LEVOBUPIVACAINE

US Previously Marketed

First approved in 1999

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H28N2O
Molecular Weight	288.4277
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LEBVLXFERQHONN-INIZCTEOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H28N2O
Molecular Weight	288.4277
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18728849

Levobupivacaine (CHIROCAINE®) is a (S)-enantiomer of bupivacaine and it is related chemically and pharmacologically to the amino amide class of local anesthetics. Local anesthetics block the generation and the conduction of nerve impulses by increasing the threshold for electrical excitation in the nerve, by slowing propagation of the nerve impulse, and by reducing the rate of rise of the action potential. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of affected nerve ﬁbers. Clinically, the order of loss of nerve function is as follows: 1) pain, 2) temperature, 3) touch, 4) proprioception and 5) skeletal muscle tone. Levobupivacaine (CHIROCAINE®) is a safer alternative for regional anesthesia than bupivacaine. It demonstrated less affinity and strength of depressant effects onto myocardial and central nervous vital centers in pharmacodynamic studies, and a superior pharmacokinetic profile.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel protein type IV alpha subunit 23 Target ID: CHEMBL3509 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24249993	Blocker 555		4.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	Primary		Approved 8583	CHIROCAINE Approved Use Chirocaine is indicated for the production of local or regional anesthesia for surgery and obstetrics, and for post-operative pain management. Launch Date 1999

C_max

Value	Dose	Analyte	Population
0.582 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	75 mg single, epidural dose: 75 mg route of administration: Epidural experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
0.811 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	112.5 mg single, epidural dose: 112.5 mg route of administration: Epidural experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
0.474 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	1 mg/kg bw single, brachial plexus block dose: 1 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
0.961 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	2 mg/kg bw single, brachial plexus block dose: 2 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
3.561 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	75 mg single, epidural dose: 75 mg route of administration: Epidural experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.93 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	112.5 mg single, epidural dose: 112.5 mg route of administration: Epidural experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.999 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	1 mg/kg bw single, brachial plexus block dose: 1 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
5.311 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	2 mg/kg bw single, brachial plexus block dose: 2 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Analyte	Population
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	75 mg single, epidural dose: 75 mg route of administration: Epidural experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	112.5 mg single, epidural dose: 112.5 mg route of administration: Epidural experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	1 mg/kg bw single, brachial plexus block dose: 1 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf	2 mg/kg bw single, brachial plexus block dose: 2 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered:	LEVOBUPIVACAINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
142.5 mg single, intravenous Dose: 142.5 mg Route: intravenous Route: single Dose: 142.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10512284	unhealthy, 77 years Health Status: unhealthy Age Group: 77 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/10512284	Sources: https://pubmed.ncbi.nlm.nih.gov/10512284
2 mg/kg single, caudal epidural Dose: 2 mg/kg Route: caudal epidural Route: single Dose: 2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16100236	unhealthy, < 3 months Health Status: unhealthy Age Group: < 3 months Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16100236	Sources: https://pubmed.ncbi.nlm.nih.gov/16100236
1.75 mg/kg single, subcutaneous Dose: 1.75 mg/kg Route: subcutaneous Route: single Dose: 1.75 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/18761239	unhealthy, >66 years Health Status: unhealthy Age Group: >66 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18761239	Sources: https://pubmed.ncbi.nlm.nih.gov/18761239

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf#page=4 Page: 4.0	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20997lbl.pdf#page=4 Page: 4.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1573604/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6149	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6149
eMolecules	36757176	https://www.emolecules.com/cgi-bin/more?vid=36757176
MolPort	MolPort-004-959-713	https://www.molport.com/shop/molecule-link/MolPort-004-959-713
ZINC	ZINC000001530812	http://zinc15.docking.org/substances/ZINC000001530812

