Atenolol

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Structural formula
(±) -Atenolol enantiomers
( R ) -Atenolol (top) and ( S ) -Atenolol (bottom), 1: 1 mixture of stereoisomers
General
Non-proprietary name Atenolol
other names
  • (±) -4 - [(2-Hydroxy-3-isopropyl-aminopropoxy) -phenyl] -acetamide
  • ( RS ) -2- [4- (2-Hydroxy-3-isopropyl-aminopropoxy) phenyl] acetamide
  • 2- (4 - {(2 RS ) -2-Hydroxy-3 - [(1-methylethyl) amino] propoxy} phenyl) acetamide ( Pharmacopoeia )
Molecular formula C 14 H 22 N 2 O 3
Brief description

white to almost white powder

External identifiers / databases
CAS number 29122-68-7
EC number 249-451-7
ECHA InfoCard 100.044.941
PubChem 2249
ChemSpider 2162
DrugBank DB00335
Wikidata Q411325
Drug information
ATC code

C07 AB03

Drug class

β-receptor blockers

Mechanism of action

selective blockade of β 1 receptors

properties
Molar mass 266.34 g · mol -1
Physical state

firmly

Melting point

147 ° C

pK s value

9.4

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

134 mg kg −1 ( LD 50mouseip )

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

Atenolol is a drug from the group of selective β 1 -adrenoreceptor blockers ( beta blockers ) and, like other beta blockers, is used to treat arterial hypertension (high blood pressure).

pharmacology

Atenolol belongs to the group of selective beta blockers because it binds specifically to the β 1 adrenoceptors . It has no intrinsic sympathomimetic activity ( ISA ). The relative potency of atenolol compared to propranolol is 1.

indication

Areas of application for this active ingredient are coronary heart diseases, acute myocardial infarction, functional cardiovascular complaints, cardiac arrhythmias, tachyarrhythmias and hypertension.

Pharmacokinetics

Atenolol, which is not particularly liposoluble, is relatively well absorbed after oral intake ( bioavailability is approx. 50%). Because of its poor solubility in fat , it should cross the blood-brain barrier more poorly and thus lead to fewer central side effects ( sedation , headaches , etc.) than propranolol, for example, which is readily soluble in fat . Atenolol has a plasma half-life of 4 to 6 hours. The plasma protein binding of atenolol is approximately 15%. Atenolol is only slightly metabolized in the liver (less than 10%) and excreted via the kidneys . It can pass into the breast milk in breastfeeding women , so the use of atenolol during breastfeeding should be discussed critically.

chemistry

Atenolol is a chiral drug. The chemical synthesis is described in the literature. This β-receptor blocker is used as a racemate , the enantiomers of active substances usually having different pharmacological effects. The active stereoisomer ( eutomer ) is the ( S ) form of atenolol.

Trade names

Monopreparations

Atenil (CH), Atenolan (A), Cardaxen (CH), Selobloc (CH), Tenormin (D, A, CH), Generika (D, A, CH)

Combination preparations
  • In combination with chlortalidone : Teneretic (D), Tenoretic (A, CH), generics (D, A, CH)
  • In combination with nifedipine : Beta-Adalat (A, CH), Nif-Ten (D, A, CH), generics (D, A, CH)

literature

  • T. Karow, R. Lang-Roth: General and special pharmacology and toxicology , 2003, pp. 62-66

Individual evidence

  1. a b c d e f data sheet Atenolol, ≥98% (TLC), powder from Sigma-Aldrich , accessed on December 19, 2019 ( PDF ).
  2. a b Entry on atenolol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. ^ V. Martinez, MI Maguregui, RM Jimenez, RM Alonso: Determination of the pKa values ​​of β-blockers by automated potentiometric titrations. In: Journal of Pharmaceutical and Biomedical Analysis . 23, 2000, pp. 459-468, doi: 10.1016 / S0731-7085 (00) 00324-1 .
  4. Ruhr University Bochum: General Pharmacology - Summarized handouts of the pharmacology lecture by Prof. Michels ( Memento from June 12, 2007 in the Internet Archive ), under "β-adrenoceptor antagonists".
  5. Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , 4th edition (2000) 2 volumes published by Thieme-Verlag Stuttgart, see there pages 145 to 146, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.
  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 .
  7. Joni Agustiana, Azlina Harun Kamaruddina, Subhash Bhatiaa: Single enantiomeric blockers — The existing technologies , Process Biochemistry 45 ( 2010 ) 1587-1604.