LEVOBUPIVACAINE HYDROCHLORIDE

US Previously Marketed

First approved in 1999

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H28N2O.ClH
Molecular Weight	324.889
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LEVOBUPIVACAINE HYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=SIEYLFHKZGLBNX-NTISSMGPSA-N

InChI=1S/C18H28N2O.ClH/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);1H/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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Safer labelling of levobupivacaine.	2002 Aug	12378684
Levobupivacaina, bupivacaina racemica e ropivacaina nel blocco del plesso brachiale.	2002 Jul-Aug	12244291
Does local anesthetic stereoselectivity or structure predict myocardial depression in anesthetized canines?	2002 Sep-Oct	12373692
The place of ropivacaine in anesthesia.	2003	12872430
Seizure after levobupivacaine for interscalene brachial plexus block.	2003 Apr	12651682
A response to 'Convulsions following axillary brachial plexus blockade with levobupivacaine', Pirotta D, Sprigge J, Anaesthesia 2002; 57: 1187-9.	2003 Apr	12648152
Epidural levobupivacaine, ropivacaine and bupivacaine in combination with sufentanil in early labour: a randomized trial.	2003 Aug	12932065
A comparison of three different concentrations of levobupivacaine for caudal block in children.	2003 Aug	12873919
Comparison of different concentrations of levobupivacaine for post-operative epidural analgesia.	2003 Aug	12859311
Levobupivacaine versus racemic bupivacaine in spinal anaesthesia for urological surgery.	2003 Dec	14719424
A prospective, randomized, double-blind comparison of epidural levobupivacaine 0.5% with epidural ropivacaine 0.75% for lower limb procedures.	2003 Dec	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 Dec	14639153
Relative analgesic potencies of levobupivacaine and ropivacaine for epidural analgesia in labor.	2003 Dec	14639148
Preoperative interscalene block for elective shoulder surgery: loss of benefit over early postoperative block after patient discharge to home.	2003 Dec	14633531
Preincisional local infiltration of levobupivacaine vs ropivacaine for pain control after laparoscopic cholecystectomy.	2003 Dec	14577025
Efficacy and safety of caudal injection of levobupivacaine, 0.25%, in children under 2 years of age undergoing inguinal hernia repair, circumcision or orchidopexy.	2003 Feb	12562483
[The choice of drugs for caudal anaesthesia in children. An overview].	2003 Jan	12577167
Accidental intravascular injection of levobupivacaine and lidocaine during the transarterial approach to the axillary brachial plexus.	2003 Jan	12514163
Interscalene brachial plexus anesthesia and analgesia for open shoulder surgery: a randomized, double-blinded comparison between levobupivacaine and ropivacaine.	2003 Jan	12505962
Central nervous system and cardiac effects from long-acting amide local anesthetic toxicity in the intact animal model.	2003 Jan-Feb	12567336
The relative toxicity of amitriptyline, bupivacaine, and levobupivacaine administered as rapid infusions in rats.	2003 Jul	12818949
Levobupivacaine versus ropivacaine for sciatic nerve block in the rat.	2003 Jul-Aug	12945022
Convulsions following axillary brachial plexus blockade with levobupivacaine.	2003 Jun	12846645
Intraoperative epidural anesthesia and postoperative analgesia with levobupivacaine for major orthopedic surgery: a double-blind, randomized comparison of racemic bupivacaine and ropivacaine.	2003 Mar	12719052
New local anesthetics. Are they worth the cost?	2003 Mar	12698830
The efficacy and safety of 0.75% levobupivacaine vs 0.75% bupivacaine for peribulbar anaesthesia.	2003 Mar	12640407
Infragluteal-parabiceps sciatic nerve block: an evaluation of a novel approach using a single-injection technique.	2003 Mar	12598276
Continuous epidural infusion of large concentration/small volume versus small concentration/large volume of levobupivacaine for postoperative analgesia.	2003 Mar	12598265
Safe dose of levobupivacaine (Chirocaine) in caudal analgesia in children.	2003 Mar	12594163
Urinary bladder scanning after day-case arthroscopy under spinal anaesthesia: comparison between lidocaine, ropivacaine, and levobupivacaine.	2003 Mar	12594142
Central nervous system toxicity following the administration of levobupivacaine for lumbar plexus block: A report of two cases.	2003 Mar-Apr	12677626
[Prevention of cardiovascular accidents during locoregional anesthesia].	2003 May	12768178
Stability of sufentanil and levobupivacaine solutions and a mixture in a 0.9% sodium chloride infusion stored in polypropylene syringes.	2003 May	12729859
Efficacy, safety, and pharmacokinetics of levobupivacaine with and without fentanyl after continuous epidural infusion in children: a multicenter trial.	2003 Nov	14576555
Comparison of the effects of intrathecal ropivacaine, levobupivacaine, and bupivacaine for Caesarean section.	2003 Nov	14570791
The relative motor blocking potencies of bupivacaine and levobupivacaine in labor.	2003 Nov	14570676
Perioperative thoracic epidural analgesia in aortic surgery: role of levobupivacaine.	2003 Oct	14673397
Levobupivacaine 0.25% compared with ropivacaine 0.25% by the caudal route in children.	2003 Oct	14580053
Pulmonary uptake of ropivacaine and levobupivacaine in rabbits.	2003 Sep	12933424
Onset time, quality of blockade, and duration of three-in-one blocks with levobupivacaine and bupivacaine.	2003 Sep	12933423
Severe phantom leg pain in an amputee after lumbar plexus block.	2003 Sep-Oct	14556141
A comparison of levobupivacaine 0.5% and racemic bupivacaine 0.5% for extradural anesthesia for caesarean section.	2003 Sep-Oct	14556128
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 Feb	14725515
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 Jan	14693626
Levobupivacaine for pediatric spinal anesthesia.	2004 Jan	14693586
Local anaesthetic sensitivities of cloned HERG channels from human heart: comparison with HERG/MiRP1 and HERG/MiRP1 T8A.	2004 Jan	14665560
Long-term stability of sufentanil citrate with levobupivacaine hydrochloride in 0.9% sodium chloride infusion PVC bags at 4 degrees C.	2004 Jul	15223079
[Levobupivacaine in obstetric analgesia and anaesthesia. Where is its place?].	2004 Jul	15221118
Evidence that intravenous vasopressors can affect rostral spread of spinal anesthesia in pregnancy.	2004 Jul	15220768
Intraoperative and postoperative analgesia with subcutaneous ring block of the penis with levobupivacaine for circumcision in children.	2004 Jun	15211412

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 18:12:21 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:21 GMT 2025`
Record UNII	J998RDZ51I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LEVOBUPIVACAINE HCL

Preferred Name

English

LEVOBUPIVACAINE HYDROCHLORIDE

Official Name

English

BUPIVACAINE (-)-FORM HYDROCHLORIDE [MI]

Common Name

English

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

Systematic Name

English

LEVOBUPIVACAINE HYDROCHLORIDE [JAN]

Common Name

English

LEVOBUPIVACAINE HCL [VANDF]

Common Name

English

LEVOBUPIVACAINE HYDROCHLORIDE [MART.]

Common Name

English

LEVOBUPIVACAINE HYDROCHLORIDE [USAN]

Common Name

English

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

Common Name

English

Levobupivacaine hydrochloride [WHO-DD]

Common Name

English

LEVOBUPIVACAINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

CHIROCAINE

Code

English

BUPIVACAINE (-)-FORM HYDROCHLORIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245