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
Legal status	UK: POM (Prescription only) US: ℞-only
Routes of administration	inhaled
Identifiers
CAS Number	28523-86-6 Y
ATC code	N01AB08 (WHO)
PubChem	CID: 5206
IUPHAR/BPS	7296
DrugBank	DB01236 Y
ChemSpider	5017 Y
UNII	38LVP0K73A Y
KEGG	D00547 Y
ChEBI	CHEBI:9130 Y
ChEMBL	CHEMBL1200694 N
Chemical data
Formula	C4H3F7O
Molecular mass	200.055 g/mol
SMILES FC(F)(F)C(OCF)C(F)(F)F
InChI InChI=1S/C4H3F7O/c5-1-12-2(3(6,7)8)4(9,10)11/h2H,1H2 Y Key:DFEYYRMXOJXZRJ-UHFFFAOYSA-N Y
NY (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.

It is one of the most commonly used volatile anesthetic agents, particularly for outpatient anesthesia, 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", but is under review for potential neurotoxicity, especially relevant to administration in infants and children, and rare reports similar to halothane hepatotoxicity. Sevoflurane is the preferred agent for mask induction due to its lesser irritation to mucous membranes.

Sevoflurane was discovered by Ross Terrell 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. During the process of waking up from the medication, it has been known to cause agitation and delirium. It is not clear if this can be prevented.

Adverse effects

Sevoflurane raises intracranial pressure and can cause respiratory depression.

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".

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.

Pharmacology

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

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.

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.

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