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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

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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
4.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CHIROCAINE

Cmax

ValueDoseCo-administeredAnalytePopulation
0.474 μg/mL
1 mg/kg bw single, brachial plexus block
LEVOBUPIVACAINE plasma
Homo sapiens
0.582 μg/mL
75 mg single, epidural
LEVOBUPIVACAINE plasma
Homo sapiens
0.811 μg/mL
112.5 mg single, epidural
LEVOBUPIVACAINE plasma
Homo sapiens
0.961 μg/mL
2 mg/kg bw single, brachial plexus block
LEVOBUPIVACAINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2.999 μg × h/mL
1 mg/kg bw single, brachial plexus block
LEVOBUPIVACAINE plasma
Homo sapiens
3.561 μg × h/mL
75 mg single, epidural
LEVOBUPIVACAINE plasma
Homo sapiens
4.93 μg × h/mL
112.5 mg single, epidural
LEVOBUPIVACAINE plasma
Homo sapiens
5.311 μg × h/mL
2 mg/kg bw single, brachial plexus block
LEVOBUPIVACAINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
1 mg/kg bw single, brachial plexus block
LEVOBUPIVACAINE plasma
Homo sapiens
3%
75 mg single, epidural
LEVOBUPIVACAINE plasma
Homo sapiens
3%
112.5 mg single, epidural
LEVOBUPIVACAINE plasma
Homo sapiens
3%
2 mg/kg bw single, brachial plexus block
LEVOBUPIVACAINE plasma
Homo sapiens

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Tox targets

PubMed

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
Record UNII
J998RDZ51I
Record Status Validated (UNII)
Record Version