Acebutolol

• ( ±)- acebutolol
• ( RS)- acebutolol
• DL- acebutolol
• Rac- acebutolol
• (RS )-3- acetyl-4 -(2- hydroxy-3- isopropylaminopropoxy ) butyranilid
• (± )-3- acetyl-4 -(2- hydroxy-3- isopropylaminopropoxy ) butyranilid
• DL-3 -acetyl-4 -(2- hydroxy-3- isopropylaminopropoxy ) butyranilid
• Rac -3 -acetyl-4 -(2- hydroxy-3- isopropylaminopropoxy ) butyranilid

• 37517-30-9 (racemate )
• 68107-81-3 ((R) - enantiomer)
• 68107-82-4 ((S) - enantiomer)
• 34381-68-5 ( racemate hydrochloride)

C07AB04

Beta blocker

Blockade of β - receptors with low β1 - selectivity and intrinsic activity of existing

119-123 ° C

Attention

• 75.2 mg · kg -1 ( LD50, mouse, i.v. racemate)
• 4 mg · kg -1 ( LD50, dog, i.v. racemate)
• 185 mg · kg -1 ( LD50, mouse, ip, racemate hydrochloride)
• 4050 mg · kg -1 ( LD50, Mouse, oral, racemate hydrochloride)
• 53 mg · kg -1 ( LD50, mouse, iv, racemate hydrochloride)
• 291 mg · kg -1 ( LD50, mouse, sc, racemate hydrochloride)
• 222 mg · kg -1 ( LD50, rat, ip, racemate hydrochloride)
• 6620 mg · kg -1 ( LD50, Rat, oral, racemate hydrochloride)
• 103 mg · kg -1 ( LD50, rat, iv, racemate hydrochloride)
• 1310 mg · kg -1 ( LD50, rat, sc, racemate hydrochloride)
• 41 mg · kg -1 ( LD50, rabbit, iv, racemate hydrochloride)
• 296 mg · kg -1 ( LD50, Rabbit, oral, racemate hydrochloride)

Template: Infobox chemical / molecular formula search available

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

• 3.1 stereochemistry

Representation and extraction

The production of acebutolol in five steps. The synthesis starts from 4-aminophenol that is implemented in the first step with butyric acid amide to 4- Butyramidophenol and in the second step with acetyl chloride to the O - acetyl-4- butyramidophenol. After the isomerization of the 2- Phenylacetatstruktur Hydroxyacetophenonstruktur at 140 ° C in the presence of aluminum chloride etherification is carried out with epichlorohydrin. The target compound is obtained by the ring opening of the epoxide moiety with isopropylamine. The reaction sequence results in the racemate.

Clinical information

Acebutolol belongs to the group of medium- long-acting beta -blockers, with a half-life of 4 to 12 hours and a duration of action up to 24 hours. The bioavailability of acebutolol is 60% and it has a low selectivity for β1 -adrenoceptors over other β -adrenoceptors on. It is excreted by the kidney and therefore should not be given to patients with renal insufficiency.

Intrinsic activity sympathominetische

The peculiarity of acebutolol and some other beta-blockers ( oxprenolol and pindolol ) is the intrinsic sympathomimetic activity (ISA).

Other Information

Stereochemistry

Acebutolol has a chiral center, is used medicinally the racemate. 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.