Bupranolol
Structural formula | ||||||||||||||||
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( 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 |
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Molecular formula | C 14 H 22 ClNO 2 | |||||||||||||||
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Drug information | ||||||||||||||||
ATC code | ||||||||||||||||
properties | ||||||||||||||||
Molar mass | 271.78 g · mol -1 | |||||||||||||||
Physical state |
firmly |
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safety instructions | ||||||||||||||||
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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
- ↑ a b c d e f Entry on Bupranolol. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ ROTE LISTE 2008 , Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-939192-20-6 .