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.
화학적 성질
white crystalline powder
용도
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.
정의
ChEBI: Levobupivacaine hydrochloride (anhydrous) is the monohydrochloride salt of levobupivacaine. It has a role as a local anaesthetic, an adrenergic antagonist, an amphiphile, an EC 3.1.1.8 (cholinesterase) inhibitor and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It contains a levobupivacaine(1+). It is an enantiomer of a dextrobupivacaine hydrochloride (anhydrous).
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.
일반 설명
Levobupivacaine belongs to the N-alkyl substituted pipecoloxylidide family and comprises amino-amide group.
Mode of action
Levobupivacaine Hydrochloride is the hydrochloride salt of levobupivacaine, an amide derivative with anesthetic property. Levobupivacaine reversibly binds voltage-gated sodium channels to modulate ionic flux and prevent the initiation and transmission of nerve impulses (stabilizing neuronal membrane), thereby resulting in analgesia and anesthesia. In comparison with racemic bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action.
