1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole

• ChemBase ID: 981
• Molecular Formular: C18H14Cl4N2O
• Molecular Mass: 416.12856
• Monoisotopic Mass: 413.9860238
• SMILES: Clc1c(C(OCc2c(Cl)cc(Cl)cc2)Cn2ccnc2)ccc(Cl)c1
• Canonical SMILES: Clc1ccc(c(c1)Cl)COC(c1ccc(cc1Cl)Cl)Cn1cncc1
• InChI: InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2
• InChIKey: BYBLEWFAAKGYCD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole
• IUPAC Traditional name: miconazole
• Brand Name: Daktarin; Femizol-M; M-zole 3 Combination Pack; M-zole 7 Dual Pack; Micatin; Miconazole 3; Miconazole 3 Combination Pack; Miconazole 7; Miconazole 7 Combination Pack; Miconazole Nitrate; Miconazole Nitrate Combination Pack; Miconazole-7; Micozole; Minostate; Monazole 7; Monistat; Monistat 1 Combination Pack; Monistat 3; Monistat 3 Combination Pack; Monistat 3 Dual-Pak; Monistat 3 Vaginal Ovules; Monistat 5; Monistat 5 Tampon; Monistat 7; Monistat 7 Combination Pack; Monistat 7 Dual-Pak; Monistat 7 Vaginal Suppositories; Monistat Dual- PAK; Monistat IV; Monistat-3 Combination Pack; Monistat-Derm; Novo-Miconazole Vaginal Ovules; Zimycan; Vusion; Desenex, Monistat, Zeasorb-AF
• Synonyms: MCZ; miconazole; Miconazole; Daktarin IV; MJR 1762; Monistat IV; NSC 17098; 1-[2,4-Dichloro-β-([2,4-dichloro-benzyl]oxy)phenethyl]imidazole; 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-1h-imidazole

Database IDs

• CAS Number: 22916-47-8
• EC Number: 245-324-5
• MDL Number: MFCD00216019
• PubChem SID: 46506017; 160964444
• PubChem CID: 4189
• CHEBI ID: 6923
• ATC CODE: G01AF04; A07AC01; A01AB09; D01AC02; S02AA13; J02AB01
• CHEMBL: 91
• Chemspider ID: 4044
• DrugBank ID: DB01110
• IUPHAR ligand ID: 2449
• KEGG ID: D00416
• Unique Ingredient Identifier: 7NNO0D7S5M
• Wikipedia Title: Miconazole
• Medline Plus: a601203

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.4261637
• LogD (pH = 7.4): 5.89066
• Log P: 5.9563684
• Molar Refractivity: 103.0676 cm^3
• Polarizability: 40.009266 Å^3
• Polar Surface Area: 27.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.86
• LOG S: -5.74
• Solubility (Water): 7.63e-04 g/l

PROPERTIES

Physical Property

• Solubility: 1g/100mL (20°C)
• Melting Point: 135°C
• Hydrophobicity(logP): 6.1

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: NI4770000

Pharmacology Properties

• Admin Routes: topical, vaginal
• Bioavailability: n/a
• Excretion: n/a
• Half Life: n/a
• Metabolism: n/a
• Legal Status: OTC (US); POM (UK)

Product Information

• Purity: 98%
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02193915

Free Base

DrugBank - DB01110

• Drug Groups: approved; investigational
• Description: An imidazole antifungal agent that is used topically and by intravenous infusion. [PubChem]
• Indication: For topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor.
• Pharmacology: Miconazole is an anti-fungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). It is used either on the skin or in the vagina for fungal infections. Miconazole was approved by the FDA in 1974. Miconazole prevents fungal organisms from producing vital substances required for growth and function. This medication is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections.
• Toxicity: Oral, mouse: LD₅₀ = 3800 mg/kg; Oral, rat: LD₅₀ = 3 gm/kg. Ingestion of the amounts of the components contained in a tube of cream are unlikely to produce overdosage and toxic effects.
• Affected Organisms: Fungi, yeast and protozoans
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S2536

Research Area: Infection
Biological Activity:
Miconazole (Monistat) is an imidazole antifungal agent. Miconazole (Monistat) is common made into miconazole nitrate (riconazole; Prilagin; R 14889; Vodol; Zeasorb AF; Zimycan). Miconazole nitrate (riconazole; Prilagin; R 14889; Vodol; Zeasorb AF; Zimycan) is commonly applied topically to the skin or to mucus membranes to cure fungal infections. Miconazole nitrate (riconazole; Prilagin; R 14889; Vodol; Zeasorb AF; Zimycan) works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes. Miconazole nitrate (riconazole; Prilagin; R 14889; Vodol; Zeasorb AF; Zimycan) can also be used against certain species of Leishmania protozoa which are a type of unicellular parasite that also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, Miconazole nitrate (riconazole; Prilagin; R 14889; Vodol; Zeasorb AF; Zimycan) also has some limited antibacterial properties. [1][2]

REFERENCES

• Chang HT et al. Life Sci. 2005 Mar 18; 76(18):2091