Levobupivacaine

Summary

Levobupivacaine (CHEMBL1201193) is an approved small-molecule local anaesthetic (ATC N01BB10); indicated across 7 conditions including neoplasm and cleft palate.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N01BB10
• Indications: 7 conditions
• Clinical trials: 139
• Chemistry: 288.4 Da · C18H28N2O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1201193
Name	Levobupivacaine
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	92253
ChEBI	CHEBI:6149
ATC	N01BB10
Molecular formula	C18H28N2O
Molecular weight	288.4
InChIKey	LEBVLXFERQHONN-INIZCTEOSA-N

SMILES: CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C

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

ChEBI definition: The (S)-(−)-enantiomer of bupivacaine.

Pharmacological roles (ChEBI): local anaesthetic, adrenergic antagonist, amphiphile, EC 3.1.1.8 (cholinesterase) inhibitor, EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor.

Also known as: (-)-bupivacaine, (s)-bupivacaine, Bupivacaine (-)-form, Bupivacaine, (-)-, Bupivacaine, (s)-, L-bupivacaine, Levobupivacaina, Levobupivacaine, Novabupi, SID11112642, SID29215441, LEVOBUPIVACAINE

Parent form; salt/anhydrous children: CHEMBL1200749

Patent coverage: 3,128 distinct patent families (9,718 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

Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Inositol monophosphatase 1, Thyrotropin receptor, Voltage-gated inwardly rectifying potassium channel KCNH2, Cytochrome P450 2D6, Cytochrome P450 1A2, Cytochrome P450 3A4.

Bioactivity

ChEMBL activities: 10 potent at pChembl ≥ 5 of 11 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P97697	8	Potency	10	nM	CHEMBL_ACT_4820579
CYP2D6	6.71	IC50	196.4	nM	CHEMBL_ACT_7755210
CYP2D6	6.3	Potency	501.2	nM	CHEMBL_ACT_4982045
CYP2D6	6.3	AC50	501.2	nM	CHEMBL_ACT_6010889
CYP1A2	5.3	AC50	5012	nM	CHEMBL_ACT_6068534
TSHR	5.2	Potency	6310	nM	CHEMBL_ACT_3912381
TSHR	5.2	Potency	6310	nM	CHEMBL_ACT_4719041
CYP3A4	5	Potency	10000	nM	CHEMBL_ACT_4949380
CYP3A4	5	Potency	10000	nM	CHEMBL_ACT_5018259
CYP3A4	5	AC50	10000	nM	CHEMBL_ACT_6053599

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

7 indications (0 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).

Indication	Trial phase	MONDO	EFO
neoplasm	3	MONDO:0005070	EFO:0000616
cleft palate	2	MONDO:0016064	HP:0000175

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

Clinical trials

Total trials: 139.

