Ligand id: 2397

Name: bupivacaine

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: bupivacaine

Structure and Physico-chemical Properties

2D Structure
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 4.32
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

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. U.S.A., 98 (11): 6482-7. [PMID:11353868]