methoxyflurane
Trade name: penthrane
Approved
May 4, 1962
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 Methoxyflurane was used for surgical, obstetric, or dental anesthesia, but was withdrawn from US market due to safety concerns, but is still in use in Australia and other countries.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. — NCATS
Clinical trial activity
30 trials · 38 clinical orgs · 1 marketing orgs
Earliest trial started Sep 1, 2007 (NCT00524927)
Timeline
Indications
Approved for
Studied for
- Acute Coronary Syndrome · Phase 3
- Acute Pain · Phase 4
- Ambulances · Phase 3
- Anesthesia, Local · Phase 2
- Angina, Unstable · Phase 4
- Hematocele · Phase 2
- Hypovolemia · Phase 4
- Neoplasms · Phase 3
- Occupational Exposure · Phase 4
- Pain Measurement · Phase 4
- Prostatic Hyperplasia · Phase 4
- Scrotum · Phase 2
- Shoulder Injuries · Phase 4
- Sinusitis · Phase 1/Phase 2
- Spermatocele · Phase 2
- ST Elevation Myocardial Infarction · Phase 3
- Testicular Hydrocele · Phase 2
- Wounds and Injuries · Phase 4
Mechanism of action
Glycine receptor (alpha-1/beta) agonist
Alpha subunit is binding site
- GABA-A receptor; anion channelPOSITIVE MODULATOR
GABA-A receptor; anion channel positive modulator
- Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1) ↗
- Gamma-aminobutyric acid receptor subunit beta-2 (GABRB2) ↗
- Gamma-aminobutyric acid receptor subunit gamma-2 (GABRG2) ↗
- Gamma-aminobutyric acid receptor subunit beta-3 (GABRB3) ↗
- Gamma-aminobutyric acid receptor subunit alpha-4 (GABRA4) ↗
- Gamma-aminobutyric acid receptor subunit gamma-3 (GABRG3) ↗
- Gamma-aminobutyric acid receptor subunit theta (GABRQ) ↗
- Gamma-aminobutyric acid receptor subunit alpha-3 (GABRA3) ↗
- Gamma-aminobutyric acid receptor subunit pi (GABRP) ↗
- Gamma-aminobutyric acid receptor subunit delta (GABRD) ↗
- Gamma-aminobutyric acid receptor subunit gamma-1 (GABRG1) ↗
- Gamma-aminobutyric acid receptor subunit beta-1 (GABRB1) ↗
- Gamma-aminobutyric acid receptor subunit epsilon (GABRE) ↗
- Gamma-aminobutyric acid receptor subunit alpha-2 (GABRA2) ↗
- Gamma-aminobutyric acid receptor subunit alpha-5 (GABRA5) ↗
- Gamma-aminobutyric acid receptor subunit alpha-6 (GABRA6) ↗
- GABA receptor alpha-1 subunit
- GABA receptor beta-2 subunit
- GABA receptor alpha-4 subunit
- GABA receptor delta subunit
- GABA receptor alpha-5 subunit
- GABA receptor alpha-6 subunit
- GABA receptor beta-3 subunit
- GABA receptor alpha-3 subunit
- GABA receptor alpha-2 subunit
- GABA-A receptor; GABA-A site (alpha1/beta2 interface)
- GABA-A receptor; alpha-3/beta-3/gamma-2
- GABA-A receptor; alpha-1/beta-3/gamma-2
- GABA-A receptor; alpha-5/beta-3/gamma-2
- GABA-A receptor; alpha-2/beta-3/gamma-2
- GABA-A receptor; alpha-1/beta-2/gamma-2
- GABA-A receptor; alpha-6/beta-3/gamma-2
- GABA-A receptor; benzodiazepine site
- GABA-A receptor; agonist GABA site
- GABA A receptor alpha-2/beta-2/gamma-2
- GABA A receptor alpha-3/beta-2/gamma-2
- GABA A receptor alpha-6/beta-2/gamma-2
- GABA A receptor alpha-1/beta-1/gamma-2
- GABA A receptor alpha-4/beta-3/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta3/delta
- Gamma-aminobutyric acid receptor subunit alpha-1/ beta-1
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-3/ beta-2
