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 Methoxyflurane was used for surgical, obstetric, or dental anesthesia, but was withdrawn from US market due to safety concerns, but is still in use in Australia and other countries.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
Renal oxalosis and azotemia after methoxyflurane anesthesia.	1970 Sep 24	5454752
[Halogenated hydrocarbon compounds in anesthesia and their effect on the liver. Liver necrosis and tubulus degeneration after repeated methoxyflurane anesthesia].	1971	5140659
Renal dysfunction associated with methoxyflurane anesthesia. A randomized, prospective clinical evaluation.	1971 Apr 12	5107910
Polyuric acute renal failure after methoxyflurane and tetracycline.	1971 Dec 11	5134563
Hepatorenal failure with renal oxalosis after methoxyflurane anesthesia.	1971 Nov	5286606
Methoxyflurane and renal dysfunction.	1971 Sep 27	5109740
[Renal tubular necrosis and cytolytic hepatitis following repeated anaesthetic inhalation of methoxyflurane].	1972 Jul-Aug	4649400
Combined nephrotoxicity of gentamicin and methoxyflurane anaesthesia in man. A case report.	1973 Apr	4705491
Letter: Partial recovery from renal failure following methoxyflurane anesthesia.	1974 Jan 14	4859609
Unilateral nephrotoxicity associated with methoxyflurane anesthesia: a case report.	1974 Mar-Apr	4856134
A comparison of renal effects and metabolism of sevoflurane and methoxyflurane in enzyme-induced rats.	1975 Nov-Dec	1239223
[Primary hyperoxaluria. Clinical, histological and crystallographic study of the ocular lesions].	1976 Feb	180940
Deuterated methoxyflurane anesthesia and renal function in Fischer 344 rats.	1982 Mar	7059030
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003 Jan 1	12464242
Modulation of T cell function by combination of epitope specific and low dose anticytokine therapy controls autoimmune arthritis.	2006 Dec 20	17183718
Multiple dendritic cell populations activate CD4+ T cells after viral stimulation.	2008 Feb 27	18301768
Isoflavones prevent bone loss following ovariectomy in young adult rats.	2008 Mar 2	18312690
Non-invasive measurements of exhaled NO and CO associated with methacholine responses in mice.	2008 May 27	18505586

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