bupivacaine   

GtoPdb Ligand ID: 2397

Synonyms: DL-Bupivacaine | Marcain® | Sensorcaine® | W-7 | Xaracoll®
bupivacaine is an approved drug (FDA (1972))
Compound class: Synthetic organic
Comment: The isomer levobupivacaine is also an approved drug but has a longer duration of action and produces less vasodilation.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 32.34
Molecular weight 288.22
XLogP 3.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C
Isomeric SMILES CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C
InChI InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)
InChI Key LEBVLXFERQHONN-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1972))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
International Nonproprietary Names
INN number INN
2279 bupivacaine
Synonyms
DL-Bupivacaine | Marcain® | Sensorcaine® | W-7 | Xaracoll®
Database Links
BindingDB Ligand 50017664
CAS Registry No. 38396-39-3
ChEBI CHEBI:3215
ChEMBL Ligand CHEMBL1098
DrugBank Ligand DB00297
DrugCentral Ligand 432
GtoPdb PubChem SID 135650032
PubChem CID 2474
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Wikipedia Bupivacaine