Labetalol

Structural formula
	Structural formula without stereochemistry (mixture of four stereoisomers)
General
Non-proprietary name	Labetalol
other names	(±) -2-Hydroxy-5- {1-hydroxy-2 - [(1-methyl-3-phenylpropyl) amino] ethyl} benzamide
Molecular formula	C 19 H 24 N 2 O 3 ; C 19 H 24 N 2 O 3 · HCl ( hydrochloride ) ;
External identifiers / databases
EC number	253-258-3
ECHA InfoCard	100.048.401
PubChem	3869
DrugBank	DB00598
Wikidata	Q958087
Drug information
ATC code	C07 AG01
properties
Molar mass	328.41 g · mol -1 ; 364.87 g · mol -1 (hydrochloride) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	660 mg kg −1 ( LD 50 , mouse , oral , labetalol) ; > 2000 mg kg −1 ( LD 50 , rat , oral , labetalol) ; 1450 mg kg −1 ( LD 50 , mouse , oral , hydrochloride) ; 2114 mg kg −1 ( LD 50 , rat , oral , hydrochloride) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Labetalol is a chemical compound from the group of salicylic acid - derivatives and benzamides . It is used as a medicine to treat hypertension ( blood pressure lowering agent ). It works as both an alpha and beta blocker . The compound was patented by Allen & Hanburys (now GlaxoSmithKline ) in 1971 ; the more water-soluble and less toxic hydrochloride is used .

Clinical information

application

Labetalol is used in arterial hypertension for long-term medication in tablet form as well as intravenously and in emergency medicine exclusively iv. It acts as an antagonist on both alpha-adrenoceptors and beta-adrenoceptors (β1 and β2).

Side effects

Side effects include arterial hypotension , lethargy , insomnia, erectile dysfunction, nausea, difficulty urinating, visual disturbances, nasal congestion and hypersensitivity reactions.

Contraindications

A relative contraindication is given in patients with asthma , congestive heart failure, any blockage of the cardiac conduction system (including SA block and AV block ), bradycardia, and cardiogenic shock .

Stereochemistry

Labetalol contains two stereocenters and consists of four stereoisomers. This is a mixture of ( R , R ) -, ( S , R ) -, ( R , S ) - and the ( S , S ) form:

Stereoisomers of Labetalol
CAS number: 75659-07-3	CAS number: 83167-24-2
CAS number: 83167-32-2	CAS number: 83167-31-1

Trade names

Monopreparations : Trandate (A, CH)

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b ^c ^d ^e Entry on Labetalol. In: Römpp Online . Georg Thieme Verlag, accessed on August 5, 2013.
^ Hermann J. Roth and Helmut Fenner, Pharmaceuticals , Deutscher Apotheker Verlag, Stuttgart 2000.
↑ ^a ^b Red List 1988 , Federal Association of the Pharmaceutical Industry eV, Editio Cantor, Aulendorf, 1988.

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[roempp-2] Entry on Labetalol. In: Römpp Online . Georg Thieme Verlag, accessed on August 5, 2013.

[3] Hermann J. Roth and Helmut Fenner, Pharmaceuticals , Deutscher Apotheker Verlag, Stuttgart 2000.

[Roth-4] Red List 1988 , Federal Association of the Pharmaceutical Industry eV, Editio Cantor, Aulendorf, 1988.