Details of the Drug

General Information of Drug (ID: DM783CH)

Drug Name
Levobupivacaine
Synonyms
Novabupi; Chirocaine (TN); Levobupivacaine (INN); Levobupivacaine [INN:BAN]; Novabupi (TN); L(-)-Bupivacaine; L-(-)-bupivacaine; L-(-)-1-Butyl-2',6'-pipecoloxylidide; (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; (S)-1-Butyl-2',6'-pipecoloxylidide; (S)-bupivacaine
Indication
Disease Entry ICD 11 Status REF
Anaesthesia 9A78.6 Approved [1]
Therapeutic Class
Anesthetics
Affected Organisms
Humans and other mammals
ATC Code
N01BB10: Levobupivacaine
N01BB: Amides
N01B: ANESTHETICS, LOCAL
N01: ANESTHETICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 288.4
Logarithm of the Partition Coefficient (xlogp) 3.4
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 8.7 mL/min/kg [3]
Elimination
0.5% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 3.3 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 13.00112 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.03% [3]
Vd
The volume of distribution (Vd) of drug is 66.91 +/- 18.23 L []
Water Solubility
The ability of drug to dissolve in water is measured as 0.17 mg/mL [2]
Chemical Identifiers
Formula
C18H28N2O
IUPAC Name
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Canonical SMILES
CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
InChI
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1
InChIKey
LEBVLXFERQHONN-INIZCTEOSA-N
Cross-matching ID
PubChem CID
92253
ChEBI ID
CHEBI:6149
CAS Number
27262-47-1
UNII
A5H73K9U3W
DrugBank ID
DB01002
TTD ID
D09QUQ
INTEDE ID
DR0934
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sodium channel unspecific (NaC) TTRK8B9 NOUNIPROTAC Blocker [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [6]
Cytochrome P450 1A2 (CYP1A2)
Main DME 		DEJGDUW CP1A2_HUMAN Substrate [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Levobupivacaine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Ivosidenib DM8S6T7 Minor Increased metabolism of Levobupivacaine caused by Ivosidenib mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [8]
Arn-509 DMT81LZ Minor Increased metabolism of Levobupivacaine caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [9]
Dronedarone DMA8FS5 Moderate Decreased metabolism of Levobupivacaine caused by Dronedarone mediated inhibition of CYP450 enzyme. Angina pectoris [BA40] [10]
Nifedipine DMSVOZT Moderate Decreased metabolism of Levobupivacaine caused by Nifedipine mediated inhibition of CYP450 enzyme. Angina pectoris [BA40] [11]
Posaconazole DMUL5EW Moderate Decreased metabolism of Levobupivacaine caused by Posaconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [11]
Desipramine DMT2FDC Minor Increased plasma concentration of Levobupivacaine and Desipramine due to competitive binding of plasma proteins. Attention deficit hyperactivity disorder [6A05] [12]
Obeticholic acid DM3Q1SM Moderate Decreased metabolism of Levobupivacaine caused by Obeticholic acid mediated inhibition of CYP450 enzyme. Autoimmune liver disease [DB96] [11]
Dalfopristin DM4LTKV Moderate Decreased metabolism of Levobupivacaine caused by Dalfopristin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [11]
Clarithromycin DM4M1SG Moderate Decreased metabolism of Levobupivacaine caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [11]
Norfloxacin DMIZ6W2 Moderate Decreased metabolism of Levobupivacaine caused by Norfloxacin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [11]
Pexidartinib DMS2J0Z Minor Increased metabolism of Levobupivacaine caused by Pexidartinib mediated induction of CYP450 enzyme. Bone/articular cartilage neoplasm [2F7B] [8]
Lapatinib DM3BH1Y Moderate Decreased metabolism of Levobupivacaine caused by Lapatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [11]
Tucatinib DMBESUA Moderate Decreased metabolism of Levobupivacaine caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [11]
Osilodrostat DMIJC9X Moderate Decreased metabolism of Levobupivacaine caused by Osilodrostat mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [11]
MK-8228 DMOB58Q Moderate Decreased metabolism of Levobupivacaine caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [11]
Nefazodone DM4ZS8M Moderate Decreased metabolism of Levobupivacaine caused by Nefazodone mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [11]
Cenobamate DM8KLU9 Minor Increased metabolism of Levobupivacaine caused by Cenobamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Stiripentol DMMSDOY Moderate Decreased metabolism of Levobupivacaine caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [11]
