U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of METHOXYFLURANE

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

HIDE SMILES / InChI

Description
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 Methoxyflurane was used for surgical, obstetric, or dental anesthesia, but was withdrawn from US market due to safety concerns, but is still in use in Australia and other countries.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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PENTHROX

Approved Use

For 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

T1/2

ValueDoseCo-administeredAnalytePopulation
5 min
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

Doses

DosePopulationAdverse 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
Other AEs: Renal failure...
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
Health Status: unhealthy
Sex: M
Population Size: 1
Sources:
Disc. AE: Hepatitis...
AEs leading to
discontinuation/dose reduction:
Hepatitis
Sources:
AEs

AEs

AESignificanceDosePopulation
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
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
Health Status: unhealthy
Sex: M
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as victim
PubMed

PubMed

TitleDatePubMed
Renal and hepatic injury associated with methoxyflurane anesthesia.
1968 Dec
Nephropathy associated with methoxyflurane anesthesia. A follow-up report.
1968 Sep 9
Hazards of methoxyflurane emulsions in man.
1968 Sep-Oct
The effect of methoxyflurane on cerebrospinal fluid pressure in patients with and without intracranial space-occupying lesions.
1969 Jul
Nephrogenic diabetes insipidus following methoxyflurane anesthesia. A report of two cases.
1969 Mar-Apr
Hepatic coma associated with methoxyflurane anesthesia. Report of a case.
1970 Aug
Halothane anesthesia following methoxyflurane-induced nephrotoxicity.
1970 Oct
Toxicity following methoxyflurane anesthesia. I. Clinical and pathological observations in two fatal cases.
1970 Oct 5
Renal oxalosis and azotemia after methoxyflurane anesthesia.
1970 Sep 24
[Halogenated hydrocarbon compounds in anesthesia and their effect on the liver. Liver necrosis and tubulus degeneration after repeated methoxyflurane anesthesia].
1971
Renal dysfunction associated with methoxyflurane anesthesia. A randomized, prospective clinical evaluation.
1971 Apr 12
Methoxyflurane anesthesia.
1971 Apr 19
Recurrent hepatitis due to methoxyflurane anesthesia.
1971 Apr 29
Polyuric acute renal failure after methoxyflurane and tetracycline.
1971 Dec 11
Exacerbation of subclinical myasthenia by occupational exposure to an anesthetic.
1971 May-Jun
Hepatorenal failure with renal oxalosis after methoxyflurane anesthesia.
1971 Nov
Methoxyflurane metabolism and renal dysfunction: clinical correlation in man.
1971 Sep
Methoxyflurane and renal dysfunction.
1971 Sep 27
Irreversible acute oliguric renal failure. A complication of methoxyflurane anesthesia.
1972 Apr 20
Renal failure and methoxyflurane. Case report.
1972 Aug
Renal failure after methoxyflurane anaesthesia.
1972 Jan
Repeated methoxyflurane analgesia for burns dressings.
1972 Jun
Dose-related methoxyflurane nephrotoxicity in rats: a biochemical and pathologic correlation.
1972 Jun
Methoxyflurane analgesia for burns dressings.
1972 Mar
Anesthetic malignant myopathy hyperthermia.
1972 Sep
Occasional occurrence of serious renal complications after methoxyflurane (Penthrane) anesthesia.
1973 Aug
Interstitial fibrosis and chronic renal failure following methoxyflurane anesthesia.
1973 Mar 12
Methoxyflurane-induced renal failure.
1973 Nov
Nephrotoxicity associated with use of methoxyflurane. Recovery following severe renal impairment.
1974
Persisting renal insufficiency after methoxyflurane anesthesia. Report of two cases and review of literature.
1974 Apr
Changes in urine osmolality and urine fluoride concentrations following methoxyflurane anaesthesia.
1974 Feb
Letter: Partial recovery from renal failure following methoxyflurane anesthesia.
1974 Jan 14
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
Generalized oxalosis with retinal involvement following methoxyflurane anesthesia.
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
Hepatorenal injury in a dog associated with methoxyflurane (a case report).
1977 Apr
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
In Vitro Use Guide
Unknown
Name Type Language
METHOXYFLURANE
GREEN BOOK   HSDB   INN   MART.   MI   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
METHOXIFLURANE
Common Name English
2,2-DICHLORO-1,1-DIFLUOROETHYL METHYL ETHER
Systematic Name English
METHOXYFLURANE [WHO-DD]
Common Name English
PENTHRANE
Brand Name English
METHOXYFLURANE [HSDB]
Common Name English
METHOXYFLURANE [USP]
Common Name English
METHYL 1,1-DIFLUORO-2,2-DICHLOROETHYL ETHER
Systematic Name English
ETHANE, 2,2-DICHLORO-1,1-DIFLUORO-1-METHOXY-
Systematic Name English
INHALAN
Common Name English
METHOXYFLURANE [USAN]
Common Name English
METHOXYFLURANE [USP-RS]
Common Name English
ANALGIZER
Common Name English
METHOXY FLURANE [JAN]
Common Name English
PENTHROX
Brand Name English
METHOXYFLURANE [INN]
Common Name English
ANECOTAN
Common Name English
METHOXYFLURANE [MART.]
Common Name English
METHOXYFLURANE [GREEN BOOK]
Common Name English
METHOXYFLURANE [MI]
Common Name English
NSC-110432
Code English
METHOXYFLURANE [VANDF]
Common Name English
DA-759
Code English
Classification Tree Code System Code
WHO-ATC N02BG09
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
NCI_THESAURUS C245
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
WHO-VATC QN02BG09
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
Code System Code Type Description
DRUG BANK
DB01028
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
NCI_THESAURUS
C75098
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
MERCK INDEX
M7337
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PRIMARY Merck Index
INN
1048
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
HSDB
7201
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
MESH
D008733
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
IUPHAR
7234
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
WIKIPEDIA
METHOXYFLURANE
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
DRUG CENTRAL
1754
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL1341
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
EPA CompTox
76-38-0
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-956-0
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
USP_CATALOG
1418004
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY USP-RS
CAS
76-38-0
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
PUBCHEM
4116
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
FDA UNII
30905R8O7B
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
EVMPD
SUB08858MIG
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY
RXCUI
6857
Created by admin on Sat Jun 26 04:17:38 UTC 2021 , Edited by admin on Sat Jun 26 04:17:38 UTC 2021
PRIMARY RxNorm