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Bupivacaine

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Also known as AnekainBR-003BucaineBupivacainaBupivacaine component of zynrelefBupivacaine liposomeExparelExparel liposomalLiposomal bupivacaineLIQ-865LIQ865PosimirRopivacaine hydrochloride impuritybupivacaine-SKY-0402SKY0402rac-bupivacaineSID160644527Bupivicaine

Summary

Bupivacaine (CHEMBL1098) is an approved small molecule (ATC N01BB01) targeting KCNJ6, KCNA5, and KCND3; indicated across 74 conditions including bone fracture and injury.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N01BB01 (+1 more)
  • Targets: 4 (KCNJ6, KCNA5, KCND3…)
  • Indications: 74 conditions
  • Clinical trials: 1,218
  • Chemistry: 288.4 Da · C18H28N2O

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1098
NameBupivacaine
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID2474
ChEBICHEBI:77431
ATCN01BB01, N01BB51
Molecular formulaC18H28N2O
Molecular weight288.4
InChIKeyLEBVLXFERQHONN-UHFFFAOYSA-N

SMILES: CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C

IUPAC name: 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

ChEBI definition: A piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline.

Also known as: Anekain, BR-003, Bucaine, Bupivacaina, Bupivacaine, Bupivacaine component of zynrelef, Bupivacaine liposome, Exparel, Exparel liposomal, Liposomal bupivacaine, LIQ-865, LIQ865

Parent form; salt/anhydrous children: CHEMBL1200396

Patent coverage: 10,327 distinct patent families (37,899 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
KCNJ6Kir3.2Antagonist4.20.1%P48051
KCNA5Kv1.55.40.2%P22460
KCND3Kv4.345.5%Q9UK17
SCN5ANav1.5Pore blocker4.160.2%Q14524

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Sodium channel alpha subunits; brain (Types I, II, III), Potassium channel subfamily K member 3, Voltage-gated inwardly rectifying potassium channel KCNH2, Potassium channel subfamily K member 3, Potassium channel subfamily K member 9.

Bioactivity

ChEMBL activities: 1 potent at pChembl ≥ 5 of 5 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
SCN1A5.27IC505400nMCHEMBL_ACT_376599

Target pathways

Aggregated over 4 target gene(s): KCNJ6, KCNA5, KCND3, SCN5A.

Top Reactome pathways

22 total, by targets touching each:

PathwayTargetsGenes
Neuronal System3KCNA5, KCND3, KCNJ6
Potassium Channels3KCNA5, KCND3, KCNJ6
Muscle contraction3KCNA5, KCND3, SCN5A
Cardiac conduction3KCNA5, KCND3, SCN5A
Voltage gated Potassium channels2KCNA5, KCND3
Neurotransmitter receptors and postsynaptic signal transmission1KCNJ6
Transmission across Chemical Synapses1KCNJ6
Developmental Biology1SCN5A
Activation of G protein gated Potassium channels1KCNJ6
G protein gated Potassium channels1KCNJ6
Inwardly rectifying K+ channels1KCNJ6
L1CAM interactions1SCN5A
Axon guidance1SCN5A
Interaction between L1 and Ankyrins1SCN5A
Phase 3 - rapid repolarisation1KCNA5
Phase 0 - rapid depolarisation1SCN5A
Phase 1 - inactivation of fast Na+ channels1KCND3
Nervous system development1SCN5A
GABA receptor activation1KCNJ6
GABA B receptor activation1KCNJ6
Activation of GABAB receptors1KCNJ6
Inhibition of voltage gated Ca2+ channels via Gbeta/gamma subunits1KCNJ6

Dominant GO biological processes

GO termTargets
monoatomic ion transport4
monoatomic ion transmembrane transport4
potassium ion transport3
regulation of heart rate by cardiac conduction3
transmembrane transport3
action potential2
protein homooligomerization2
regulation of atrial cardiac muscle cell membrane repolarization2
potassium ion transmembrane transport2
atrial cardiac muscle cell action potential2
potassium ion export across plasma membrane2
regulation of monoatomic ion transmembrane transport1
potassium ion import across plasma membrane1
response to hypoxia1
Notch signaling pathway1

