Isoflurane

Structural formula
	1: 1 mixture of ( S ) -isoflurane (left) and ( R ) -isoflurane (right)
General
Non-proprietary name	Isoflurane
other names	Foran; Aerran; ( RS ) -Difluoromethoxy-1-chloro-2,2,2-trifluoroethane; (±) -Difluoromethoxy-1-chloro-2,2,2-trifluoroethane; rac -Difluoromethoxy-1-chloro-2,2,2-trifluoroethane;
Molecular formula	C 3 H 2 ClF 5 O
Brief description	colorless, ethereal-smelling liquid
External identifiers / databases
EC number	247-897-7
ECHA InfoCard	100,043,528
PubChem	3763
ChemSpider	3631
DrugBank	DB00753
Wikidata	Q413918
Drug information
ATC code	N01 AB06
Drug class	Inhalation anesthetic
properties
Molar mass	184.49 g mol −1
density	1.45 g cm −3
boiling point	48.5 ° C
Vapor pressure	320 h Pa (20 ° C) ; 440 hPa (25 ° C) ;
solubility	not miscible or difficult to mix with water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 336-373
	P: 304 + 340 + 312
Toxicological data	6,920 mg kg −1 ( LD 50 , rat , oral )
Global warming potential	510
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isoflurane is a volatile anesthetic belonging to the Flurane group . It is a structural isomer of enflurane and has been used for anesthesia in Germany since 1984 . Isoflurane has good hypnotic and muscle-relaxing effects, but only has a weak analgesic effect .

Chemistry and pharmacology

The rate of metabolism of isoflurane is very low (0.2%), which is why the narcotic can also be used in patients with liver damage. The blood-gas distribution coefficient of isoflurane is 1.46; at a concentration of 1% by volume in the alveoli , the concentration in the blood is therefore 1.46% by volume. Isoflurane is chiral ; it is used as a racemate [1: 1 mixture of ( S ) -isoflurane and ( R ) -isoflurane]. The synthesis of isoflurane, starting from 2,2,2-trifluoroethanol and dimethyl sulfate , is described in the literature.

Side effects

Isoflurane causes blood vessels to widen ( vasodilation ) and, depending on the dose, leads to a drop in arterial blood pressure and an increase in heart rate . It reduces the blood flow to the heart and, depending on the dose, the cardiac output . The blood flow to the kidneys is also reduced, the glomerular filtration rate and urine production are decreased. The active ingredient also reduces breathability, so it has a respiratory depressive effect . Isoflurane irritates the mucous membranes and is therefore only partially suitable for induction of anesthesia.

environment

The lifetime in the atmosphere is 3.2 years, the global warming potential 510 and the emissions are (estimated) 880 tons per year.

Others

As a result of the drastic increase in demand in recent weeks due to the Covid-19 pandemic , the manufacturer Baxter reported a supply bottleneck for propofol and isoflurane at the Federal Institute for Drugs and Medical Devices in 2020 . The authority sees "partially restricted availability" and delivery delays, but no delivery interruptions.

Trade names

Monopreparations : Forane (A), Forene (D, CH), various generics (D, A, CH)

literature

Michaele Alef, Gerhard Oechtering: Practice of inhalation anesthesia. Enke-Verlag, Stuttgart 2003, ISBN 3-8304-1015-8 .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on isoflurane in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .

↑ Isoflurane data sheet at AlfaAesar, accessed on March 17, 2010 ( PDF )(JavaScript required) .

↑ ^a ^b Martin K. Vollmer, Tae Siek Rhee, Matt Rigby, Doris Hofstetter, Matthias Hill, Fabian Schoenenberger, Stefan Reimann: Modern inhalation anesthetics: Potent greenhouse gases in the global atmosphere . In: Geophysical Research Letters . tape 42 , no. 5 , March 16, 2015, p. 1606–1611 , doi : 10.1002 / 2014GL062785 .

^ Axel Kleemann , Jürgen Engel, Bernd Kutscher, Dietmar Reichert: Pharmaceutical Substances. Syntheses, Patents, Applications. 2 volumes. 4th edition. Thieme, Stuttgart et al. 2001, ISBN 1-58890-031-2 ; online since 2003 with biannual additions and updates.

↑ Reinhard Larsen: Anesthesia and intensive medicine in cardiac, thoracic and vascular surgery. (1st edition 1986) 5th edition. Springer, Berlin / Heidelberg / New York et al. 1999, ISBN 3-540-65024-5 , pp. 8-10.

↑ Martin U. Müller: Strong demand for supply bottlenecks for anesthetic drugs. In: spiegel.de. April 10, 2020, accessed April 13, 2020 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on isoflurane in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .