Vecuronium

Structural formula
General
Non-proprietary name	Vecuronium
other names	[(2 S , 3 S , 5 S , 8 R , 9 S , 10 S , 13 S , 14 S , 16 S , 17 R ) -3-acetyloxy-10,13-dimethyl-16- (1-methylpiperidine- 1-ium-1-yl) -2-piperidin-1-yl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1 H - cyclopenta [ a ] phenanthren-17-yl] acetate bromide ( IUPAC )
Molecular formula	C 34 H 57 BrN 2 O 4
Brief description	odorless, white, crystalline powder
External identifiers / databases
EC number	256-723-9
ECHA InfoCard	100.051.549
PubChem	39764
ChemSpider	36357
DrugBank	DBSALT001200
Wikidata	Q27108523
Drug information
ATC code	M03 AC03
Drug class	Muscle relaxant
properties
Molar mass	637.73 g · mol -1
Physical state	firmly
Melting point	228 ° C
boiling point	from 350 ° C decomposition
solubility	easily soluble in water and ethanol ; sparingly soluble in methanol ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Vecuronium bromide; Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	0.13 mg kg −1 ( LD 50 , woman , oral ) ; 0.123 mg kg −1 ( LD 50 , woman , parenteral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vecuronium is the non-proprietary name (INN) for a non-depolarizing, medium long-acting muscle relaxant that has been introduced into clinical practice 1980th It represents a further development of the long-acting pancuronium and, like this, belongs to the group of amino steroids . In contrast to the pancuronium, the vecuronium has only one quaternary amine center ( mono-quaternary relaxant ) at a physiological pH value .

The bromide is used pharmaceutically .

Pharmacological properties

Vecuronium is a potent muscle relaxant, the effective dose for a 95% effect (ED ₉₅ ) is 0.05 mg / kg body weight. The attack time after a usual intubation dose (double ED ₉₅ ) is 2-3 minutes, the clinical duration of action after a single dose is 30-40 minutes. The volume of distribution is determined by the hydrophilicity small of the molecule as in the other non-depolarizing muscle relaxants and amounts to 0.2-0.5 liters per kg of body weight. The plasma clearance is 2.5–5 ml / kg body weight / min.

About 30% of the vecuronium is excreted via the kidneys , the rest via the biliary route, some of which is converted into metabolites by the liver . This results in 3-hydroxy-, 3,17-hydroxy- and 17-hydroxyvecuronium, of which the former shows a 50% potency, while the other metabolites are hardly effective. The duration of action may be prolonged with repeated or continuous administration, mainly due to the accumulation of the 3-hydroxy metabolite. This can also be the case with liver failure , although this only plays a minor role after a single dose. A renal failure will not affect the duration of action.

application

Vecuronium is used as a non-depolarizing muscle relaxant to create good intubation conditions (for endotracheal intubation ) during induction of anesthesia and / or for surgical interventions that require relaxation of the skeletal muscles . Vecuronium (bromide) is supplied as a soluble powder ( lyophilisate ) that is dissolved in water for use; As this simplifies storage and does not require cooling, Vecuronium is often used in emergency medicine . However, it is not suitable for rapid sequence induction , which limits its application.

There is an incompatibility with the barbiturate thiopental , so that these active ingredients have to be administered separately.

In the US states of Florida and Oklahoma , vecuronium is said to be used together with hydromorphone and potassium chloride for execution after the usual barbiturates were no longer available. In April 2014, the first such execution in McAlester State Prison failed spectacularly.

Side effects

The side effect profile corresponds to that of other non-depolarizing muscle relaxants; Independent breathing of the patient is no longer possible due to the complete paralysis of the skeletal muscles, which is why airway protection and controlled ventilation must be carried out. Vecuronium is characterized by circulatory stability and has almost no blocking effects on muscarinic acetylcholine receptors (no vagolysis , no triggering of tachycardia ). Also, no relevant histamine release is caused.

Application restrictions

Although Vecuronium does not cross the placenta , there are no studies in humans for safety during pregnancy, so its use is not recommended. However, it can be used in children.

Trade names

Vecuronium is commercially available as a bromide in Germany, Austria and Switzerland under the name Norcuron and in Germany also as a generic.

literature

Rossaint, Werner, Zwissler (ed.): The anesthesiology. General and special anesthesiology, pain therapy and intensive care medicine. Springer, Berlin; 2nd edition 2008. ISBN 978-3-540-76301-7
Heck, Fresenius: Revision course anesthesiology . Springer, Berlin; 5th edition 2007. ISBN 978-3-540-46575-1
Technical information for Norcuron ^®

Individual evidence

↑ ^a ^b ^c ^d F. v. Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hagers Handbook of Pharmaceutical Practice. 5th edition, Vol. 7, fabrics A – D, Springer / Birkhäuser, 1995, ISBN 978-3-540-52688-9 , p. 97.
↑ ^a ^b ^c Entry on Vecuronium in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Data sheet Vecuronium bromide from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).
↑ Anesthesia and Analgesia Vol. 66, p. 188, 1987.
^ British Journal of Anesthesia. Vol. 57, pp. 807, 1985.
↑ Oklahoma plans to use untested three-drug combination in two executions. The Guardian, April 1, 2014 .
↑ Oklahoma blames inmate's vein for botched execution; attorney questions 'untried' lethal injection. AP, April 30, 2014.
↑ An execution stirs up the United States. Tages-Anzeiger, May 3, 2014.

[hager-1] F. v. Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hagers Handbook of Pharmaceutical Practice. 5th edition, Vol. 7, fabrics A – D, Springer / Birkhäuser, 1995, ISBN 978-3-540-52688-9 , p. 97.

[chemid-2] Entry on Vecuronium in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-3] Data sheet Vecuronium bromide from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).

[4] Anesthesia and Analgesia Vol. 66, p. 188, 1987.

[5] British Journal of Anesthesia. Vol. 57, pp. 807, 1985.

[6] Oklahoma plans to use untested three-drug combination in two executions. The Guardian, April 1, 2014 .

[7] Oklahoma blames inmate's vein for botched execution; attorney questions 'untried' lethal injection. AP, April 30, 2014.

[8] An execution stirs up the United States. Tages-Anzeiger, May 3, 2014.