bupivacaine

Ligand id: 2397

Name: bupivacaine

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Structure and Physico-chemical Properties

2D Structure
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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 3.57
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

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
Comments
The isomer levobupivacaine is also an approved drug but has a longer duration of action and produces less vasodilation.
Database Links
BindingDB Ligand 50017664
CAS Registry No. 38396-39-3
ChEBI CHEBI:3215
ChEMBL Ligand CHEMBL1098
DrugBank Ligand DB00297
GtoPdb PubChem SID 135650032
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
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Search UniChem for chemical match using the InChIKey LEBVLXFERQHONN-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone LEBVLXFERQHONN
Wikipedia Bupivacaine