Sevoflurane Explained

Verifiedfields:changed
Watchedfields:changed
Verifiedrevid:464389790
Tradename:Ultane, others
Pregnancy Au:B2
Routes Of Administration:Inhalation
Class:Anesthetic
Atc Prefix:N01
Atc Suffix:AB08
Legal Au:S4
Legal Br:C1
Legal Br Comment:[1]
Legal Ca:Rx-only
Legal Uk:POM
Legal Us:Rx-only
Legal Us Comment:[2] [3]
Legal Eu:Rx-only
Legal Eu Comment:[4] [5] [6] [7]
Metabolism:Liver by CYP2E1
Metabolites:Hexafluoroisopropanol
Elimination Half-Life:15–23 hours
Excretion:Kidney
Iuphar Ligand:7296
Cas Number:28523-86-6
Pubchem:5206
Drugbank:DB01236
Chemspiderid:5017
Unii:38LVP0K73A
Kegg:D00547
Chebi:9130
Chembl:1200694
Iupac Name:1,1,1,3,3,3-Hexafluoro-2-(fluoromethoxy)propane
C:4
H:3
F:7
O:1
Smiles:FC(F)(F)C(OCF)C(F)(F)F
Stdinchi:1S/C4H3F7O/c5-1-12-2(3(6,7)8)4(9,10)11/h2H,1H2
Density:1.53
Stdinchikey:DFEYYRMXOJXZRJ-UHFFFAOYSA-N
Boiling Point:58.5

Sevoflurane, sold under the brand name Sevorane, among others, 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.[8] While its offset may be faster than agents other than desflurane in a few circumstances, its offset is more often similar to that of the much older agent isoflurane. While sevoflurane is only half as soluble as isoflurane in blood, the tissue blood partition coefficients of isoflurane and sevoflurane are quite similar. For example, in the muscle group: isoflurane 2.62 vs. sevoflurane 2.57. In the fat group: isoflurane 52 vs. sevoflurane 50. As a result, the longer the case, the more similar will be the emergence times for sevoflurane and isoflurane.[9] [10] [11]

It is on the World Health Organization's List of Essential Medicines.[12]

Medical uses

It is one of the most commonly used volatile anesthetic agents, particularly for outpatient anesthesia,[13] across all ages, as well as in veterinary medicine. Together with desflurane, sevoflurane is replacing isoflurane and halothane in modern anesthesia practice. It is often administered in a mixture of nitrous oxide and oxygen.

Physiological effects

Sevoflurane is a potent vasodilator, as such it induces a dose dependent reduction in blood pressure and cardiac output. It is a bronchodilator, however, in patients with pre-existing lung pathology, it may precipitate coughing and laryngospasm. It reduces the ventilatory response to hypoxia and hypercapnia, and impedes hypoxic pulmonary vasoconstriction. Sevoflurane vasodilatory properties also cause it to increase intracranial pressure and cerebral blood flow. However, it reduces cerebral metabolic rate. [14] [15]

Adverse effects

Sevoflurane has an excellent safety record,[13] but is under review for potential hepatotoxicity, and may accelerate Alzheimer's.[16] There were rare reports involving adults with symptoms similar to halothane hepatotoxicity.[13] Sevoflurane is the preferred agent for mask induction due to its lesser irritation to mucous membranes.

Sevoflurane is an inhaled anesthetic that is often used to induce and maintain anesthesia in children for surgery. During the process of awakening from the medication, it has been associated with a high incidence (>30%) of agitation and delirium in preschool children undergoing minor noninvasive surgery. It is not clear if this can be prevented.[17]

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".[18]

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.[19]

In 2021, researchers at Massachusetts General Hospital published in Communications Biology research that sevoflurane may accelerate existing Alzheimer's or existing tau protein to spread: "These data demonstrate anesthesia-associated tau spreading and its consequences. [...] This tau spreading could be prevented by inhibitors of tau phosphorylation or extracellular vesicle generation." According to Neuroscience News, "Their previous work showed that sevoflurane can cause a change (specifically, phosphorylation, or the addition of phosphate) to tau that leads to cognitive impairment in mice. Other researchers have also found that sevoflurane and certain other anesthetics may affect cognitive function."[16]

Additionally, there has been some investigation into potential correlation of sevoflurane use and renal damage (nephrotoxicity).[20] However, this should be subject to further investigation, as a recent study shows no correlation between sevoflurane use and renal damage as compared to other control anesthetic agents.[21]

Pharmacology

The exact mechanism of the action of general anaesthetics has not been delineated.[22] Sevoflurane acts as a positive allosteric modulator of the GABAA receptor in electrophysiology studies of neurons and recombinant receptors.[23] [24] [25] [26] However, it also acts as an NMDA receptor antagonist,[27] potentiates glycine receptor currents, and inhibits nAChR[28] and 5-HT3 receptor currents.[29] [30] [31]

History

Sevoflurane was discovered by Ross Terrell.[32] The rights for sevoflurane worldwide were held by AbbVie. It is available as a generic drug.

Global-warming potential

Sevoflurane is a greenhouse gas. The twenty-year global-warming potential, GWP(20), for sevoflurane is 349.[33]

Degradation

Sevoflurane will degrade into what is most commonly referred to as compound A (fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether) when in contact with CO2 absorbents, and this degradation tends to enhance with decreased fresh gas flow rates, increased temperatures, and increased sevoflurane concentration.[34] Compound A is what some believe is in correlation with renal damage.[35]

Further reading

Notes and References

  1. Web site: Anvisa . Brazilian Health Regulatory Agency . 31 March 2023 . RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial . Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control. live . https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 . 3 August 2023 . 16 August 2023 . . pt-BR . 4 April 2023.
  2. Web site: Ultane- sevoflurane liquid . DailyMed . 18 August 2022 . 29 June 2024.
  3. Web site: Sojourn- sevoflurane liquid . DailyMed . 26 June 2024 . 29 June 2024.
  4. Web site: SevoFlo EPAR . European Medicines Agency . 14 August 2007 . 29 June 2024.
  5. Web site: SevoFlo PI . Union Register of medicinal products . 13 December 2002 . 29 June 2024.
  6. Web site: Sevohale (previously known as Sevocalm) EPAR . European Medicines Agency . 29 July 2016 . 29 June 2024.
  7. Web site: Sevohale PI . Union Register of medicinal products . 24 June 2016 . 29 June 2024.
  8. Sakai EM, Connolly LA, Klauck JA . Inhalation anesthesiology and volatile liquid anesthetics: focus on isoflurane, desflurane, and sevoflurane . Pharmacotherapy . 25 . 12 . 1773–1788 . December 2005 . 16305297 . 10.1592/phco.2005.25.12.1773 . 40873242 .
  9. Maheshwari K, Ahuja S, Mascha EJ, Cummings KC, Chahar P, Elsharkawy H, Kurz A, Turan A, Sessler DI . 6 . Effect of Sevoflurane Versus Isoflurane on Emergence Time and Postanesthesia Care Unit Length of Stay: An Alternating Intervention Trial . Anesthesia and Analgesia . 130 . 2 . 360–366 . February 2020 . 30882520 . 10.1213/ANE.0000000000004093 . free .
  10. Sloan MH, Conard PF, Karsunky PK, Gross JB . Sevoflurane versus isoflurane: induction and recovery characteristics with single-breath inhaled inductions of anesthesia . Anesthesia and Analgesia . 82 . 3 . 528–532 . March 1996 . 8623956 . 10.1213/00000539-199603000-00018 . free .
  11. Smith I, Ding Y, White PF . Comparison of induction, maintenance, and recovery characteristics of sevoflurane-N2O and propofol-sevoflurane-N2O with propofol-isoflurane-N2O anesthesia . Anesthesia and Analgesia . 74 . 2 . 253–259 . February 1992 . 1731547 . 10.1213/00000539-199202000-00015 . 12345796 . free .
  12. Book: ((World Health Organization)) . The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) . 2023 . 10665/371090 . World Health Organization . World Health Organization . Geneva . WHO/MHP/HPS/EML/2023.02 . free .
  13. Livertox: Clinical and Research Information on Drug-Induced Liver Injury . Drug Record: Sevoflurane . 2 July 2014 . 31643176 . 15 August 2014 .
  14. Web site: Sevoflurane . 30521202 . 2022 . Edgington TL, Muco E, Maani CV . StatPearls .
  15. Green WB . The ventilatory effects of sevoflurane . Anesthesia and Analgesia . 81 . 6 Suppl . S23–S26 . December 1995 . 7486144 . 10.1097/00000539-199512001-00004 .
  16. Web site: 16 May 2021. Anesthetic May Affect Tau Spread in the Brain to Promote Alzheimer's Disease Pathology. 17 May 2021. Neuroscience News. en-US.
  17. Costi D, Cyna AM, Ahmed S, Stephens K, Strickland P, Ellwood J, Larsson JN, Chooi C, Burgoyne LL, Middleton P . 6 . Effects of sevoflurane versus other general anaesthesia on emergence agitation in children . The Cochrane Database of Systematic Reviews . 2014 . 9 . CD007084 . September 2014 . 25212274 . 10.1002/14651858.CD007084.pub2 . 10898224 .
