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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Bioactivity Comments
Many of the tetrahydroisoquinolinium class of neuromuscular blocking agents are associated with histamine release following bolus administration, with outward symptoms including short-lived cutaneous flushing. Transient hypotension and reflex tachycardia may occur.
Note that we have mapped this drug to the relevant α subunit of the experimentally tested nACh receptor complexes [3].
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
nicotinic acetylcholine receptor α3 subunit Hs Antagonist Antagonist 7.9 – 9.1 pIC50 - 3
⤷ pIC50 7.9 – 9.1 (IC50 1.16x10-8 – 9x10-10 M) [3]
Description: Antagonism of ACh activation of human α3β2 or α3β4 nACh receptors expressed in Xenopus oocytes, at different ACh concentrations.
nicotinic acetylcholine receptor α7 subunit Hs Antagonist Antagonist 7.9 – 8.3 pIC50 - 3
⤷ pIC50 7.9 – 8.3 (IC50 1.3x10-8 – 5.6x10-9 M) [3]
Description: Antagonism of ACh activation of human α7 nACh receptors expressed in Xenopus oocytes, at different ACh concentrations.
nicotinic acetylcholine receptor α4 subunit Hs Antagonist Antagonist 7.7 – 8.1 pIC50 - 3
⤷ pIC50 7.7 – 8.1 (IC50 2.11x10-8 – 7.9x10-9 M) [3]
Description: Antagonism of ACh activation of human α4β2 nACh receptors expressed in Xenopus oocytes, at different ACh concentrations.
nicotinic acetylcholine receptor α1 subunit Hs Antagonist Antagonist 7.0 pIC50 - 3
⤷ pIC50 7.0 (IC50 9.7x10-8 M) [3]
Description: Antagonism of ACh activation of α1β1εδ nACh receptors expressed in Xenopus oocytes.