Fosphenytoin DMOX3LB Minor Increased metabolism of Levobupivacaine caused by Fosphenytoin mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Rufinamide DMWE60C Minor Increased metabolism of Levobupivacaine caused by Rufinamide mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Phenobarbital DMXZOCG Minor Increased metabolism of Levobupivacaine caused by Phenobarbital mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [11]
Tazemetostat DMWP1BH Minor Increased metabolism of Levobupivacaine caused by Tazemetostat mediated induction of CYP450 enzyme. Follicular lymphoma [2A80] [8]
Itraconazole DMCR1MV Moderate Decreased metabolism of Levobupivacaine caused by Itraconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [11]
Miconazole DMPMYE8 Moderate Decreased metabolism of Levobupivacaine caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [11]
Rifampin DMA8J1G Minor Increased metabolism of Levobupivacaine caused by Rifampin mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [8]
Rifapentine DMCHV4I Minor Increased metabolism of Levobupivacaine caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [9]
Fosamprenavir DM4W9B3 Moderate Decreased metabolism of Levobupivacaine caused by Fosamprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [11]
Cobicistat DM6L4H2 Moderate Decreased metabolism of Levobupivacaine caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [11]
Saquinavir DMG814N Moderate Decreased metabolism of Levobupivacaine caused by Saquinavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [11]
Etravirine DMGV8QU Minor Increased metabolism of Levobupivacaine caused by Etravirine mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [9]
Darunavir DMN3GCH Moderate Decreased metabolism of Levobupivacaine caused by Darunavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [11]
Atazanavir DMSYRBX Moderate Decreased metabolism of Levobupivacaine caused by Atazanavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [11]
Teriflunomide DMQ2FKJ Minor Increased metabolism of Levobupivacaine caused by Teriflunomide mediated induction of CYP450 enzyme. Hyper-lipoproteinaemia [5C80] [8]
Givosiran DM5PFIJ Moderate Decreased metabolism of Levobupivacaine caused by Givosiran mediated inhibition of CYP450 enzyme. Inborn porphyrin/heme metabolism error [5C58] [11]
Amobarbital DM0GQ8N Minor Increased metabolism of Levobupivacaine caused by Amobarbital mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [8]
Crizotinib DM4F29C Moderate Decreased metabolism of Levobupivacaine caused by Crizotinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
Ceritinib DMB920Z Moderate Decreased metabolism of Levobupivacaine caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
PF-06463922 DMKM7EW Minor Increased metabolism of Levobupivacaine caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [9]
Osimertinib DMRJLAT Minor Increased metabolism of Levobupivacaine caused by Osimertinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [9]
Capmatinib DMYCXKL Moderate Decreased metabolism of Levobupivacaine caused by Capmatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
Selpercatinib DMZR15V Moderate Decreased metabolism of Levobupivacaine caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
Primaquine DMWQ16I Moderate Decreased metabolism of Levobupivacaine caused by Primaquine mediated inhibition of CYP450 enzyme. Malaria [1F40-1F45] [11]
Idelalisib DM602WT Moderate Decreased metabolism of Levobupivacaine caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [11]
IPI-145 DMWA24P Moderate Decreased metabolism of Levobupivacaine caused by IPI-145 mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [11]
Vemurafenib DM62UG5 Minor Increased metabolism of Levobupivacaine caused by Vemurafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [9]
Dabrafenib DMX6OE3 Minor Increased metabolism of Levobupivacaine caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [9]
Danazol DML8KTN Moderate Decreased metabolism of Levobupivacaine caused by Danazol mediated inhibition of CYP450 enzyme. Menstrual cycle bleeding disorder [GA20] [11]
Exjade DMHPRWG Moderate Decreased metabolism of Levobupivacaine caused by Exjade mediated inhibition of CYP450 enzyme. Mineral absorption/transport disorder [5C64] [11]
Fedratinib DM4ZBK6 Moderate Decreased metabolism of Levobupivacaine caused by Fedratinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [11]
