Levobupivacaine hydrochloride
Synonym(s):(S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride;(S)-bupivacaine hydrochloride;1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
- CAS NO.:27262-48-2
- Empirical Formula: C18H29ClN2O
- Molecular Weight: 324.89
- MDL number: MFCD01704265
- EINECS: 1308068-626-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-28 19:50:54
What is Levobupivacaine hydrochloride?
Description
Levobupivacaine was first launched in the US for the production of local anesthesia for surgery and obstetrics and for post-operative pain management. It is the (S)-enantiomer of the long acting, highly potent local anesthetic bupivacaine (Marcaine) that can be prepared by a three step sequence from (S)-pipecolic acid or from (S)-lysine by oxidative deamination and stereospecific ring closure to (S)-pipecolamide core structure. Levobupivacaine exhibits its long-acting local anesthetic effect by blocking neuronal sodium channel ion flow in nerve axons. Clinical studies demonstrated an efficacy and a general profile closely resembling those of the racemic bupivacaine currently in use; however, it produced an enhanced safety profile, in particular substantially reduced (about one-third) cardiotoxicity (less effect on myocardial contractility and QT, prolongation) and CNS depressive side effects. Onset and duration of blockade were also equivalent or even better.
The Uses of Levobupivacaine hydrochloride
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.
Properties of Levobupivacaine hydrochloride
Melting point: | 254 °C (dec.)(lit.) |
storage temp. | 2-8°C |
solubility | H2O: soluble20mg/mL, clear |
form | powder |
color | white to beige |
Safety information for Levobupivacaine hydrochloride
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Levobupivacaine hydrochloride
InChIKey | SIEYLFHKZGLBNX-NTISSMGPSA-N |
SMILES | C([C@@H]1CCCCN1CCCC)(=O)NC1C(=CC=CC=1C)C.Cl |&1:1,r| |
Abamectin manufacturer
ANANTH LABS
Dishman Carbogen Amcis Ltd (Dishman Group)
Sanvin Group of Companies (Pioneer Agro Industries)
Surajlok Chemicals Pvt Ltd (Neon Laboratories Ltd)
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