PubMed

Title	Date	PubMed
Long-term stability of sufentanil citrate with levobupivacaine hydrochloride in 0.9% sodium chloride infusion PVC bags at 4 degrees C.	2004-07	15223079
[Levobupivacaine in obstetric analgesia and anaesthesia. Where is its place?].	2004-07	15221118
Evidence that intravenous vasopressors can affect rostral spread of spinal anesthesia in pregnancy.	2004-07	15220768
Intraoperative and postoperative analgesia with subcutaneous ring block of the penis with levobupivacaine for circumcision in children.	2004-06	15211412
Epidural test dose with levobupivacaine and ropivacaine: determination of ED(50) motor block after spinal administration.	2004-06	15096445
Postoperative analgesia in infants and children: new developments.	2004-05	15181422
High-dose bupivacaine, levobupivacaine and ropivacaine in axillary brachial plexus block.	2004-05	15101856
Can ropivacaine and levobupivacaine be used as test doses during regional anesthesia?	2004-04	15087628
Density of spinal anaesthetic solutions of bupivacaine, levobupivacaine, and ropivacaine with and without dextrose.	2004-04	14766715
Epidural levobupivacaine 0.1% or ropivacaine 0.1% combined with morphine provides comparable analgesia after abdominal surgery.	2004-02	14742376
Paravertebral analgesia with levobupivacaine increases postoperative flap tissue oxygen tension after immediate latissimus dorsi breast reconstruction compared with intravenous opioid analgesia.	2004-02	14739814
Comparison of patient-controlled epidural bolus administration of 0.1% ropivacaine and 0.1% levobupivacaine, both with 0.0002% fentanyl, for analgesia during labour.	2004-02	14725515
Pharmacokinetics of levobupivacaine 0.25% following caudal administration in children under 2 years of age.	2004-02	14722171
Changes in transcutaneous carbon dioxide, oxygen saturation, and respiratory rate after interscalene block.	2004-01	14746417
A comparison of duration of analgesia of intrathecal 2.5 mg of bupivacaine, ropivacaine, and levobupivacaine in combined spinal epidural analgesia for patients in labor.	2004-01	14693626
Levobupivacaine for pediatric spinal anesthesia.	2004-01	14693586
Local anaesthetic sensitivities of cloned HERG channels from human heart: comparison with HERG/MiRP1 and HERG/MiRP1 T8A.	2004-01	14665560
Levobupivacaine versus racemic bupivacaine in spinal anaesthesia for urological surgery.	2003-12	14719424
A prospective, randomized, double-blind comparison of epidural levobupivacaine 0.5% with epidural ropivacaine 0.75% for lower limb procedures.	2003-12	14690101
A randomized sequential allocation study to determine the minimum effective analgesic concentration of levobupivacaine and ropivacaine in patients receiving epidural analgesia for labor.	2003-12	14639153
Relative analgesic potencies of levobupivacaine and ropivacaine for epidural analgesia in labor.	2003-12	14639148
Preoperative interscalene block for elective shoulder surgery: loss of benefit over early postoperative block after patient discharge to home.	2003-12	14633531
Preincisional local infiltration of levobupivacaine vs ropivacaine for pain control after laparoscopic cholecystectomy.	2003-12	14577025
Efficacy, safety, and pharmacokinetics of levobupivacaine with and without fentanyl after continuous epidural infusion in children: a multicenter trial.	2003-11	14576555
Comparison of the effects of intrathecal ropivacaine, levobupivacaine, and bupivacaine for Caesarean section.	2003-11	14570791
The relative motor blocking potencies of bupivacaine and levobupivacaine in labor.	2003-11	14570676
Severe phantom leg pain in an amputee after lumbar plexus block.	2003-10-14	14556141
A comparison of levobupivacaine 0.5% and racemic bupivacaine 0.5% for extradural anesthesia for caesarean section.	2003-10-14	14556128
Perioperative thoracic epidural analgesia in aortic surgery: role of levobupivacaine.	2003-10	14673397
Levobupivacaine 0.25% compared with ropivacaine 0.25% by the caudal route in children.	2003-10	14580053
Pulmonary uptake of ropivacaine and levobupivacaine in rabbits.	2003-09	12933424
Onset time, quality of blockade, and duration of three-in-one blocks with levobupivacaine and bupivacaine.	2003-09	12933423
Levobupivacaine versus ropivacaine for sciatic nerve block in the rat.	2003-08-29	12945022
Epidural levobupivacaine, ropivacaine and bupivacaine in combination with sufentanil in early labour: a randomized trial.	2003-08	12932065
The central nervous system and cardiovascular effects of levobupivacaine and ropivacaine in healthy volunteers.	2003-08	12873927
A comparison of three different concentrations of levobupivacaine for caudal block in children.	2003-08	12873919
Comparison of different concentrations of levobupivacaine for post-operative epidural analgesia.	2003-08	12859311
The relative toxicity of amitriptyline, bupivacaine, and levobupivacaine administered as rapid infusions in rats.	2003-07	12818949
[Chirocaine in ophthalmology].	2003-06	12898725
Convulsions following axillary brachial plexus blockade with levobupivacaine.	2003-06	12846645
Convulsions following axillary brachial plexus blockade with levobupivacaine.	2003-06	12846644
[Prevention of cardiovascular accidents during locoregional anesthesia].	2003-05	12768178
Stability of sufentanil and levobupivacaine solutions and a mixture in a 0.9% sodium chloride infusion stored in polypropylene syringes.	2003-05	12729859
Central nervous system toxicity following the administration of levobupivacaine for lumbar plexus block: A report of two cases.	2003-04-05	12677626
Seizure after levobupivacaine for interscalene brachial plexus block.	2003-04	12651682
A response to 'Convulsions following axillary brachial plexus blockade with levobupivacaine', Pirotta D, Sprigge J, Anaesthesia 2002; 57: 1187-9.	2003-04	12648152
Intraoperative epidural anesthesia and postoperative analgesia with levobupivacaine for major orthopedic surgery: a double-blind, randomized comparison of racemic bupivacaine and ropivacaine.	2003-03	12719052
New local anesthetics. Are they worth the cost?	2003-03	12698830
The efficacy and safety of 0.75% levobupivacaine vs 0.75% bupivacaine for peribulbar anaesthesia.	2003-03	12640407
The place of ropivacaine in anesthesia.	2003	12872430