  18. Vlisides P, Xie Z . Neurotoxicity of general anesthetics: an update . Current Pharmaceutical Design . 18 . 38 . 6232–6240 . 2012 . 22762477 . 10.2174/138161212803832344 .
  19. Sun L . Early childhood general anaesthesia exposure and neurocognitive development . British Journal of Anaesthesia . 105 . Suppl 1 . i61–i68 . December 2010 . 21148656 . 3000523 . 10.1093/bja/aeq302 .
  20. Book: Edgington TL, Muco E, Naani CV . Sevoflurane . 2023 . http://www.ncbi.nlm.nih.gov/books/NBK534781/ . StatPearls . 5 November 2023 . Treasure Island (FL) . StatPearls Publishing . 30521202 .
  21. Sondekoppam RV, Narsingani KH, Schimmel TA, McConnell BM, Buro K, Özelsel TJ . The impact of sevoflurane anesthesia on postoperative renal function: a systematic review and meta-analysis of randomized-controlled trials . Canadian Journal of Anaesthesia . 67 . 11 . 1595–1623 . November 2020 . 32812189 . 10.1007/s12630-020-01791-5 . free .
  22. Web site: Perkins B . How does anesthesia work? . . 7 February 2005 . 30 June 2016.
  23. Jenkins A, Franks NP, Lieb WR . Effects of temperature and volatile anesthetics on GABA(A) receptors . Anesthesiology . 90 . 2 . 484–491 . February 1999 . 9952156 . 10.1097/00000542-199902000-00024 . free .
  24. Wu J, Harata N, Akaike N . Potentiation by sevoflurane of the gamma-aminobutyric acid-induced chloride current in acutely dissociated CA1 pyramidal neurones from rat hippocampus . British Journal of Pharmacology . 119 . 5 . 1013–1021 . November 1996 . 8922750 . 1915958 . 10.1111/j.1476-5381.1996.tb15772.x .
  25. Krasowski MD, Harrison NL . The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations . British Journal of Pharmacology . 129 . 4 . 731–743 . February 2000 . 10683198 . 1571881 . 10.1038/sj.bjp.0703087 .
  26. Book: Schüttler J, Schwilden H . Modern Anesthetics. 8 January 2008. Springer Science & Business Media. 978-3-540-74806-9. 32–.
  27. Brosnan RJ, Thiesen R . Increased NMDA receptor inhibition at an increased Sevoflurane MAC . BMC Anesthesiology . 12 . 1 . 9 . June 2012 . 22672766 . 3439310 . 10.1186/1471-2253-12-9 . free .
  28. Book: Van Dort CJ . Regulation of Arousal by Adenosine A(1) and A(2A) Receptors in the Prefrontal Cortex of C57BL/6J Mouse . 2008 . 978-0-549-99431-2 . 120– . University of Michigan .
  29. Book: Schüttler J, Schwilden H . Modern Anesthetics . 8 January 2008. Springer Science & Business Media . 978-3-540-74806-9 . 74–.
  30. Suzuki T, Koyama H, Sugimoto M, Uchida I, Mashimo T . The diverse actions of volatile and gaseous anesthetics on human-cloned 5-hydroxytryptamine3 receptors expressed in Xenopus oocytes . Anesthesiology . 96 . 3 . 699–704 . March 2002 . 11873047 . 10.1097/00000542-200203000-00028 . 6705116 . free .
  31. Hang LH, Shao DH, Wang H, Yang JP . Involvement of 5-hydroxytryptamine type 3 receptors in sevoflurane-induced hypnotic and analgesic effects in mice . Pharmacological Reports . 62 . 4 . 621–626 . 2010 . 20885002 . 10.1016/s1734-1140(10)70319-4 . 4754446 . 10.1.1.587.5552 .
  32. Burns WB, Eger EI . Ross C. Terrell, PhD, an anesthetic pioneer . Anesthesia and Analgesia . 113 . 2 . 387–389 . August 2011 . 21642612 . 10.1213/ane.0b013e3182222b8a . 19988772 . free . Obituaries .
  33. Ryan SM, Nielsen CJ . Global warming potential of inhaled anesthetics: application to clinical use . Anesthesia and Analgesia . 111 . 1 . 92–98 . July 2010 . 20519425 . 10.1213/ane.0b013e3181e058d7 . . 20737354 . free .
  34. Web site: Carbon Dioxide Absorbent - an overview ScienceDirect Topics . 5 November 2023 . www.sciencedirect.com.
  35. Eger EI, Koblin DD, Bowland T, Ionescu P, Laster MJ, Fang Z, Gong D, Sonner J, Weiskopf RB . 6 . Nephrotoxicity of sevoflurane versus desflurane anesthesia in volunteers . Anesthesia and Analgesia . 84 . 1 . 160–168 . January 1997 . 8989018 . 10.1213/00000539-199701000-00029 .

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