Details
Stereochemistry | ACHIRAL |
Molecular Formula | C3H4Cl2F2O |
Molecular Weight | 164.966 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(F)(F)C(Cl)Cl
InChI
InChIKey=RFKMCNOHBTXSMU-UHFFFAOYSA-N
InChI=1S/C3H4Cl2F2O/c1-8-3(6,7)2(4)5/h2H,1H3
Molecular Formula | C3H4Cl2F2O |
Molecular Weight | 164.966 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB01028Curator's Comment: description was created based on several sources, including
https://www.fda.gov/ohrms/dockets/98fr/04p-0379-nwl0001.pdf
Sources: https://www.drugbank.ca/drugs/DB01028
Curator's Comment: description was created based on several sources, including
https://www.fda.gov/ohrms/dockets/98fr/04p-0379-nwl0001.pdf
Methoxyflurane is an inhalation anesthetic. Methoxyflurane was used for surgical, obstetric, or dental anesthesia, but was withdrawn from US market due to safety concerns, but is still in use in Australia and other countries. Methoxyflurane induces muscle relaxation and reduces pains sensitivity by altering tissue excitability by decreasing the extent of gap junction mediated cell-cell coupling and altering the activity of the channels that underlie the action potential.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0007268 Sources: https://www.ncbi.nlm.nih.gov/pubmed/550880 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | PENTHROX Approved UseFor emergency relief of pain by self administration in conscious haemodynamically stable patients with trauma and associated pain, under supervision of personnel trained in its use. For the relief of pain in monitored conscious patients who require analgesia for surgical procedures such as the change of dressings. |
Doses
Dose | Population | Adverse events |
---|---|---|
60 mL 1 times / day multiple, respiratory Highest studied dose Dose: 60 mL, 1 times / day Route: respiratory Route: multiple Dose: 60 mL, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Renal failure... Other AEs: Renal failure (grade 5, 2 patients) Sources: |
2 mL 2 times / day multiple, respiratory Dose: 2 mL, 2 times / day Route: respiratory Route: multiple Dose: 2 mL, 2 times / day Sources: |
unhealthy |
Disc. AE: Hepatitis... AEs leading to discontinuation/dose reduction: Hepatitis Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Renal failure | grade 5, 2 patients | 60 mL 1 times / day multiple, respiratory Highest studied dose Dose: 60 mL, 1 times / day Route: respiratory Route: multiple Dose: 60 mL, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hepatitis | Disc. AE | 2 mL 2 times / day multiple, respiratory Dose: 2 mL, 2 times / day Route: respiratory Route: multiple Dose: 2 mL, 2 times / day Sources: |
unhealthy |
PubMed
Title | Date | PubMed |
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Renal oxalosis and azotemia after methoxyflurane anesthesia. | 1970 Sep 24 |
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[Halogenated hydrocarbon compounds in anesthesia and their effect on the liver. Liver necrosis and tubulus degeneration after repeated methoxyflurane anesthesia]. | 1971 |
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Renal dysfunction associated with methoxyflurane anesthesia. A randomized, prospective clinical evaluation. | 1971 Apr 12 |
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Polyuric acute renal failure after methoxyflurane and tetracycline. | 1971 Dec 11 |
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Hepatorenal failure with renal oxalosis after methoxyflurane anesthesia. | 1971 Nov |
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Methoxyflurane and renal dysfunction. | 1971 Sep 27 |
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[Renal tubular necrosis and cytolytic hepatitis following repeated anaesthetic inhalation of methoxyflurane]. | 1972 Jul-Aug |
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Combined nephrotoxicity of gentamicin and methoxyflurane anaesthesia in man. A case report. | 1973 Apr |
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Letter: Partial recovery from renal failure following methoxyflurane anesthesia. | 1974 Jan 14 |
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Unilateral nephrotoxicity associated with methoxyflurane anesthesia: a case report. | 1974 Mar-Apr |
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A comparison of renal effects and metabolism of sevoflurane and methoxyflurane in enzyme-induced rats. | 1975 Nov-Dec |
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[Primary hyperoxaluria. Clinical, histological and crystallographic study of the ocular lesions]. | 1976 Feb |
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Deuterated methoxyflurane anesthesia and renal function in Fischer 344 rats. | 1982 Mar |
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Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
|
Modulation of T cell function by combination of epitope specific and low dose anticytokine therapy controls autoimmune arthritis. | 2006 Dec 20 |
|
Multiple dendritic cell populations activate CD4+ T cells after viral stimulation. | 2008 Feb 27 |
|
Isoflavones prevent bone loss following ovariectomy in young adult rats. | 2008 Mar 2 |
|
Non-invasive measurements of exhaled NO and CO associated with methacholine responses in mice. | 2008 May 27 |
Patents
Sample Use Guides
One bottle of PENTHROX® (1.5 mL or 3 mL) to be vaporised in a PENTHROX inhaler. On finishing the initial bottle, another bottle may be used. Up to 6 mL may be administered per day. The refilling must be conducted in a well ventilated area to reduce environmental exposure to Methoxyflurane vapour.
Route of Administration:
Respiratory
Substance Class |
Chemical
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Record UNII |
30905R8O7B
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Record Status |
Validated (UNII)
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WHO-ATC |
N02BG09
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CFR |
21 CFR 216.24
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NCI_THESAURUS |
C245
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WHO-VATC |
QN02BG09
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Code System | Code | Type | Description | ||
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DB01028
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C75098
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1418004
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100000081436
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m7337
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1048
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7201
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6843
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D008733
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7234
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METHOXYFLURANE
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1754
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CHEMBL1341
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DTXSID7025556
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200-956-0
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76-38-0
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4116
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30905R8O7B
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110432
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30905R8O7B
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SUB08858MIG
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6857
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PRIMARY | RxNorm |
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TARGET -> INHIBITOR | |||
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TARGET -> AGONIST |
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TARGET -> AGONIST |
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Related Record | Type | Details | ||
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METABOLITE TOXIC -> PARENT |
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
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METABOLITE TOXIC -> PARENT |
Fluoride ion produced clinical toxicity in form of nephrotoxicity in man.
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Related Record | Type | Details | ||
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ACTIVE MOIETY |