Oxiconazole
Solid powder
Chemical Compounds
Oxiconazole is a broad spectrum imidazole derivative with antifungal activity. Although the exact mechanism of action has yet to be fully elucidated, oxiconazole, like other azole antifungals, most likely inhibits the cytochrome P450-dependent demethylation of lanosterol. This prevents the synthesis of ergosterol which is a crucial component of fungal cell membrane. By disrupting fungal cell membrane synthesis and integrity, oxiconazole alters fungal cell membrane permeability, promotes loss of essential intracellular components and eventually inhibits fungal cell growth.
Oxiconazole is an oxime O-ether that is the 2,4-dichlorobenzyl ether of the oxime obtained by formal condensation of hydroxylamine with the carbonyl group of acetopnenone in which the phenyl group is substituted by chlorines at positions 2 and 4, and in which one of the hydrogens of the methyl group is replaced by a 1H-imidazol-1-yl group. An antifungal agent, it is used (generally as the nitrate salt) in creams and powders for the topical treatment of fungal skin infections. It has a role as an antiinfective agent. It is a member of imidazoles, an oxime O-ether, a dichlorobenzene, an imidazole antifungal drug and a conazole antifungal drug. It is a conjugate base of an oxiconazole(1+).
Oxiconazole is an antifungal agent that is commonly found in topical formulations. It is marketed under the brand names Oxistat and Oxistat, and is used in the treatment of various skin infections such as athlete's foot, jock itch and ringworm. 429.1 g/mol
Oxiconazole is an oxime O-ether that is the 2,4-dichlorobenzyl ether of the oxime obtained by formal condensation of hydroxylamine with the carbonyl group of acetopnenone in which the phenyl group is substituted by chlorines at positions 2 and 4, and in which one of the hydrogens of the methyl group is replaced by a 1H-imidazol-1-yl group. An antifungal agent, it is used (generally as the nitrate salt) in creams and powders for the topical treatment of fungal skin infections. It has a role as an antiinfective agent. It is a member of imidazoles, an oxime O-ether, a dichlorobenzene, an imidazole antifungal drug and a conazole antifungal drug. It is a conjugate base of an oxiconazole(1+).
Oxiconazole is an antifungal agent that is commonly found in topical formulations. It is marketed under the brand names Oxistat and Oxistat, and is used in the treatment of various skin infections such as athlete's foot, jock itch and ringworm. 429.1 g/mol
Formulation:
429.1 g/mol
Source:
Usage:
Oxiconazole
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-277976
CAS Number: 64211-45-6
Molecular Formula: C18H13Cl4N3O
Molecular Weight: 429.1 g/mol
| CAS Number | 64211-45-6 |
|---|---|
| Product Name | Oxiconazole |
| Molecular Formula | C18H13Cl4N3O |
| Molecular Weight | 429.1 g/mol |
| Appearance | Solid powder |
| InChI | InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18+ |
| InChI Key | QRJJEGAJXVEBNE-HKOYGPOVSA-N |
| Isomeric SMILES | C1=CC(=C(C=C1Cl)Cl)CO/N=C(\CN2C=CN=C2)/C3=C(C=C(C=C3)Cl)Cl |
| IUPAC Name | (Z)-1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methoxy]-2-imidazol-1-ylethanimine |
| Canonical SMILES | C1=CC(=C(C=C1Cl)Cl)CON=C(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl |
| Description | Oxiconazole is a broad spectrum imidazole derivative with antifungal activity. Although the exact mechanism of action has yet to be fully elucidated, oxiconazole, like other azole antifungals, most likely inhibits the cytochrome P450-dependent demethylation of lanosterol. This prevents the synthesis of ergosterol which is a crucial component of fungal cell membrane. By disrupting fungal cell membrane synthesis and integrity, oxiconazole alters fungal cell membrane permeability, promotes loss of essential intracellular components and eventually inhibits fungal cell growth. Oxiconazole is an oxime O-ether that is the 2,4-dichlorobenzyl ether of the oxime obtained by formal condensation of hydroxylamine with the carbonyl group of acetopnenone in which the phenyl group is substituted by chlorines at positions 2 and 4, and in which one of the hydrogens of the methyl group is replaced by a 1H-imidazol-1-yl group. An antifungal agent, it is used (generally as the nitrate salt) in creams and powders for the topical treatment of fungal skin infections. It has a role as an antiinfective agent. It is a member of imidazoles, an oxime O-ether, a dichlorobenzene, an imidazole antifungal drug and a conazole antifungal drug. It is a conjugate base of an oxiconazole(1+). Oxiconazole is an antifungal agent that is commonly found in topical formulations. It is marketed under the brand names Oxistat and Oxistat, and is used in the treatment of various skin infections such as athlete's foot, jock itch and ringworm. |
| Other CAS Number | 64211-45-6 64211-46-7 |
| Pictograms | Irritant |
| Related CAS | 64211-46-7 (nitrate) |
| Shelf Life | >3 years if stored properly |
| SMILES | C1=CC(=C(C=C1Cl)Cl)CON=C(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl |
| Solubility | Soluble in DMSO |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Synonyms | (Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-O-(2,4-dichlorobenzyl) ethanone oxime nitrate 2',4'-dichloro-2-imidazol-1-ylacetophenone (Z)-(O-(2,4-dichlorobenzyl)oxime), mononitrate Fonx Gyno-Myfungar Myfungar Oceral oxiconazole oxiconazole mononitrate, (Z)-isomer oxiconazole nitrate Oxistat Oxizole oxyconazole RO-13-8996 Salongo Sgd 301-76 |
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| PubChem Compound | Oxiconazole |
| Last Modified | Mar 14 2022 |