Page last updated: 2024-12-05

methoxyflurane

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Description

Methoxyflurane is a general anesthetic, commonly used for its fast onset of action and its relative safety. It was synthesized in 1954, Its mechanism of action involves enhancing inhibitory neurotransmission by potentiating the effects of GABA at GABA receptors. Methoxyflurane is metabolized by the liver and excreted in the urine. While effective, its use has decreased due to concerns over potential hepatotoxicity, leading to its limited use in modern anesthesia. However, it remains studied for its potential application in veterinary anesthesia and its use in controlled environments, Due to its unique properties and potential applications, methoxyflurane continues to be a subject of research.'
```

angiotensin II amide: a diuretic peptide; from the central nervous system of the leech Erpobdella octoculata [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Methoxyflurane: An inhalation anesthetic. Currently, methoxyflurane is rarely used for surgical, obstetric, or dental anesthesia. If so employed, it should be administered with NITROUS OXIDE to achieve a relatively light level of anesthesia, and a neuromuscular blocking agent given concurrently to obtain the desired degree of muscular relaxation. (From AMA Drug Evaluations Annual, 1994, p180) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

methoxyflurane : An ether in which the two groups attached to the central oxygen atom are methyl and 2,2-dichloro-1,1-difluoroethyl. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5890
MeSH IDM0013605
PubMed CID4116
CHEMBL ID1341
CHEBI ID6843
SCHEMBL ID121229
MeSH IDM0013605

Synonyms (114)

Synonym
D02939
angiotensin amide (usan)
angiotensinamide (inn)
5-valine-angiotensin ii-.beta.-amide
l-phenylalanine, n-[1-[n-[n-[n-[n-(n(sup2)-l-asparaginyl-l-arginyl)-l-valyl]-l-tyrosyl]-l-valyl]-l-histidyl]-l-prolyl]-
5-valine-angiotensin ii aspartic-.beta.-amide
angiotensin ii aspartic-.beta.-amide, 5-l-valine
nsc107678
1-l-asparagine-5-l-valine-angiotensin ii
angiotensin (ciba)
1-aspartic acid-.beta.-amide 5-valine-angiotensin ii
angiotensin ii amide
[1-asparagine-5-valine]-angiotensin ii
angiotensinamid
bdbm410295
us10370388, compound angiotensin
ethane, 2,2-dichloro-1,1-difluoro-1-methoxy-
pentran
metofane
2,1-difluoro-1-methoxyethane
76-38-0
inhalan
nsc-110432
ether,2-dichloro-1,1-difluoroethyl methyl
ethane,2-dichloro-1,1-difluoro-1-methoxy-
methoxyfluran
metoxifluran
pentrane
2,1-difluoroethyl methyl ether
anecotan
methoflurane
methoxane
metoxfluran
analgizer
nsc110432
methofane
methoxyflurane
penthrane
wln: gygxffo1
metofane (van)
penthrane (van)
einecs 200-956-0
methofluranum
methoxifluranum
ingalan
ccris 5840
metossiflurano [dcit]
methoxyfluranum [inn-latin]
methoxyflurane [anaesthetics, volatile]
2,2-dichloro-1,1-difluoroethyl methyl ether
ether, 2,2-dichloro-1,1-difluoroethyl methyl
hsdb 7201
metoxiflurano [inn-spanish]
brn 1737766
C07517
methyl 1,1-difluoro-2,2-dichloroethyl ether
DB01028
methoxyfluoran
D00544
methoxyflurane (usp/inn)
penthrane (tn)
2,2-dichloro-1,1-difluoro-1-methoxyethane
NCGC00168747-01
penthrox
chebi:6843 ,
methoxiflurane
methoxy flurane
CHEMBL1341
da-759
tox21_112626
dtxsid7025556 ,
cas-76-38-0
dtxcid405556
(2,2-dichloro-1,1-difluoroethyl) methyl ether
AKOS006228995
methoxyfluorane
metoxiflurano
metossiflurano
30905r8o7b ,
methoxyfluranum
methoxyflurane [usan:usp:inn:ban]
unii-30905r8o7b
gtpl7234
methoxy flurane [jan]
methoxyflurane [hsdb]
methoxyflurane [usan]
methoxyflurane [vandf]
methoxyflurane [green book]
methoxyflurane [usp-rs]
methoxyflurane [mi]
methoxyflurane [who-dd]
methoxyflurane [usp monograph]
methoxyflurane [inn]
methoxyflurane [mart.]
