Acebutolol

Prent is a redirect to this article. For the German actress see Lilian Prent .

Structural formula
1: 1 mixture of two stereoisomers - simplified structural formula without stereochemistry
General
Non-proprietary name	Acebutolol
other names	N - {3-Acetyl-4- [2-hydroxy-3- (isopropylamino) propoxy] phenyl} butanamide ( IUPAC ) (±) -Acebutolol ( RS ) -Acebutolol DL -Acebutolol rac -acebutolol ( RS ) -3-acetyl-4- (2-hydroxy-3-isopropylaminopropoxy) butyranilide (±) -3-Acetyl-4- (2-hydroxy-3-isopropylaminopropoxy) butyranilide DL -3-acetyl-4- (2-hydroxy-3-isopropylaminopropoxy) butyranilide rac -3-acetyl-4- (2-hydroxy-3-isopropylaminopropoxy) butyranilide
Molecular formula	C 18 H 28 N 2 O 4
External identifiers / databases
CAS number 37517-30-9 (racemate) 68107-81-3 [( R ) -enantiomer] 68107-82-4 [( S ) -enantiomer] 34381-68-5 (racemate, hydrochloride) EC number 253-539-0 ECHA InfoCard 100.048.654 PubChem 1978 ChemSpider 1901 DrugBank DB01193 Wikidata Q418857
Drug information
ATC code	C07 AB04
Drug class	Beta blockers
Mechanism of action	Blockade of β receptors with poor β 1 selectivity and intrinsic activity present
properties
Molar mass	336.43 g mol −1
Physical state	firmly
Melting point	119-123 ° 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: 312-332 P: 280
Toxicological data	75.2 mg kg −1 ( LD 50 ,  mouse ,  iv , racemate) 4 mg kg −1 ( LD 50 ,  dog ,  iv , racemate) 185 mg kg −1 ( LD 50 ,  mouse ,  ip , racemate, hydrochloride) 4050 mg kg −1 ( LD 50 ,  mouse ,  oral , racemate, hydrochloride) 53 mg kg −1 ( LD 50 ,  mouse ,  iv , racemate, hydrochloride) 291 mg kg −1 ( LD 50 ,  mouse ,  sc , racemate, hydrochloride) 222 mg kg −1 ( LD 50 ,  rat ,  ip , racemate, hydrochloride) 6620 mg kg −1 ( LD 50 ,  rat ,  oral , racemate, hydrochloride) 103 mg kg −1 ( LD 50 ,  rat ,  iv , racemate, hydrochloride) 1310 mg kg −1 ( LD 50 ,  rat ,  sc , racemate, hydrochloride) 41 mg kg −1 ( LD 50 ,  rabbit ,  iv , racemate, hydrochloride) 296 mg kg −1 ( LD 50 ,  rabbit ,  oral , racemate, hydrochloride)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acebutolol is an organic chemical compound that is one of the aromatics and amides . The substance is used as a drug belonging to the group of beta blockers .

Presentation and extraction

Acebutolol is made in five steps. The synthesis is based on 4-aminophenol , which is converted in the first step with butyric anhydride to form the acid amide 4-butyramidophenol and in the second step with acetyl chloride to form O- acetyl-4-butyramidophenol. After isomerization ( Fries rearrangement ) of the phenyl acetate structure to the 2-hydroxyacetophenone structure at 140 ° C. in the presence of aluminum chloride , an etherification with epichlorohydrin takes place . The target compound results from the ring opening of the epoxy function with isopropylamine . The synthesis sequence gives the racemate .

Clinical information

Acebutolol belongs to the group of medium-acting beta blockers, with a half-life of 4 to 12 hours and a duration of action of up to 24 hours. The bioavailability of acebutolol is 60% and it has a low selectivity for β ₁ -adrenoceptors over other β-adrenoceptors . It is excreted by the kidneys and should therefore not be given to patients with renal insufficiency.

Intrinsic sympathetic activity

The specialty of acebutolol and some other beta blockers ( oxprenolol and pindolol ) is their intrinsic sympathomimetic activity (ISA).

Other Information

Stereochemistry

Acebutolol has a chiral center, the racemate is used medicinally . The two enantiomers of a chiral drug almost always show a different pharmacology and pharmacokinetics, which was previously often ignored due to ignorance of stereochemical relationships. The active stereoisomer ( eutomer ) is ( S ) -form of acebutolol.

Acebutolol enantiomers
CAS No .: 68107-81-3	CAS No .: 68107-82-4

literature

• T. Karow / R. Lang-Roth General and Special Pharmacology and Toxicology 2003 pp. 62 - 66.
• G. Herold Internal Medicine 2004.

Individual evidence

1. ↑ Entry on acebutolol. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
2. ↑ ^{a b} Data sheet Acebutolol hydrochloride from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
3. ↑ Entry on acebutolol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
4. ↑ ^{a b c d e f g h i j k l m} A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2000), Thieme-Verlag Stuttgart , ISBN 978-1-58890-031-9
5. ↑ Patent GB 1247384 (May & Baker, 1967).
6. ↑ Verma, KK; Tyagi, P .: in Anal. Chem. 56 (1984) 2157.
7. ↑ EJ Ariëns (1984): Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology . In: Eur J Clin Pharmacol . 26 (2); 663-668; PMID 6092093 .
8. ↑ Joni Agustiana, Azlina Harun Kamaruddina, Subhash Bhatiaa: Single enantiomeric blockers — The existing technologies , Process Biochemistry 45 ( 2010 ) 1587-1604.

Trade names

Monopreparations

Prent (D)

Combination preparations

Acebutolol in combination with Mefrusid : Sali-Prent (D), Acebutolol in combination with Nifedipine : Tredalat (D)

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