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Chemical Compound Review

Anecotan     2,2-dichloro-1,1-difluoro-1- methoxy-ethane

Synonyms: Metofane, Pentrane, Analgizer, Ingalan, Inhalan, ...
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Disease relevance of methoxyflurane


Psychiatry related information on methoxyflurane


High impact information on methoxyflurane

  • Inhalation anesthesia with ether or methoxyflurane was accomplished with a closed recirculatory system that allowed a short induction time for anesthesia and a good control over the concentration of anesthetic [1].
  • Survival rates during the 10 weekly instillations were least for the Brevital-treated group and greatest for the methoxyflurane-treated group [1].
  • The gerbils were treated with either saline vehicle or 10 mg/kg i.p. of one of the test drugs 30 minutes before and again 2 hours after a 10-minute period of bilateral carotid artery occlusion or sham occlusion under light methoxyflurane anesthesia [9].
  • The effects of seven anesthetics (thiopentone, 50 mg/kg ip; pentobarbitone, 50 mg/kg ip; chloral hydrate, 300 mg/kg ip; urethane, 1,5 g/kg, 1/2ip, 1/2sc; ether; methoxyflurane, 1,5%; halothane, 2%) on basal serum TSH concentrations and on the cold-induced as well as the TRH-induced TSH responses were studied in Sprague-Dawley rats [10].
  • 2. When ether or methoxyflurane was added to the gas stream that superfused the surface of the preparations, the population e.p.s.p.s. and population spikes were depressed at lower concentrations than those required to depress the compound action potential of the afferent fibres [11].

Chemical compound and disease context of methoxyflurane


Biological context of methoxyflurane


Anatomical context of methoxyflurane


Associations of methoxyflurane with other chemical compounds


Gene context of methoxyflurane

  • P450 2E1 is the principal, but not exclusive enzyme responsible for the metabolism of methoxyflurane, which also appears to be catalyzed by P450s 1A2, 2C9/10, and 2D6 [29].
  • Obligatory role of cytochrome b5 in the microsomal metabolism of methoxyflurane [30].
  • The EC50 concentration for 5-HT decreased from 1.86 +/- 0.02 microM to 1.07 +/- 0.11 microM (means +/- s.e.mean) due to the presence of 1 MAC (270 microM) methoxyflurane [31].
  • The mutant proteins have been expressed in Saccharomyces cerevisiae, purified and assayed for their ability to support the cytochrome P450-catalyzed metabolism of the cytochrome b5 requiring substrate methoxyflurane (G. Vergères and L. Waskell, 1992, J. Biol. Chem. 267, 12583-12591) [32].
  • The mutant protein receives electrons from NADPH cytochrome P450 reductase and provides the second electron to cytochrome P450 to catalyze the metabolism of methoxyflurane, a substrate which requires cytochrome b5 for its metabolism, at the same rate as the wild type protein [33].

Analytical, diagnostic and therapeutic context of methoxyflurane


  1. Effect of anesthetic agent on lung tumor induction in hamsters given benzo[a]pyrene-ferric oxide. Henry, M.C., Port, C.D. J. Natl. Cancer Inst. (1978) [Pubmed]
  2. Spectrum and subcellular determinants of fluorinated anesthetic-mediated proximal tubular injury. Lochhead, K.M., Kharasch, E.D., Zager, R.A. Am. J. Pathol. (1997) [Pubmed]
  3. Mycoplasma pneumoniae pneumonia in a mouse model. Wubbel, L., Jafri, H.S., Olsen, K., Shelton, S., Barton Rogers, B., Gambill, G., Patel, P., Keyser, E., Cassell, G., McCracken, G.H. J. Infect. Dis. (1998) [Pubmed]
  4. Ultra-long-duration local anesthesia produced by injection of lecithin-coated methoxyflurane microdroplets. Haynes, D.H., Kirkpatrick, A.F. Anesthesiology (1985) [Pubmed]
  5. Effects of pressure and anesthetics on conduction and synaptic transmission. Kendig, J.J., Trudell, J.R., Cohen, E.N. J. Pharmacol. Exp. Ther. (1975) [Pubmed]
  6. The effects of abused inhalants on mouse behavior in an elevated plus-maze. Bowen, S.E., Wiley, J.L., Balster, R.L. Eur. J. Pharmacol. (1996) [Pubmed]
  7. Analgesic effect in humans of subanaesthetic isoflurane concentrations evaluated by experimentally induced pain. Petersen-Felix, S., Arendt-Nielsen, L., Bak, P., Roth, D., Fischer, M., Bjerring, P., Zbinden, A.M. British journal of anaesthesia. (1995) [Pubmed]
  8. A comparison of the analgesic effects of methoxyflurane-nitrous oxide and nitrous oxide alone during labour related to the Eysenck personality inventory test. Arozenius, S., Dahlgren, B.E., Lindwall, L., Akerlind, I. Acta obstetricia et gynecologica Scandinavica. (1980) [Pubmed]
  9. Quantitative analysis of effects of kappa-opioid agonists on postischemic hippocampal CA1 neuronal necrosis in gerbils. Hall, E.D., Pazara, K.E. Stroke (1988) [Pubmed]
  10. Anesthetics and thyrotropin secretion in the rat. Männistö, P.T., Saarinen, A., Ranta, T. Endocrinology (1976) [Pubmed]
  11. The action of ether and methoxyflurane on synaptic transmission in isolated preparations of the mammalian cortex. Richards, C.D., Russell, W.J., Smaje, J.C. J. Physiol. (Lond.) (1975) [Pubmed]
  12. Fertility, reproduction, and postnatal survival in mice chronically exposed to isoflurane. Mazze, R.I. Anesthesiology (1985) [Pubmed]
  13. A return to trichloroethylene for obstetric anaesthesia. Crawford, J.S., Davies, P. British journal of anaesthesia. (1975) [Pubmed]
  14. Preservation of the hypoxic pulmonary vasoconstrictor mechanism during methoxyflurane anaesthesia in the dog. Marin, J.L., Carruthers, B., Chakrabarti, M.K., Sykes, M.K. British journal of anaesthesia. (1979) [Pubmed]
  15. The effects of anesthesia on osmotic blood-brain barrier disruption. Gumerlock, M.K., Neuwelt, E.A. Neurosurgery (1990) [Pubmed]
  16. Glycine toxicity after high-dose i.v. infusion of 1.5% glycine in the mouse. Olsson, J., Hahn, R.G. British journal of anaesthesia. (1999) [Pubmed]
  17. Kinetics of methoxyflurane biotransformation with reference to substrate inhibition. Adler, L., Brown, B.R., Thompson, M.F. Anesthesiology (1976) [Pubmed]
  18. The effects of central injections of adenosine analogs on blood pressure and heart rate in the rat. Barraco, R.A., Phillis, J.W., Campbell, W.R., Marcantonio, D.R., Salah, R.S. Neuropharmacology (1986) [Pubmed]
  19. Fluoride in bone of rats anesthetized during gestation with enflurane or methoxyflurane. Fiserova-Bergerova, V. Anesthesiology (1976) [Pubmed]
  20. [Renal effects and metabolism of sevoflurane in Fisher 3444 rats: an in-vivo and in-vitro comparison with methoxyflurane]. Cook, T.L., Beppu, W.J., Hitt, B.A., Kosek, J.C., Mazze, R.I. Anesthesiology (1975) [Pubmed]
  21. Effects of anesthetics, dibucaine and methoxyflurane on the ATPase activity and physical state of Tetrahymena surface membranes. Saeki, H., Nozawa, Y., Shimonaka, H., Kawai, K., Ito, M., Yamamoto, M. Biochem. Pharmacol. (1979) [Pubmed]
  22. Multiple environments of fluorinated anesthetics in intact tissues observed with 19F NMR spectroscopy. Wyrwicz, A.M., Li, Y.E., Schofield, J.C., Burt, C.T. FEBS Lett. (1983) [Pubmed]
  23. Anesthetic solubility coefficients for maternal and fetal blood. Gibbs, C.P., Munson, E.S., Tham, M.K. Anesthesiology (1975) [Pubmed]
  24. Inhibition by enflurane and methoxyflurane of postdrive hyperpolarization in canine Purkinje fibers. Pratila, M., Vogel, S., Sperelakis, N. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  25. Anesthetic biotransformation and renal function in obese patients during and after methoxyflurane or halothane anesthesia. Young, S.R., Stoelting, R.K., Peterson, C., Madura, J.A. Anesthesiology (1975) [Pubmed]
  26. Maternal and neonatal plasma inorganic fluoride levels after methoxyflurane analgesia for labor and delivery. Clark, R.B., Beard, A.G., Thompson, D.S., Barclay, D.L. Anesthesiology (1976) [Pubmed]
  27. Uptake and clearance of inhalation anesthetics in man. Fiserova-Bergerova, V., Holaday, D.A. Drug Metab. Rev. (1979) [Pubmed]
  28. Patterns of resting discharge in neurons of the raccoon main cuneate nucleus. Pubols, B.H., Haring, J.H., Rowinski, M.J. J. Neurophysiol. (1989) [Pubmed]
  29. Identification of cytochrome P450 2E1 as the predominant enzyme catalyzing human liver microsomal defluorination of sevoflurane, isoflurane, and methoxyflurane. Kharasch, E.D., Thummel, K.E. Anesthesiology (1993) [Pubmed]
  30. Obligatory role of cytochrome b5 in the microsomal metabolism of methoxyflurane. Canova-Davis, E., Chiang, J.Y., Waskell, L. Biochem. Pharmacol. (1985) [Pubmed]
  31. Actions of general anaesthetics on 5-HT3 receptors in N1E-115 neuroblastoma cells. Jenkins, A., Franks, N.P., Lieb, W.R. Br. J. Pharmacol. (1996) [Pubmed]
  32. Kinetics of the reduction of cytochrome b5 with mutations in its membrane-binding domain. Wu, F.F., Vergères, G., Waskell, L. Arch. Biochem. Biophys. (1994) [Pubmed]
  33. The function of tyrosine 74 of cytochrome b5. Vergères, G., Chen, D.Y., Wu, F.F., Waskell, L. Arch. Biochem. Biophys. (1993) [Pubmed]
  34. Activation of locus coeruleus enhances the responses of olfactory bulb mitral cells to weak olfactory nerve input. Jiang, M., Griff, E.R., Ennis, M., Zimmer, L.A., Shipley, M.T. J. Neurosci. (1996) [Pubmed]
  35. Renal function in newborns and mothers exposed to methoxyflurane analgesia for labor and delivery. Clark, R.B., Beard, A.G., Thompson, D.S. Anesthesiology (1979) [Pubmed]
  36. Hepatitis following the use of methoxyflurane in obstetric analgesia. Rubinger, D., Davidson, J.T., Melmed, R.N. Anesthesiology (1975) [Pubmed]
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