SCHEMBL121229
KS-5167
2,2-dichloro-1,1-difluoroethylmethylether
benzenepropanoic acid, 4-methoxy-.alpha.-oxo-
mfcd00040144
SR-01000944693-1
sr-01000944693
Q411594
CS-0009624
HY-B0718
methoxyflurane (usan:usp:inn:ban)
1,1-difluoro-2,2-dichloroethyl methyl ether
methoxyflurane (mart.)
methoxyflurane (usp-rs)
metoxiflurano (inn-spanish)
methoxyflurane (usp monograph)
n02bg09
da759
methoxyfluranum (inn-latin)
Z1201617823

Research Excerpts

Overview

Methoxyflurane is an inhalation analgesic used in the emergency department (ED) but also has minimal sedative properties. It is self-administered in a controlled low dose from the Penthrox(®) inhaler for short-term pain relief.

ExcerptReferenceRelevance
"Methoxyflurane is an historical anaesthetic agent that has undergone a renaissance with the introduction of a smaller dose in a handheld 'Penthrox' device. "( Penthrox enables quicker management of fractures, dislocations and more: learning lessons from expedited care of trauma patients during the COVID-19 pandemic.
Angel, CK; Brennan, C; Dias, A; Gray Stephens, C; Middleton, RG; Skinner, E, 2023
)
2.35
"Methoxyflurane (MTX) is an inhalation agent that has several potential benefits for limiting various types of pain in ambulance care."( Ambulance nurses' experiences of pain management with Penthrox® in Swedish ambulance care: A mixed method study.
Ivarsson, B; Johansson, A; Svensson, A; Wihlborg, J, 2023
)
2.35
"Methoxyflurane is a fluorinated hydrocarbon gas which has analgesic properties when inhaled."( Inhaled methoxyflurane (Penthrox) for analgesia in trauma: a systematic review protocol.
Eager, MM; Nolan, GS; Ramjeeawon, A; Taylor, N; Tonks, K, 2021
)
1.78
"Methoxyflurane is a volatile, fluorinated anesthetic agent with analgesic properties. "( Methoxyflurane for Procedural Analgesia at 4470 m Altitude.
Heath, EC; Mason, NP; Wilkes, M, 2018
)
3.37
"Methoxyflurane is an inhalation analgesic used in the emergency department (ED) but also has minimal sedative properties. "( Inhaled methoxyflurane for the reduction of acute anterior shoulder dislocation in the emergency department.
Blom, CJ; Kelliher, JH; McNicholl, B; Umana, E, 2019
)
2.39
"Methoxyflurane is a volatile, halogenated analgesic, self-administered in a controlled low dose from the Penthrox(®) inhaler for short-term pain relief. "( Analgesic use of inhaled methoxyflurane: Evaluation of its potential nephrotoxicity.
Dayan, AD, 2016
)
2.18
"Methoxyflurane is an anesthetic whose metabolism by cytochrome P-450LM2 has been shown to be dependent upon a heat-stable microsomal protein (Canova-Davis, E., and Waskell, L. "( The identification of the heat-stable microsomal protein required for methoxyflurane metabolism as cytochrome b5.
Canova-Davis, E; Waskell, L, 1984
)
1.94
"Methoxyflurane appears to be an enzyme-inducing agent similar to spironolactone, whereas enflurane does not appear to be an inducing agent for any of the enzymes studied."( Do methoxyflurane and enflurane induce hepatic drug-metabolizing enzymes?
Harrison, GG; Ivanetich, KM; Lucas, SA; Marsh, JA, 1979
)
1.6

Effects

Methoxyflurane has been used for general anesthesia at The Montreal Children's Hospital since its clinical introduction in 1960. It has been administered to more than 5000 patients undergoing most types of pediatric operations.

