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Chemical Compound Review

Novabupi     (2S)-1-butyl-N-(2,6- dimethylphenyl)piperid...

Synonyms: Novabupi (TN), SureCN34537, CHEBI:6149, CHEMBL1201193, AC1L3NQM, ...
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Disease relevance of C07887


Psychiatry related information on C07887


High impact information on C07887

  • While all local anaesthetics can cause direct negative inotropic effects, ropivacaine and levobupivacaine are less cardiotoxic than bupivacaine judging by the larger doses tolerated in laboratory animal preparations before the onset of serious cardiotoxicity (particularly electro-mechanical dissociation or malignant ventricular arrhythmias) [6].
  • The tolerability profiles of levobupivacaine and bupivacaine were very similar in clinical trials [2].
  • In studies of surgical anaesthesia in adults, levobupivacaine provided sensory block for up to 9 hours after epidural administration of < or = 202.5 mg, 6.5 hours after intrathecal 15 mg, and 17 hours after brachial plexus block with 2 mg/kg [2].
  • Stereoselective differences have been observed between the 2 enantiomers and the racemic mixture, with levobupivacaine exhibiting a slightly higher degree of plasma protein binding, a lower volume of distribution, a higher plasma clearance, and a shorter t 1/2 beta than the R-(+)-enantiomer [7].
  • In experiment 2, colorectal distension-induced response in heart rate was less depressed in rats given levobupivacaine than in those given the other anesthetics [8].