Nilotinib DM7HXWT Moderate Decreased metabolism of Levobupivacaine caused by Nilotinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [11]
Dasatinib DMJV2EK Moderate Decreased metabolism of Levobupivacaine caused by Dasatinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [11]
Netupitant DMEKAYI Moderate Decreased metabolism of Levobupivacaine caused by Netupitant mediated inhibition of CYP450 enzyme. Nausea/vomiting [MD90] [11]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Levobupivacaine caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [11]
Abametapir DM2RX0I Moderate Decreased metabolism of Levobupivacaine caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [13]
Lefamulin DME6G97 Moderate Decreased metabolism of Levobupivacaine caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [14]
Lonafarnib DMGM2Z6 Moderate Decreased metabolism of Levobupivacaine caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [11]
Enzalutamide DMGL19D Minor Increased metabolism of Levobupivacaine caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [9]
Bicalutamide DMZMSPF Moderate Decreased metabolism of Levobupivacaine caused by Bicalutamide mediated inhibition of CYP450 enzyme. Prostate cancer [2C82] [11]
Temsirolimus DMS104F Moderate Increased plasma concentrations of Levobupivacaine and Temsirolimus due to competitive inhibition of the same metabolic pathway. Renal cell carcinoma [2C90] [15]
Dexamethasone DMMWZET Minor Increased metabolism of Levobupivacaine caused by Dexamethasone mediated induction of CYP450 enzyme. Rheumatoid arthritis [FA20] [9]
Voxelotor DMCS6M5 Moderate Decreased metabolism of Levobupivacaine caused by Voxelotor mediated inhibition of CYP450 enzyme. Sickle-cell disorder [3A51] [11]
Telotristat ethyl DMDIYFZ Moderate Increased metabolism of Levobupivacaine caused by Telotristat ethyl mediated induction of CYP450 enzyme. Small intestine developmental anomaly [DA90] [11]
Larotrectinib DM26CQR Moderate Decreased metabolism of Levobupivacaine caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [11]
Armodafinil DMGB035 Minor Increased metabolism of Levobupivacaine caused by Armodafinil mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [9]
LEE011 DMMX75K Moderate Decreased metabolism of Levobupivacaine caused by LEE011 mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [11]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Levobupivacaine caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [16]
Elagolix DMB2C0E Minor Increased metabolism of Levobupivacaine caused by Elagolix mediated induction of CYP450 enzyme. Uterine fibroid [2E86] [8]
Bretylium DM1FX74 Moderate Increased risk of bradycardia by the combination of Levobupivacaine and Bretylium. Ventricular tachyarrhythmia [BC71] [17]
Propafenone DMPIBJK Moderate Decreased metabolism of Levobupivacaine caused by Propafenone mediated inhibition of CYP450 enzyme. Ventricular tachyarrhythmia [BC71] [11]
Amiodarone DMUTEX3 Moderate Increased risk of bradycardia by the combination of Levobupivacaine and Amiodarone. Ventricular tachyarrhythmia [BC71] [17]
⏷ Show the Full List of 70 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7211).
2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Block of neuronal tetrodotoxin-resistant Na+ currents by stereoisomers of piperidine local anesthetics. Anesth Analg. 2000 Dec;91(6):1499-505.
6 Clinical profile of levobupivacaine in regional anesthesia: A systematic review. J Anaesthesiol Clin Pharmacol. 2013 Oct;29(4):530-9.
7 Pharmacokinetics of levobupivacaine after caudal epidural administration in infants less than 3 months of age. Br J Anaesth. 2005 Oct;95(4):524-9.
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9 Product Information. Chirocaine (levobupivacaine) Organon, West Orange, NJ.
10 Product Information. Multaq (dronedarone). sanofi-aventis , Bridgewater, NJ.
11 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
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13 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
14 Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
15 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
16 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.
17 Keidar S, Grenadier E, Palant A "Sinoatrial arrest due to lidocaine injection in sick sinus syndrome during amiodarone administration." Am Heart J 104 (1982): 1384-5. [PMID: 7148661]