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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
Structure of METHOXYFLURANE

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

HIDE SMILES / InChI

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

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 Methoxyflurane was used for surgical, obstetric, or dental anesthesia, but was withdrawn from US market due to safety concerns, but is still in use in Australia and other countries.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.
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
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
Health Status: unhealthy
Sex: M
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
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
Health Status: unhealthy
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as victim
PubMed

PubMed

TitleDatePubMed
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
Polyuric acute renal failure after methoxyflurane and tetracycline.
1971 Dec 11
Hepatorenal failure with renal oxalosis after methoxyflurane anesthesia.
1971 Nov
Methoxyflurane and renal dysfunction.
1971 Sep 27
[Renal tubular necrosis and cytolytic hepatitis following repeated anaesthetic inhalation of methoxyflurane].
1972 Jul-Aug
Combined nephrotoxicity of gentamicin and methoxyflurane anaesthesia in man. A case report.
1973 Apr
Letter: Partial recovery from renal failure following methoxyflurane anesthesia.
1974 Jan 14
Unilateral nephrotoxicity associated with methoxyflurane anesthesia: a case report.
1974 Mar-Apr
A comparison of renal effects and metabolism of sevoflurane and methoxyflurane in enzyme-induced rats.
1975 Nov-Dec
[Primary hyperoxaluria. Clinical, histological and crystallographic study of the ocular lesions].
1976 Feb
Deuterated methoxyflurane anesthesia and renal function in Fischer 344 rats.
1982 Mar
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:36:46 GMT 2025
Edited
by admin
on Mon Mar 31 17:36:46 GMT 2025
Record UNII
30905R8O7B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENTHRANE
Preferred Name English
METHOXYFLURANE
GREEN BOOK   HSDB   INN   MART.   MI   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
METHOXIFLURANE
Common Name English
METHOXYFLURANE [USP MONOGRAPH]
Common Name English
2,2-Dichloro-1,1-difluoroethyl methyl ether
Systematic Name English
METHOXYFLURANE [HSDB]
Common Name English
Methoxyflurane [WHO-DD]
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 Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
CFR 21 CFR 216.24
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
NCI_THESAURUS C245
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
WHO-VATC QN02BG09
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
Code System Code Type Description
DRUG BANK
DB01028
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
NCI_THESAURUS
C75098
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
RS_ITEM_NUM
1418004
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
SMS_ID
100000081436
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
MERCK INDEX
m7337
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY Merck Index
INN
1048
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
HSDB
7201
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
CHEBI
6843
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PRIMARY
MESH
D008733
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
IUPHAR
7234
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
WIKIPEDIA
METHOXYFLURANE
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
DRUG CENTRAL
1754
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
ChEMBL
CHEMBL1341
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
EPA CompTox
DTXSID7025556
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-956-0
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
CAS
76-38-0
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
PUBCHEM
4116
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
FDA UNII
30905R8O7B
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
NSC
110432
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
DAILYMED
30905R8O7B
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
EVMPD
SUB08858MIG
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY
RXCUI
6857
Created by admin on Mon Mar 31 17:36:46 GMT 2025 , Edited by admin on Mon Mar 31 17:36:46 GMT 2025
PRIMARY RxNorm
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> AGONIST
TARGET -> AGONIST
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METABOLITE TOXIC -> PARENT
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
METABOLITE TOXIC -> PARENT
Fluoride ion produced clinical toxicity in form of nephrotoxicity in man.
Related Record Type Details
ACTIVE MOIETY