Chemical compound and disease context of C07887


Biological context of C07887


Anatomical context of C07887


Associations of C07887 with other chemical compounds


Gene context of C07887


Analytical, diagnostic and therapeutic context of C07887


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  2. Levobupivacaine: a review of its pharmacology and use as a local anaesthetic. Foster, R.H., Markham, A. Drugs (2000) [Pubmed]
  3. Cardiac and CNS toxicity of levobupivacaine: strengths of evidence for advantage over bupivacaine. Gristwood, R.W. Drug safety : an international journal of medical toxicology and drug experience. (2002) [Pubmed]
  4. Direct cardiac effects of intracoronary bupivacaine, levobupivacaine and ropivacaine in the sheep. Chang, D.H., Ladd, L.A., Copeland, S., Iglesias, M.A., Plummer, J.L., Mather, L.E. Br. J. Pharmacol. (2001) [Pubmed]
  5. Analgesia and effectiveness of levobupivacaine compared with ropivacaine in patients undergoing an axillary brachial plexus block. Cline, E., Franz, D., Polley, R.D., Maye, J., Burkard, J., Pellegrini, J. AANA journal. (2004) [Pubmed]
  6. Cardiotoxicity with modern local anaesthetics: is there a safer choice? Mather, L.E., Chang, D.H. Drugs (2001) [Pubmed]
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  8. Comparative somatic and visceral antinociception and neurotoxicity of intrathecal bupivacaine, levobupivacaine, and dextrobupivacaine in rats. Muguruma, T., Sakura, S., Kirihara, Y., Saito, Y. Anesthesiology (2006) [Pubmed]
  9. Effects of CNS site-directed carotid arterial infusions of bupivacaine, levobupivacaine, and ropivacaine in sheep. Ladd, L.A., Chang, D.H., Wilson, K.A., Copeland, S.E., Plummer, J.L., Mather, L.E. Anesthesiology (2002) [Pubmed]
  10. Dexmedetomidine decreases the convulsive potency of bupivacaine and levobupivacaine in rats: involvement of alpha2-adrenoceptor for controlling convulsions. Tanaka, K., Oda, Y., Funao, T., Takahashi, R., Hamaoka, N., Asada, A. Anesth. Analg. (2005) [Pubmed]
  11. Safety and efficacy of levobupivacaine for postoperative pain relief after the surgical removal of impacted third molars: a comparison with lignocaine and adrenaline. Rood, J.P., Coulthard, P., Snowdon, A.T., Gennery, B.A. The British journal of oral & maxillofacial surgery. (2002) [Pubmed]
  12. Caudal 0.2% ropivacaine is less effective during surgery than 0.2% levobupivacaine and 0.2% bupivacaine: a double-blind, randomized, controlled trial. Ingelmo, P.M., Locatelli, B.G., Sonzogni, V., Gattoni, C., Cadisco, A., Lorini, M., Sora, G.N., Fumagalli, R. Paediatric anaesthesia. (2006) [Pubmed]
  13. Efficacy, safety, and pharmacokinetics of levobupivacaine with and without fentanyl after continuous epidural infusion in children: a multicenter trial. Lerman, J., Nolan, J., Eyres, R., Schily, M., Stoddart, P., Bolton, C.M., Mazzeo, F., Wolf, A.R. Anesthesiology (2003) [Pubmed]
  14. Molecular mechanisms of the inhibitory effects of bupivacaine, levobupivacaine, and ropivacaine on sarcolemmal adenosine triphosphate-sensitive potassium channels in the cardiovascular system. Kawano, T., Oshita, S., Takahashi, A., Tsutsumi, Y., Tomiyama, Y., Kitahata, H., Kuroda, Y., Nakaya, Y. Anesthesiology (2004) [Pubmed]
  15. Effect of age on the clinical profile and systemic absorption and disposition of levobupivacaine after epidural administration. Simon, M.J., Veering, B.T., Stienstra, R., van Kleef, J.W., Burm, A.G. British journal of anaesthesia. (2004) [Pubmed]
  16. Vasoactive characteristics of bupivacaine and levobupivacaine with and without adjuvant epinephrine in peripheral human skin. Newton, D.J., McLeod, G.A., Khan, F., Belch, J.J. British journal of anaesthesia. (2005) [Pubmed]
  17. The efficacy and safety of three concentrations of levobupivacaine administered as a continuous epidural infusion in patients undergoing orthopedic surgery. Murdoch, J.A., Dickson, U.K., Wilson, P.A., Berman, J.S., Gad-Elrab, R.R., Scott, N.B. Anesth. Analg. (2002) [Pubmed]
  18. Levobupivacaine 0.125% and lidocaine 0.5% for intravenous regional anesthesia in volunteers. Atanassoff, P.G., Aouad, R., Hartmannsgruber, M.W., Halaszynski, T. Anesthesiology (2002) [Pubmed]
  19. Effect of bupivacaine and levobupivacaine on exocytotic norepinephrine release from rat atria. Joseph, A., Montiague, R., Effendi, A.R., Urbanska, R.A., Vogel, S., Winnie, A.P., Rabito, S.F. Anesthesiology (2005) [Pubmed]
  20. Effects of levobupivacaine and ropivacaine on rat sciatic nerve blood flow. Bouaziz, H., Iohom, G., Estèbe, J.P., Campana, W.M., Myers, R.R. British journal of anaesthesia. (2005) [Pubmed]
  21. A comparison of median effective doses of intrathecal levobupivacaine and ropivacaine for labor analgesia. Sia, A.T., Goy, R.W., Lim, Y., Ocampo, C.E. Anesthesiology (2005) [Pubmed]
  22. Infragluteal-parabiceps sciatic nerve block: an evaluation of a novel approach using a single-injection technique. Sukhani, R., Candido, K.D., Doty, R., Yaghmour, E., McCarthy, R.J. Anesth. Analg. (2003) [Pubmed]
  23. The efficacy and safety of epidural infusions of levobupivacaine with and without clonidine for postoperative pain relief in patients undergoing total hip replacement. Milligan, K.R., Convery, P.N., Weir, P., Quinn, P., Connolly, D. Anesth. Analg. (2000) [Pubmed]
  24. Comparative effects of levobupivacaine and racemic bupivacaine on excitotoxic neuronal death in culture and N-methyl-D-aspartate-induced seizures in mice. Marganella, C., Bruno, V., Matrisciano, F., Reale, C., Nicoletti, F., Melchiorri, D. Eur. J. Pharmacol. (2005) [Pubmed]
  25. Local anaesthetic sensitivities of cloned HERG channels from human heart: comparison with HERG/MiRP1 and HERG/MiRP1 T8A. Friederich, P., Solth, A., Schillemeit, S., Isbrandt, D. British journal of anaesthesia. (2004) [Pubmed]
  26. Pharmacokinetics of levobupivacaine after caudal epidural administration in infants less than 3 months of age. Chalkiadis, G.A., Anderson, B.J., Tay, M., Bjorksten, A., Kelly, J.J. British journal of anaesthesia. (2005) [Pubmed]
  27. Hyperbaric spinal levobupivacaine: a comparison to racemic bupivacaine in volunteers. Alley, E.A., Kopacz, D.J., McDonald, S.B., Liu, S.S. Anesth. Analg. (2002) [Pubmed]
  28. A comparison of epidural levobupivacaine 0.75% with racemic bupivacaine for lower abdominal surgery. Kopacz, D.J., Allen, H.W., Thompson, G.E. Anesth. Analg. (2000) [Pubmed]
  29. Relative analgesic potencies of levobupivacaine and ropivacaine for epidural analgesia in labor. Polley, L.S., Columb, M.O., Naughton, N.N., Wagner, D.S., van de Ven, C.J., Goralski, K.H. Anesthesiology (2003) [Pubmed]
  30. The placental transfer and fetal effects of levobupivacaine, racemic bupivacaine, and ropivacaine. Santos, A.C., Karpel, B., Noble, G. Anesthesiology (1999) [Pubmed]
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