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.
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View more information in the IUPHAR Pharmacology Education Project: bupivacaine

2D Structure
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Physico-chemical Properties
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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
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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)
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
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kv1.5 Hs Channel blocker - 5.4 pKd - 1
pKd 5.4 [1]
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