Atracurium

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Atracurium
Systematic (IUPAC) name
5-[3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoate
Identifiers
CAS number  ?
ATC code  ?
PubChem 10034347
Chemical data
Formula C53H72N2O12+2
Mol. mass 929.14498
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes  ?

[edit] Description

A non-depolarizing neuromuscular blocking agent with short duration of action. Its lack of significant cardiovascular effects and its lack of dependence on good kidney function for elimination provide clinical advantage over alternate non-depolarizing neuromuscular blocking agents.

Atracurium is a neuromuscular-blocking drug or skeletal muscle relaxant in the category of non-depolarizing neuromuscular-blocking drugs, used adjunctively in anesthesia to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.

Side effects owing to histamine liberation are rash, reflex increase in heart rate, low blood pressure and bronchospasm.

It is a bisbenzyltetrahydroisoquinolinium mixture of 10 stereoisomers. Atracurium was first synthesized, in 1974 by George H. Dewar, in John B. Stenlake's medicinal chemistry research group at Strathclyde University, Scotland. It is the first non-depolarising non-steroidal skeletal muscle relaxant rationally designed to undergo chemodegradation in vivo. Atracurium was licensed to Burroughs Wellcome Co., which developed atracurium and eventually marketed it (as a mixture of all ten stereoisomers) under the name Tracrium. Atracurium's rate of degradation in vivo is influenced by pH and temperature.

Atracurium was succeeded by cisatracurium, which is the R-cis R-cis isomer constituent of atracurium. The pharmacodynamic and adverse effects profile of cisatracurium proved to be superior to that of atracurium. Cisatracurium was made available worldwide as Nimbex in 1995, with its clinical development solely undertaken by Burroughs Wellcome Co.

Atracurium is classified as an intermediate-acting non-depolarising neuromuscular blocking agent.

[edit] General Properties

*Molecular Weight

929.14498

*Molecular Formula

C53H72N2O12+2

*IUPAC NAME

5-[3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl3-[(1R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoate

*Canonical Smiles

C[N+]1(CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC)CCC(=O)OCCCCCOC(=O)CC[N+]4(CCC5=CC(=C(C=C5C4CC6=CC(=C(C=C6)OC)OC)OC)OC)C

*Isomeric Smiles

C[N+]1(CCC2=CC(=C(C=C2[C@H]1CC3=CC(=C(C=C3)OC)OC)OC)OC)CCC(=O)OCCCCCOC(=O)CC[N+]4(CCC5=CC(=C(C=C5[C@H]4CC6=CC(=C(C=C6)OC)OC)OC)OC)C

*XLogP

N/A

*Topological Polar Surface Area

126

[edit] External Links

Link to BIAdb Database