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Levobupivacaine

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Last Updated: 03 November 2020

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General | Latest Info

Levobupivacaine

Chemical and physical data
3D model ( JSmol )Interactive image
FormulaC 18 H 28 N 2 O
Molar mass288.435 gmol 1
Clinical data
AHFS / Drugs.comMicromedex Detailed Consumer Information
ATC codeN01BB10 ( WHO )
Pregnancy categoryAU : B3,
Routes of administrationParenteral
Identifiers
CAS Number27262-47-1 Y
ChEBICHEBI:6149 Y
ChEMBLChEMBL1201193 N
ChemSpider83289 Y
CompTox Dashboard ( EPA )DTXSID8048496
DrugBankDB01002 Y
IUPHAR/BPS7211
PubChem CID92253
UNIIA5H73K9U3W
Legal status
Legal statusAU : S4 (Prescription only)
Pharmacokinetic data
Bioavailabilityn/a
Elimination half-life2-2.6 hours
ExcretionRenal 70%, faecal 24%
MetabolismHepatic

EditorWe have read and paid attention to an article by Mann and colleagues. 1 We found that it was a very interesting paper as it offered further information about levobupivacaine and bupivacaine usage in spinal anaesthesia. The authors describe spinal blocks with low dose of both local anaesthetic agents for lower limb arthroplasty surgery. Mann and colleagues use 7. 5-10 mg of bupivacaine 0. 25 %, and identical volumes of levobupivacaine. In bupivacaine group, satisfactory sensory block was achieved for duration of arthroplasty surgery. However, they report failure to achieve adequate sensory block and fast block regression in the levobupivacaine group, so they had to use 12. 5-15 mg of levobupivacaine to compensate for this failure. Several studies have compared the potencies of both local anaesthetics. Authors comment on one of them, and state that there is minor discrepancy between ED 50 of levobupivacaine and bupivacaine. 2 Yet some controversy exists as to whether calculated values for ED 50 can be directly translated into clinical practice when dose closer to ED 95 are habitually used 3 traditionally, levobupivacaine dose used for spinal anaesthesia has been 15 mg. This dose provides adequate sensory and motor block for most surgical procedures lasting 6. 5 h. 4 up-and-down sequential design study performed on patients undergoing hip replacement surgery recommends minimum effective local anaesthetic dose of levobupivacaine of 11. 7 mg. 5 Smaller doses have been used in ambulatory surgery, and they allow more rapid recovery and subsequent quicker hospital discharges. 6 7 So we agree with Mann and colleagues that low doses of levobupivacaine used for lower limb arthroplasty are insufficient. Our experience in these Local anaesthetics in knee arthroscopy with 12. 5 mg of isobaric levobupivacaine and bupivacaine 0. 5 % have been recently publish. 8 Similar haemodynamic parameters, and sensory and motor block duration, were found for both anaesthetics. However, we detect some significant differences between both local anaesthetics, despite many studies indicating that they are clinically indistinguishable. Sensory and motor block onset was faster in the bupivacaine group. This is important because the onset of motor block is one of the important qualities of local anaesthetic agent used for spinal anaesthesia because delayed onset time can cause delay in starting surgery, which may be too time-consuming. Moreover, greater sensory block with longer postoperative painless period was achieved in the bupivacaine group. We think that bupivacaine density was more hypobaric than that of levobupivacaine, and that the higher level of maximum sensory block seen for bupivacaine may thus be related to its baricity. So bupivacaine may be more recommendable for surgery requiring greater sensory block and longer postoperative analgesia, like major orthopaedic surgery. We believe that low-dose local anaesthetics are ideal agents to be used in ambulatory surgery, where rapid return of ambulatory function is desirable because hospital discharge home is possible for these patients on the same day of surgery.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

Related video

28 March 2018Levobupivacaine(LB) is a better anesthetic than LB & lidocaine combination in breast cancer surgery

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Cardiovascular

Levobupivacaine demonstrates less affinity and strength of inhibitory effect on inactivated state of cardiac sodium channels than racemic parent or dextrobupivacaine in in vitro animal tissue experimental studies. It also shows less depressant effect on atrioventricular conduction and QRS complex duration, and provokes less impairment of contractile function of the isolated animal heart. Levobupivacaine was also less potent in blocking clone human heart sodium and potassium channels. Similarly, in vivo animal studies show that cardio-toxic dose of intravenous bupivacaine and its pure S-enantiomers follow order ropivacaine > levobupivacaine > bupivacaine. The estimated mean fatal dose through severe arrhythmias after intravenous administration of levobupivacaine in sheep is 277 mg, which is significantly larger than the fatal dose of bupivacaine of 156 mg. In regards to reversibility of cardio-toxic effects, evidence is less clear. It was show in anaesthetized open chest dogs receiving continuous infusion of local anesthetic until cardiovascular collapse that animals receiving bupivacaine were more likely to have fatal outcome than animals receiving levobupivacaine and ropivacaine but differences were not significant. In another study, there was no difference in the number of successfully resuscitated anaesthetized rats after administration of bupivacaine, levobupivacaine or ropivacaine. However, less epinephrine was required for successful resuscitation of rats receiving ropivacaine than those receiving levobupivacaine or bupivacaine.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

Long-acting Agents

The choice of local anaesthetic is influenced by several factors; it must provide effective anaesthesia and analgesia for duration of procedure and meet expectations for post-operative pain management. Of primary concern is patient safety. Bupivacaine, currently the most widely used long acting local anaesthetic agent in both surgery and obstetrics, generally has a good safety record but its use has resulted in fatal cardiotoxicity, usually after accidental intravascular injection. Hence, for several years there has been a need for long-acting local anaesthetic, similar to bupivacaine, but with improved cardiovascular safety profile. Levobupivacaine, single enantiomer version of bupivacaine, offers a new long-acting local anaesthetic, clinically equivalent in anaesthetic potency to bupivacaine, but with a reduced toxicity profile. Preclinical studies, from in vitro in single ion channels to whole large animal models, have unquestionably demonstrated that levobupivacaine is significantly less CNS toxic and cardiotoxic than bupivacaine. Cardiotoxicity is less easy to study in man, as clinical signs are not usually seen until CNS toxicity is mark, and well beyond that which is tolerable to volunteers or patients. Nevertheless, levobupivacaine has been shown to have less effect on myocardial contractility and QTc prolongation, early signs of cardiotoxicity, than bupivacaine in healthy subjects. In clinical use, levobupivacaine has been shown to be equally efficacious as bupivacaine at comparable doses and concentrations, and has been found to produce similar anaesthetic characteristics. As levobupivacaine now becomes commercially available, databases available with which to make efficacy and safety comparisons with other local anaesthetics will increase, and the true value of this new long-acting local anaesthetic should become even more apparent.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

Background

Inguinal Hernia is one of the most common diseases in the elderly. The Italian National Health System is gear to recognize the role of local Anesthesia for surgical treatment of inguinal Hernia. Treatment of this type of pathology is exclusively surgical and relies almost always on the contribution of local anesthesia. While in the past, Hernia Surgery was carried out mainly by general Anesthesia, in recent years there has been growing emphasis on the role of local Anesthesia. This type of Anesthesia has significantly improved treatment of inguinal Hernia, significantly reducing recurrences, complications, recovery time and return to normal working activities. Hernia Surgery should be approached according to technique as simple and safe as possible that is at the same time accepted by patient and easily realizable by surgeon. Inguinal hernioplasty is now the most performed surgery in the departments of general Surgery. For this reason, it is necessary to find solutions which can be adapted to each individual case, combining experience and innovation. Surgery can be customized according to physique, age, comorbidity, lifestyle and size of Hernia. We are talking more and more about tailored Surgery, so-call personalized Surgery, individualize, build on the needs and characteristics of the patient. The Concept of tailor Surgery encompasses not only technical-surgical and prosthetic choices but also anesthetic. According to recent guidelines of European Hernia Society, published in Hernia in 2009, repair of Hernia in primary election can always take advantage of local anesthesia. This is a Grade recommendation, with high scientific impact. Simultaneous use of local anesthetic drugs with long duration of action, but very powerful such as Levobupivacaine, in addition to drugs equally potent, but duration of immediate action, such as Mepivacaine, allows optimization of Anesthesia / analgesia both intra-and post-operatively. Finally, do not forget that we are talking about local assist Anesthesia and therefore the contribution of anesthetist, and the overall effectiveness of Anesthesia, are essential to ensure maximum comfort for patients intraoperatively. Why do surgeons have to practice this kind of anesthesia? Because this type of Anesthesia consists of several phases: first, percutaneous, may be made without distinction by the surgeon or anesthesiologist, while the last phase, incisional, is exclusively of surgical pertinence, as it is the task of the surgeon to identify points of landmarks, locate and infiltrate properly. Local assist Anesthesia by truncal block / incisional has several advantages: safety, even in patients at risk; effectiveness, commitment to anesthetic proportionate intervention, minimally invasive anesthetic technique, simple and reproducible. Currently, local assist Anesthesia is the procedure of choice in primary unilateral inguinal hernias treated in election. There are no absolute contraindications to anesthetic block. If anything, there are relative contraindications: poor patient, especially at young age, morbid obesity, bilateral hernioplasty, bulky inguinal hernias. The aim of this study was to compare two local anesthetics, Levobupivacaine and bupivacaine, commonly used in surgical treatment of inguinal Hernia.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

Methods

Parturients at 7 cm of cervical dilation or less who requested EPIDURAL analgesia were allocated to one of two groups in this double-blind, randomize, prospective study. After lumbar EPIDURAL catheter placement, 20 ml of test solution was give: levobupivacaine or ropivacaine. Concentration of local anesthetic was determined by the response of previous patient in that group to higher or lower concentration using up-down sequential allocation. Analgesic efficacy was assessed using 100-mm visual analog pain scale scores, with 10 mm or less within 30 min defined as effective. Effective result direct 0. 01 % wt / vol decrement for next patient. Ineffective result direct 0. 01 % wt / vol increment. EPIDURAL bupivacaine provides excellent analgesia for labor and delivery and remains the most widely used local anesthetic for obstetric analgesia. However, concerns regarding its potential for cardiovascular toxicity have prompted search for alternative agents. Levobupivacaine and ropivacaine are relatively recently introduced amino amide local anesthetics that are structurally similar to bupivacaine. Both agents have been associated with less central nervous system and cardiac toxicity relative to bupivacaine when equal concentrations were compare.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

Results

BUPIVACAINE and levobupivacaine are long-acting local anesthetics that provide greater sensory than motor blockade and are often used in conjunction with opioids in epidural analgesia. When infused with opioid at the level of nerve roots involved in pain transmission, synergism results in improved pain relief associated with decreased opioid requirement and decreased side effects. Therefore, local anesthetic is used at concentration which if used on its own would have inadequate analgesic effect, along with opioid, again at dose that would be insufficient if administered alone, but when used in combination, can provide good quality pain relief. However, disadvantages of potential motor and sympathetic blockade with local anesthetic use must be realizedambulation. Must be restrict, and precautions against hypotension must be implement.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

Discussion

63-yr-old, 77-kg man with localized prostate cancer but no other medical history present for brachytherapy. The patient was premedicated with 10 mg of oral diazepam and 1 G oral paracetamol 60 min before anesthesia. At time of arrival in the operating room, saline infusion was start, and monitors were connect: five-lead electrocardiogram, end-tidal carbon dioxide, end-tidal sevoflurane concentration, noninvasive arterial blood pressure, pulse oximetry, Entropy index, and peripheral nerve stimulator. For prophylaxis, infusion of 200 mg ciprofloxacin was started 5 min before induction of anesthesia. General anesthesia was induced with thiopental, fentanyl, and rocuronium. Tracheal intubation was perform, and control ventilation was start. Patients ' arterial blood pressure and heart rate were 152 / 95 mmHg and 75 beats / min, respectively, initially, and 125 / 85 mmHg and 70 beats / min 5 min after induction. Ten minutes after induction, arterial blood pressure was 85 / 60 mmHg, heart rate was 60 beats / min, and end-tidal carbon dioxide was 32 mmHg. To increase arterial blood pressure, patient was given 1 mg of intravenous etilefrine. Five minutes later, when infusion of the prescribed antibiotic dose was complete, it was noticed that the administered infusion was not antibiotic but 125 mg of Levobupivacaine. Levobupivacaine, which was intended for epidural infusion, was packed in a similar 100-ml plastic infusion bag as an antibiotic. At the same time, arterial blood pressure was not measurable noninvasively, and there was no pulse in the left radial artery. The Electrocardiogram showed a heart rate of 55 beats / min, and there were no changes in level or rhythm. There were no changes in Entropy indexes or end-tidal carbon dioxide, either. The patient was immediately given 0. 2 mg of intravenous epinephrine, and his arterial blood pressure increased to 85 / 65 mmHg. His left radial artery was cannulate, blood gas analysis was perform, and the oxygen fraction in ventilator was increased to 100 %. His blood gas values were as follow: pH, 7. 37; partial pressure of carbon dioxide, 45 mmHg; base excess, 0. 9 mmHg; partial pressure of oxygen, 187 mmHg. Seven minutes later, arterial blood pressure decreased again, to 62 / 45 mmHg, and 0. 1 mg of epinephrine was given intravenously. Arterial blood pressure then increased to 95 / 55 mmHg, and the infusion of norepinephrine was start. Norepinephrine was infused during the first 5 min at a dose of 0. 17 G kg 1 min 1 and thereafter at 0. 09 G kg 1 min 1 over next 70 min until end of anesthesia. When systolic blood pressure stabilized at a level of 95-100 mmHg after starting norepinephrine infusion, surgical procedure was perform. During this period, there were numerous extra supraventricular beats, multiple transitory changes in levels, and short periods of nodal rhythm. After the operation, patient awaken normally, and he was kept in the recovery room overnight for monitoring. There were no changes in his postoperative electrocardiogram, and his glucose, electrolyte, and troponin plasma concentrations were normal. Arterial Levobupivacaine concentrations were 1. 74 mg / l at 40 min, 0. 81 mg / l at 100 min, and 0. 60 mg / l at 160 min.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

Additional information

Levobupivacaine was compared in two concentrations with racemic bupivacaine 0. 5 % of 76 patients undergoing hand surgery under supraclavicular block. Standard volume of 0. 4 ml. Kg 1 was used for all patients. Higher dermatomes were blocked more consistently and complete block was achieved in a higher percentage of patients who received Levobupivacaine 0. 5 % than in those who receive Levobupivacaine 0. 25 % or bupivacaine 0. 5 %. Investigators were unable to demonstrate a dose-response effect, although there was tendency for Levobupivacaine 0. 25 % to have slower onset, shorter duration of action and lower overall success rate than Levobupivacaine 0. 5 % or bupivacaine 0. 5 %. Mean duration of sensory analgesia was longer for Levobupivacaine 0. 5 %, but this do not reach significance because of wide variability; Levobupivacaine 0. 25 % last similar duration to bupivacaine 0. 5 %, 892 min vs. 896 min, respectively. In 66 male patients undergoing inguinal herniorrhaphy, Anaesthetic and analgesic efficacy of Levobupivacaine 0. 25 % and bupivacaine 0. 25 % was compare. Fifty millilitres of study Solution was administered and perioperative Pain Scores and satisfaction ratings were record. No difference was found between groups in postoperative Pain Scores in supine position, while rising from supine position to sitting and while walking. There was no difference in use of postoperative analgesics between the two groups. Two studies have been performed with Levobupivacaine in children. In the first study, 38 children aged 6 months to 12 years undergoing herniorrhaphy were randomly allocated to receive either ilioinguinal and iliohypogastric nerve block with Levobupivacaine 0. 5 % 0. 25 ml. Kg 1 or no block at end of surgery. Of those completing study, nine out of 20 receiving Levobupivacaine and 11 out of 15 with no block require additional postoperative analgesia. The Time to first request for analgesia was significantly different at Median duration of 118 min for Levobupivacaine and 31 min in those without block. This initial study in Children demonstrates that Levobupivacaine in concentration of 0. 5 % was effective for postoperative pain control in children undergoing herniorrhaphy. The second study was twocentre, open label study in 49 children under 2 years of age having caudal anaesthesia for circumcision, herniorrhaphy or orchidopexy. Levobupivacaine 0. 25 % was administered at a dose of 2 mg. Kg 1 and the degree of pain was measured using Children's Hospital of Ontario Pain Scale. Almost 90 % of children had satisfactory postoperative pain relief, with a mean time to request for analgesia of 7. 6 h. Levobupivacaine proven equally efficacious in children above and below 2 years of age, but the mean time to additional analgesia was slightly longer in older children.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