Patents

Sample Use Guides

In Vivo Use Guide

Surgical anaesthesia: epidural for surgery 10-20 mL (50-150 mg), epidural for cesarean section 20-30 mL (100-150 mg), peripheral nerve 30 mL or 0.4 mL/kg (75-150 mg or 1-2 mg/kg), ophthalmic 5-15 mL (37.5-112.5 mg), local infiltration 60 mL (150 mg). Pain management: epidural for labor analgesia 10-20 mL (25-50 mg), epidural for post-operative pain 4-10 mL/h (5-25 mg/h).

Route of Administration: Intravenous

In Vitro Use Guide

The antagonist activity of levobupivacaine was tested at the human nicotinic acetylcholine (nACh), murine N-methyl-d-aspartate (NMDA), murine gamma-aminobutyric acid(A) (GABA(A)), and human 5-hydroxytryptamine(3A) (5-HT(3A)) receptors expressed in Xenopus oocytes using a 2-voltage clamp technique. The IC50 of levobupivacaine were 950 uM, 65 uM and 85 uM for NMDA, 5-HT(3A), and nACh receptors, respectively. Inhibition of the GABA(A) receptor required concentrations in excess of 10 mM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:50:37 GMT 2025` Edited by `admin` on `Mon Mar 31 18:50:37 GMT 2025`
Record UNII	A5H73K9U3W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVOBUPIVACAINE

Official Name

English

NOVABUPI

Preferred Name

English

BUPIVACAINE, (-)-

Common Name

English

BUPIVACAINE (-)-FORM [MI]

Common Name

English

Levobupivacaine [WHO-DD]

Common Name

English

(S)-1-BUTYL-N-(2,6-DIMETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE

Systematic Name

English

BUPIVACAINE (-)-FORM

Common Name

English

LEVOBUPIVACAINE [MART.]

Common Name

English

(S)-1-BUTYL-2',6'-PIPECOLOXYLIDIDE

Common Name

English

(-)-BUPIVACAINE

Common Name

English

levobupivacaine [INN]

Common Name

English

BUPIVACAINE, (S)-

Common Name

English

(S)-BUPIVACAINE

Common Name

English

ROPIVACAINE HYDROCHLORIDE MONOHYDRATE IMPURITY A [EP IMPURITY]

Common Name

English

L-BUPIVACAINE

Common Name

English

LEVOBUPIVACAINE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245