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Compound Detail

CHEMBL1201193

LEVOBUPIVACAINE
💊 Approved Drug
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💊 Approved Drug
CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201193
Name LEVOBUPIVACAINE
Phase Approved
Structure Type MOL
InChI Key LEBVLXFERQHONN-INIZCTEOSA-N
Therapeutic ✓ Yes

Known Names

(-)-bupivacaine (s)-bupivacaine Bupivacaine (-)-form Bupivacaine, (-)- Bupivacaine, (s)- L-bupivacaine Levobupivacaina Levobupivacaine Novabupi
2
Targets
2
Activities
1
Assay Types
0
PK Parameters
6
Publications
9
Known Names
7
Indications

Molecular Properties

288.4
MW (Da)
3.90
ALogP
2
HBA
1
HBD
32.3
PSA (Ų)
0.89
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -caine
USAN Year 1998

Extended Properties

Molecular Formula C18H28N2O
MW 288.44
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -1.36

Indications

Back Pain Neoplasms Pain Pregnancy Abdominal Pain Cleft Palate Postoperative Complications

ATC Classification

N01BB10
levobupivacaine
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS

Activity Summary

IC50 2 meas. best 6.71

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 2D6
CHEMBL289
 IC50 6.71 6.71 196.4 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.68 4.68 20893.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 2D6 IC50 = 196.4 nM 6.71 DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 20892.96 nM 4.68 Inhibition of human ERG 21185626

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 214
21550810 10.1016/j.bmc.2011.04.030 Lipid bilayer 6
21550810 10.1016/j.bmc.2011.04.030 Canis familiaris 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
21185626 10.1016/j.ejmech.2010.11.042 Voltage-gated inwardly rectifying potassium channel KCNH2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine