My watch list
my.chemeurope.com  
Login  

Isoflurane



Isoflurane
Systematic (IUPAC) name
2-chloro-2-(difluoromethoxy)-1,1,1-trifluoro-ethane
Identifiers
CAS number 26675-46-7
ATC code N01AB06
PubChem 3763
DrugBank APRD00212
Chemical data
Formula C3H2ClF5O 
Mol. mass 184.5 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes  ?

Isoflurane (2-chloro-2-(difluoromethoxy)-1,1,1-trifluoro-ethane) is a halogenated ether used for inhalational anesthesia. Together with enflurane and halothane, it replaced the flammable ethers used in the pioneer days of surgery. Its use in human medicine is now starting to decline, being replaced with sevoflurane, desflurane and the intravenous anaesthetic propofol. Isoflurane is still frequently used for veterinary anaesthesia.

Isoflurane is always administered in conjunction with air and/or pure oxygen. Often nitrous oxide is also used. Although its physical properties means that anaesthesia can be induced more rapidly than with halothane, its pungency can irritate the respiratory system, negating this theoretical advantage conferred by its physical properties. It is usually used to maintain a state of general anesthesia that has been induced with another drug, such as thiopentone or propofol. It vaporizes readily, but is a liquid at room temperature. It is completely non-flammable.

A major advantage of isoflurane is that the patent covering its use has expired, therefore it is very economical to use.

Contents

Physical properties

Molecular weight 184.5g/mol
Boiling point (at 1 atm): 48.5 °C
Density (at 25 °C): 1.496 g/mL
MAC : 1.15 vol %
Vapor pressure: 238 mmHg 31.7 kPa (at 20°C)
295 mmHg 39.3 kPa (at 25°C)
367 mmHg 48.9 kPa (at 30°C)
450 mmHg 60.0 kPa (at 35°C)
Water Solubility Insoluble
Blood:Gas Partition coefficient: 1.4
Oil:Gas Partition coefficient: 98

Mechanism of action

Isoflurane reduces pain sensitivity (analgesia) and relaxes muscles. The mechanism by which general anesthetics produce the anesthetic state is not clearly understood but likely involves interactions with multiple receptor sites to interfere with synaptic transmission. Isoflurane binds to GABA receptors, glutamate receptors and glycine receptors, and also inhibits conduction in activated potassium channels. Glycine inhibition helps to inhibit motor function, while bonding to glutamate receptors mimics the efects of NDMA. It activates calcium ATPase through an increase in membrane fluidity, and binds to the D subunit of ATP synthase and NADH dehydrogenase. In addition, a number of general anesthetics attenuate gap junction commmunication, which could contribute to anesthetic action.

Possible link to cognitive decline

Isoflurane exposure has been shown to induce cognitive decline in mice.[1] Exposure of cultured human cells to isoflurane has been reported to induce apoptosis and accumulation and aggregation of amyloid beta protein.[2] Further research will be required to establish whether or not clinical exposure to isoflurane leads to dementia (Alzheimer's disease).[3][4]

References

  1. ^ S. L. Bianchi, T. Tran, C. Liu, S. Lin, Y. Li, J. M. Keller, R. G. Eckenhoff, M. F. Eckenhoff (2007). "Brain and behavior changes in 12-month-old Tg2576 and nontransgenic mice exposed to anesthetics". Neurobiology of Aging 28 (in press): in press. doi:10.1016/j.neurobiolaging.2007.02.009.
  2. ^ Z. Xie, Y. Dong, U. Maeda, R. D. Moir, W. Xia, D. J. Culley, G. Crosby, R. E. Tanzi (2007). "The Inhalation Anesthetic Isoflurane Induces a Vicious Cycle of Apoptosis and Amyloid β-Protein Accumulation". Journal of Neuroscience 27 (6): 1247-1254. doi:10.1523/JNEUROSCI.5320-06.2007.
  3. ^ M. C. Lewis, I. Nevoa, M. A. Paniaguaa, A. Ben-Aric, E. Prettoa, S. Eisdorfera, E. Davidsona, I. Matotc, C. Eisdorfer (2007). "Uncomplicated general anesthesia in the elderly results in cognitive decline: Does cognitive decline predict morbidity and mortality?". Medical Hypotheses 68 (3): 484-492. doi:10.1016/j.mehy.2006.08.030.
  4. ^ Reinberg, Steven. "Anesthetic Linked to Alzheimer's Risk", HealthDay News, 15 January 2007. Retrieved on 2007-08-08. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Isoflurane". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE