atracurium   Click here for help

GtoPdb Ligand ID: 9537

Synonyms: atracurium besilate | atracurium dibesylate | BW 33A [1] | Tracrium®
Approved drug Immunopharmacology Ligand
atracurium is an approved drug (FDA (1983), UK (1999))
Compound class: Synthetic organic
Comment: Atracurium (besylate) is a intermediate-duration non-depolarizing neuromuscular blocking agent, delivered by bolus injection in to a vein. It is a complex molecule with potential to exist as multiple stereoisomers.The INN for this drug stipulates the besylate salt, represented in PubChem CID 47320. We show the structure for the parent molecule, with no specified stereochemistry.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 26
Topological polar surface area 126.44
Molecular weight 928.51
XLogP 6.44
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc2c(cc1OC)CC[N+](C2Cc1ccc(c(c1)OC)OC)(C)CCC(=O)OCCCCCOC(=O)CC[N+]1(C)CCc2c(C1Cc1ccc(c(c1)OC)OC)cc(c(c2)OC)OC
Isomeric SMILES COc1cc2c(cc1OC)CC[N+](C2Cc1ccc(c(c1)OC)OC)(C)CCC(=O)OCCCCCOC(=O)CC[N+]1(C)CCc2c(C1Cc1ccc(c(c1)OC)OC)cc(c(c2)OC)OC
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
InChI Key YXSLJKQTIDHPOT-UHFFFAOYSA-N
References
1. Basta SJ, Ali HH, Savarese JJ, Sunder N, Gionfriddo M, Cloutier G, Lineberry C, Cato AE. (1982)
Clinical pharmacology of atracurium besylate (BW 33A): a new non-depolarizing muscle relaxant.
Anesth Analg, 61 (9): 723-9. [PMID:6213181]
2. Fanelli V, Morita Y, Cappello P, Ghazarian M, Sugumar B, Delsedime L, Batt J, Ranieri VM, Zhang H, Slutsky AS. (2016)
Neuromuscular Blocking Agent Cisatracurium Attenuates Lung Injury by Inhibition of Nicotinic Acetylcholine Receptor-α1.
Anesthesiology, 124 (1): 132-40. [PMID:26540149]
3. Jonsson M, Gurley D, Dabrowski M, Larsson O, Johnson EC, Eriksson LI. (2006)
Distinct pharmacologic properties of neuromuscular blocking agents on human neuronal nicotinic acetylcholine receptors: a possible explanation for the train-of-four fade.
Anesthesiology, 105 (3): 521-33. [PMID:16931985]