Indications & clinical

Indications

74 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
bone fracture3MONDO:0005315EFO:0003931
injury3MONDO:0021178EFO:0000546
breast neoplasm3MONDO:0021100EFO:0003869
chronic pancreatitis3MONDO:0005003EFO:0000342
neoplasm3MONDO:0005070EFO:0000616
exocrine pancreatic carcinoma3MONDO:0005192EFO:0002618
rotator cuff syndrome3MONDO:0007028EFO:1001250
liver disorder3MONDO:0005154EFO:0001421
non-small cell lung carcinoma3MONDO:0005233EFO:0003060
hemorrhoid3MONDO:0004872EFO:0009552
osteoarthritis, knee3MONDO:0005416EFO:0004616
urethral stricture3MONDO:0002127HP:0012227
peritoneal neoplasm3MONDO:0006901MONDO:0002087
radiculopathy3MONDO:0002959MONDO:0002959
lung neoplasm3MONDO:0021117MONDO:0021117
female reproductive organ cancer3MONDO:0001416EFO:1001331
ileus3MONDO:0004567MONDO:0004567
osteoarthritis3MONDO:0005178MONDO:0005178
migraine disorder3MONDO:0005277MONDO:0005277
pancreatic neoplasm3MONDO:0021040EFO:0003860
radius fracture3MONDO:0005325EFO:0003957
pain agnosia3MONDO:0000675EFO:1001484
hypotensive disorder2MONDO:0005468EFO:0005251
hip fracture2MONDO:0005327EFO:0003964
osteoarthritis, hip2MONDO:0006629EFO:1000786
hypospadias2MONDO:0005345EFO:0004209
palmar fibromatosis2MONDO:0006345EFO:0004229
appendicitis2MONDO:0005649EFO:0007149
femoral neck fracture2MONDO:0043589EFO:1001792
mucositis2MONDO:0020579EFO:1001898
plantar fasciitis2MONDO:0004833EFO:1001909
cleft palate2MONDO:0016064HP:0000175
spinal stenosis2MONDO:0005965EFO:0007490
blood coagulation disease2MONDO:0001531EFO:0009314
pulpitis2MONDO:0006937EFO:1001139
lacrimal apparatus disorder2MONDO:0001854HP:0009926
atrial fibrillation2MONDO:0004981EFO:0000275
musculoskeletal system disorder2MONDO:0002081EFO:0009676
ptosis2MONDO:0000728MONDO:0000728
complex regional pain syndrome2MONDO:0019369EFO:1001998
HIV infectious disease1MONDO:0005109EFO:0000764
brain neoplasm1MONDO:0021211EFO:0003833
intracranial vasospasm1MONDO:0006812EFO:1000994
aorta coarctation1MONDO:0007345EFO:1001267
sinusitis1MONDO:0005961EFO:0007486
morbid obesity1MONDO:0005139EFO:0001074
neuralgia0MONDO:0021667EFO:0005762
soft tissue sarcoma0MONDO:0018078EFO:1001968
post-traumatic stress disorder0MONDO:0005146EFO:0001358
lung disorder0MONDO:0005275EFO:0003818
subarachnoid hemorrhage0MONDO:0005099EFO:0000713

23 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 1,218.

Phase distribution

PhaseTrials
PHASE4451
Not specified428
PHASE3111
PHASE2104
PHASE143
PHASE2/PHASE340
EARLY_PHASE129
PHASE1/PHASE212

