U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of LEVOBUPIVACAINE

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
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.

Originator

Curator's Comment: Darwin Discovery Ltd., distributed by Purdue Pharma L.P.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

9.3381119E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.474 μg/mL
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
0.582 μg/mL
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
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
0.961 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
2.999 μg × h/mL
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
3.561 μg × h/mL
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
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
5.311 μg × h/mL
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
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%
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%
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%
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

Doses

DosePopulationAdverse events​
142.5 mg single, intravenous
Dose: 142.5 mg
Route: intravenous
Route: single
Dose: 142.5 mg
Sources:
unhealthy, 77 years
n = 1
Health Status: unhealthy
Age Group: 77 years
Sex: F
Population Size: 1
Sources:
2 mg/kg single, caudal epidural
Dose: 2 mg/kg
Route: caudal epidural
Route: single
Dose: 2 mg/kg
Sources:
unhealthy, < 3 months
n = 22
Health Status: unhealthy
Age Group: < 3 months
Sex: M+F
Population Size: 22
Sources:
1.75 mg/kg single, subcutaneous
Dose: 1.75 mg/kg
Route: subcutaneous
Route: single
Dose: 1.75 mg/kg
Sources:
unhealthy, >66 years
n = 12
Health Status: unhealthy
Age Group: >66 years
Sex: M+F
Population Size: 12
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Local anaesthesia in elective inguinal hernia repair: a randomised, double-blind study comparing the efficacy of levobupivacaine with racemic bupivacaine.
2002
Effects of levobupivacaine, ropivacaine and bupivacaine on HERG channels: stereoselective bupivacaine block.
2002 Dec
Safety and efficacy of levobupivacaine for postoperative pain relief after the surgical removal of impacted third molars: a comparison with lignocaine and adrenaline.
2002 Dec
Convulsions following axillary brachial plexus blockade with levobupivacaine.
2002 Dec
The place of ropivacaine in anesthesia.
2003
Seizure after levobupivacaine for interscalene brachial plexus block.
2003 Apr
A response to 'Convulsions following axillary brachial plexus blockade with levobupivacaine', Pirotta D, Sprigge J, Anaesthesia 2002; 57: 1187-9.
2003 Apr
Epidural levobupivacaine, ropivacaine and bupivacaine in combination with sufentanil in early labour: a randomized trial.
2003 Aug
The central nervous system and cardiovascular effects of levobupivacaine and ropivacaine in healthy volunteers.
2003 Aug
A comparison of three different concentrations of levobupivacaine for caudal block in children.
2003 Aug
A prospective, randomized, double-blind comparison of epidural levobupivacaine 0.5% with epidural ropivacaine 0.75% for lower limb procedures.
2003 Dec
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
Relative analgesic potencies of levobupivacaine and ropivacaine for epidural analgesia in labor.
2003 Dec
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
[The choice of drugs for caudal anaesthesia in children. An overview].
2003 Jan
Accidental intravascular injection of levobupivacaine and lidocaine during the transarterial approach to the axillary brachial plexus.
2003 Jan
Interscalene brachial plexus anesthesia and analgesia for open shoulder surgery: a randomized, double-blinded comparison between levobupivacaine and ropivacaine.
2003 Jan
Central nervous system and cardiac effects from long-acting amide local anesthetic toxicity in the intact animal model.
2003 Jan-Feb
Levobupivacaine versus ropivacaine for sciatic nerve block in the rat.
2003 Jul-Aug
Convulsions following axillary brachial plexus blockade with levobupivacaine.
2003 Jun
Intraoperative epidural anesthesia and postoperative analgesia with levobupivacaine for major orthopedic surgery: a double-blind, randomized comparison of racemic bupivacaine and ropivacaine.
2003 Mar
New local anesthetics. Are they worth the cost?
2003 Mar
The efficacy and safety of 0.75% levobupivacaine vs 0.75% bupivacaine for peribulbar anaesthesia.
2003 Mar
Infragluteal-parabiceps sciatic nerve block: an evaluation of a novel approach using a single-injection technique.
2003 Mar
Continuous epidural infusion of large concentration/small volume versus small concentration/large volume of levobupivacaine for postoperative analgesia.
2003 Mar
Urinary bladder scanning after day-case arthroscopy under spinal anaesthesia: comparison between lidocaine, ropivacaine, and levobupivacaine.
2003 Mar
Central nervous system toxicity following the administration of levobupivacaine for lumbar plexus block: A report of two cases.
2003 Mar-Apr
Efficacy, safety, and pharmacokinetics of levobupivacaine with and without fentanyl after continuous epidural infusion in children: a multicenter trial.
2003 Nov
Comparison of the effects of intrathecal ropivacaine, levobupivacaine, and bupivacaine for Caesarean section.
2003 Nov
The relative motor blocking potencies of bupivacaine and levobupivacaine in labor.
2003 Nov
Perioperative thoracic epidural analgesia in aortic surgery: role of levobupivacaine.
2003 Oct
Pulmonary uptake of ropivacaine and levobupivacaine in rabbits.
2003 Sep
Onset time, quality of blockade, and duration of three-in-one blocks with levobupivacaine and bupivacaine.
2003 Sep
A comparison of levobupivacaine 0.5% and racemic bupivacaine 0.5% for extradural anesthesia for caesarean section.
2003 Sep-Oct
Can ropivacaine and levobupivacaine be used as test doses during regional anesthesia?
2004 Apr
Density of spinal anaesthetic solutions of bupivacaine, levobupivacaine, and ropivacaine with and without dextrose.
2004 Apr
Epidural levobupivacaine 0.1% or ropivacaine 0.1% combined with morphine provides comparable analgesia after abdominal surgery.
2004 Feb
Paravertebral analgesia with levobupivacaine increases postoperative flap tissue oxygen tension after immediate latissimus dorsi breast reconstruction compared with intravenous opioid analgesia.
2004 Feb
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
Pharmacokinetics of levobupivacaine 0.25% following caudal administration in children under 2 years of age.
2004 Feb
Changes in transcutaneous carbon dioxide, oxygen saturation, and respiratory rate after interscalene block.
2004 Jan
Levobupivacaine for pediatric spinal anesthesia.
2004 Jan
Local anaesthetic sensitivities of cloned HERG channels from human heart: comparison with HERG/MiRP1 and HERG/MiRP1 T8A.
2004 Jan
Long-term stability of sufentanil citrate with levobupivacaine hydrochloride in 0.9% sodium chloride infusion PVC bags at 4 degrees C.
2004 Jul
[Levobupivacaine in obstetric analgesia and anaesthesia. Where is its place?].
2004 Jul
Evidence that intravenous vasopressors can affect rostral spread of spinal anesthesia in pregnancy.
2004 Jul
Intraoperative and postoperative analgesia with subcutaneous ring block of the penis with levobupivacaine for circumcision in children.
2004 Jun
Epidural test dose with levobupivacaine and ropivacaine: determination of ED(50) motor block after spinal administration.
2004 Jun
Postoperative analgesia in infants and children: new developments.
2004 May
High-dose bupivacaine, levobupivacaine and ropivacaine in axillary brachial plexus block.
2004 May
Patents

