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Merck

SML1092

Levobupivacaine hydrochloride

≥98% (HPLC)

Synonym(s):

(S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride, (S)-bupivacaine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H28N2O · HCl
CAS Number:
27262-48-2
Molecular Weight:
324.89
NACRES:
NA.77
PubChem Substance ID:
329825469
UNSPSC Code:
12352200
MDL number:
MFCD01704265

Key Documents

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Product Name

Levobupivacaine hydrochloride, ≥98% (HPLC)

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

SMILES string

CC1=C(NC([C@H]2N(CCCC)CCCC2)=O)C(C)=CC=C1.Cl

InChI key

SIEYLFHKZGLBNX-NTISSMGPSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -10 to -14°, c = 1.0 in H2O

storage condition

desiccated

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... SCN4A(6329)

Application

Levobupivacaine hydrochloride has been used as an analyte in tandem mass spectrometry. It may be used to test its inhibitory effect on phosphorylation of extracellular signal-regulated kinase (ERK) mediated by capsaicin It may also be used as a component of poly(D,L-lactide-co-glycolide) (PLGA) microparticles for testing its sustainable release by electrospraying technique

Biochem/physiol Actions

Levobupivacaine hydrochloride is a sodium channel blocker used as a long-acting local anaesthetic for epidural anesthesia. Levobupivacaine is the (S)-isomer of bupivacaine, with efficacy similar to that of bupivacaine with a reduced risk of cardiotoxicity.
Levobupivacaine hydrochloride is a sodium channel blocker.
Levobupivacaine mediates its action by blocking the action potential and sodium passage in neuronal membrane.

General description

Levobupivacaine belongs to the N-alkyl substituted pipecoloxylidide family and comprises amino-amide group.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000503851
0000503851
0000481776
0000481776
0000140078

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Joanne Guay et al.
The Cochrane database of systematic reviews, 3, CD006715-CD006715 (2019-03-02)
General anaesthesia combined with epidural analgesia may have a beneficial effect on clinical outcomes. However, use of epidural analgesia for cardiac surgery is controversial due to a theoretical increased risk of epidural haematoma associated with systemic heparinization. This review was
Different effects of local anesthetics on extracellular signal-regulated kinase phosphorylation in rat dorsal horn neurons
Zhang L, et al.
European Journal of Pharmacology, 734(6), 132-136 (2014)
Salima Qudsi-Sinclair et al.
Pain practice : the official journal of World Institute of Pain, 17(5), 578-588 (2016-09-20)
Knee osteoarthritis is a disease that affects a third of the population over 65 years of age, and it is increasingly becoming a motive for consultation and a source of pain and disability. The gold standard surgical treatment is a total
Lianxi Zhang et al.
European journal of pharmacology, 734, 132-136 (2014-04-15)
Local anesthetics, which are widely known to be neuronal voltage-gated Na(+) channel blockers, also affect a variety of other ion channels, N-methyl-d-asparate (NMDA) receptors and α-amino-3-hydroxy-5-methyl-4-izoxazolepropionic acid (AMPA) receptors. Glutamate, which is released from presynaptic fibers, activates extracellular signal-regulated kinase
Crina L Burlacu et al.
Therapeutics and clinical risk management, 4(2), 381-392 (2008-08-30)
In recent years levobupivacaine, the pure S (-)-enantiomer of bupivacaine, emerged as a safer alternative for regional anesthesia than its racemic parent. It demonstrated less affinity and strength of depressant effects onto myocardial and central nervous vital centers in pharmacodynamic
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