Sevoflurane

Base Information

• Chemical Name: Sevoflurane
• CAS No.: 28523-86-6
• Molecular Formula: C4H3F7O
• Molecular Weight: 200.056
• Hs Code.: 29091990
• European Community (EC) Number: 643-089-7
• ICSC Number: 1436
• NSC Number: 760367
• UNII: 38LVP0K73A
• DSSTox Substance ID: DTXSID8046614
• Nikkaji Number: J20.100F
• Wikipedia: Sevoflurane
• Wikidata: Q419394
• NCI Thesaurus Code: C47717
• RXCUI: 36453
• Pharos Ligand ID: DF3TK2LS5D6J
• Metabolomics Workbench ID: 43446
• ChEMBL ID: CHEMBL1200694
• Mol file: 28523-86-6.mol

Synonyms:BAX 3084;fluoromethyl hexafluoroisopropyl ether;fluoromethyl-2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether;sevoflurane;sevorane;Ultane

Chemical Property of Sevoflurane

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 311mmHg at 25°C
• Melting Point: 58 °C
• Refractive Index: 1.266
• Boiling Point: 49.5 °C at 760 mmHg
• Flash Point: 58 °C
• PSA: 9.23000
• Density: 1.505 g/cm³
• LogP: 2.42320
• Storage Temp.: Refrigerator
• Solubility.: Slightly soluble in water, miscible with ethanol (96 per cent).
• Water Solubility.: Slightly miscible with water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 200.00721185
• Heavy Atom Count: 12
• Complexity: 121

Purity/Quality:

99%min ^*data from raw suppliers

1,1,1,3,3,3-Hexafluoro-2-(fluoromethoxy)propane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36/37/39-36/37-23

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anesthetics, Halogenated
• Canonical SMILES: C(OC(C(F)(F)F)C(F)(F)F)F
• Recent ClinicalTrials: Total Knee Replacement TIVA With Robotic Arm Assisted
• Recent EU Clinical Trials: CARDIOPROTECTIVE-NEPHROPROTECTIVE EFFECTS OF SEVOFLURAN IN COMPARISON WITH PROPOFOL IN DOUBLE VALVULAR SURGERY. USE OF SEVOFLURANE AS A PILLAR OF PROTECTION IN EXTRACORPOREA CIRCULATION AND POSTOPERATIVE SEDATION
• Recent NIPH Clinical Trials: A Study on the Efficacy of Opioid-Free Anesthesia in Pediatric Cardiac Surgery
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. The substance may cause effects on the central nervous system and cardiovascular system. Exposure at high levels could cause unconsciousness.
• Description: Sevoflurane is a rapidly acting, potent inhalation anesthetic with rapid uptake and and elimination. While somewhat less potent than halothane, sevoflurane does not induce arrhythmias and reportedly has no effect on renal function. Sevoflurane is a halogenated ether with anesthetic properties. It enhances the activity of GABAA and glycine receptors and inhibits the activity of nicotinic acetylcholine receptors (nAChRs) and glutamate receptors. Sevoflurane enhances the responses of α2β1 subunit-containing GABAA and α1 subunit-containing glycine receptors at submaximal agonist concentrations in HEK293 cells (EC50s = 0.45 and 0.36 mM, respectively). Sevoflurane (360 μM) also increases the amplitude of GABAA receptor responses to GABA stimulation for receptors with an α1β2γ2 subunit composition. It inhibits binding of the high affinity nicotinic agonist epibatidine to nAChRs in mouse brain membranes (IC50 = 0.77 mM). Formulations containing sevoflurane have been used in the induction and maintenance of general anesthesia.
• Uses: antibacterial 1,1,1,3,3,3-Hexafluoro-2-(fluoromethoxy)propane is an volatile anesthetic which inhibited activation of inflammatory neutrophil and granulocyte in human blood during simulated extracorporeal circulati on. Fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether is a volatile anesthetic, which inhibits the activation of inflammatory neutrophil and granulocyte in human blood during simulated extracorporeal circulation. It also serves as an antibacterial and used as an inhalational anaesthetic for induction and maintenance of general anesthesia. Further, it finds application in anesthesia of children and infants to make them asleep for surgery. In addition to this, it is used in veterinary medicine.
• Therapeutic Function: Anesthetic
• Biological Functions: Sevoflurane (Ultane) is the most recently introduced inhalation anesthetic. It has low tissue and blood solubility, which allows for rapid induction and emergence and makes it useful for outpatient and ambulatory procedures. It has the advantage of not being pungent, a characteristic that permits a smooth inhalation induction, and is particularly useful in pediatric anesthesia. Hypotension is produced by sevoflurane as systemic vasodilation occurs and cardiac output decreases. Since it does not directly produce tachycardia, it is a useful alternative to consider in patients with myocardial ischemia. However, a concern for reflex-induced tachycardia remains. Sevoflurane undergoes hepatic biotransformation (about 3% of the inhaled dose), and it is somewhat degraded by conventional CO2 absorbents. The degradation product from the absorbent has been reported to be nephrotoxic, although the report is controversial and not substantiated by more recent studies. Sevoflurane’s actions on skeletal muscle and on vascular regulation within the CNS are similar to those described for the other halogenated hydrocarbon anesthetics.
• Clinical Use: Sevoflurane has been shown to cause epileptic changeson EEGs and case reports of seizures during surgery, especiallyin children, have been reported.

Technology Process of Sevoflurane

There total 25 articles about Sevoflurane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether (26103-07-1) → sevoflurane (28523-86-6)

Guidance literature:

With diisopropylethylamine hydrofluoride; for 16h; Heating;

DOI:10.1016/S0022-1139(01)00396-7

Reference yield: 93.0%

1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether (26103-07-1) → 1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + sevoflurane (28523-86-6)

Guidance literature:

With hydrogenchloride; potassium fluoride; water; Aliquat HTA-1; at 100 ℃; for 3h; Product distribution / selectivity;

Reference yield: 91.43%

fluoroiodomethane (373-53-5) + 1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) → sevoflurane (28523-86-6)

Guidance literature:

With triethylamine; In acetonitrile; at 60 ℃; for 8h; Product distribution / selectivity; Inert atmosphere; Sealed vesselaturated gas;

upstream raw materials:

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether

1,1,1,3',3',3'-hexafluoro-propanol

bis(2-chloromethyl)ether

Downstream raw materials:

1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane

fluoromethyl-2,2-difluoro-1-(trifluoromethyl)vinyl ether

(Z)-1,3,3,3-Tetrafluoro-2-fluoromethoxy-1-methoxy-propene

1,1,1,3,3,3-hexafluoro-2-methoxypropane

Refernces

• 1、 -. "Preparation method of chloromethyl hexafluoroisopropyl ether". Paragraph 0025; 0026. . Retrieved 2018/11/03.
• 2、 -. "PROCESS FOR THE MANUFACTURING OF SEVOFLURANE". Paragraph 0027. . Retrieved 2013/03/26.