Sample Use Guides

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
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 Fri Dec 16 22:45:30 UTC 2022
Edited
by admin
on Fri Dec 16 22:45:30 UTC 2022
Record UNII
A5H73K9U3W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOBUPIVACAINE
INN   MART.   VANDF   WHO-DD  
INN  
Official 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
MI  
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
NOVABUPI
Brand 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
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
WHO-VATC QN01BB10
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
WHO-ATC N01BB10
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
Code System Code Type Description
LACTMED
Levobupivacaine
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
PUBCHEM
92253
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
EPA CompTox
DTXSID8048496
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
CAS
27262-47-1
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
NCI_THESAURUS
C87594
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
MERCK INDEX
M2769
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY Merck Index
FDA UNII
A5H73K9U3W
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
WIKIPEDIA
LEVOBUPIVACAINE
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
IUPHAR
7211
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
ChEMBL
CHEMBL1201193
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
CHEBI
6149
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
CAS
41148-30-5
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
SUPERSEDED
RXCUI
259453
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY RxNorm
MESH
C476513
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
EVMPD
SUB08464MIG
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
DRUG CENTRAL
4
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
DRUG BANK
DB01002
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
DAILYMED
A5H73K9U3W
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
INN
7465
Created by admin on Fri Dec 16 22:45:30 UTC 2022 , Edited by admin on Fri Dec 16 22:45:30 UTC 2022
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY