Sevoflurane

Sevoflurane
Systematic (IUPAC) name
1,1,1,3,3,3-Hexafluoro-2-(fluoromethoxy)propane
Clinical data
Trade names Sojourn, Ultane, Sevorane
AHFS/Drugs.com Consumer Drug Information
Routes of
administration		 inhaled
Legal status
Legal status
Identifiers
CAS Number 28523-86-6 YesY
ATC code N01AB08 (WHO)
PubChem CID 5206
IUPHAR/BPS 7296
DrugBank DB01236 YesY
ChemSpider 5017 YesY
UNII 38LVP0K73A YesY
KEGG D00547 YesY
ChEBI CHEBI:9130 YesY
ChEMBL CHEMBL1200694 N
Chemical data
Formula C4H3F7O
Molar mass 200.055 g/mol
 NYesY (what is this?)  (verify)

Sevoflurane (1,1,1,3,3,3-hexafluoro-2-(fluoromethoxy)propane; synonym, fluoromethyl hexafluoroisopropyl ether), is a sweet-smelling, nonflammable, highly fluorinated methyl isopropyl ether used as an inhalational anaesthetic for induction and maintenance of general anesthesia. After desflurane, it is the volatile anesthetic with the fastest onset and offset.[1]

It is one of the most commonly used volatile anesthetic agents, particularly for outpatient anesthesia,[2] and including in anesthesia of children and infants, and in veterinary medicine. Together with desflurane, sevoflurane is replacing isoflurane and halothane in modern anesthesiology. It is often administered in a mixture of nitrous oxide and oxygen.

Sevoflurane "has an excellent safety record",[2] but is under review for potential neurotoxicity, especially relevant to administration in infants and children, and rare reports similar to halothane hepatotoxicity.[2] Sevoflurane is the preferred agent for mask induction due to its lesser irritation to mucous membranes.

Sevoflurane was discovered by Ross Terrell[3] and independently by Bernard M Regan. A detailed report of its development and properties appeared in 1975 in a paper authored by Richard Wallin, Bernard Regan, Martha Napoli and Ivan Stern it was introduced into clinical practice initially in Japan in 1990. The rights for sevoflurane in the US and other countries were held by Abbott Laboratories; it is available as a generic drug. Sevoflurane's name derives from the seven fluorine atoms in its substituents, alongside a standard suffix for such agents.

Medical uses

Sevoflurane is an inhaled anaesthetic that is often used to put children asleep for surgery.[4] During the process of waking up from the medication, it has been known to cause agitation and delirium.[4] It is not clear if this can be prevented.[4]

Adverse effects

Sevoflurane raises intracranial pressure and can cause respiratory depression.[5]

Studies examining a current significant health concern, anesthetic-induced neurotoxicity (including with sevoflurane, and especially with children and infants) are "fraught with confounders, and many are underpowered statistically", and so are argued to need "further data... to either support or refute the potential connection".[6]

Concern regarding the safety of anaesthesia is especially acute with regard to children and infants, where preclinical evidence from relevant animal models suggest that common clinically important agents, including sevoflurane, may be neurotoxic to the developing brain, and so cause neurobehavioural abnormalities in the long term; two large-scale clinical studies (PANDA and GAS) were ongoing as of 2010, in hope of supplying "significant [further] information" on neurodevelopmental effects of general anaesthesia in infants and young children, including where sevoflurane is used.[7]

Pharmacology

The exact mechanism of the action of general anaesthetics have not been delineated.[8] Sevoflurane is thought to potentially acts as a positive allosteric modulator of the GABAA receptor.[9] However, it also acts as an NMDA receptor antagonist,[10] potentiates glycine receptor currents,[9] and inhibits nACh[11] and 5-HT3 receptor currents.[9][12][13]

Physical properties

Boiling point: 58.6 °C (at 101.325 kPa)
Density: 1.517–1.522 g/cm³ (at 20 °C)
MAC : 2.1 vol %
Molecular weight: 200 u
Vapor pressure: 157 mmHg (22.9 kPa) (at 20 °C)
197 mmHg (26.3 kPa) (at 25 °C)
317 mmHg (42.3 kPa) (at 36 °C)
Blood:Gas partition coefficient: 0.68
Oil:Gas partition coefficient: 47

Bispectral index

Sevoflurane has lower values of controversial bispectral index than desflurane.[14][15]

