METHOXYFLURANE

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 Search

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 Methoxyflurane was used for surgical, obstetric, or dental anesthesia, but was withdrawn from US market due to safety concerns, but is still in use in Australia and other countries.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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
synaptic transmission 2 Target ID: GO:0007268 Sources: https://www.ncbi.nlm.nih.gov/pubmed/550880	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.medsafe.govt.nz/profs/Datasheet/p/penthroxinh.pdf	Primary		Approved 8583	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

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: https://pubmed.ncbi.nlm.nih.gov/32593381 https://pubmed.ncbi.nlm.nih.gov/3452163/	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/32593381 https://pubmed.ncbi.nlm.nih.gov/3452163/	Other AEs: Renal failure... Other AEs: Renal failure (grade 5, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/32593381 https://pubmed.ncbi.nlm.nih.gov/3452163/
2 mL 2 times / day multiple, respiratory Dose: 2 mL, 2 times / day Route: respiratory Route: multiple Dose: 2 mL, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3971205	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3971205	Disc. AE: Hepatitis... AEs leading to discontinuation/dose reduction: Hepatitis Sources: https://pubmed.ncbi.nlm.nih.gov/3971205

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: https://pubmed.ncbi.nlm.nih.gov/32593381 https://pubmed.ncbi.nlm.nih.gov/3452163/	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/32593381 https://pubmed.ncbi.nlm.nih.gov/3452163/
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: https://pubmed.ncbi.nlm.nih.gov/3971205	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3971205

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946		substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2E1 729 CYP1A2 1197 CYP2A6 626 CYP2B6 776

Drug as victim

Target	Modality	Activity
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8214760/	major
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8214760/	minor
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8214760/	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/7879937/	yes
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/7879937/	yes
CYP3A4 1946	substrate 4014 Sources: DOI: 10.1097/00000542-199503000-00011	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6843	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6843
ChemicalBook	CB6314297	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6314297
eMolecules	891340	https://www.emolecules.com/cgi-bin/more?vid=891340
MolPort	MolPort-000-153-984	https://www.molport.com/shop/molecule-link/MolPort-000-153-984
ZINC	ZINC000000896988	http://zinc15.docking.org/substances/ZINC000000896988

PubMed

Title	Date	PubMed
Human kidney methoxyflurane and sevoflurane metabolism. Intrarenal fluoride production as a possible mechanism of methoxyflurane nephrotoxicity.	1995-03	7879937
[Massive oxalosis of the kidney in association with anesthesia using methoxyflurane].	1984-08	6499021
Methoxyflurane hepatitis: two cases following obstetric analgesia.	1983-02	6133801
Hepatitis and renal tubular acidosis after anesthesia with methoxyflurane.	1982-10-01	6985498
Deuterated methoxyflurane anesthesia and renal function in Fischer 344 rats.	1982-03	7059030
Hepatic and renal effects of low concentrations of methoxyflurane in exposed delivery ward personnel.	1980-12	7218059
[Adverse effects of modern inhalation anesthetics. 2. Control of amounts and elimination of escaping anesthesia gases].	1978-12-14	721016
Methoxyflurane-induced nephrotoxicity: influence of food intake on some biochemical indicators of renal function in Fischer 344 rats.	1978-09	725934
Anesthetic indices--further data.	1978-03	626424
Methoxyflurane hepatitis.	1977-11	918705
Hepatorenal injury in a dog associated with methoxyflurane (a case report).	1977-04	585515
Influence of phenobarbital pretreatment on methoxyflurane and sodium fluoride nephropathy in Fischer 344 Rats.	1976-08	982456
The effect of enflurane, isoflurane, fluroxene, methoxyflurane and diethyl ether anesthesia on ouabain tolerance in the dog.	1976-05-01	5922
Generalized oxalosis with retinal involvement following methoxyflurane anesthesia.	1974-09	4852146
Incidence of tubular degeneration with microlithiasis following methoxyflurane compared with other anesthetic agents.	1974-05-01	4856932
Methoxyflurane nephropathy.	1974-05	4829511
Persisting renal insufficiency after methoxyflurane anesthesia. Report of two cases and review of literature.	1974-04	4818422
Unilateral nephrotoxicity associated with methoxyflurane anesthesia: a case report.	1974-03-01	4856134
The syndrome of methoxyflurane-associated hepatitis.	1974-03	4816183
Changes in urine osmolality and urine fluoride concentrations following methoxyflurane anaesthesia.	1974-02	4834480
Letter: Partial recovery from renal failure following methoxyflurane anesthesia.	1974-01-14	4859609
Nephrotoxicity associated with use of methoxyflurane. Recovery following severe renal impairment.	1974	4853325
Methoxyflurane-induced renal failure.	1973-11	4767174
Occasional occurrence of serious renal complications after methoxyflurane (Penthrane) anesthesia.	1973-08	4722675
Interstitial fibrosis and chronic renal failure following methoxyflurane anesthesia.	1973-03-12	4739327
Anesthetic malignant myopathy hyperthermia.	1972-09	5081936
Renal failure and methoxyflurane. Case report.	1972-08	5083024
Repeated methoxyflurane analgesia for burns dressings.	1972-06	5045566
Dose-related methoxyflurane nephrotoxicity in rats: a biochemical and pathologic correlation.	1972-06	5033780
Irreversible acute oliguric renal failure. A complication of methoxyflurane anesthesia.	1972-04-20	5061073
Methoxyflurane analgesia for burns dressings.	1972-03	5024149
Renal failure after methoxyflurane anaesthesia.	1972-01	5007641
Polyuric acute renal failure after methoxyflurane and tetracycline.	1971-12-11	5134563
Hepatorenal failure with renal oxalosis after methoxyflurane anesthesia.	1971-11	5286606
Methoxyflurane and renal dysfunction.	1971-09-27	5109740
Methoxyflurane metabolism and renal dysfunction: clinical correlation in man.	1971-09	5095537
Exacerbation of subclinical myasthenia by occupational exposure to an anesthetic.	1971-05-01	5103772
Recurrent hepatitis due to methoxyflurane anesthesia.	1971-04-29	5551804
Methoxyflurane anesthesia.	1971-04-19	5107940
Renal dysfunction associated with methoxyflurane anesthesia. A randomized, prospective clinical evaluation.	1971-04-12	5107910
[Halogenated hydrocarbon compounds in anesthesia and their effect on the liver. Liver necrosis and tubulus degeneration after repeated methoxyflurane anesthesia].	1971	5140659
Toxicity following methoxyflurane anesthesia. I. Clinical and pathological observations in two fatal cases.	1970-10-05	5469063
Halothane anesthesia following methoxyflurane-induced nephrotoxicity.	1970-10	5525298
Renal oxalosis and azotemia after methoxyflurane anesthesia.	1970-09-24	5454752
Hepatic coma associated with methoxyflurane anesthesia. Report of a case.	1970-08	5455938
The effect of methoxyflurane on cerebrospinal fluid pressure in patients with and without intracranial space-occupying lesions.	1969-07	5798834
Nephrogenic diabetes insipidus following methoxyflurane anesthesia. A report of two cases.	1969-03-01	5813072
Renal and hepatic injury associated with methoxyflurane anesthesia.	1968-12	5725736
Nephropathy associated with methoxyflurane anesthesia. A follow-up report.	1968-09-09	5695293
Hazards of methoxyflurane emulsions in man.	1968-09-01	4876884

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

PENTHRANE

Preferred Name

English

METHOXYFLURANE

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