Details
Stereochemistry | ACHIRAL |
Molecular Formula | C3H4Cl2F2O |
Molecular Weight | 164.9661 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(C(Cl)Cl)(F)F
InChI
InChIKey=RFKMCNOHBTXSMU-UHFFFAOYSA-N
InChI=1S/C3H4Cl2F2O/c1-8-3(6,7)2(4)5/h2H,1H3
Molecular Formula | C3H4Cl2F2O |
Molecular Weight | 164.9661 |
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 Methoxyflurane was used for surgical, obstetric, or dental anesthesia, but was withdrawn from US market due to safety concerns, but is still in use in Australia and other countries.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 |
---|---|---|---|---|
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. |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3706798/ |
0.047 % other, respiratory dose: 0.047 % route of administration: Respiratory experiment type: OTHER co-administered: |
METHOXYFLURANE unknown | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
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 n = 2 Health Status: unhealthy Population Size: 2 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 n = 1 |
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 n = 2 Health Status: unhealthy Population Size: 2 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 n = 1 |
PubMed
Title | Date | PubMed |
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Renal and hepatic injury associated with methoxyflurane anesthesia. | 1968 Dec |
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Nephropathy associated with methoxyflurane anesthesia. A follow-up report. | 1968 Sep 9 |
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Hazards of methoxyflurane emulsions in man. | 1968 Sep-Oct |
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The effect of methoxyflurane on cerebrospinal fluid pressure in patients with and without intracranial space-occupying lesions. | 1969 Jul |
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Hepatic coma associated with methoxyflurane anesthesia. Report of a case. | 1970 Aug |
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Halothane anesthesia following methoxyflurane-induced nephrotoxicity. | 1970 Oct |
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Toxicity following methoxyflurane anesthesia. I. Clinical and pathological observations in two fatal cases. | 1970 Oct 5 |
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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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Methoxyflurane anesthesia. | 1971 Apr 19 |
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Recurrent hepatitis due to methoxyflurane anesthesia. | 1971 Apr 29 |
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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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Irreversible acute oliguric renal failure. A complication of methoxyflurane anesthesia. | 1972 Apr 20 |
|
Renal failure and methoxyflurane. Case report. | 1972 Aug |
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Renal failure after methoxyflurane anaesthesia. | 1972 Jan |
|
[Renal tubular necrosis and cytolytic hepatitis following repeated anaesthetic inhalation of methoxyflurane]. | 1972 Jul-Aug |
|
Repeated methoxyflurane analgesia for burns dressings. | 1972 Jun |
|
Methoxyflurane analgesia for burns dressings. | 1972 Mar |
|
Anesthetic malignant myopathy hyperthermia. | 1972 Sep |
|
Combined nephrotoxicity of gentamicin and methoxyflurane anaesthesia in man. A case report. | 1973 Apr |
|
Nephrotoxicity from methoxyflurane anaesthesia: a 6-year retrospective study. | 1973 Apr |
|
An animal model for combined methoxyflurane and gentamicin nephrotoxicity. | 1973 Apr |
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Occasional occurrence of serious renal complications after methoxyflurane (Penthrane) anesthesia. | 1973 Aug |
|
Strain differences in metabolism and susceptibility to the nephrotoxic effects of methoxyflurane in rats. | 1973 Feb |
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Methoxyflurane (penthrane) inhalation in labor. | 1973 Jun |
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Nephrotoxicity associated with use of methoxyflurane. Recovery following severe renal impairment. | 1974 |
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Persisting renal insufficiency after methoxyflurane anesthesia. Report of two cases and review of literature. | 1974 Apr |
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Changes in urine osmolality and urine fluoride concentrations following methoxyflurane anaesthesia. | 1974 Feb |
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Letter: Partial recovery from renal failure following methoxyflurane anesthesia. | 1974 Jan 14 |
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The syndrome of methoxyflurane-associated hepatitis. | 1974 Mar |
|
Unilateral nephrotoxicity associated with methoxyflurane anesthesia: a case report. | 1974 Mar-Apr |
|
Methoxyflurane nephropathy. | 1974 May |
|
Incidence of tubular degeneration with microlithiasis following methoxyflurane compared with other anesthetic agents. | 1974 May-Jun |
|
Letter: Nonoliguric renal failure and enflurane. | 1974 Oct |
|
Generalized oxalosis with retinal involvement following methoxyflurane anesthesia. | 1974 Sep |
|
The etiology of methoxyflurane nephrotoxicity. | 1974 Sep |
|
Influence of phenobarbital pretreatment on methoxyflurane and sodium fluoride nephropathy in Fischer 344 Rats. | 1976 Aug |
|
The effect of enflurane, isoflurane, fluroxene, methoxyflurane and diethyl ether anesthesia on ouabain tolerance in the dog. | 1976 May-Jun |
|
Methoxyflurane hepatitis. | 1977 Nov |
|
[Adverse effects of modern inhalation anesthetics. 2. Control of amounts and elimination of escaping anesthesia gases]. | 1978 Dec 14 |
|
Anesthetic indices--further data. | 1978 Mar |
|
Methoxyflurane-induced nephrotoxicity: influence of food intake on some biochemical indicators of renal function in Fischer 344 rats. | 1978 Sep |
|
Hepatic and renal effects of low concentrations of methoxyflurane in exposed delivery ward personnel. | 1980 Dec |
|
Deuterated methoxyflurane anesthesia and renal function in Fischer 344 rats. | 1982 Mar |
|
Hepatitis and renal tubular acidosis after anesthesia with methoxyflurane. | 1982 Oct-Dec |
|
Methoxyflurane hepatitis: two cases following obstetric analgesia. | 1983 Feb |
|
[Massive oxalosis of the kidney in association with anesthesia using methoxyflurane]. | 1984 Aug |
|
Human kidney methoxyflurane and sevoflurane metabolism. Intrarenal fluoride production as a possible mechanism of methoxyflurane nephrotoxicity. | 1995 Mar |
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
Created
by
admin
on
Edited
Sat Jun 26 04:17:38 UTC 2021
by
admin
on
Sat Jun 26 04:17:38 UTC 2021
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Record UNII |
30905R8O7B
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Record Status |
Validated (UNII)
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Record Version |
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-
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WHO-ATC |
N02BG09
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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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PRIMARY | |||
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C75098
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PRIMARY | |||
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M7337
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PRIMARY | Merck Index | ||
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1048
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PRIMARY | |||
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7201
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PRIMARY | |||
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D008733
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PRIMARY | |||
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7234
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PRIMARY | |||
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METHOXYFLURANE
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1754
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CHEMBL1341
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76-38-0
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200-956-0
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PRIMARY | |||
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1418004
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PRIMARY | USP-RS | ||
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76-38-0
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4116
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30905R8O7B
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SUB08858MIG
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6857
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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TARGET -> AGONIST | |||
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TARGET -> AGONIST |
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 |