Compound Detail
CHEMBL1098
BUPIVACAINE 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL1098 |
| Name | BUPIVACAINE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | LEBVLXFERQHONN-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
5
Targets
6
Activities
1
Assay Types
19
PK Parameters
20
Publications
16
Known Names
20
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
Acute Pain Hernia Pain Analgesia Ankle Fractures Breast Neoplasms Breast Neoplasms Breech Presentation Carcinoma, Non-Small-Cell Lung Chronic Pain Cough Fractures, Bone Genital Neoplasms, Female Hallux Valgus Hemorrhoids Hernia, Inguinal Ileus Liver Diseases Lung Neoplasms Lung Neoplasms
ATC Classification
N01BB01
bupivacaine
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS
N01BB51
bupivacaine, combinations
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS
Activity Summary
IC50 6 meas. best 5.27
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682 | IC50 | 5.27 | 5.27 | 5400.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 5.27 | 5.27 | 5370.3 | 2 |
| Potassium channel subfamily K member 3 CHEMBL2321613 | IC50 | 4.39 | 4.39 | 41000.0 | 1 |
| Potassium channel subfamily K member 3 CHEMBL4294 | IC50 | 4.39 | 4.39 | 41000.0 | 1 |
| Potassium channel subfamily K member 9 CHEMBL4295 | IC50 | 4.0 | 4.0 | 100000.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 4.3 | mL.min-1.kg-1 | Homo sapiens |
| CL | 4.2 | mL.min-1.kg-1 | Homo sapiens |
| CL | 4.3 | mL.min-1.kg-1 | Homo sapiens |
| CL | 4.3 | mL.min-1.kg-1 | Homo sapiens |
| Fu | 0.056 | - | Homo sapiens |
| Fu | 0.056 | - | Homo sapiens |
| Fu | 0.89 | - | Homo sapiens |
| Fu | 0.278 | - | Rattus norvegicus |
| Fu | 0.17 | - | Sus scrofa |
| Fu | 0.232 | - | Homo sapiens |
| Fu | 0.195 | - | Macaca fascicularis |
| Fu | 0.211 | - | Canis lupus familiaris |
| Fu | 0.204 | - | Cavia porcellus |
| Fu | 0.274 | - | Mus musculus |
| Fu | 0.098 | - | Rattus norvegicus |
| Fu | 0.19 | - | Sus scrofa |
| Fu | 0.15 | - | Rattus norvegicus |
| MRT | 3.3 | hr | Homo sapiens |
| T1/2 | 3.1 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Sodium channel alpha subunits; brain (Types I, II, III) | IC50 | = | 5400.0 | nM | 5.27 | Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol... | 2579237 |
| Unchecked | IC50 | = | 5400.0 | nM | 5.27 | Displacement of [3H]-BTX-B from neuronal voltage-gated sodium channel in rat cer... | 19346132 |
| Unchecked | IC50 | = | 5370.32 | nM | 5.27 | Displacement of [3H]-BTX-B from neuronal voltage-gated sodium channel in rat cer... | 19346132 |
| Potassium channel subfamily K member 3 | IC50 | = | 41000.0 | nM | 4.39 | Inhibition of human TASK1 expressed in Xenopus oocytes by whole cell voltage cla... | 31260312 |
| Potassium channel subfamily K member 3 | IC50 | = | 41000.0 | nM | 4.39 | Inhibition of rat TASK1 expressed in African green monkey COS7 cells by outside-... | 31260312 |
| Potassium channel subfamily K member 9 | IC50 | = | 100000.0 | nM | 4.0 | Inhibition of rat TASK3 expressed in African green monkey COS7 cells by outside-... | 31260312 |
Literature References
Data from ChEMBL 36 via Core Engine