Top trials by phase / activity

NCTPhaseStatusTitle
NCT02381353PHASE4ACTIVE_NOT_RECRUITINGExparel Injection for Postoperative Orbital Pain
NCT03737292PHASE4RECRUITINGLiposomal Bupivacaine Versus Plain Bupivacaine After Intercostal Injections For Pain Management After Thoracoscopy
NCT03968822PHASE4ACTIVE_NOT_RECRUITINGIntralipid® 20% for Reversal of Local Anesthetics
NCT04003506PHASE4NOT_YET_RECRUITINGEffectiveness of Adductor Canal Block Using Liposomal Bupivacaine
NCT04575688PHASE4ENROLLING_BY_INVITATIONPeriarticular Injection Versus Popliteal Block
NCT04577690PHASE4RECRUITINGPECS Study for CIED Implantation Surgery
NCT04680221PHASE4ACTIVE_NOT_RECRUITINGStopping Opioid Overuse in Obstetrics to Halt Exposure Trial
NCT05285566PHASE4RECRUITINGPain Control for Undergoing Costal Cartilage Harvesting
NCT05391971PHASE4ACTIVE_NOT_RECRUITINGEffects of Stellate Ganglion Block in Post-traumatic Stress Disorder
NCT05425979PHASE4ENROLLING_BY_INVITATIONMepivacaine Versus Bupivacaine Onset Time in Ultrasound-guided Ankle Blocks
NCT05602636PHASE4RECRUITINGAnalgesic Effect of Supraclavicular Block and Interscalene Analgesia Versus an Intercostobrachial Nerve Block Versus PCA in Forearm Surgery
NCT05605639PHASE4RECRUITINGPhrenic Nerve Infiltration in Neck Pain
NCT05972018PHASE4RECRUITINGLiposomal Bupivacaine/Bupivacaine in Rectus Sheath Blocks Versus Ropivacaine in Rectus Sheath Blocks And Catheters
NCT05996133PHASE4RECRUITINGMultifidus Cervicis Plane Block Vs. Sham Block For Posterior Cervical Spine Fusion Surgery
NCT06006624PHASE4ENROLLING_BY_INVITATIONExparel vs Block for ACL Reconstruction
NCT06189781PHASE4RECRUITINGPain Injection Versus Epidural Anesthesia for Hip Surgery in Pediatric Patients With Cerebral Palsy
NCT06252662PHASE4RECRUITINGLiposomal Bupivacaine Vs Bupivacaine with Dexmedetomidine in Erector Spinae Plane Blocks for Mastectomies
NCT06271707PHASE4RECRUITINGStellate Ganglion Block
NCT06381401PHASE4RECRUITINGBupivacaine 0.125% Versus Bupivacaine 0.25% in Superficial Cervical Plexus Block for Tympanomastoid Surgeries in Adults
NCT06416891PHASE4NOT_YET_RECRUITINGEffect of Adding Dexamethasone to Bupivacaine 0.25% in SCPB on Surgical Field Visibility During Tympanomastoid Surgery
NCT06432127PHASE4NOT_YET_RECRUITINGRole of Ultrasound Guide Greater Occipital Nerve Block at Second Cervical Vertebra in Migraine Headache Prophylaxis
NCT06465992PHASE4ENROLLING_BY_INVITATIONLiposomal Bupivacaine With Dexamethasone for Foot Surgery
NCT06474949PHASE4NOT_YET_RECRUITINGLocal Anesthetic for Plateau Fractures
NCT06557018PHASE4RECRUITINGEfficacy and Safety of Liposomal Bupivacaine Using Periarticular Injection in Total Knee Arthroplasty
NCT06569953PHASE4RECRUITINGEfficacy and Safety of Liposomal Bupivacaine Injection for Paravertebral Nerve Block in the Treatment of Acute and Chronic Pain After Thoracoscopic Pneumonectomy: A Multicenter, Randomized, Double-blind, Controlled Clinical Trial
NCT06574022PHASE4RECRUITINGPost-mastectomy Recovery: Comparing Preoperative PECS-II Blocks With Intraoperative Pectoral Blocks
NCT06575010PHASE4ENROLLING_BY_INVITATIONExparel v Dexamethasone in RCR
NCT06590402PHASE4RECRUITINGAnterior Femoral and Adductor Canal Nerve Blocks in Peds Knees
NCT06619340PHASE4ENROLLING_BY_INVITATIONEXPAREL IPSA Block in Knee Arthroplasty
NCT06644261PHASE4RECRUITINGTransvaginal Versus Fluoroscopy-guided Trans Gluteal Pudendal Nerve Block for Pudendal Neuralgia
NCT06653621PHASE4NOT_YET_RECRUITINGEffect of Bupivacaine Liposomes or Bupivacaine for Femoral Triangle or Adductor Block on Analgesia After Total Knee Replacement
NCT06677827PHASE4NOT_YET_RECRUITINGEffect of Adding Magnesium Sulphate as Adjuvant to Bupivacaine in Ultrasound Guided External Oblique Intercostal Plane Block in Upper Abdominal Cancer Surgery.to Assess the Total Postoperative Opioid Consumption in the First 24 h and Evaluate Post Operative VAS Score
NCT06685705PHASE4NOT_YET_RECRUITINGComparative Study Between Intrathecal Magnesium Sulfate, Neostigmine and Fentanyl as Adjuvant for Bubivacaine in Postoperative Analgesia in Lower Abdominal Surgeries
NCT06694077PHASE4NOT_YET_RECRUITINGSuprazygomatic Maxillary Nerve Block for Management of Postoperative Pain in Adenotonsillectomy Patients
NCT06720337PHASE4NOT_YET_RECRUITINGComparative Study Between the Analgesic Effect of Dexmedetomidine and Magnesium Sulfate as Adjuvant to Bupivacaine Using Ultrasound-Guided Transversus Abdominis Plane Block in Abdominal Hysterectomy : A Randomized Double-blinded Study
NCT06737341PHASE4NOT_YET_RECRUITINGBupivacaine Liposomes or Bupivacaine for CMB on Postoperative Analgesia in Laparoscopic Hepatobiliary Pancreatic Surgery
NCT06747975PHASE4NOT_YET_RECRUITINGPreventative Effect of Combining Dexamethasone with Ondansetron on Postoperative Nausea, Vomiting and Shivering in Children Undergoing Caudal Anesthesia on Hypospadias Surgery
NCT06752525PHASE4NOT_YET_RECRUITINGOpioid Sparing Effect of Sphenopalatine Ganglion Block in Functional Endoscopic Sinus Surgery: a Randomized Controlled Clinical Trial.
NCT06752629PHASE4NOT_YET_RECRUITINGComparison Between Dexmedetomidine and Fentanyl As an Adjuvant to Bupivacaine in the Paravertebral Nerve Block in Laparoscopic Cholecystectomy for Postoperative Analgesia: Randomized Comparative Clinical Trial.
NCT06783764PHASE4ACTIVE_NOT_RECRUITINGComparative Study Between Combined Modified Pectoral Nerve Block (PECSΙΙ) and Transversus Thoracic Plane Block Versus Erector Spinae Plane Block for Post-operative Analgesia Following Breast Surgeries, (randomized Clinical Trial Study)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

