atracurium   

GtoPdb Ligand ID: 9537

Synonyms: atracurium besilate | atracurium dibesylate | BW 33A [1] | Tracrium®
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.
2D Structure
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Physico-chemical Properties
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1983), UK (1999))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
5-[3-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl 3-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoate
International Nonproprietary Names
INN number INN
4734 atracurium besilate
Synonyms
atracurium besilate | atracurium dibesylate | BW 33A [1] | Tracrium®
Database Links
BindingDB Ligand 92478
ChEMBL Ligand CHEMBL1360
DrugCentral Ligand 259
GtoPdb PubChem SID 336446923
PubChem CID 47319
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