Miconazole nitrate

Base Information

• Chemical Name: Miconazole nitrate
• CAS No.: 22832-87-7
• Deprecated CAS: 75319-48-1
• Molecular Formula: C18H15Cl4N3O4
• Molecular Weight: 479.147
• Hs Code.: 2933290000
• European Community (EC) Number: 245-256-6,922-010-2
• NSC Number: 757119,169434
• UNII: VW4H1CYW1K
• DSSTox Substance ID: DTXSID50996767
• Wikidata: Q27292045
• NCI Thesaurus Code: C29257
• RXCUI: 42790
• Metabolomics Workbench ID: 67836
• ChEMBL ID: CHEMBL1559
• Mol file: 22832-87-7.mol

Synonyms:Brentan;Dactarin;Miconasil Nitrate;Miconazole;Miconazole Nitrate;Monistat;Nitrate, Miconasil;Nitrate, Miconazole;R 14,889;R-14,889;R14,889

Chemical Property of Miconazole nitrate

Chemical Property:

• Appearance/Colour: White crystal powder
• Melting Point: 170-185 °C
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 555.1 °C at 760 mmHg
• Flash Point: 289.5 °C
• PSA: 93.10000
• Density: 1.451g/cm3
• LogP: 6.63030
• Storage Temp.: Store at RT
• Solubility.: pyridine: soluble50mg/mL
• Water Solubility.: Slightly soluble in water. Soluble in propylene glycol or pyridine.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 478.978717
• Heavy Atom Count: 29
• Complexity: 441

Purity/Quality:

99% ^*data from raw suppliers

Miconazole nitrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43-40
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-]
• Recent ClinicalTrials: Study Evaluating the Efficacy and Safety of Miconazole Nitrate + Domiphen Bromide Vaginal Cream in the Treatment of Subjects With Acute Vulvovaginal Candidiasis
• Recent EU Clinical Trials: A Phase 2, Randomized, Double-Blind, Active-Controlled Study to Evaluate the Efficacy and Safety of Miconazole Nitrate 2% + Domiphen Bromide Vaginal cream in the Treatment of Subjects with Acute Vulvovaginal Candidiasis
• Drug Interactions: 1. When it is used in combination with anticoagulant drugs such as coumarin or indandione derivative, it can enhance the effects of the later drugs, leading to prolonged prothrombin time. The patient should be subject to close observation and monitoring of prothrombin time as well as adjustment of the dosage of the anti-coagulation drugs. 2. Miconazole nitrate can be used to increase the cyclosporine blood concentration and could increase the risk of renal toxicity. Therefore, when these two drugs are used in combination, we should monitor the blood concentration of cyclosporine. 3. Rifampicin may enhance the metabolism of this product, increase the liver toxicity. When being used in combination with this drug, it can reduce the plasma concentration of this product, leading to the treatment failure. Being used in combination with isoniazid may also reduce the blood concentration of this product. Thus, we should be cautious when use those above drugs in combination with each other. 4. Combination with phenytoin and miconazole nitrate can cause changes in metabolism of these two drugs, and prolong the peak time of this product. When use the two drugs in combination, we should closely monitor their reactions. 5. Combination with hypoglycemic agent can lead to severe hypoglycemia due to inhibit the metabolism of the drug. 6. Combination with cisapride should be tabooed because this can lead to inhibition of the cytochrome P450 metabolic pathways, further causing arrhythmia. There is also risk of arrhythmia when apply miconazole nitrate in combination with astemizole or terfenadin. Therefore, this should also be avoided.
• Uses: It is a kind of broad-spectrum anti-fungal drug and can be applied to the treatment of deep fungal infections. Antifungal (topical). An antifungal agent that inhibits platelet cyclooxygenase Miconazole 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.
• Description: Miconazole 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.
• Therapeutic Function: Antifungal
• Clinical Use: 1-[2-(2,4-Dichlorophenyl)-2-[2,4-dichlorophenyl]-methoxy]ethyl]-1H-imidazole mononitrate (Monistat,Micatin) is a weak base with a pKa of 6.65. The nitric acidsalt occurs as white crystals that are sparingly soluble inwater and most organic solvents.The free base is available in an injectable form, solubilized with polyethylene glycol and castor oil, and intended for the treatment of serious systemic fungal infections, such as candidiasis, coccidioidomycosis, cryptococcosis, petriellidiosis, and paracoccidioidomycosis. It may also be used for the treatment of chronic mucocutaneous candidiasis. Although serious toxic effects from the systemic administration of miconazole are comparatively rare, thrombophlebitis, pruritus, fever, and gastrointestinal upset are relatively common. Miconazole nitrate is supplied in various dosage forms (cream, lotion, powder, and spray) for the treatment of tinea infections and cutaneous candidiasis. Vaginal creams and suppositories are also available for the treatment of vaginal candidiasis. A concentration of 2% of the salt is used in most topical preparations.

Technology Process of Miconazole nitrate

There total 1 articles about Miconazole nitrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ miconasole nitrate (22832-87-7,27656-15-1,75319-48-1)

Guidance literature:

Reference yield: 65.0%

miconasole nitrate (22832-87-7,27656-15-1,75319-48-1) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 1-[β-(2,4-dichlorophenyl)-phenethyl]imidazole (61023-62-9)

Guidance literature:

miconasole nitrate; With sodium hydroxide; In chloroform;

benzene; With trifluorormethanesulfonic acid; In chloroform; at 25 ℃; for 4h;

DOI:10.1021/jo802798x

Reference yield:

miconasole nitrate (22832-87-7,27656-15-1,75319-48-1) → 2,4 dichlorobenzoic acid (50-84-0) + 2,4-dichlorobenzaldeyhde (874-42-0) + 1-(2,4-Dichloro-phenyl)-2-imidazol-1-yl-ethanol; compound with nitric acid (61258-52-4) + 1-[2,4-dichloro-β-(2,4-dichlorophenylcarbonyloxy)phenethyl]-imidazole nitrate (68601-96-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); oxygen; In ethanol; at 77.5 ℃; for 3.4h; under 5171.5 Torr; Further byproducts given;

DOI:10.1016/S0040-4020(01)82309-7

Downstream raw materials:

(2,4-dichlorophenyl)methanol

2,4 dichlorobenzoic acid

2,4-dichlorobenzaldeyhde

1-(2,4-Dichloro-phenyl)-2-imidazol-1-yl-ethanol; compound with nitric acid

Refernces