ExcerptReferenceRelevance
"Methoxyflurane has a high blood/gas partition coefficient and a low vapor pressure. "( Precautions when using methoxyflurane.
Dyson, D, 1992
)
2.04
"Methoxyflurane has been used for general anesthesia at The Montreal Children's Hospital since its clinical introduction in 1960, and has been administered to more than 5000 patients undergoing most types of pediatric operations. "( METHOXYFLURANE ANESTHESIA IN PEDIATRICS: A CLINICAL REPORT.
DAVENPORT, HT; QUAN, P, 1964
)
3.13
"Methoxyflurane (Metofane) has been widely used as an open-circuit anaesthetic in small laboratory animals for several decades. "( A replacement for methoxyflurane (Metofane) in open-circuit anaesthesia.
Davis, C; Gitelman, I; Itah, R, 2004
)
2.1
"Methoxyflurane has been demonstrated to produce renal dysfunction when administered in high concentrations for prolonged periods of time to obese patients."( Effects of anesthetics on the kidney.
Deutsch, S, 1975
)
0.98
"Methoxyflurane has a high blood/gas partition coefficient and a low vapor pressure. "( Precautions when using methoxyflurane.
Dyson, D, 1992
)
2.04

Treatment

ExcerptReferenceRelevance
"Methoxyflurane treatment was rated 'Excellent', 'Very Good' or 'Good' by 77.6% of patients, 74.5% of physicians and 72.5% of nurses."( Methoxyflurane Analgesia in Adult Patients in the Emergency Department: A Subgroup Analysis of a Randomized, Double-blind, Placebo-controlled Study (STOP!).
Coffey, F; Dissmann, P; Lomax, M; Mirza, K, 2016
)
2.6

Toxicity

Methoxyflurane was well tolerated, with the majority of adverse reactions being mild, transient and in line with anticipated pharmacological action. Adverse events (all non-serious) were reported by 17% of methoxy flurane- treated patients and 3% of SAT-treated patients.

ExcerptReferenceRelevance
" The occasionally observed liver and kidney injuries indicate a potential formation of toxic metabolites."( [The biotransformation of inhalation anaesthetics and its relevance to clinical side effects (author's transl)].
Rietbrock, I, 1975
)
0.25
" The possibility that methoxyflurane increases alcohol dehydrogenase-dependent oxidation of allyl alcohol to acrolein, the proposed toxic metabolite, was evaluated by measuring the rate of acrolein formation in the presence of allyl alcohol and liver cytosol."( Methoxyflurane enhances allyl alcohol hepatotoxicity in rats. Possible involvement of increased acrolein formation.
Barsotti, DA; Dent, JG; Kershaw, WC; Lage, GL; Leonard, TB,
)
1.89
" No adverse effects on reproduction or fetal development were demonstrated following exposure to trace (2 ppm) and subanesthetic (60 ppm) concentrations of methoxyflurane for 4 hours daily on days 6 through 15 of pregnancy."( Developmental toxicity of methoxyflurane in mice.
Mazze, RI; Sievenpiper, TS; Wharton, RS, 1980
)
0.76
"Methoxyflurane nephrotoxicity is mediated by cytochrome P450-catalyzed metabolism to toxic metabolites."( Human kidney methoxyflurane and sevoflurane metabolism. Intrarenal fluoride production as a possible mechanism of methoxyflurane nephrotoxicity.
Hankins, DC; Kharasch, ED; Thummel, KE, 1995
)
2.1
" This was followed by toxic effects on peritoneal organs and surfaces, except for sevoflurane, which did not produce any lesions."( Fluorinated anesthetics differ in toxic effects on peritoneum and subjacent tissues.
Levine, S; Saltzman, A,
)
0.13
"Methoxyflurane nephrotoxicity results from biotransformation; inorganic fluoride is a toxic metabolite."( New insights into the mechanism of methoxyflurane nephrotoxicity and implications for anesthetic development (part 1): Identification of the nephrotoxic metabolic pathway.
Kharasch, ED; Liggitt, HD; Park, SB; Schroeder, JL; Sheffels, P; Whittington, D, 2006
)
2.05
" Phenobarbital increases in methoxyflurane toxicity do not seem attributable to methoxyflurane dechlorination, MDFA toxicity, or MDFA metabolism to another toxic metabolite, suggesting that nephrotoxicity is attributable to methoxyflurane O-demethylation."( New insights into the mechanism of methoxyflurane nephrotoxicity and implications for anesthetic development (part 1): Identification of the nephrotoxic metabolic pathway.
Kharasch, ED; Liggitt, HD; Park, SB; Schroeder, JL; Sheffels, P; Whittington, D, 2006
)
0.9
" Fluoride is one of many methoxyflurane metabolites and may itself cause toxicity and/or reflect formation of other toxic metabolite(s)."( New insights into the mechanism of methoxyflurane nephrotoxicity and implications for anesthetic development (part 2): Identification of nephrotoxic metabolites.
Ensign, D; Kharasch, ED; Liggitt, HD; Schroeder, JL; Whittington, D, 2006
)
0.91
" Because their co-formation is unique to methoxyflurane compared with other volatile anesthetics and they are more toxic than fluoride alone, this suggests a new hypothesis of methoxyflurane nephrotoxicity."( New insights into the mechanism of methoxyflurane nephrotoxicity and implications for anesthetic development (part 2): Identification of nephrotoxic metabolites.
Ensign, D; Kharasch, ED; Liggitt, HD; Schroeder, JL; Whittington, D, 2006
)
0.88
"This article reviews the evidence for the analgesic efficacy of methoxyflurane in both prehospital and ED settings, as well as the adverse event profile associated with methoxyflurane use."( Review article: Efficacy and safety of methoxyflurane analgesia in the emergency department and prehospital setting.
Babl, FE; Grindlay, J, 2009
)
0.86
"MEOF was safe and performed better than placebo for analgesia in BMB procedures."( A randomised, double-blind, placebo-controlled study to assess the safety and efficacy of methoxyflurane for procedural pain of a bone marrow biopsy.
Bressel, M; Milner, A; Spruyt, O; Wein, S; Westerman, D, 2014
)
0.62
" Methoxyflurane was well tolerated, with the majority of adverse reactions being mild, transient and in line with anticipated pharmacological action."( STOP!: a randomised, double-blind, placebo-controlled study of the efficacy and safety of methoxyflurane for the treatment of acute pain.
Coffey, F; Dissmann, P; Hartshorn, S; Hunt, P; Locker, T; Mirza, K; Wright, J, 2014
)
1.53
" The pathogenesis of the renal damage and clinical use of methoxyflurane are discussed here with evidence that a low but effective analgesic dose is not associated with the risk of renal adverse effects."( Analgesic use of inhaled methoxyflurane: Evaluation of its potential nephrotoxicity.
Dayan, AD, 2016
)
0.98
" Adverse events (all non-serious) were reported by 17% of methoxyflurane-treated patients and 3% of SAT-treated patients."( Analgesic Efficacy, Practicality and Safety of Inhaled Methoxyflurane Versus Standard Analgesic Treatment for Acute Trauma Pain in the Emergency Setting: A Randomised, Open-Label, Active-Controlled, Multicentre Trial in Italy (MEDITA).
Bonafede, E; Carpinteri, G; Fabbri, A; Farina, A; Gangitano, G; Intelligente, F; Mercadante, S; Ruggiano, G; Sblendido, A; Serra, S; Soldi, A; Voza, A, 2019
)
1.01
" Moreover, patients will be actively monitored with regard to the occurrence of side effects of evaluated therapies, as well as adverse events that may be related to insufficient platelet inhibition (no-reflow phenomenon assessed immediately after PCI, administration of GPIIb/IIIa inhibitors during PCI, acute stent thrombosis)."( ANalgesic Efficacy and safety of MOrphiNe versus methoxyflurane in patients with acute myocardial infarction: the rationale and design of the ANEMON-SIRIO 3 study: a multicentre, open-label, phase II, randomised clinical trial.
Adamski, P; Buszko, K; Gasior, M; Gorący, J; Kleinrok, A; Kosobucka, A; Kubica, A; Kubica, J; Lesiak, M; Nadolny, K; Navarese, E; Niezgoda, P; Wojakowski, W, 2021
)
0.88
" Single analgesic doses in modern use generally appear safe for patients."( Methoxyflurane toxicity: historical determination and lessons for modern patient and occupational exposure.
Allison, SJ; Chase, JG; Docherty, PD; Pons, D, 2021
)
2.06
" There were no observed adverse events."( Efficacy and safety of methoxyflurane (Penthrox) for pain control during water vapor thermal therapy (Rezum) for benign prostatic enlargement.
Bhojani, N; Chughtai, B; Elterman, DS; Zorn, KC, 2022
)
1.03

Pharmacokinetics

ExcerptReferenceRelevance
" The effects of methoxyflurane anesthesia, administration of atropine with and without diazepam were determined on the serum half-life (t1/2), clearance rate (CL), and the volume of distribution (Vd) following intramuscular (IM) administration of HI-6 (30 mg kg-1)."( Pharmacokinetics of the acetylcholinesterase oxime reactivator, HI-6, in rhesus monkeys (Macaca mulatta): effect of atropine, diazepam, and methoxyflurane anesthesia.
Briggs, CJ; Clement, JG; Lee, MJ; Simons, KJ, 1990
)
0.83

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

Methoxyflurane shifted the 5-HT dose-response curve. renal abnormalities did not occur except in rats treated also with phenobarbital; these animals developed polyuria and morphologic lesion typically associated with F--induced nephrotoxicity.

ExcerptRelevanceReference
" Ouabain dosage needed to cause ventricular tachycardia was significantly higher than that of pentobarbital with all agents except fluroxene, as was the LD50."( The effect of enflurane, isoflurane, fluroxene, methoxyflurane and diethyl ether anesthesia on ouabain tolerance in the dog.
Albrecht, RF; Cairoli, VJ; El-Etr, AA; Grossman, RK; Ivankovich, AD; Miletich, DJ,
)
0.39
" When the data were normalized for anesthetic potency, all agents exhibited a parallel dose-response curve."( In vitro inhibition of rho-aminohippurate transport by halogenated anesthetics.
Bastron, RD; Kaloyanides, GJ; Perkins, FM, 1977
)
0.26
" The dose-response curves in all anesthetics remained unaltered in the presence of either 3 x 10(-7) M dl-propranolol or 1 x 10(-6) M atropine."( Mechanisms of chronotropic effects of volatile inhalation anesthetics.
Krisna, G; Paradise, RR,
)
0.13
")Key workd: Potency, anesthetic, MAC, AD50, AD95; Pharmacology, dose-response curves."( MAC expanded: AD50 and AD95 values of common inhalation anesthetics in man.
de Jong, RH; Eger, EI, 1975
)
0.25
"The arrhythmogenic dosage of epinephrine, administered by constant intravenous infusion, was measured in five dogs during enflurane, methoxyflurane and halothane anaesthesia."( Doses of epinephrine causing arrhythmia during enflurane, methoxyflurane and halothane anaesthesia in dogs.
Munson, ES; Tucker, WK, 1975
)
0.7
" The predominant factors in the production of methoxyflurane nephrotoxicity appear to be high methoxyflurane dosage and serum inorganic fluoride concentration."( Methoxyflurane nephropathy.
Mazze, RI, 1976
)
1.96
" Methoxyflurane dosage was sufficiently low that renal abnormalities did not occur except in rats treated also with phenobarbital; these animals developed polyuria and the morphologic lesion typically associated with F--induced nephrotoxicity."( A comparison of renal effects and metabolism of sevoflurane and methoxyflurane in enzyme-induced rats.
