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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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)
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]