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Chemical Compound Review

Marcaine     1-butyl-N-(2,6- dimethylphenyl)piperidine- 2...

Synonyms: Marcaina, Anekain, Bloqueina, Carbostesin, Sensorcaine, ...
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Disease relevance of Marcaine

  • 3. This synergistic effect of systemic morphine on the extent of neural blockade with epidural bupivacaine may have an important role in improving postoperative pain relief [1].
  • However, accidental intravascular injection of bupivacaine can produce severe arrhythmias and cardiac depression [2].
  • METHODS AND RESULTS: Forty patients with unstable angina refractory to standard anti-anginal therapy were randomized to receive either continuous epidural infusion of bupivacaine (TEA, Th1 to Th5) or to standard anti-anginal therapy including beta-blockers, calcium antagonists, aspirin, heparin, and nitroglycerin infusion (control group) [3].
  • Bupivacaine also inhibited alcohol-induced GIRK currents in the absence of functional pertussis toxin-sensitive G proteins [4].
  • In contrast, fibers from the esophagus (which we show to be more fatigable than flexor digitorum brevis fibers) and from the highly glycolytic extensor digitorum longus didn't undergo pyridine nucleotide oxidation upon the addition of bupivacaine and were resistant to bupivacaine toxicity [5].

Psychiatry related information on Marcaine


High impact information on Marcaine

  • RESULTS: The patients who received epidural fentanyl or bupivacaine prior to surgical incision (preemptive analgesia) experienced 33% less pain while hospitalized (P=.007) [11].
  • METHODS: In a randomised, double-blind trial, 60 patients scheduled for lower-limb amputation were randomly assigned epidural bupivacaine (0.25% 4-7 mL/h) and morphine (0.16-0.28 mg/h) for 18 h before and during the operation (29 patients; blockade group) or epidural saline (4-7 mL/h) and oral or intramuscular morphine (31 patients; control group) [12].
  • For standard epidural analgesia, 25 mg (10 mL of 0.25%) bupivacaine was injected into the epidural space, followed by top-ups of 6-10 mL 0.25% bupivacaine, as required [13].
  • Bupivacaine inhibited GIRK channels within seconds of application, regardless of whether channels were activated through the muscarinic receptor or directly via coexpressed G protein G(beta)gamma subunits [4].
  • Mechanism underlying bupivacaine inhibition of G protein-gated inwardly rectifying K+ channels [4].

Chemical compound and disease context of Marcaine


Biological context of Marcaine

  • After bupivacaine inhalation, the heart rate response (0.27 +/- 1.04 beats/min/%) was unchanged from control [19].
  • In contrast, low levels of bupivacaine block produced significant increases in tonic BP (158.8 +/- 6.4 versus 169.0 +/- 6.5 mm Hg BP), whereas there was no effect on dynamic baroreflex sensitivity (-0.85 +/- 0.08 versus -0.73 +/- 0.08 mm Hg BP/mm Hg CSP) [20].
  • It was blocked with high affinity by tetrodotoxin (IC50, approximately 10 nmol/L) and local anesthetics (bupivacaine and lidocaine; IC50, approximately 100 nmol/L) and by Cd2+ (IC50, approximately 300 mumol/L) [21].
  • These results suggest that (1) the bupivacaine binding site is located in the inner mouth of the pore, (2) stereoselective block displays subfamily selectivity, and (3) a polar interaction with T505 combined with hydrophobic interactions with L508 and V512 are required for stereoselective block [22].
  • Its levels are highest during a period of fetal development that coincides with the emergence of specific fiber types and transiently increases in regenerating muscles damaged by bupivacaine [23].

Anatomical context of Marcaine


Associations of Marcaine with other chemical compounds


Gene context of Marcaine

  • CONCLUSION: Ipsilateral or contralateral sciatic blockade using either bupivacaine or tetrodotoxin does not inhibit carrageenan-induced activation of cytokines and p-38 MAPK in spinal cord and DRGs [28].
  • In the current study, the authors examined cytokine and p38 mitogen-activated protein kinase (MAPK) activation in lumbar dorsal root ganglia (DRGs) and spinal cord after carrageenan paw injections and sciatic blocks with either bupivacaine or tetrodotoxin [28].
  • Cells were preincubated with bupivacaine before and during the transient addition of substance P [29].
  • These results demonstrated that bupivacaine degradation into PPX was mediated in humans by CYP3A [30].
  • Five days after bupivacaine injection, IGF-II mRNA was increased 46-fold in young rats but was only increased fourfold in adult rats [31].

Analytical, diagnostic and therapeutic context of Marcaine


  1. Systemic morphine enhances spread of sensory analgesia during postoperative epidural bupivacaine infusion. Lund, C., Mogensen, T., Hjortsø, N.C., Kehlet, H. Lancet (1985) [Pubmed]
  2. Stereoselective block of cardiac sodium channels by bupivacaine in guinea pig ventricular myocytes. Valenzuela, C., Snyders, D.J., Bennett, P.B., Tamargo, J., Hondeghem, L.M. Circulation (1995) [Pubmed]
  3. Anti-ischemic and anti-anginal effects of thoracic epidural anesthesia versus those of conventional medical therapy in the treatment of severe refractory unstable angina pectoris. Olausson, K., Magnusdottir, H., Lurje, L., Wennerblom, B., Emanuelsson, H., Ricksten, S.E. Circulation (1997) [Pubmed]
  4. Mechanism underlying bupivacaine inhibition of G protein-gated inwardly rectifying K+ channels. Zhou, W., Arrabit, C., Choe, S., Slesinger, P.A. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  5. Bupivacaine myotoxicity is mediated by mitochondria. Irwin, W., Fontaine, E., Agnolucci, L., Penzo, D., Betto, R., Bortolotto, S., Reggiani, C., Salviati, G., Bernardi, P. J. Biol. Chem. (2002) [Pubmed]
  6. Amygdala-prefrontal cortical circuitry regulates effort-based decision making. Floresco, S.B., Ghods-Sharifi, S. Cereb. Cortex (2007) [Pubmed]
  7. Phantom limb pain in amputees during the first 12 months following limb amputation, after preoperative lumbar epidural blockade. Bach, S., Noreng, M.F., Tjéllden, N.U. Pain (1988) [Pubmed]
  8. Postoperative sleep disturbance: influences of opioids and pain in humans. Cronin, A.J., Keifer, J.C., Davies, M.F., King, T.S., Bixler, E.O. Sleep. (2001) [Pubmed]
  9. Dynamic changes in acetylcholine output in the medial striatum during place reversal learning. Ragozzino, M.E., Choi, D. Learn. Mem. (2004) [Pubmed]
  10. Inflammatory pain and hypersensitivity are selectively reversed by epidural bupivacaine and are developmentally regulated. Howard, R.F., Hatch, D.J., Cole, T.J., Fitzgerald, M. Anesthesiology (2001) [Pubmed]
  11. Preemptive epidural analgesia and recovery from radical prostatectomy: a randomized controlled trial. Gottschalk, A., Smith, D.S., Jobes, D.R., Kennedy, S.K., Lally, S.E., Noble, V.E., Grugan, K.F., Seifert, H.A., Cheung, A., Malkowicz, S.B., Gutsche, B.B., Wein, A.J. JAMA (1998) [Pubmed]
  12. Randomised trial of epidural bupivacaine and morphine in prevention of stump and phantom pain in lower-limb amputation. Nikolajsen, L., Ilkjaer, S., Christensen, J.H., Krøner, K., Jensen, T.S. Lancet (1997) [Pubmed]
  13. Randomised comparison of combined spinal-epidural and standard epidural analgesia in labour. Collis, R.E., Davies, D.W., Aveling, W. Lancet (1995) [Pubmed]
  14. Ropivacaine. A review of its pharmacology and therapeutic use in regional anaesthesia. Markham, A., Faulds, D. Drugs (1996) [Pubmed]
  15. Local anesthetics worsen renal function after ischemia-reperfusion injury in rats. Lee, H.T., Krichevsky, I.E., Xu, H., Ota-Setlik, A., D'Agati, V.D., Emala, C.W. Am. J. Physiol. Renal Physiol. (2004) [Pubmed]
  16. Levobupivacaine: a review of its pharmacology and use as a local anaesthetic. Foster, R.H., Markham, A. Drugs (2000) [Pubmed]
  17. Management of intractable back pain from caudal ependymoma with spinal methylprednisolone, bupivacaine and morphine. Lema, M.J., Shady, J.A., Zoll, J.G., West, C.R. Pain (1992) [Pubmed]
