Chemical Property of Levobupivacaine hydrochloride
Chemical Property:
- Appearance/Colour:white crystalline powder
- Vapor Pressure:2.24E-07mmHg at 25°C
- Melting Point:254 °C (dec.)(lit.)
- Boiling Point:423.4 °C at 760 mmHg
- Flash Point:209.9 °C
- PSA：23.55000
- LogP:4.74080
- Storage Temp.:2-8°C
- Solubility.:H2O: soluble20mg/mL, clear
- Hydrogen Bond Donor Count:2
- Hydrogen Bond Acceptor Count:2
- Rotatable Bond Count:5
- Exact Mass:324.1968412
- Heavy Atom Count:22
- Complexity:321
- Purity/Quality:
-
99% *data from raw suppliers
(S)-(-)-BupivacaineHydrochloride *data from reagent suppliers
Safty Information:
- Pictogram(s):
T+, 
Xn
- Hazard Codes:T+,Xn
- Statements:
26/27/28-20/21/22-28
- Safety Statements:
22-36/37/39-45-36/37-53
- MSDS Files:
-
SDS file from LookChem
Useful:
- Canonical SMILES:CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
- Isomeric SMILES:CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C.Cl
- Recent ClinicalTrials:TAP Block Versus Local Anesthesia Wound Infiltration for Postoperative Pain Relief After Appendicectomy in Children
- Recent EU Clinical Trials:PAIN CONTROL WITH THE USE OF WALANT IN TOTAL TRAPEZECTOMY. RANDOMIZED CLINICAL TRIAL
- Recent NIPH Clinical Trials:Randomized clinical trial on patient-controlled epidural analgesia versus intravenous patient-controlled analgesia for laparoscopiccoloectomy within an enhanced recovery pathway.
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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.
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Uses
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.
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Therapeutic Function
Local anesthetic
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Biological Functions
Levobupivacaine hydrochloride (Chirocaine) is the
S-enantiomer of bupivacaine. It too has long action.
Animal studies show that it has less CNS and cardiac
toxicity than does bupivacaine. It also is slightly more
motor sparing than is bupivacaine.