Beppu, WJ; Cook, TL; Hitt, BA; Kosek, JC; Mazze, RI,
)
1.28
" The methoxydifluoroacetate is largely excreted without further metabolism, although a small percentage of this metabolite is broken down to yield fluoride and oxalate, as determined by urine analysis of rats dosed with synthetic methoxydifluoroacetate."( In vivo nuclear magnetic resonance studies of hepatic methoxyflurane metabolism. II. A reevaluation of hepatic metabolic pathways.
London, RE; Perlman, ME; Selinsky, BS, 1988
)
0.52
"Three weeks after dosing male Fischer 344 rats with streptozotocin to induce diabetes, enflurane was administered ip, and 1 h later, fluoride levels were measured in plasma and livers were removed."( Effect of streptozotocin-induced diabetes in the rat on the metabolism of fluorinated volatile anesthetics.
Conney, AH; Pantuck, CB; Pantuck, EJ, 1987
)
0.27
" When administered over the dosage range 1-16% (v/v) intradermally, or by injections into muscle, or by repeat injections every 4 days for 16 days, all animals regained their pretreatment response to painful stimulations, and there was no evidence of gross injury to tissue."( Ultra-long-duration local anesthesia produced by injection of lecithin-coated methoxyflurane microdroplets.
Haynes, DH; Kirkpatrick, AF, 1985
)
0.5
" Except for a greater respiratory gas flow and inspiratory-expiratory gas flow ratio and a lesser inspiratory-expiratory time ratio with methoxyflurane, there was no anesthetic- or dose-response effect on respiratory variables."( Circulatory and respiratory effects of methoxyflurane in dogs: comparison of halothane.
Farver, TB; Steffey, EP; Woliner, MJ, 1984
)
0.74
" The effects of various isoniazid dosage regimens on the hepatic microsomal defluorination rates of enflurane were compared with those of several other ether anesthetics, and the conditions for production of maximal enflurane defluorination rates were determined."( Metabolism by rat hepatic microsomes of fluorinated ether anesthetics following isoniazid administration.
Mazze, RI; Rice, SA; Sbordone, L, 1980
)
0.26
" Methoxyflurane shifted the 5-HT dose-response curve to lower 5-HT concentrations, without significantly changing the Hill coefficient or maximum response."( Actions of general anaesthetics on 5-HT3 receptors in N1E-115 neuroblastoma cells.
Franks, NP; Jenkins, A; Lieb, WR, 1996
)
1.2
" The addition of methoxyflurane significantly potentiated the anaesthetic and analgesic properties of the high dosage ketamine-xylazine combination."( Evaluation of anaesthetic regimens in guineapigs.
Crenshaw, D; Hinson, A; Radde, GR; Toth, LA, 1996
)
0.63
" The different relative positions of the dose-response curves for EEG and MLAEP changes compared with antinociception (MAC) changes suggest differences in the mechanisms of action of these three agents."( Comparison of the effects of halothane, isoflurane and methoxyflurane on the electroencephalogram of the horse.
Johnson, CB; Taylor, PM, 1998
)
0.55
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
inhalation anaestheticnull
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
hepatotoxic agentA role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
nephrotoxic agentA role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
Ethanol metabolism resulting in production of ROS by CYP2E1117
Ethanol metabolism production of ROS by CYP2E1117

Bioassays (51)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID496826Antimicrobial activity against Entamoeba histolytica2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID496818Antimicrobial activity against Trypanosoma brucei brucei2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID496825Antimicrobial activity against Leishmania mexicana2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID496824Antimicrobial activity against Toxoplasma gondii2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID107968Evaluated in vitro for anesthetic activity in man and minimum alveolar concentration (MAC) was determined1982Journal of medicinal chemistry, Jul, Volume: 25, Issue:7
Hydrogen bonding and anesthetic potency.
