Methoxyflurane
N02B - Other analgesics and antipyretics
ATC N02BG09
Small molecule
Topical
Withdrawn
Black-box warning
JFDA label: Penthrox 99.9%
⚠ Black-Box Warning
- Withdrawn: hepatotoxicity — ChEMBL drug_warning (Withdrawn) | United States | Serious, irreversible, and even fatal nephrotoxicity and hepatotoxicity
- Withdrawn: nephrotoxicity — ChEMBL drug_warning (Withdrawn) | United States | Serious, irreversible, and even fatal nephrotoxicity and hepatotoxicity
Mechanism of Action
Agonist of Glycine receptor (alpha-1/beta) — Glycine receptor (alpha-1/beta) agonist; Positive Modulator of GABA-A receptor; anion channel — GABA-A receptor; anion channel positive modulator
| Target | Action | Gene / class |
|---|---|---|
| GABA-A receptor; anion channel efficacy | POSITIVE MODULATOR | |
| Glycine receptor (alpha-1/beta) efficacy | AGONIST |
Indications
Approved
- Fever — Fever
- Pain — pain
Off-label
- Neoplasms
- Wounds and Injuries
Chemistry & Properties
| Formula | C3H4Cl2F2O |
|---|---|
| Molecular weight | 164.97 g/mol |
| IUPAC name | 2,2-dichloro-1,1-difluoro-1-methoxyethane |
| CAS | 76-38-0 |
| PubChem CID | 4116 |
| InChIKey | RFKMCNOHBTXSMU-UHFFFAOYSA-N |
| logP | 2.03 (XLogP 2.2) |
| Polar surface area | 9.23 Ų |
| H-bond acceptors / donors | 1 / 0 |
| Drug-likeness (QED) | 0.57 |
| Lipinski violations | 0 |
SMILES
COC(F)(F)C(Cl)ClBiology & Pharmacokinetics
Pharmacokinetics
| BBB penetrant | Yes (logBB 0.2) |
|---|
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP1A2 | Substrate | — |
| CYP2B6 | Substrate | — |
| CYP2C19 | Inhibitor | — |
| CYP2C19 | Substrate | — |
| CYP2C8 | Inhibitor | — |
| CYP3A4 | Substrate | — |
Transporters
BCRP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)
Drug–drug interactions (51, DDInter)
| Interacting drug | Severity | Management |
|---|---|---|
| Deferasirox | major | |
| Demeclocycline | major | |
| Diatrizoate | major | |
| Doxycycline | major | |
| Epinephrine | major | |
| Everolimus | major | |
| Iohexol | major | |
| Iopamidol | major | |
| Iopromide | major | |
| Iothalamic acid | major | |
| Ioversol | major | |
| Ioxilan | major | |
| Minocycline | major | |
| Sirolimus | major | |
| Tacrolimus | major | |
| Temsirolimus | major | |
| Tetracycline | major | |
| Amikacin | moderate | |
| Amikacin (liposome) | moderate | |
| Amphotericin B | moderate | |
| Amphotericin B (cholesteryl sulfate) | moderate | |
| Amphotericin B (lipid complex) | moderate | |
| Amphotericin B (liposomal) | moderate | |
| Balsalazide | moderate | |
| Celecoxib | moderate | |
| Ceritinib | moderate | |
| Cisplatin | moderate | |
| Clofarabine | moderate | |
| Codeine | moderate | |
| Cyclosporine | moderate | |
| Diclofenac | moderate | |
| Ethanol | moderate | |
| Exenatide | moderate | |
| Flucytosine | moderate | |
| Flurbiprofen | moderate | |
| Gentamicin | moderate | |
| Hydrocodone | moderate | |
| Ibuprofen | moderate | |
| Iobenguane (I-131) | moderate | |
| Mesalazine | moderate |
Showing 40 of 51.
Registered Products (1)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| Penthrox | Inhaler 99.9 % | 3 ml | Nairoukh Drug Store | — |