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SML1092

Sigma-Aldrich

Levobupivacaine hydrochloride

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C18H28N2O · HCl
Número de CAS:
27262-48-2
Peso molecular:
324.89
MDL number:
MFCD01704265
UNSPSC Code:
12352200
PubChem Substance ID:
329825469
NACRES:
NA.77

Quality Level

100

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

SMILES string

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

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

InChI key

SIEYLFHKZGLBNX-NTISSMGPSA-N

Gene Information

human ... SCN4A(6329)

General description

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

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 mediates its action by blocking the action potential and sodium passage in neuronal membrane.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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
Tianci Li et al.
Journal of anesthesia, 33(1), 17-25 (2018-11-15)
Retrospective studies indicate that the use of regional anaesthesia causes a reduction in cancer recurrence after oncological surgery, which could be due to anaesthetic's negating effect on immunosuppression related to the surgical stress response. Local anaesthetics may also exert direct
Katrin Rössger et al.
Metabolic engineering, 21, 81-90 (2013-11-28)
In recent years, using trigger-inducible mammalian gene switches to design sophisticated transcription-control networks has become standard practice in synthetic biology. These switches provide unprecedented precision, complexity and reliability when programming novel mammalian cell functions. Metabolite-responsive repressors of human-pathogenic bacteria are
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
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