Atracurium besilate

Atracurium besilate

Clinical data
AHFS/Drugs.com	Monograph
Pregnancy category	C
Routes of administration	IV
ATC code	M03AC04 (WHO)
Legal status
Legal status	Worldwide: Prescription only
Pharmacokinetic data
Bioavailability	100% (IV)
Protein binding	82%
Metabolism	Hofmann elimination (retro-Michael addition) and ester hydrolysis by nonspecific esterases
Biological 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
Synonyms	Atracurium besylate
CAS Number	64228-79-1 Y
PubChem CID	47319
DrugBank	DB00732 Y
ChemSpider	43067 Y
UNII	40AX66P76P
ChEBI	CHEBI:2914 Y
ChEMBL	CHEMBL1360 Y
Chemical and physical data
Formula	C53H72N2O122+
Molar mass	929.145 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OCCCCCOC(=O)CC[N+]2(C(c1c(cc(OC)c(OC)c1)CC2)Cc3ccc(OC)c(OC)c3)C)CC[N+]5(C)C(c4cc(OC)c(OC)cc4CC5)Cc6ccc(OC)c(OC)c6
InChI InChI=1S/C53H72N2O12/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/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3/q+2 Y Key:YXSLJKQTIDHPOT-UHFFFAOYSA-N Y
NY (what is this?)

Atracurium besilate is a medication used in addition to other medications to provide skeletal muscle relaxation during surgery or mechanical ventilation. It can also be used to help with endotracheal intubation but suxamethonium (succinylcholine) is generally preferred if this needs to be done quickly. It is given by injection into a vein. Effects are greatest at about 4 minutes and last for up to an hour.

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

Atracurium was approved for medical use in the United States in 1983. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Atracurium is available as a generic medication. The wholesale cost in the developing world is about 1.69 to 1.87 USD per dose.