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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: bupivacaine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key LEBVLXFERQHONN-UHFFFAOYSA-N
References
1. Franqueza L, Longobardo M, Vicente J, Delpón E, Tamkun MM, Tamargo J, Snyders DJ, Valenzuela C. (1997)
Molecular determinants of stereoselective bupivacaine block of hKv1.5 channels.
Circ Res, 81 (6): 1053-64. [PMID:9400387]
2. Qu YJ, Bondarenko VE, Xie C, Wang S, Awayda MS, Strauss HC, Morales MJ. (2007)
W-7 modulates Kv4.3: pore block and Ca2+-calmodulin inhibition.
Am J Physiol Heart Circ Physiol, 292 (5): H2364-77. [PMID:17220193]
3. Schwoerer AP, Scheel H, Friederich P. (2015)
A Comparative Analysis of Bupivacaine and Ropivacaine Effects on Human Cardiac SCN5A Channels.
Anesth Analg, 120 (6): 1226-34. [PMID:25692452]
4. Yeung SY, Ohya S, Sergeant GP, Pucovský V, Greenwood IA. (2006)
Pharmacological and molecular evidence for the involvement of Kv4.3 in ultra-fast activating K+ currents in murine portal vein myocytes.
Br J Pharmacol, 149 (6): 676-86. [PMID:17016508]
5. Zhou W, Arrabit C, Choe S, Slesinger PA. (2001)
Mechanism underlying bupivacaine inhibition of G protein-gated inwardly rectifying K+ channels.
Proc Natl Acad Sci USA, 98 (11): 6482-7. [PMID:11353868]