Fluroxene

Fluroxene (INN, USAN; brand name Fluoromar), or 2,2,2-trifluoroethyl vinyl ether, is a volatile, inhalational anesthetic, and was the first halogenated hydrocarbon anesthetic to be introduced.[1][2] It was synthesized in 1951, and was introduced for clinical use in 1954, but was voluntarily withdrawn from the market in 1974 due to its potential flammability and accumulating evidence that it could cause organ toxicity.[2][1][3] In any case, prior to being discontinued, it had largely been superseded by halothane.[4] Fluroxene is metabolized to 2,2,2-trifluoroethanol, a compound responsible for some of the toxicity seen with fluroxene use.[5][6]

Fluroxene
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • (2,2,2-trifluoroethoxy)ethene
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.006.344
Chemical and physical data
FormulaC4H5F3O
Molar mass126.078 g·mol−1
3D model (JSmol)
SMILES
  • C=COCC(F)(F)F
InChI
  • InChI=1S/C4H5F3O/c1-2-8-3-4(5,6)7/h2H,1,3H2
  • Key:DLEGDLSLRSOURQ-UHFFFAOYSA-N

See also

References
  1. Stoelting RK, Hillier SC (11 January 2012). Pharmacology and Physiology in Anesthetic Practice. Lippincott Williams & Wilkins. pp. 142–. ISBN 978-1-4511-6583-8.
  2. Barash PG, Cullen BF, Stoelting RK, Cahalan M, Stock MC (1 January 2011). Clinical Anesthesia. Lippincott Williams & Wilkins. pp. 113–. ISBN 978-1-4511-2297-8.
  3. Lichtiger M, Moya F (1 January 1978). Introduction to the practice of anesthesia. Medical Dept., Harper & Row. ISBN 978-0-06-141534-0.
  4. Acta anaesthesiologica Belgica. Acta Medica Belgica. 1974.
  5. Fiserova-Bergerova V (December 1977). "Metabolism and toxicity of 2,2,2-trifluoroethyl vinyl ether". Environmental Health Perspectives. 21: 225–30. doi:10.1289/ehp.7721225. PMC 1475355. PMID 25763.
  6. Kaminsky LS, Fraser JM (1988). "Multiple aspects of the toxicity of fluroxene and its metabolite 2,2,2-trifluoroethanol". Critical Reviews in Toxicology. 19 (2): 87–112. doi:10.3109/10408448809014901. PMID 2906849.
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