Central nervous toxicity

Chronically prepared nonpregnant and pregnant sheep were randomized to receive intravenous infusion of 0. 52 % levobupivacaine, 0. 52 % BUPIVACAINE, or 0. 50 % ropivacaine at a constant rate of 0. 1 ml x kg x min Until circulatory collapse. Investigators were blind to the identity of local anesthetic. Physiologic parameters, including cardiac rhythm, were monitored throughout the study. Arterial blood samples were obtained before infusion and at onset of toxic manifestations. These were analyzed for total and free serum drug concentrations as well as arterial blood pH and gas tensions. Doses of all three drugs required to produce convulsions were lower in pregnant than nonpregnant animals. However, as infusion continue, there were no significant differences between pregnant and nonpregnant women in the dose of drug required to produce more advanced manifestations of toxicity: hypotension, apnea, and circulatory collapse. The mean cumulative dose and serum concentration at each toxic manifestation was lowest for BUPIVACAINE, intermediate for levobupivacaine, and highest for ropivacaine in both pregnant and nonpregnant animals. For all three local anesthetics, there were no significant differences between pregnant and nonpregnant ewes in total and free serum drug concentrations, except that at circulatory collapse, these were higher in pregnant animals. BUPIVACAINE is probably the most commonly used drug for epidural analgesia in obstetrics, although its margin of safety is narrower than that of less potent agents such as lidocaine and mepivacaine. 1-3 Indeed, unintended intravascular injection of BUPIVACAINE during attempted epidural anesthesia for labor or cesarean delivery has resulted in almost simultaneous convulsions and cardiovascular collapse, often refractory to resuscitation. 4 5 As a result, there has been a search for alternative drugs with desirable blocking properties of BUPIVACAINE but having a greater margin of safety. Development of new long-acting amides has taken advantage of the fact that most amide local anesthetics have a chiral center, carbon atom bond to four different molecules, and thus can exist as dextro and levorotatory stereoisomers. This is important because levorotatory isomer of most long-acting amide local anesthetics generally have lower potential for systemic toxicity than dextro form of drug. 6 Until recently, formulations of local anesthetic for clinical use have contained racemic mixture of both levorotatory and dextrorotatory isomers. Thirty-eight pregnant ewes near term of gestation and 37 nonpregnant ewes were studied in protocol approved by the Institutional Animal Care and Use Committee of State University of New York-Stony Brook and Montefiore Medical Center. Only water was provided to animals the night before surgery. Neck cutdown was performed during general endotracheal anesthesia with 2-3 % halothane in nitrous oxide and oxygen, and two polyethylene catheters were insert, side by side, into common carotid artery for simultaneous blood sampling and monitoring. An additional single catheter was placed in the jugular vein. The Ewes were then allowed to recover for at least 5 days. Antibiotics and analgesic were administered for 2 days postoperatively. On day of study, ewe was weigh and contained in a cart with freedom to stand or lie down.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

Sources

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions.

* Please keep in mind that all text is machine-generated, we do not bear any responsibility, and you should always get advice from professionals before taking any actions

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