Desflurane

Suprane · i653 · Desfluran · esflurane · DESFLURANE · DESFLURANE USP · Desflurane (0.5 mL) · Desflurane USP/EP/BP

https://huagongshe.com/en/chemical/42113

Identifiers & Physical Properties

CAS No.	57041-67-5
Molecular formula	C3H2F6O
Average molar mass	168.04 g/mol
Monoisotopic mass	168.000984 g/mol
SMILES	FC(F)OC(F)C(F)(F)F
InChIKey	DPYMFVXJLLWWEU-UHFFFAOYSA-N
PubChem CID	42113
ChEMBL	CHEMBL1200733
ChEBI	CHEBI:4445
EC No.	688-023-8
DTXSID	DTXSID80866606

Chemical & Physical Properties

XLogP	2.6
Topological polar surface area	9.2
Hydrogen bond donors	0
Hydrogen bond acceptors	7
Rotatable bonds	2
Heavy atoms	10
Formal charge	0
Complexity	97.7
Drugs	Pharmaceuticals -> Nervous system -> AnestheticsPharmaceuticals -> Anesthetics
LogP (partition coefficient)	1.9
Odor	Slight non-pungent odor
Density	1.44Relative density (water = 1): 1.51,47 g/cm3
Color/Form	Liquid
Solubility	Negligible3.54e+00 g/LSolubility in water: poorPractically insoluble in water, miscible with anhydrous ethanol.
Human Drugs	Breast FeedingLactationAnesthetics, InhalationFDA approved drugs -> Active ingredient
Boiling point	23.5 °C74.3 °F23-24°C
Vapor density	1.44
Vapor pressure	88.53 kPa at 20 °Capproximately 700 mm Hg at 22-23 °CVapor pressure, kPa at 20 °C: 89700 [email protected] °F
Physical Description	LiquidCOLOURLESS LIQUID.Colorless liquid.
Other Experimental Properties	VolatilePartition coefficient at 37 °C: (blood/gas): 0.424(saline/gas): 0.225(oil/gas): 18.7Hydroxyl radical reaction rate constant = 4.40X10-15 cu cm/molec-sec at 25 °C
Refractive index	1.3577 (estimate)
Physical state	liquid
Color	Clear
Henry's law constant	1.4×10-4 mol/(m3Pa) at 25℃, HSDB (2015)
Major applications	pharmaceutical (small molecule)
InChI	1S/C3H2F6O/c4-1(3(7,8)9)10-2(5)6/h1-2H
InChIKey	DPYMFVXJLLWWEU-UHFFFAOYSA-N
SMILES	FC(F)(F)C(F)OC(F)F
CAS DataBase Reference	57041-67-5(CAS DataBase Reference)
FDA UNII	CRS35BZ94Q
NCI Drug Dictionary	desflurane
ATC code	N01AB07
EPA Substance Registry System	Ethane, 2-(difluoromethoxy)-1,1,1,2-tetrafluoro-, (+-)- (57041-67-5)
UNSPSC Code	41116107
NACRES	NA.24
GHS pictogram	GHS07
Signal word	Warning
GHS hazard statements	H315-H319-H335
GHS precautionary statements	P271-P261-P280
Target organs	Central nervous system, Respiratory system
Hazard symbols	Xi
Safety statements (S)	23
Water hazard class (WGK)	WGK 3
Hazard Note	Irritant
Hazard class	GASEye Irrit. 2Repr. 2STOT SE 3
Customs code	2909191800
Storage class	10 - Combustible liquids
Hazardous substances data	57041-67-5(Hazardous Substances Data)

Safety & Regulations

GHS classification	This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.DangerH315 (40%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P260, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fire hazards	Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.
FDA requirements	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including desflurane, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Chemical Dangers	Decomposes on contact with hot surfaces or flames. This produces corrosive gases such as hydrogen fluoride.
Physical Dangers	The vapour is heavier than air and may accumulate in lowered spaces causing a deficiency of oxygen.
Hazard Classes and Categories	Skin Irrit. 2 (40%)
Critical Temperature and Pressure	Critical temperature: 376.46 Kcritical pressure: 2610.3 kPa
Hazardous Reactivities and Incompatibilities	No discernible degradation occurs in the presence of strong acids. Desflurane does not corrode stainless steel, brass, aluminum, anodized aluminum, nickel plated brass, copper, or beryllium.Desflurane is chemically stable. The only known degradation reaction is through prolonged direct contact with soda lime producing low levels of fluoroform (CHF3). The amount of CHF3 obtained is similar to that produced with MAC-equivalent doses of isoflurane.
Fire fighting	In case of fire in the surroundings, use appropriate extinguishing media.
First aid measures	Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Applications & Uses

Description

Desflurane is a new inhalation anesthetic introduced for induction and maintenance of general anesthesia in adults. Due to reports of respiratory irritation, desflurane may be used only for maintenance in children. Although almost structurally identical to isoflurane, a halogen replacement gives desflurane an improved pharmacokinetic profile. It is less soluble in blood and tissue and produces a fast onset of action and a more rapid recovery from anesthesia.

History

Desflurane was first synthesized by Russel et al U.S. at the 29. of July 1975. The synthesis was started by using floural methyl hemiacetal (CF3CH(OH)OCH3) and converting it to 1,2,2,2- tetraflouroethyl methyl ether (CF3CHFOCH3). Next step was chlorinating two hydrogen atoms of the methyl-group to CF3CHFOCHCl2. This next to last molecule was charged with HF in the presence of antimony pentachloride (SBCL5) to Desflurane. But this way of synthesizing Desfluran was not usable for industrial synthesis, because of the less yield of Desflurane and the expensive educts.

Uses

Anesthetic.

General Description

Desflurane is a nonflammable, colorless, very volatile liquidpackaged in amber-colored vials. The boiling point is22.8°C, and it requires a vaporizer specifically designed fordesflurane. The manufacturer states that the vials can bestored at room temperature. Desflurane has a blood:gas partitioncoefficient of 0.42, an MAC of 7.3% and an oil:gaspartition coefficient of 18.7. The low blood:gas partition coefficientleads to fast induction times and short recoverytimes. Desflurane is not recommended for induction anesthesiain children because of the high incidence of laryngospasms(50%), coughing (72%), breath holding (68%),and increase in secretions (21%). Desflurane can producea dose-dependent decrease in blood pressure and concentrationsexceeding 1 MAC may cause transient increases inheart rate. Desflurane can react with desiccated carbon dioxideabsorbents to produce carbon monoxide that may resultin elevated levels of carboxyhemoglobin.24.

Preparation & Synthesis

Preparation

Isoflurane and bromine trifluoride were reacted overnight at room temperature to synthesize desflurane in 62% yield.