Phase distribution

Phase	Trials
PHASE4	64
Not specified	42
PHASE3	13
PHASE2/PHASE3	8
PHASE2	8
PHASE1/PHASE2	2
PHASE1	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02004834	PHASE4	ACTIVE_NOT_RECRUITING	Levobupivacaine and Lidocaine for Paravertebral Block Causes Greater Hemodynamic Oscillations Than Levobupivacaine
NCT03121261	PHASE4	ACTIVE_NOT_RECRUITING	The Effect of Local Anesthetic and Clonidine on the Cutaneous Silent Period During Spinal Anesthesia
NCT04397484	PHASE4	RECRUITING	Prospective RCT Lidocaine & Levobupivacaine on Block Dynamics After Subparaneural Popliteal Sciatic Nerve Block
NCT06369870	PHASE4	RECRUITING	Interpectoral-pectoserratus Plane Block for Minimally Invasive Aortic Valve Replacement Via Right Anterior Minithoracotomy
NCT06695468	PHASE4	NOT_YET_RECRUITING	Efficacy and Safety of Adding Dexmedetomidine to Levobupivacaine in Rectus Sheath Block Compared to Quadratus Lumborum Block in Patients Undergoing Lower Abdominal Cancer Surgery: A Randomized Clinical Trial
NCT00552864	PHASE4	COMPLETED	Comparison of Ropivacaine and Levobupivacaine in High Thoracic Epidural Anesthesia
NCT00836316	PHASE4	COMPLETED	Levobupivacaine During Cholecystectomy
NCT00860899	PHASE4	COMPLETED	Postoperative Pain and SIRS After Preoperative Analgesia With Clonidine or Levobupivacaine
NCT00926666	PHASE4	UNKNOWN	A Dose Finding Study for Pain Relief of a Broken Hip
NCT00970086	PHASE4	TERMINATED	Transversus Abdominis Plane Block for Pain Relieve in Children Undergoing Groin Surgery
NCT00974961	PHASE4	UNKNOWN	Levobupivacaine on Heart Rate Variability (HRV) in Spinal Anesthesia
NCT01106001	PHASE4	COMPLETED	Study to Test the Efficacy of Periarticular Levo Bupivicaine Injection Following Primary Hip Arthroplasty
NCT01158586	PHASE4	UNKNOWN	Postoperative Patient Controlled Epidural Analgesia After Total Knee Arthroplasty With 2ug/ml Fentanyl Combine With 0.2% Ropivacaine or 0.2% Levobupivcaine
NCT01160965	PHASE4	WITHDRAWN	Ropivacaine 0.75% Versus Levobupivacaine 0.5% for Conversion of Labour Epidural
NCT01172197	PHASE4	TERMINATED	Comparison of Levobupivacaine and Ropivacaine for Femoral Neural Block
NCT01199406	PHASE4	COMPLETED	Pain Reduction After Cholecystectomy
NCT01312077	PHASE4	UNKNOWN	The Analgesic Efficacy of Periarticular Infiltration of Local Anaesthetic for Total Hip Replacement
NCT01312415	PHASE4	UNKNOWN	The Analgesic Efficacy of Local Anaesthetic Wound Infiltration Versus Intrathecal Morphine for Total Knee Replacement
NCT01597479	PHASE4	COMPLETED	Ultrasound Guided Distal Peripheral Nerve Blocks and Postoperative Pain.
NCT01785693	PHASE4	COMPLETED	Interest of a Bi-truncal Nerve Block (Femoral + Sciatic) Extended, Systematically Associated With General Anesthesia, in the Femoropopliteal Bypass: Study of Post-operative Analgesia and Peripheral Circulation Downstream
NCT01916915	PHASE4	COMPLETED	Usage of Tramadol With Levobupivacaine for Pain Treatment After Cesarean Section
NCT01918917	PHASE4	COMPLETED	Adding Intra-articular Dexmedetomidine to Levobupivacaine for Postoperative Analgesia in Arthroscopic Knee Surgery
NCT01921361	PHASE4	COMPLETED	The Effects of Dexmedetomidine on Peroperative Shivering Incidence Under Spinal Anesthesia
NCT01929252	PHASE4	COMPLETED	Postoperative Analgesic Effect Of Dexmedetomidine Administration in Wound Infiltration for Total Abdominal Hysterectomy
NCT01938755	PHASE4	COMPLETED	Hyperbaric Levobupivacaine for Spinal Anaesthesia
NCT01960543	PHASE4	COMPLETED	Effects of Bupivacaine and Levobupivacaine on Cerebral Oxygenation During Intrathecal Anesthesia in Elderly Patients
NCT01989312	PHASE4	COMPLETED	The Simultaneous Use of Supraclavicular and Distal Blocks
NCT02025374	PHASE4	COMPLETED	Hyperbaric Bupivacaine and Hyperbaric Levobupivacaine in C/S
NCT02037711	PHASE4	COMPLETED	Intraperitoneal Application of Levobupivacaine During Laparoscopic Surgery in Kids.
NCT02082067	PHASE4	WITHDRAWN	Total Knee Prosthesis With Continuous Block of Adductor Canal and Outcome
NCT02162121	PHASE4	COMPLETED	Stimulating Catheter for Lumbar Plexus Block: Better Postoperative Analgesia?
NCT02185716	PHASE4	COMPLETED	Transversus Abdominis Plane Block (TAP) for Laparoscopic Cholecystectomy Surgery
NCT02201784	PHASE4	COMPLETED	Spinal Anaesthesia With Levobupivacaine 0.5% and Ropivacaine 0.75% for Lower Limb Orthopaedic Surgery
NCT02465008	PHASE4	SUSPENDED	Analgesic Effect of Levobupivacaine in Breast Augmentation
NCT02497040	PHASE4	COMPLETED	The Effects of Scalp Block With Bupivacaine Versus Levobupivacaine
NCT02544282	PHASE4	COMPLETED	Large-scale Prospective Double-blind Randomized Controlled Trial of Pecs II Block for Breast Surgery
NCT02557386	PHASE4	UNKNOWN	Optimal Volume of Bupivacaine in Adductor Canal Nerve Block
NCT02558569	PHASE4	COMPLETED	The Use of Fentanyl in General Anesthesia for Craniotomy With or Without 0.5% Levobupivacaine Scalp Block
NCT02567487	PHASE4	UNKNOWN	TAP Block With Two Different Doses of Levobupivacaine
NCT02689024	PHASE4	TERMINATED	Delirium in Elderly Patients With Trauma of the Hip

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.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).