- Gamma-aminobutyric acid receptor subunit alpha-3/ beta-3/gamma-3
- Gamma-aminobutyric acid receptor subunit alpha-3/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-3/beta-3/theta
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-3/gamma-3
- Gamma-aminobutyric acid receptor subunit alpha-6/beta-3
- GABA-A receptor alpha-1/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-1/beta-2/delta
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-2/delta
- Gamma-aminobutyric acid receptor subunit beta-1/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-1/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-2/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-1/delta
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2
- GABA receptor beta-1 subunit
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-1/gamma-2
Approval history
- approvedPriority reviewMay 4, 1962
Chemistry & pharmacology
SMILES
COC(F)(F)C(Cl)Cl- Mol. weight
- 164.966 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- Yes
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Topical
Oral
No
Parenteral
No
Topical
Yes
Sources
- WikipediaMethoxyflurane ↗
- NCATS30905R8O7B ↗
- ChEMBLCHEMBL1341 ↗
Also known as
- methoflurane
- methoflurane
- methoflurane
- methoxane
- methoxiflurane
- methoxiflurane
- methoxyfluoran
- methoxyfluoran
- methoxyfluran
- methoxyfluran
- methoxyfluran
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyflurane
- methoxyfluranum
- methoxyfluranum
- methyl 1,1-difluoro-2,2-dichloroethyl ether
- methyl 1,1-difluoro-2,2-dichloroethyl ether
- metofane
- metofane
- metofane
- metoxfluran
- metoxifluran
- metoxiflurano
- metoxiflurano
- penthrane
- penthrane
- penthrane
- penthrane
- penthrox
- pentrane
- pentrane
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07295054 | Phase 4 | Feb 28, 2026 | University of Toronto |
| NCT07017452 | Phase 3 | Aug 31, 2025 | University of Manitoba |
| NCT07046572 | N/A | Jul 24, 2025 | University of Toronto |
| NCT06899724 | N/A | Jun 1, 2025 | Dr. John A. Thiel Medical Professional Corporation, University of Saskatchewan |
| NCT06750302 | Phase 1/Phase 2 (Phase 2) | Nov 24, 2024 | University of British Columbia |
| NCT06495372 | Phase 3 | Aug 31, 2024 | University of Western Brittany |
| NCT06392087 | Phase 4 | Aug 1, 2024 | University of Ottawa |
| NCT07192198 | Phase 2 | Apr 17, 2024 | University of Manitoba |
| NCT05821517 | Phase 4 | May 1, 2023 | University of Nice Sophia Antipolis |
| NCT05766397 | Phase 4 | Apr 30, 2023 | Mayday Fund, University of Ottawa |
| NCT05137184 | Phase 3 | Nov 12, 2021 | Norwegian Air Ambulance Foundation, Singapore Eye Research Institute, Sykehuset Innlandet HF, University of Oslo |
| NCT04618497 | Phase 3 | Oct 28, 2020 | Government of Hong Kong |
| NCT04476173 | Phase 3 | Jun 1, 2020 | Nicolaus Copernicus University |
| NCT04442919 | Phase 4 | Jun 1, 2020 | Nicolaus Copernicus University |
| NCT04412642 | Phase 4 | May 31, 2020 | University of Toronto |
| NCT04287803 | Phase 4 | Apr 30, 2020 | University of Ottawa |
| NCT04292808 | N/A | Mar 31, 2020 | Verso Surgery Centre |
| NCT04029012 | Phase 4 | Sep 30, 2019 | Can-Am HIFU Inc. |
| NCT03849027 | Phase 4 | May 31, 2019 | University of Cape Town |
| NCT03927729 | N/A | May 31, 2019 | University Hospital, Tours |