AID496831Antimicrobial activity against Cryptosporidium parvum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID497005Antimicrobial activity against Pneumocystis carinii2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID603950In-vitro air to lung partition coefficients of the compound, logK(lung) (human/rat)2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID496828Antimicrobial activity against Leishmania donovani2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID496830Antimicrobial activity against Leishmania major2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID496832Antimicrobial activity against Trypanosoma brucei rhodesiense2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID496823Antimicrobial activity against Trichomonas vaginalis2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID409952Inhibition of human brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID496829Antimicrobial activity against Leishmania infantum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID496820Antimicrobial activity against Trypanosoma brucei2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID112346Evaluated in vitro for anesthetic activity in mice and ED50 value was reported1982Journal of medicinal chemistry, Jul, Volume: 25, Issue:7
Hydrogen bonding and anesthetic potency.
AID496817Antimicrobial activity against Trypanosoma cruzi2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID496819Antimicrobial activity against Plasmodium falciparum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID28398Partition coefficient was determined in oil/gas system and value was reported1982Journal of medicinal chemistry, Jul, Volume: 25, Issue:7
Hydrogen bonding and anesthetic potency.
AID59016Evaluated in vitro for anesthetic activity in dog and minimum alveolar concentration (MAC) was determined1982Journal of medicinal chemistry, Jul, Volume: 25, Issue:7
Hydrogen bonding and anesthetic potency.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID603952In-vitro blood to lung partition coefficients of the compound, logP(lung) (human/rat)2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID496827Antimicrobial activity against Leishmania amazonensis2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID603951In-vitro air to blood partition coefficients of the compound, logK(blood) (human/rat)2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.
AID409947Inhibition of human recombinant MAOB at 1 mM by fluorimetric method2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID496821Antimicrobial activity against Leishmania2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,724)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901547 (89.73)18.7374
1990's65 (3.77)18.2507
2000's24 (1.39)29.6817
2010's45 (2.61)24.3611
2020's43 (2.49)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 79.07

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index79.07 (24.57)
Research Supply Index7.68 (2.92)
Research Growth Index4.79 (4.65)
Search Engine Demand Index142.53 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (79.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials70 (3.34%)5.53%
Reviews0 (0.00%)6.00%
Reviews130 (6.20%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies47 (2.24%)4.05%
Observational0 (0.00%)0.25%
Observational5 (0.24%)0.25%
Other8 (100.00%)84.16%
Other1,844 (87.98%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (22)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Determination of Analgesic Equipotent Doses of Inhaled Metoxyflurane vs. Intravenous Fentanyl Using Cold Pressor Test (CPT) in Volunteers: A Randomized, Double Blind, Placebo-controlled Crossover Study. [NCT03894800]Phase 412 participants (Actual)Interventional2019-04-23Completed
A Phase IV Real World Study on the Use of Low Dose Methoxyflurane (PENTHROX™) for the Treatment of Moderate to Severe Trauma Pain in the Canadian Emergency Department [NCT03868436]Phase 499 participants (Actual)Interventional2019-04-08Completed
An Open-Label Study to Assess the Efficacy and Safety of Low Dose Methoxyflurane (PENTHROX®) for Pain Control During Outpatient Aesthetic Surgeries and Facial Filler Injections [NCT04292808]0 participants (Actual)Interventional2020-07-31Withdrawn(stopped due to Covid caused too many delays)
Use of Methoxyflurane (Penthrox) as an Antalgic in Hospital Trauma [NCT03927729]34 participants (Actual)Interventional2019-06-07Completed