143 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
BelzutifanPubChemApprovedKCNA5, KCND3, SCN5A
DARIFENACINChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
DARUNAVIRChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
DEFERASIROXChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
DiltiazemChEMBL + PubChemPhase 4 (approved)KCNA5, SCN5A
DULOXETINEChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
FLECAINIDEChEMBL + PubChemPhase 4 (approved)KCNA5, SCN5A
LamotrigineChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
LidocaineChEMBL + PubChemPhase 4 (approved)KCNA5, SCN5A
MoxifloxacinChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
NEBIVOLOLChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
NelfinavirChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
PALIPERIDONEChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
PalonosetronChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
PropafenoneChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
QUINIDINEChEMBL + PubChemPhase 4 (approved)KCNA5, SCN5A
SilodosinChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
SOLIFENACINChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
SUNITINIBChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
TOLTERODINEChEMBL + PubChemPhase 4 (approved)KCND3, SCN5A
NIFEDIPINEChEMBLPhase 4 (approved)KCNA5, SCN5A
SERTINDOLEChEMBLPhase 4 (approved)KCNA5, SCN5A
VERNAKALANTChEMBLPhase 4 (approved)KCNA5, SCN5A
DesvenlafaxinePubChemApprovedKCND3, SCN5A
TadalafilPubChemApprovedKCND3, SCN5A
DronedaroneChEMBL + PubChemPhase 4 (approved)KCNA5
VARDENAFILChEMBL + PubChemPhase 4 (approved)KCND3
AMIODARONEChEMBLPhase 4 (approved)SCN5A
AMITRIPTYLINEChEMBLPhase 4 (approved)SCN5A
AMLODIPINEChEMBLPhase 4 (approved)SCN5A
ASENAPINEChEMBLPhase 4 (approved)SCN5A
ASTEMIZOLEChEMBLPhase 4 (approved)SCN5A
BAZEDOXIFENEChEMBLPhase 4 (approved)SCN5A
BENZONATATEChEMBLPhase 4 (approved)SCN5A
BEPRIDILChEMBLPhase 4 (approved)SCN5A
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)SCN5A
CARBAMAZEPINEChEMBLPhase 4 (approved)SCN5A
CARVEDILOLChEMBLPhase 4 (approved)SCN5A
CHLORPROMAZINEChEMBLPhase 4 (approved)SCN5A
CISAPRIDEChEMBLPhase 4 (approved)SCN5A
CLEMASTINEChEMBLPhase 4 (approved)SCN5A
CLOZAPINEChEMBLPhase 4 (approved)SCN5A
DABIGATRAN ETEXILATEChEMBLPhase 4 (approved)SCN5A
DASATINIBChEMBLPhase 4 (approved)SCN5A
DESIPRAMINEChEMBLPhase 4 (approved)SCN5A
DIBUCAINEChEMBLPhase 4 (approved)SCN5A
DIPHENHYDRAMINEChEMBLPhase 4 (approved)SCN5A
DOMPERIDONEChEMBLPhase 4 (approved)SCN5A
DROPERIDOLChEMBLPhase 4 (approved)SCN5A
ETIDOCAINEChEMBLPhase 4 (approved)SCN5A
FEDRATINIBChEMBLPhase 4 (approved)SCN5A
FELODIPINEChEMBLPhase 4 (approved)SCN5A
FLUPHENAZINEChEMBLPhase 4 (approved)SCN5A
FLUVOXAMINEChEMBLPhase 4 (approved)SCN5A
HALOPERIDOLChEMBLPhase 4 (approved)SCN5A
IMIPRAMINEChEMBLPhase 4 (approved)SCN5A
ISRADIPINEChEMBLPhase 4 (approved)SCN5A
LETERMOVIRChEMBLPhase 4 (approved)SCN5A
LOPERAMIDEChEMBLPhase 4 (approved)SCN5A
LOPINAVIRChEMBLPhase 4 (approved)SCN5A

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot