Methoxyflurane
| File:Methoxyflurane.svg | |
| File:Methoxyflurane-3D-balls.png | |
| Systematic (IUPAC) name | |
|---|---|
|
2,2-dichloro-1,1-difluoro-1-methoxy-ethane | |
| Clinical data | |
| Pregnancy category | |
| Routes of administration | Inhalation |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Metabolism | 70% |
| Identifiers | |
| CAS Number | 76-38-0 |
| ATC code | N01AB03 (WHO) |
| PubChem | CID 4116 |
| DrugBank | APRD00744 |
| Synonyms | 2,2-dichloro-1,1-difluoroethyl methyl ether |
| Chemical data | |
| Formula | C3H4Cl2F2O |
| Molar mass | 164.966 g/mol[[Script error: No such module "String".]] |
| (verify) | |
Methoxyflurane (C3H4Cl2F2O, or 2,2-dichloro-1,1-difluoroethyl methyl ether) was commonly used as an inhalational anaesthetic in the 1960s and early 1970s. It is classified as a halogenated hydrocarbon under the ATC code N01 (Anesthetics) subgroup of the Anatomical Therapeutic Chemical Classification System, but its chemical structure is more accurately characterised as a halogenated ether.
The clinical use of methoxyflurane in human medicine has largely been abandoned because of detrimental effects on the kidneys, due to fluoride ions being produced by its metabolism in the kidney, and detrimental effects on the liver, including hepatic necrosis requiring liver transplant or causing death. The kidney effect was considered to be dose-dependent, smaller doses for shorter periods being considered relatively safer. The concurrent use of tetracyclines and methoxyflurane has been reported to result in fatal renal toxicity.[1]
Its minimum alveolar concentration (MAC) is 0.2%, hence it is extremely potent. It has a high lipid solubility (oil:gas coefficient around 950) giving it a very slow onset/offset, this being undesirable for anesthetic purposes.
Even so, methoxyflurane is a powerful analgesic (pain-relieving) agent, at well below full anaesthetic doses. The vapour is sometimes said to have a pleasant, fruity aroma.
Uses
Methoxyflurane is widely used as an emergency analgesic in Australia. It is used extensively in the Australian Defence Force and Australian ambulance services, with St John Ambulance offering certification for first-aiders to administer it under remote and trauma conditions. As of 2010, methoxyflurane was listed under the Pharmaceutical Benefits Scheme for emergency treatment only[2].
Methoxyflurane is also widely used as an anesthetic and analgesic in rodents in a lab animal setting.
References
- ↑ "By-Mycin 50mg Capsules". medicines.ie. 2009-12-14. Retrieved 2010-07-29.
- ↑ "Methoxyflurane (Penthrox) for analgesia (doctors bag listing)". NPS RADAR. 14 May 2010. Retrieved 14 May 2010. C1 control character in
|title=at position 48 (help)
External links
- Info at New Zealand Medicines Safety Authority
- Drug information at Drugs.com
- Safety data sheet
- Use in medical research
- Info at Drug Digest
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