Atracurium

Structural formula
	Counterions ( anions ) not shown
General
Non-proprietary name	Atracurium
other names	5- (3- {1 - [(3,4-Dimethoxyphenyl) methyl] -6,7-dimethoxy-2-methyl-3,4-dihydro-1 H -isoquinolin-2-yl} propanoyloxy) pentyl-3- {1 - [(3,4-dimethoxyphenyl) methyl] -6,7-dimethoxy-2-methyl-3,4-dihydro-1 H -isoquinolin-2-yl} propanoate ( IUPAC ); Atracurium besylate;
Molecular formula	C 65 H 82 N 2 O 18 S 2 (besilate)
External identifiers / databases
EC number	264-743-4
ECHA InfoCard	100,058,840
PubChem	47320
ChemSpider	43068
DrugBank	DB00732
Wikidata	Q165660
Drug information
ATC code	M03 AC04
Drug class	Muscle relaxants
properties
Molar mass	1243.48 g mol −1 (besilate)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Besilat;	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 50 mg kg −1 ( LD 50 , rat , oral , besilate)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Atracurium is a drug from the group of non-depolarizing muscle relaxants that is used in operations and in intensive care medicine .

The benzenesulfonic acid salt (besilate) is used in finished medicinal products .

Clinical information

Application areas (indications)

Atracurium is used to relax the muscles (relax the muscles) for surgery or other medical procedures, such as: B. to achieve mechanical ventilation .

Drug interactions

A prolongation or enhancement of the effect with simultaneous use with aminoglycosides , loop diuretics , magnesium , lithium , suxamethonium or volatile anesthetics is possible.

Adverse effects (side effects)

A release of histamine can cause reddening of the skin, cardiac arrhythmia , drop in blood pressure , tachycardia and bronchospasm , depending on the dose . In contrast to atracurium, the cis -isomer cisatracurium does not lead to a release of histamine. The metabolite laudanosine is attributed to triggering cerebral cramps.

Pharmacological properties

Mechanism of action (pharmacodynamics)

Atracurium as a peripheral muscle relaxant binds competitively to the acetylcholine receptor of the motor endplate without triggering depolarization. The effect of the acetylcholine is blocked.

metabolism

1/3 of the atracurium disintegrates spontaneously ( Hofmann elimination ), 2/3 are cleaved unspecifically by esterases in the blood plasma ( ester hydrolysis ). The degradation products are pentamethyl diacrylate , laudanosine , quaternary acids and alcohol.

Other Information

Chemical information

Structure of isoquinoline, from which the benzylisoquinoline derivatives are derived.

The benzyl isoquinoline derivative atracurium chemically belongs to the esters , tetrahydropyridine derivatives and phenol ethers . It is a mixture of ten different stereoisomers .

History

Atracurium was synthesized by John B. Stenlake in 1974. Atracurium was approved in Germany in 1987.

Trade names

Monopreparations

Tracrium (D, A, CH), various generics (D)

literature

HW Striebel: The anesthesia . Schattauer, 2003, ISBN 3-7945-1985-X .
Wolfgang Forth , D. Henschler, W. Rummel, U. Förstermann, K. Starke: General and special pharmacology and toxicology . Urban & Fischer, 2001, ISBN 3-437-42520-X .

Individual evidence

↑ Data sheet Atracurium besylate from Sigma-Aldrich , accessed on May 5, 2011 ( PDF ).
↑ Data sheet atracurium besilate (PDF) from EDQM , accessed on June 20, 2009.
↑ 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. 37.

[Sigma-1] Data sheet Atracurium besylate from Sigma-Aldrich , accessed on May 5, 2011 ( PDF ).

[Ph._Eur.-2] Data sheet atracurium besilate (PDF) from EDQM , accessed on June 20, 2009.

[3] 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. 37.