  18. A re-examination of tetrodotoxin for prolonged duration local anesthesia. Kohane, D.S., Yieh, J., Lu, N.T., Langer, R., Strichartz, G.R., Berde, C.B. Anesthesiology (1998) [Pubmed]
  19. Contribution of pulmonary receptors to the heart rate response to acute hypoxemia in rabbits. Kato, H., Menon, A.S., Chen, F.J., Slutsky, A.S. Circulation (1988) [Pubmed]
  20. Selective contribution of two types of carotid sinus baroreceptors to the control of blood pressure. Seagard, J.L., Hopp, F.A., Drummond, H.A., Van Wynsberghe, D.M. Circ. Res. (1993) [Pubmed]
  21. A novel tetrodotoxin-sensitive Na+ current in cultured human coronary myocytes. Quignard, J.F., Ryckwaert, F., Albat, B., Nargeot, J., Richard, S. Circ. Res. (1997) [Pubmed]
  22. Molecular determinants of stereoselective bupivacaine block of hKv1.5 channels. Franqueza, L., Longobardo, M., Vicente, J., Delpón, E., Tamkun, M.M., Tamargo, J., Snyders, D.J., Valenzuela, C. Circ. Res. (1997) [Pubmed]
  23. Molecular dissection of DNA sequences and factors involved in slow muscle-specific transcription. Calvo, S., Vullhorst, D., Venepally, P., Cheng, J., Karavanova, I., Buonanno, A. Mol. Cell. Biol. (2001) [Pubmed]
  24. Electrical activity and cytosolic calcium regulate levels of tetrodotoxin-sensitive sodium channels in cultured rat muscle cells. Sherman, S.J., Catterall, W.A. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  25. Evidence for a specific receptor site for lidocaine, quinidine, and bupivacaine associated with cardiac sodium channels in guinea pig ventricular myocardium. Clarkson, C.W., Hondeghem, L.M. Circ. Res. (1985) [Pubmed]
  26. Increased adipogenicity of cells from regenerating skeletal muscle. Yamanouchi, K., Yada, E., Ishiguro, N., Hosoyama, T., Nishihara, M. Exp. Cell Res. (2006) [Pubmed]
  27. Influence of bupivacaine on mepivacaine protein binding. Hartrick, C.T., Dirkes, W.E., Coyle, D.E., Raj, P.P., Denson, D.D. Clin. Pharmacol. Ther. (1984) [Pubmed]
  28. Effects of bupivacaine and tetrodotoxin on carrageenan-induced hind paw inflammation in rats (Part 2): cytokines and p38 mitogen-activated protein kinases in dorsal root ganglia and spinal cord. Beloeil, H., Ji, R.R., Berde, C.B. Anesthesiology (2006) [Pubmed]
  29. Local anesthetics inhibit substance P binding and evoked increases in intracellular Ca2+. Li, Y.M., Wingrove, D.E., Too, H.P., Marnerakis, M., Stimson, E.R., Strichartz, G.R., Maggio, J.E. Anesthesiology (1995) [Pubmed]
  30. Oxidative metabolism of bupivacaine into pipecolylxylidine in humans is mainly catalyzed by CYP3A. Gantenbein, M., Attolini, L., Bruguerolle, B., Villard, P.H., Puyoou, F., Durand, A., Lacarelle, B., Hardwigsen, J., Le-Treut, Y.P. Drug Metab. Dispos. (2000) [Pubmed]
  31. Association of insulin-like growth factor mRNA expressions with muscle regeneration in young, adult, and old rats. Marsh, D.R., Criswell, D.S., Hamilton, M.T., Booth, F.W. Am. J. Physiol. (1997) [Pubmed]
  32. Bupivacaine concentration and obstetric delivery. Marcoux, S., Mailloux, J., Fontaine, J.Y., Leclerc, M. Lancet (1987) [Pubmed]
  33. Hepatitis B virus transmission associated with a multiple-dose vial in a hemodialysis unit. Alter, M.J., Ahtone, J., Maynard, J.E. Ann. Intern. Med. (1983) [Pubmed]
  34. Selective reinnervation of intercostal muscles transplanted from different segmental levels to a common site. Wigston, D.J., Sanes, J.R. J. Neurosci. (1985) [Pubmed]
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