Veterinary medicine

Sevoflurane had "become a popular inhalation anesthetic in veterinary practice" with a rapid induction and recovery from anesthesia due to a relatively low blood/gas solubility coefficient.[16]

References

  1. ↑ Sakai EM, Connolly LA, Klauck JA (December 2005). "Inhalation anesthesiology and volatile liquid anesthetics: focus on isoflurane, desflurane, and sevoflurane". Pharmacotherapy 25 (12): 1773–88. doi:10.1592/phco.2005.25.12.1773. PMID 16305297.
  2. 1 2 3 Livertox: Clinical and Research Information on Drug-Induced Liver Injury (2014) "Drug Record: Sevoflurane", U.S. National Library of Medicine, 2 July 2014 update, see , accessed 15 August 2014.
  3. ↑ Burns, William; Edmond I Eger II (August 2011). "Ross C. Terrell, PhD, an Anesthetic Pioneer". Anesth. Analg. 2 113 (113): 387–9. doi:10.1213/ane.0b013e3182222b8a.
  4. 1 2 3 Costi, D; Cyna, AM; Ahmed, S; Stephens, K; Strickland, P; Ellwood, J; Larsson, JN; Chooi, C; Burgoyne, LL; Middleton, P (Sep 12, 2014). "Effects of sevoflurane versus other general anaesthesia on emergence agitation in children.". The Cochrane database of systematic reviews 9: CD007084. doi:10.1002/14651858.CD007084.pub2. PMID 25212274.
  5. ↑ "Sevoflurane".
  6. ↑ Vlisides, P; Xie, Z. (2012). "Neurotoxicity of general anesthetics: an update". Curr Pharm Design 18 (38): 6232–40. doi:10.2174/138161212803832344. PMID 22762477.
  7. ↑ Sun, L. (2010). "Early childhood general anaesthesia exposure and neurocognitive development". Br J Anaesth 105 (Suppl 1): i61–8. doi:10.1093/bja/aeq302. PMID 21148656.
  8. ↑ http://www.scientificamerican.com/article/how-does-anesthesia-work/
  9. 1 2 3 Jürgen Schüttler; Helmut Schwilden (8 January 2008). Modern Anesthetics. Springer Science & Business Media. pp. 32–. ISBN 978-3-540-74806-9.
  10. ↑ Brosnan, Robert J; Thiesen, Roberto (2012). "Increased NMDA receptor inhibition at an increased Sevoflurane MAC". BMC Anesthesiology 12 (1): 9. doi:10.1186/1471-2253-12-9. ISSN 1471-2253.
  11. ↑ Christa J. Van Dort (2008). Regulation of Arousal by Adenosine A(1) and A(2A) Receptors in the Prefrontal Cortex of C57BL/6J Mouse. ProQuest. pp. 120–. ISBN 978-0-549-99431-2.
  12. ↑ Suzuki T, Koyama H, Sugimoto M, Uchida I, Mashimo T (March 2002). "The diverse actions of volatile and gaseous anesthetics on human-cloned 5-hydroxytryptamine3 receptors expressed in Xenopus oocytes". Anesthesiology 96 (3): 699–704. doi:10.1097/00000542-200203000-00028. PMID 11873047.
  13. ↑ Hang LH, Shao DH, Wang H, Yang JP (2010). "Involvement of 5-hydroxytryptamine type 3 receptors in sevoflurane-induced hypnotic and analgesic effects in mice" (PDF). Pharmacol Rep 62 (4): 621–6. doi:10.1016/s1734-1140(10)70319-4. PMID 20885002.
  14. ↑ Kim JK (Feb 2014). "Relationship of bispectral index to minimum alveolar concentration during isoflurane, sevoflurane or desflurane anaesthesia.". J Int Med Res 42 (1): 130–7. doi:10.1177/0300060513505525. PMID 24366495.
  15. ↑ Kreuer S (Oct 2009). "Comparative pharmacodynamic modeling of desflurane, sevoflurane and isoflurane.". J Clin Monit Comput. 23 (8): 299–305. doi:10.1007/s10877-009-9196-6. PMID 19711188.
  16. ↑ ITAMI, Takaharu; et al. (2011). "Cardiovascular Effects of Tramadol in Dogs Anesthetized with Sevoflurane". Journal of Veterinary Medical Science 73 (12): 1603–1609. doi:10.1292/jvms.11-0227.

Further reading

External links

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