化合物详情
CAS27262-47-1
分子式C18H28N2O
分子量288.43 g/mol g/mol
危化品
Levobupivacaine is the (S)-()-enantiomer of bupivacaine. It has a role as a local anaesthetic, an EC 3.1.1.8 (cholinesterase) inhibitor, an adrenergic antagonist, an amphiphile and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is a conjugate base of a levobupivacaine(1+). It is an enantiomer of a dextrobupivacaine.
科学粮草官-词典编辑部,修订于:2026-07-06

Toxicity
ToxicitySymptoms
nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures, depression (drowsiness, loss of consciousness, respiratory depression and apnea). [Wikipedia]
Treatment
If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Toxicity Data
LD50: 5.1mg/kg in rabbit, intravenous; 18mg/kg in rabbit, oral; 207mg/kg in rabbit, parenteral; 63mg/kg in rat, subcutaneous.
Health Effects
Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central...
Exposure Routes
The plasma concentration of levobupivacaine following therapeutic administration depends on dose and also on route of administration, because absorption from the site of administration is affected by the vascularity of the tissue. Peak levels in blood were reached approximately 30 minutes after epidural administration, and doses up to 150 mg resulted in mean C<sub>max</sub> levels of up to 1.2 ug/mL.
Toxicity Summary
Levobupivacaine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibi...
Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation
A retrospective medical record study in China compared women who received patient-controlled epidural analgesia during labor (n = 527) to those who did not (n = 395). Epidural analgesia included 0.1% levobupivacaine and 5 mg of sufentanil in 10 mL of saline. All women completed a questionnaire regarding their breastfeeding experience at 6 months postpartum. There were no statistically significant differences between the groups in the proportion who initiated breastfeeding within 1 hour after birth or who exclusively or partially breastfed their infants at 1, 3, or 6 months postpartum.





