Basic information
- CAS
22832-87-7- Standard SMILES
Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)c(Cl)c1.O=[N+]([O-])O- InChIKey
MCCACAIVAXEFAL-UHFFFAOYSA-N- Molecular formula
- C18H15Cl4N3O4
- Average molar mass
- 479.1 g/mol
- Monoisotopic mass
- 476.98166668
Overview
Miconazole is an antifungal prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of mucocutaneouscandidiasis, including:
Names & identifiers
- Preferred name
- Miconazole Nitrate
- IUPAC
- 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole;nitric acid
- English name
- Miconazole nitrate
- Molecular formula
- C18H14Cl4N2O.HNO3
- Molecular weight
- 479.14
Names & synonyms
Miconazole nitrate22832-87-7DermonistatMicatinMonistat-DermMiconazole 7Monistat 3Monistat 5Monistat 7M-zole 7 Dual PackPriconazoleM-zole 3 Combination Pack
Show more names
monistatTocris BioscienceIsoconazole IMpurity C Nitrate (Miconazole Nitrate)EcobiVodolDaktarFloridAflorixBrentanHi-Pick
Miconazole 1Miconazole 3Monistat Dual-pakMonistat 3 Combination PackMonistat 7 Combination PackMonistat-3 Combination PackBaza cream antifungalBaza cream
Database identifiers
- CAS
22832-87-7- PubChem CID
- 68553
- DTXSID
DTXSID50996767- ChEMBL
CHEMBL1559- UNII
- VW4H1CYW1K
- EC Number
- 245-256-6、922-010-2
Properties
Computed structural properties
- Topological polar surface area
- 93.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 441
Experimental & physicochemical properties
Solubility26.3 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
FDA approved animal drugs -> Active ingredient
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Collision Cross Section189.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 170 · 170-185 C
- Density
- 1.5 · 1.5000 (rough estimate)
- refractive index
- 1.62 · 1.6200 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 50 mg/mL · pyridine: soluble50mg/mL
- form
- Solid
- color
- white to off-white
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 161 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
REACH registered substance: Miconazole nitrate (EC: 245-256-6)
Miconazole nitrate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-, mononitrate: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Exposure RoutesTopical
Toxicity Summary
Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Signs and Symptoms
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
2% MICONAZOLE NITRATE CREAM
Azoles [CS]; Azole Antifungal [EPC]
ANTI-FUNGAL MICONAZOLE ATHLETES FOOT SPRAY TALC FREE
Azole Antifungal [EPC]; Azoles [CS]
ANTI-FUNGAL POWDER MICONAZOLE NITRATE TALC FREE
Azoles [CS]; Azole Antifungal [EPC]
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism.
Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2C9.
Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A.
Uses & manufacturing
Uses
For topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by <i>Trichophyton rubrum</i>, <i>Trichophyton mentagrophytes</i>, and <i>Epidermophyton floccosum</i>, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor.
Household ProductsInformation on 1 consumer products that contain Miconazole Nitrate in the following categories is provided:
Applications
UsesIt is a kind of broad-spectrum anti-fungal drug and can be applied to the treatment of deep fungal infections.
DescriptionMiconazole is a widely used antifungal imidazole that acts by inhibiting the 14α-demethylation of lanosterol, which consequently leads to the inhibition of ergosterol synthesis in fungal cell membranes. Additionally, miconazole has been shown to induce reactive oxygen species in fungal biofilms, demonstrating a MIC value of ≥256 μM against Candida spp.
Related reactions
2 records
Compound notes
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