Pindolol

Structural formula
	( R ) -pindolol (top) and ( S ) -pindolol (bottom), 1: 1 stereoisomeric mixture
General
Non-proprietary name	Pindolol
other names	(±) -pindolol; ( RS ) -pindolol; rac -pindolol; DL -pindolol; (±) -1- (1 H -indol-4-yloxy) -3- (1-methylethylamino) propan-2-ol; ( RS ) -1- (1 H -indol-4-yloxy) -3- (1-methylethylamino) propan-2-ol; DL -1- (1 H -indol-4-yloxy) -3- (1-methylethylamino) propan-2-ol; rac -1- (1 H -indol-4-yloxy) -3- (1-methylethylamino) propan-2-ol;
Molecular formula	C 14 H 20 N 2 O 2
External identifiers / databases
EC number	236-867-9
ECHA InfoCard	100.033.501
PubChem	4828
ChemSpider	4662
DrugBank	DB00960
Wikidata	Q418101
Drug information
ATC code	C07 AA03
Drug class	Beta blockers
properties
Molar mass	248.32 g · mol -1
Physical state	firmly
Melting point	167-171 ° C
solubility	Water: 7880 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: 302-315-319-335
	P: 261-305 + 351 + 338
Toxicological data	263 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pindolol is a drug from the group of beta blockers and is used, among other things, to treat arterial hypertension (high blood pressure). It can also be used in rescue medicine to treat supraventricular tachycardia that can occur after administration of nitroglycerin .

Clinical information

Pindolol belongs to the group of nonselective beta blockers because it does not specifically bind to the β ₁ -adrenoceptors . The relative potency compared to propranolol is 5. Pindolol has intrinsic sympathomimetic activity ( ISA ), as do the beta blockers acebutolol and oxprenolol . In contrast to beta blockers without ISA, beta blockers with ISA do not have a beneficial effect on myocardial infarction. Beta blockers with ISA are said to lead to sleep disorders more often than beta blockers without ISA.

Responsiveness

Even when taken as intended, the ability to react can be so reduced that active participation in road traffic or the use of machines is not recommended.

Pharmacological properties

Pharmacokinetics

The fat-soluble pindolol is well absorbed after oral intake and has a plasma half-life of 3 to 6 hours. It is subject to a lower first-pass effect than propranolol, its bioavailability is very variable and fluctuates between 40 and 90%. The plasma protein binding of pindolol is 60%. 40% of the pindolol is excreted in the kidneys.

Other Information

Stereochemistry

The importance of the enantiomeric purity of the synthetically produced active ingredients is being given increasing attention, because the two enantiomers of a chiral drug almost always show different pharmacodynamics and pharmacokinetics. In the past, this was often ignored due to a lack of knowledge of stereochemical relationships. In this respect it is worth mentioning that pindolol is used as a racemate . The active stereoisomer ( eutomer ) is the ( S ) form of pindolol.

Trade names

Monopreparations

Glauco-Stulln (D), Viskaldix (D, CH), Visken (D, A, CH)

Combination preparations

Viskenite (A)

literature

T. Karow / R. Lang-Roth: General and special pharmacology and toxicology . 2003 p. 62 - p. 66
G. Herold: Internal Medicine 2004

Individual evidence

↑ ^a ^b ^c Entry on pindolol in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ ^a ^b data sheet pindolol from Sigma-Aldrich , accessed on April 20, 2011 ( PDF ).
↑ EJ Ariëns, Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology , European Journal of Clinical Pharmacology 26 (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.

[ChemIDplus-1] Entry on pindolol in the ChemIDplus database of the United States National Library of Medicine (NLM)

[Sigma-2] ta sheet pindolol from Sigma-Aldrich , accessed on April 20, 2011 ( PDF ).

[Ariëns-3] EJ Ariëns, Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology , European Journal of Clinical Pharmacology 26 (1984) 663-668. PMID 6092093 .

[Agustiana-4] Joni Agustiana, Azlina Harun Kamaruddina, Subhash Bhatiaa: Single enantiomeric β-blockers — The existing technologies , Process Biochemistry 45 ( 2010 ) 1587-1604.