Compound Detail
CHEMBL1200396
BUPIVACAINE HYDROCHLORIDE 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL1200396 |
| Name | BUPIVACAINE HYDROCHLORIDE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | SIEYLFHKZGLBNX-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
| Parent Compound | CHEMBL1098 |
| Active Moiety | CHEMBL1098 |
2
Targets
6
Activities
1
Assay Types
0
PK Parameters
13
Publications
23
Known Names
19
Indications
1
Mechanisms
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 | 1972 |
| Availability | Prescription |
| Chirality | Racemic |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Sodium channel protein type IV alpha subunit blocker | BLOCKER | Sodium channel protein type 4 subunit alpha | ✓ | ✓ |
Indications
Anesthesia Pain Cleft Palate Hallux Valgus Hemorrhoids Neoplasms Osteoarthritis, Knee Peritoneal Neoplasms Radiculopathy Radius Fractures Breast Neoplasms Hernia, Inguinal Migraine Disorders Wounds and Injuries Chronic Pain HIV Infections Neuralgia, Postherpetic Hot Flashes Parathyroid Neoplasms
Drug Warnings
Black Box Warning
cardiotoxicity
Black Box Warning
misuse
Black Box Warning
neurotoxicity
Black Box Warning
hematological toxicity
Black Box Warning
vascular toxicity
Activity Summary
IC50 6 meas. best 6.4
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Cytochrome P450 2D6 CHEMBL289 | IC50 | 6.4 | 6.4 | 400.0 | 1 |
| Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240 | IC50 | 4.66 | 4.3933 | 22000.0 | 3 |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Cytochrome P450 2D6 | IC50 | = | 400.0 | nM | 6.4 | DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) | - |
| Voltage-gated inwardly rectifying potassium channel KCNH2 | IC50 | = | 22000.0 | nM | 4.66 | Inhibition of wild-type human ERG channel expressed in CHO cells by whole-cell p... | 21624711 |
| Voltage-gated inwardly rectifying potassium channel KCNH2 | IC50 | = | 32000.0 | nM | 4.5 | Inhibition of wild-type human ERG channel expressed in HEK293 cells assessed as ... | 21624711 |
| Voltage-gated inwardly rectifying potassium channel KCNH2 | IC50 | = | 95000.0 | nM | 4.02 | Inhibition of human ERG Y652A mutant channel expressed in CHO cells by whole-cel... | 21624711 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 21624711 | 10.1016/j.ejmech.2011.05.015 | Voltage-gated inwardly rectifying potassium channel KCNH2 | 6 |
| 21624711 | 10.1016/j.ejmech.2011.05.015 | Unchecked | 2 |
| - | 10.6019/CHEMBL4495565 | SARS-CoV-2 | 2 |
| - | 10.6019/CHEMBL4808148 | Histone deacetylase 6 | 2 |
| 23571415 | 10.1124/mol.112.084152 | Solute carrier organic anion transporter family member 1B3 | 1 |
| 23571415 | 10.1124/mol.112.084152 | Solute carrier organic anion transporter family member 1B1 | 1 |
| 23956101 | 10.1093/toxsci/kft176 | Bile salt export pump | 1 |
| 23956101 | 10.1093/toxsci/kft176 | ATP-binding cassette sub-family C member 2 | 1 |
| 23956101 | 10.1093/toxsci/kft176 | ATP-binding cassette sub-family C member 3 | 1 |
| 23956101 | 10.1093/toxsci/kft176 | ATP-binding cassette sub-family C member 4 | 1 |
| - | 10.1101/2020.04.03.023846 | SARS-CoV-2 | 1 |
| - | 10.21203/rs.3.rs-23951/v1 | SARS-CoV-2 | 1 |
| - | 10.6019/CHEMBL4495564 | Replicase polyprotein 1ab | 1 |
Data from ChEMBL 36 via Core Engine