bupivacaine   Click here for help

GtoPdb Ligand ID: 2397

Synonyms: DL-Bupivacaine | Exparel® | Marcain® | Posimir® | Sensorcaine® | W-7 | Xaracoll®
Approved drug
bupivacaine is an approved drug (FDA (1972), EMA (2020))
Compound class: Synthetic organic
Comment: The isomer levobupivacaine is also an approved drug but has a longer duration of action and produces less vasodilation.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: bupivacaine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Bioactivity Comments
We have been unable to find publicly available affinity data for this drug (at human sodium channels) to substantiate its MMOA.
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kv1.5 Hs Channel blocker - 5.4 pKd - 1
pKd 5.4 [1]
Nav1.5 Hs Channel blocker Pore blocker 4.2 – 5.7 pIC50 - 3
pIC50 5.7 (IC50 2.18x10-6 M) Blockade of inactivated channel [3]
pIC50 4.2 (IC50 6.95x10-5 M) Open-channel block [3]
Kv4.3 Mm Channel blocker - 4.0 – 4.5 pIC50 - 2,4
pIC50 4.5 [4]
pIC50 4.0 [2]
Kir3.2 N/A Gating inhibitor Antagonist 4.0 – 4.2 pIC50 - 5
pIC50 4.0 – 4.2 [5]
Voltage: -110.0 – -40.0 mV