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Sevoflurane (1,1,1,3,3,3-hexafluoro-2-(fluoromethoxy)propane), also called fluoromethyl hexafluoroisopropyl ether, is a sweet-smelling, nonflammable, highly fluorinated methyl isopropyl ether used for induction and maintenance of general anesthesia. Together with desflurane, it is replacing isoflurane and halothane in modern anesthesiology.^{[citation needed]} It is often administered in a mixture of nitrous oxide and oxygen. After desflurane, it is the volatile anesthetic with the fastest onset and offset.^[1] Though desflurane has the lowest blood/gas coefficient of the currently used volatile anesthetics, sevoflurane is the preferred agent for mask induction due to its lesser irritation to mucous membranes.

First reports of sevoflurane appeared in the literature in 1971. The agent was developed by ^[2]Ross Terrell, PhD. It was introduced into clinical practice initially in Japan in 1990. Its name comes from having seven fluorine atoms. The rights for sevoflurane in the US and other countries were held by Abbott Laboratories. It is now available as a generic drug.

Toxic breakdown products[edit source | edit]

Sevoflurane forms at least two degradation products, compound A [fluoromethyl-2,2-difluoro-1-(trifluoromethyl)vinyl ether]^[3] also called PIFE (pentafluoroisopropenyl fluoromethyl ether) and Compound B [1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane],^[4] also called PMFE (pentafluoromethoxy isopropyl fluoromethyl ether) on contact with the soda lime in a rebreathing apparatus, which absorbs exhaled carbon dioxide, especially at higher temperatures and when the soda lime is desiccated. Hydrofluoric acid is formed in the same reaction as compound A. Compound A has been shown to cause renal necrosis in rats. In humans, direct histological evidence of renal toxicity has not been demonstrated, although there is dose-related proteinuria, glycosuria and enzymuria. During low-flow anaesthesia, when the lower fresh gas flow leads to decreased flushing of the circuit and increased temperature of the soda lime, compound A may build up to clinically significant levels, although there have never been any reports of adverse events in humans. As a result, sevoflurane is sometimes administered with a minimum fresh gas flow of 2 liters per minute, making it a relatively expensive choice for maintaining general anesthesia. Only two countries currently have recommended minimum flow rates of 2L/min; Canada and Australia. Recent generic competition in select markets has also significantly lowered the unit cost of sevoflurane, making it more cost effective.

Animal studies[edit source | edit]

Sevoflurane has been implicated in neuronal degeneration in infant mice. This activity is thought to occur via blockade of NMDA receptors or hyperactivity of GABA neurotransmission. In one study, the researchers showed exposure of infant mice to inhaled sevoflurane resulted in learning deficits and abnormal social behaviour.^[5]

Sevoflurane raises intracranial pressure and can cause respiratory depression.^[6]

Physical properties[edit source | edit]

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

References[edit source | edit]

^ 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.
^ Burns, William; Edmond I Eger II (August 2011). "Ross C. Terrell, PhD, an Anesthetic Pioneer". Anesth. Analg. 2 113 (113): 387–9.
^ Stabernack CR, Eger EI 2nd, Warnken UH, Förster H, Hanks DK, Ferrell LD (2003). "Sevoflurane degradation by carbon dioxide absorbents may produce more than one nephrotoxic compound in rats". Can J Anaesth 50 (3): 249–52. doi:10.1007/BF03017793. PMID 12620947.
^ Schmidt, R.; Roeder, M.; Oeckler, O.; Simon, A.; Schurig, V. (2000). "Separation and absolute configuration of the enantiomers of a degradation product of the new inhalation anesthetic sevoflurane". Chirality 12 (10): 751–5. doi:10.1002/1520-636X(2000)12:10<751::AID-CHIR8>3.0.CO;2-H. PMID 11054834.
^ Satomoto M, Satoh Y, Terui K, et al. (March 2009). "Neonatal exposure to sevoflurane induces abnormal social behaviors and deficits in fear conditioning in mice". Anesthesiology 110 (3): 628–37. doi:10.1097/ALN.0b013e3181974fa2. PMID 19212262.
^ Sevoflurane.

External links[edit source | edit]

"Propofol and Sevoflurane Anesthesia".

UpToDate Contents

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1. 麻酔および麻酔剤選択の概要 overview of anesthesia and anesthetic choices
2. 重症患者における鎮静鎮痛剤：特性、投与レジメン、および副作用 sedative analgesic medications in critically ill patients properties dosage regimens and adverse effects
3. 小児における急性重症喘息の増悪：集中治療室（ICU）でのマネージメント acute severe asthma exacerbations in children intensive care unit management
4. 全身麻酔に引き続く記憶を伴う術中覚醒 awareness with recall following general anesthesia
5. 非心臓手術施行時の肥満患者に対する麻酔 anesthesia for the obese patient undergoing non cardiac surgery

English Journal

Comparison of the Surgical Pleth Index with autonomic nervous system modulation on cardiac activity during general anaesthesia: A randomised cross-over study.

Colombo R, Raimondi F, Corona A, Rivetti I, Pagani F, Porta VD, Guzzetti S.Author information From the Anaesthesiology and Intensive Care Unit (RC, FR, AC, IR, FP, VDP); Accident and Emergency Department, Azienda Ospedaliera Luigi Sacco, Milan, Italy (SG).AbstractBACKGROUND: Surgical plethysmographic index (SPI) has been proposed as a tool to measure the nociception/antinociception balance during general anaesthesia. Untreated nociception may increase sympathetic tone, but the relationship between SPI and the autonomic nervous system (ANS) is poorly understood.
European journal of anaesthesiology.Eur J Anaesthesiol.2014 Feb;31(2):76-84. doi: 10.1097/01.EJA.0000436116.06728.b3.
BACKGROUND: Surgical plethysmographic index (SPI) has been proposed as a tool to measure the nociception/antinociception balance during general anaesthesia. Untreated nociception may increase sympathetic tone, but the relationship between SPI and the autonomic nervous system (ANS) is poorly understo
PMID 24284309

Tropisetron alleviate early post-operative pain after gynecological laparoscopy in sevoflurane based general anaesthesia: A randomized, parallel-group, factorial study.

Mei W, Li M, Yu Y, Cheung CW, Cao F, Nie B, Zhang Z, Wang P, Tian Y.Author information Department of Anaesthesiology and Pain Medicine, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, China.AbstractBACKGROUND: Studies have suggested that 5-hydroxytryptamine-3A (5-HT-3A) receptor antagonists may have analgesic effects. This randomized, double-blind, placebo-controlled, factorial study tested the hypothesis that 5-HT-3A receptor antagonist tropisetron attenuates post-operative pain in women receiving either sevoflurane or propofol based anaesthesia.
European journal of pain (London, England).Eur J Pain.2014 Feb;18(2):238-48. doi: 10.1002/j.1532-2149.2013.00365.x. Epub 2013 Jul 19.
BACKGROUND: Studies have suggested that 5-hydroxytryptamine-3A (5-HT-3A) receptor antagonists may have analgesic effects. This randomized, double-blind, placebo-controlled, factorial study tested the hypothesis that 5-HT-3A receptor antagonist tropisetron attenuates post-operative pain in women rece
PMID 23868810

The use of a double-lumen central venous catheter for airway management in pediatric patients undergoing laryngeal papillomatosis surgery.

Zhu ZR, Hu ZY, Jiang YL, Xu LL, McQuillan PM.Author information Department of Anesthesiology, The Children's Hospital, School of Medicine, Zhejiang University, Hangzhou, China.AbstractPURPOSE: To evaluate the efficacy and safety of a spontaneous ventilation anesthesia technique with insufflation of oxygen and volatile agent through a double-lumen central venous catheter (DLCVC) in pediatric patients undergoing suspension laryngoscopic surgery for laryngeal papillomatosis.
Paediatric anaesthesia.Paediatr Anaesth.2014 Feb;24(2):157-63. doi: 10.1111/pan.12253. Epub 2013 Aug 19.
PURPOSE: To evaluate the efficacy and safety of a spontaneous ventilation anesthesia technique with insufflation of oxygen and volatile agent through a double-lumen central venous catheter (DLCVC) in pediatric patients undergoing suspension laryngoscopic surgery for laryngeal papillomatosis.METHODS:
PMID 24033557

Japanese Journal

Preliminary Report : Intravenous Droperidol Decreases the Bispectral Index during General Anesthesia with Sevoflurane and Remifentanil

ADACHI Yushi U.,TANAKA Katsuhiro,SUZUKI Shogo
麻酔 62(1), 71-74, 2013-01
NAID 40019551937

高濃度セボフルラン導入によるラリンジアルマスク挿入時における亜酸化窒素の有用性

西山友貴
麻酔 61(11), 1221-1225, 2012-11
NAID 40019480556

歯科治療が予定された封入体筋炎患者にロクロニウム, スガマデクス, セボフルランによる全身麻酔を行った1例

曽我部健,野口いづみ,戸井尚子,砂川秀樹,河原博
日本歯科麻酔学会雑誌 40(3), 318-319, 2012-07-15
NAID 10030799116

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「セボフルラン」

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
Pregnancy cat.	?
Legal status	POM (UK) ℞-only (US)
Routes	inhaled
Identifiers
CAS number	28523-86-6
ATC code	N01AB08
PubChem	CID 5206
DrugBank	DB01236
ChemSpider	5017
UNII	38LVP0K73A
KEGG	D00547
ChEBI	CHEBI:9130
ChEMBL	CHEMBL1200694
Chemical data
Formula	C4H3F7O
Mol. 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 ; Key:DFEYYRMXOJXZRJ-UHFFFAOYSA-N ;
(what is this?) (verify);

　　[★]

英: sevoflurane
商: セボフレン、セボネス
関: 吸入麻酔薬

イソフルランよりMACが高いが、臭気なくセボフルランがよい例がある。
悪性高熱症は少ないが起こりうる。
肝臓でわずかに代謝を受ける(3%)。

[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] Burns, William; Edmond I Eger II (August 2011). "Ross C. Terrell, PhD, an Anesthetic Pioneer". Anesth. Analg. 2 113 (113): 387–9.

[3] Stabernack CR, Eger EI 2nd, Warnken UH, Förster H, Hanks DK, Ferrell LD (2003). "Sevoflurane degradation by carbon dioxide absorbents may produce more than one nephrotoxic compound in rats". Can J Anaesth 50 (3): 249–52. doi:10.1007/BF03017793. PMID 12620947.

[4] Schmidt, R.; Roeder, M.; Oeckler, O.; Simon, A.; Schurig, V. (2000). "Separation and absolute configuration of the enantiomers of a degradation product of the new inhalation anesthetic sevoflurane". Chirality 12 (10): 751–5. doi:10.1002/1520-636X(2000)12:10<751::AID-CHIR8>3.0.CO;2-H. PMID 11054834.

[5] Satomoto M, Satoh Y, Terui K, et al. (March 2009). "Neonatal exposure to sevoflurane induces abnormal social behaviors and deficits in fear conditioning in mice". Anesthesiology 110 (3): 628–37. doi:10.1097/ALN.0b013e3181974fa2. PMID 19212262.

[6] Sevoflurane.

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sevoflurane