bupivacaine

Ligand id: 2397

Name: bupivacaine

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: bupivacaine

Structure and Physico-chemical Properties

2D Structure
Calculated 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 4.32
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1972))
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
Database Links
BindingDB Ligand 50017664
CAS Registry No. 38396-39-3
ChEBI CHEBI:3215
ChEMBL Ligand CHEMBL1098
DrugBank Ligand DB00297
PubChem CID 2474
Search Google for chemical match using the InChIKey LEBVLXFERQHONN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone LEBVLXFERQHONN
Search PubMed clinical trials bupivacaine
Search PubMed titles bupivacaine
Search PubMed titles/abstracts bupivacaine
Search UniChem for chemical match using the InChIKey LEBVLXFERQHONN-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone LEBVLXFERQHONN
Wikipedia Bupivacaine
Comments
The isomer levobupivacaine is also an approved drug but has a longer duration of action and produces less vasodilation.