Esmolol

Structural formula
	( S ) -form (top) and ( R ) -form (bottom): 1: 1 mixture of the stereoisomers
General
Non-proprietary name	Esmolol
other names	(±) -Methyl 3- {4- [2-hydroxy-3- (isopropylamino) propoxy] phenyl} propionate; ( RS ) -Methyl 3- {4- [2-hydroxy-3- (isopropylamino) propoxy] phenyl} propionate; DL -Methyl 3- {4- [2-hydroxy-3- (isopropylamino) propoxy] phenyl} propionate; rac -Methyl 3- {4- [2-hydroxy-3- (isopropylamino) propoxy] phenyl} propionate;
Molecular formula	C 16 H 25 NO 4
External identifiers / databases
PubChem	59768
ChemSpider	53916
DrugBank	DB00187
Wikidata	Q418139
Drug information
ATC code	C07 AB09
Drug class	β-receptor blockers
properties
Molar mass	295.37 g mol −1 (free base) ; 331.84 g mol −1 (monohydrochloride) ;
Melting point	48–50 ° C (free base); 85–86 ° C (hydrochloride);
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Hydrochloride; Caution
H and P phrases	H: 319
	P: 305 + 351 + 338
Toxicological data	71 mg kg −1 ( LD 50 , rat , iv ) ; 93 mg kg −1 ( LD 50 , mouse , iv ) ; 32 mg kg −1 ( LD 50 , dog , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Esmolol is a drug from the group of sympatholytics , which is used as the shortest-acting cardioselective β ₁ blocker .

pharmacology

Its half-life is about nine minutes because, unlike other beta blockers, esmolol is not broken down in an organ-bound manner, but rather is eliminated via esterases - hydrolases . For this reason, esmolol may need to be given continuously intravenously. The effects and side effects are the same as those of beta blockers. In medicine, esmolol is mainly used for diagnostic purposes and in emergency medicine because of its short duration of action. Here it is used at an initial dose of 0.5 to 1.5 mg / kg for one minute in supraventricular paroxysmal tachycardias , non-compensatory sinus tachycardias requiring therapy and hyperkinetic cardiac syndrome . Cardiovascular stable and chronically ill patients receive long-acting beta blockers in tablet form.

Stereoisomerism

Esmolol is a chiral drug with a stereocenter . The active isomer ( eutomer ) is the ( S ) -esmolol. Esmolol is used as a racemate , i.e. as a 1: 1 mixture of the ( S ) form and ( R ) form.

synthesis

The synthesis of racemic esmolol starts from methyl 3- (4-hydroxyphenyl) propionate, which is etherified with epichlorohydrin in the first step in the presence of potassium carbonate . In the second step, isopropylamine is added to the epoxy function of the intermediate compound .

Individual evidence

↑ ^a ^b ^c P.W. Erhardt, CM Woo, WG Anderson, RJ Gorczynski: Ultra-short-acting .beta.-adrenergic receptor blocking agents. 2. (Aryloxy) propanolamines containing esters on the aryl function in J. Med. Chem. 25 (1982) 1408-1412. doi : 10.1021 / jm00354a003 .
↑ ^a ^b data sheet Esmolol hydrochloride from Sigma-Aldrich , accessed on May 25, 2011 ( PDF ).
↑ ^a ^b ^c A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001), Thieme-Verlag Stuttgart, ISBN 978-1-58890-031- 9 .
↑ Reinhard Larsen: Anesthesia and intensive medicine in cardiac, thoracic and vascular surgery. (1st edition 1986) 5th edition. Springer, Berlin / Heidelberg / New York et al. 1999, ISBN 3-540-65024-5 , p. 60 f.
^ D. Kühn, J. Luxem, K. Runggaldier: Rescue Service (3rd edition) . Urban & Fischer Verlag, Munich 2004, ISBN 3-437-46191-5 .
↑ Joni Agustiana, Azlina Harun Kamaruddina, Subhash Bhatiaa: Single enantiomeric β-blockers - The existing technologies. , Process Biochemistry 45 (2010) 1587-1604. doi : 10.1016 / j.procbio.2010.06.022 .

Trade names

Monopreparations

Brevibloc (D, A, CH), Esmolol Amomed (A), Esmocard (D), Esmolol Orpha (CH)

[Erhardt-1] P.W. Erhardt, CM Woo, WG Anderson, RJ Gorczynski: Ultra-short-acting .beta.-adrenergic receptor blocking agents. 2. (Aryloxy) propanolamines containing esters on the aryl function in J. Med. Chem. 25 (1982) 1408-1412. doi : 10.1021 / jm00354a003 .

[Sigma-2] ta sheet Esmolol hydrochloride from Sigma-Aldrich , accessed on May 25, 2011 ( PDF ).

[Kleemann-3] A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001), Thieme-Verlag Stuttgart, ISBN 978-1-58890-031- 9 .

[4] Reinhard Larsen: Anesthesia and intensive medicine in cardiac, thoracic and vascular surgery. (1st edition 1986) 5th edition. Springer, Berlin / Heidelberg / New York et al. 1999, ISBN 3-540-65024-5 , p. 60 f.

[RD_-_urbanufischer-5] D. Kühn, J. Luxem, K. Runggaldier: Rescue Service (3rd edition) . Urban & Fischer Verlag, Munich 2004, ISBN 3-437-46191-5 .

[Agustiana-6] Joni Agustiana, Azlina Harun Kamaruddina, Subhash Bhatiaa: Single enantiomeric β-blockers - The existing technologies. , Process Biochemistry 45 (2010) 1587-1604. doi : 10.1016 / j.procbio.2010.06.022 .