Alprenolol

Structural formula
	( R ) -Alprenolol (above) and ( S ) -Alprenolol (below), 1: 1 stereoisomer mixture
General
Non-proprietary name	Alprenolol
other names	( RS ) -1- (2-Allylphenoxy) -3- (isopropylamino) -2-propanol; (±) -1- (1-Methylethylamino) -3- (2-prop-2-enylphenoxy) -propan-2-ol ( IUPAC ) ;
Molecular formula	C 15 H 23 NO 2 ; C 15 H 23 NO 2 HCl ( hydrochloride ) ;
Brief description	white, crystalline powder or colorless crystals (hydrochloride)
External identifiers / databases
EC number	237-140-9
ECHA InfoCard	100,033,750
PubChem	2119
ChemSpider	2035
DrugBank	DB00866
Wikidata	Q201370
Drug information
ATC code	C07 AA01
Drug class	Beta blockers
properties
Molar mass	249.35 g mol −1 ; 285.81 g mol −1 (hydrochloride) ;
Melting point	56 ° C (free base); 107-109 ° C (hydrochloride) ;
solubility	Water: 547 mg l −1 at 25 ° C
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	90 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Alprenolol is a drug from the group of beta blockers and was used, among other things, to treat arterial hypertension (high blood pressure). It was patented by AB Hässle as a beta blocker in 1969 and is no longer on the market worldwide.

Pharmacology and pharmacokinetics

Alprenolol has a similar chemical structure to oxprenolol and, like oxprenolol , belongs to the non-selective beta blockers, since it does not specifically bind to the β ₁ -adrenoceptors . Like the beta blockers acebutolol and pindolol, it has intrinsic sympathomimetic activity ( ISA ) in contrast to metoprolol . The relative potency of Alprenolol compared to Propranolol is 0.3. The conditionally fat-soluble alprenolol has a plasma half-life of 2 to 3 hours. The bioavailability of alprenolol is classified with 10% more likely to be low.

particularities

All beta blockers with ISA are said to lead to sleep disorders more often than beta blockers without ISA. In high doses, alprenolol has a membrane-stabilizing effect similar to that of quinidine . This effect also occurs with propranolol and oxprenolol.

Stereochemistry

Alprenolol is used as a racemate [1: 1 mixture of the ( R ) - and ( S ) form of the active ingredient], although the importance of the enantiomeric purity of the synthetically produced active ingredients is increasingly being given attention, also with alprenolol. The two enantiomers of a chiral drug almost always show different pharmacology and pharmacokinetics. In the past, this was often ignored due to a lack of knowledge of stereochemical relationships. The active stereoisomer ( eutomer ) is the ( S ) form of alprenolol.

Individual evidence

↑ European Pharmacopoeia Commission (Ed.): EUROPEAN PHARMACOPOE 6TH EDITION . tape 6.0-6.2 , 2008.
↑ IB Simon, VP Vvedenskii, II Levshina, IS Chekman, ZP Shchechenko: Synthesis of some O-allylphenoxyalkanolamine derivatives with β-adrenoblocking activity in Pharm. Chem. J. 8 (1974) 137-139, doi : 10.1007 / BF00771150 .
↑ ^a ^b ^c Entry on alprenolol in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ ^a ^b Data sheet Alprenolol hydrochloride from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).
↑ Sager, G. et al. (1985): Adrenergic ligand binding in human serum . In: Biochem. Pharmacol. 34 (15); 2812-2815; PMID 4015719 .
↑ Ariëns, EJ. (1984): Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology . In: Eur J Clin Pharmacol . 26 (2) (1984) 663-668; PMID 6092093 .
↑ Joni Agustiana, Azlina Harun Kamaruddina, Subhash Bhatiaa: Single enantiomeric β-blockers — The existing technologies , Process Biochemistry 45 ( 2010 ) 1587-1604.

literature

T. Karow / R. Lang-Roth: General and special pharmacology and toxicology . 2003, 62-66.
Estler: Toxikologie und Pharmakologie Schattauer 1994, ISBN 3-7945-1645-1 .

[Ph._Eur._6-1] European Pharmacopoeia Commission (Ed.): EUROPEAN PHARMACOPOE 6TH EDITION . tape 6.0-6.2 , 2008.

[2] IB Simon, VP Vvedenskii, II Levshina, IS Chekman, ZP Shchechenko: Synthesis of some O-allylphenoxyalkanolamine derivatives with β-adrenoblocking activity in Pharm. Chem. J. 8 (1974) 137-139, doi : 10.1007 / BF00771150 .

[ChemIDplus-3] Entry on alprenolol in the ChemIDplus database of the United States National Library of Medicine (NLM)

[Sigma-4] Data sheet Alprenolol hydrochloride from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).

[Sager-5] Sager, G. et al. (1985): Adrenergic ligand binding in human serum . In: Biochem. Pharmacol. 34 (15); 2812-2815; PMID 4015719 .

[Ariëns-6] Ariëns, EJ. (1984): Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology . In: Eur J Clin Pharmacol . 26 (2) (1984) 663-668; PMID 6092093 .

[Agustiana-7] Joni Agustiana, Azlina Harun Kamaruddina, Subhash Bhatiaa: Single enantiomeric β-blockers — The existing technologies , Process Biochemistry 45 ( 2010 ) 1587-1604.