 22 ClNO 2
External identifiers / databases
CAS number
PubChem 2475
ChemSpider 2381
DrugBank DB08808
Wikidata Q425838
Drug information
ATC code

C07 AA19

properties
Molar mass 271.78 g · mol -1
Physical state

firmly

Melting point

220–222 ° C (hydrochloride, racemate )

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
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bupranolol (trade name: Betadrenol) is an unselective beta blocker without intrinsic activity (ISA), but with a strong membrane-stabilizing effect. The effectiveness is comparable to that of propranolol .

Stereochemistry

Bupranolol is a chiral compound that contains an asymmetrically substituted carbon atom. The compound is therefore usually a 1: 1 mixture ( racemate ) of two mirror-image molecules ( enantiomers ), which can differ in physiological effects and in rotation value. The drug used is the racemate.

The individual stereoisomers can be isolated in a targeted manner by suitable synthesis strategies (see also: enantiomerically pure drug synthesis ) or separation processes ( racemate resolution ).

dosage

Like other beta blockers, bupranolol is used to treat high blood pressure and tachycardia . The starting dose is 50 mg twice a day. This can be increased to 100 mg up to four times a day. Bupranolol eye drops (0.05-0.5%) are used to treat glaucoma .

pharmacology

Bupranolol is quickly and almost completely absorbed from the intestine. Over 90% of the amount consumed is subject to the first pass effect . Bupranolol has a plasma half-life of 2 to 4 hours and rarely reaches plasma levels above 1 µg / l at therapeutic doses. The main metabolite of bupranonol is carboxybupranolol (4-chloro-3- [3- (1,1-dimethylethylamino) -2-hydroxypropyloxy] benzoic acid), 88% of which is eliminated via the kidneys within 24 hours .

Contraindications and Interactions

Contraindications and interactions are essentially the same as for propranolol and other non-selective beta-blockers.

literature

  • Dinnendahl, V, Fricke, U (Eds.): Drug profiles , 21st edition, Volume 2, Govi ​​Pharmazeutischer Verlag, Eschborn, 2007, ISBN 978-3-7741-98-46-3 .

Individual evidence

  1. a b c d e f Entry on Bupranolol. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.
  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.
  3. ROTE LISTE 2008 , Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-939192-20-6 .