Atracurium besilate

Atracurium besilate
Clinical data
Trade names	Tracrium, Acurium
Other names	Atracurium besylate
AHFS/Drugs.com	Monograph
Pregnancy; category	C;
Routes of; administration	IV
ATC code	M03AC04 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100% (IV)
Protein binding	82%
Metabolism	Hofmann elimination (retro-Michael addition) and ester hydrolysis by nonspecific esterases
Elimination half-life	17–21 minutes
Identifiers
	IUPAC name 2,2'-{1,5-Pentanediylbis[oxy(3-oxo-3,1-propanediyl)]}bis[1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium] dibenzenesulfonate;
CAS Number	64228-81-5 ;
PubChem CID	47320;
DrugBank	DB00732 ;
ChemSpider	43068 ;
UNII	40AX66P76P;
KEGG	D00758;
ChEBI	CHEBI:2915 ;
ChEMBL	ChEMBL1200527 ;
CompTox Dashboard (EPA)	DTXSID6022630 ;
ECHA InfoCard	100.058.840
Chemical and physical data
Formula	C65H82N2O18S2
Molar mass	1243.49 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	85 to 90 °C (185 to 194 °F)
	SMILES C[N+]1(CCc2cc(c(cc2C1Cc3ccc(c(c3)OC)OC)OC)OC)CCC(=O)OCCCCCOC(=O)CC[N+]4(CCc5cc(c(cc5C4Cc6ccc(c(c6)OC)OC)OC)OC)C.c1ccc(cc1)S(=O)(=O)[O-].c1ccc(cc1)S(=O)(=O)[O-];
	InChI InChI=1S/C53H72N2O12.2C6H6O3S/c1-54(22-18-38-32-48(62-7)50(64-9)34-40(38)42(54)28-36-14-16-44(58-3)46(30-36)60-5)24-20-52(56)66-26-12-11-13-27-67-53(57)21-25-55(2)23-19-39-33-49(63-8)51(65-10)35-41(39)43(55)29-37-15-17-45(59-4)47(31-37)61-6;27-10(8,9)6-4-2-1-3-5-6/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3;21-5H,(H,7,8,9)/q+2;;/p-2 ; Key:XXZSQOVSEBAPGS-UHFFFAOYSA-L ;
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Atracurium besilate, also known as atracurium besylate, is a medication used in addition to other medications to provide skeletal muscle relaxation during surgery or mechanical ventilation.^[1] It can also be used to help with endotracheal intubation but suxamethonium (succinylcholine) is generally preferred if this needs to be done quickly.^[1] It is given by injection into a vein.^[1] Effects are greatest at about 4 minutes and last for up to an hour.^[1]

Common side effects include flushing of the skin and low blood pressure.^[1]^[2] Serious side effects may include allergic reactions; however, it has not been associated with malignant hyperthermia.^[1]^[2] Prolonged paralysis may occur in people with conditions like myasthenia gravis.^[1] It is unclear if use in pregnancy is safe for the baby.^[1] Atracurium is in the neuromuscular-blocker family of medications and is of the non-depolarizing type.^[1] It works by blocking the action of acetylcholine on skeletal muscles.^[1]

Atracurium was approved for medical use in the United States in 1983.^[1] It is on the World Health Organization's List of Essential Medicines.^[3] Atracurium is available as a generic medication.^[1]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l "Atracurium Besylate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
^ ^a ^b "Atracurium Besilate 10 mg/ml Injection - (eMC)". www.medicines.org.uk. March 2015. Archived from the original on 20 December 2016. Retrieved 16 December 2016.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[AHFS2016-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l "Atracurium Besylate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.

[UK2015-2] "Atracurium Besilate 10 mg/ml Injection - (eMC)". www.medicines.org.uk. March 2015. Archived from the original on 20 December 2016. Retrieved 16 December 2016.

[WHO21st-3] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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