MethOxyflUraNe at moderaTe High AltItudes for PAIN Management: A Randomised, Double-blind, Cross-over Study [NCT03849027]Phase 424 participants (Anticipated)Interventional2019-05-31Not yet recruiting
METHOXYFLURANE or Virtual Reality Headset vs Standard Analgesic Management for the Reduction of Anterior Shoulder Dislocation [NCT05821517]Phase 4150 participants (Anticipated)Interventional2023-05-01Recruiting
Multicentre, Randomised, Double-blind Study Assessing the Efficacy and Safety of Penthrox® Combined With a Standard Analgesia (SoC) in Comparison to a Placebo Combined With a Standard Analgesia (SoC) in Adult Patients Admitted to the Emergency Department [NCT03798899]Phase 4360 participants (Actual)Interventional2018-05-14Completed
Pilot Study to Assess the Feasibility of Self-administered Low Dose Methoxyflurane for Pain Relief During Minor Out-patient Urologic Procedures [NCT04412642]Phase 410 participants (Anticipated)Interventional2020-05-31Not yet recruiting
A Randomized Controlled, Open-label, Non-inferiority, Three Arm Clinical Study to Assess Inhalation of Low-dose Methoxyflurane, Intranasal Fentanyl, and Intravenous Morphine for Acute Pain in the Pre-hospital Setting [NCT05137184]Phase 3338 participants (Actual)Interventional2021-11-12Completed
Reduction of Anterior Shoulder Dislocation Facilitated by Inhaled Low Dose Methoxyflurane - a Pilot Study [NCT03853954]20 participants (Actual)Interventional2019-06-01Completed
A Phase 3 Double-blind Placebo-controlled Randomized Trial of Methoxyflurane With Periprostatic Local Anaesthesia to Reduce the Discomfort of Transrectal Ultrasound-guided Prostate Biopsy [NCT02604225]Phase 3420 participants (Actual)Interventional2015-12-31Completed
A Pilot Study on the Use of Methoxyflurane (Penthrox®) for Pain Control in the Emergency Department [NCT04618497]Phase 340 participants (Actual)Interventional2020-10-28Completed
ANalgesic Efficacy and Safety of MOrphiNe Versus Methoxyflurane in Patients With Acute Myocardial Infarction [NCT04476173]Phase 3200 participants (Anticipated)Interventional2020-06-01Recruiting
Influence of METHoxyflurane on ANtiplatelet Effect of Ticagrelor in Patients With Unstable Angina Pectoris - METHANE Study [NCT04442919]Phase 475 participants (Anticipated)Interventional2020-06-01Recruiting
A Randomised, Double Blind, Multi-centre, Placebo Controlled Study to Evaluate the Efficacy and Safety of Methoxyflurane (Penthrox) for the Treatment of Acute Pain in Patients Presenting to an Emergency Department With Minor Trauma [NCT01420159]Phase 3300 participants (Actual)Interventional2011-08-31Completed
A Phase IV, Randomized, Double Blind, Single Centre, Placebo Controlled Study to Assess the Safety and Efficacy of Methoxyflurane [Penthrox] for the Treatment of Incident Pain in Participants Undergoing a Bone Marrow Biopsy Procedure [NCT00524927]Phase 4110 participants (Anticipated)Interventional2007-09-30Completed
Evaluation of Occupational Exposure of Methoxyflurane to Paramedics in the Back of an Ontario, Canada Approved Ambulance. [NCT05766397]Phase 430 participants (Anticipated)Interventional2023-04-30Not yet recruiting
Efficacy and Safety of Methoxyflurane Vaporized (PENTHROX®) in the Treatment of Acute Trauma Pain in Pre-hospital Setting and in the Emergency Department in Italy: a Multicentre, Randomized, Controlled, Open-label Study [NCT03585374]Phase 3272 participants (Actual)Interventional2018-02-08Completed
Prehospital Analgesia in Adults Using Inhaled (PAIN) Methoxyflurane : A Feasibility Study [NCT04287803]Phase 497 participants (Actual)Interventional2021-04-12Completed
A Pilot Study to Assess Efficacy and Safety of Methoxyflurane for Pain Control During Convective Thermal Therapy Using Rezūm System in Benign Prostatic Hyperplasia (BPH) [NCT04029012]Phase 410 participants (Actual)Interventional2019-09-10Completed
A Randomised, Double-blind, Multicentre, Placebo Controlled Study to Evaluate the Safety and Efficacy of Methoxyflurane (PENTHROX®) for the Treatment of Acute Pain in Children and Adolescents From 6 to Less Than 18 Years of Age (Presenting to an Emergency [NCT03215056]Phase 3222 participants (Anticipated)Interventional2017-06-30Recruiting
Open Randomized Clinical Trial to Compare Pain Relief Between Methoxyflurane and Standard of Care for Treating Patients With Trauma Pain in Spanish Emergency Units. [NCT03256903]Phase 3310 participants (Actual)Interventional2017-07-07Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]