Miconazole

Base Information

• Chemical Name: Miconazole
• CAS No.: 22916-47-8
• Deprecated CAS: 75319-47-0
• Molecular Formula: C18H14Cl4N2O
• Molecular Weight: 416.134
• Hs Code.: 2933290000
• European Community (EC) Number: 245-324-5
• NSC Number: 170986
• UNII: 7NNO0D7S5M
• DSSTox Substance ID: DTXSID6023319
• Nikkaji Number: J11.471E
• Wikipedia: Miconazole
• Wikidata: Q410534
• NCI Thesaurus Code: C62048
• RXCUI: 6932
• Pharos Ligand ID: D38GAS72Z2X2
• Metabolomics Workbench ID: 43338
• ChEMBL ID: CHEMBL91
• Mol file: 22916-47-8.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

Chemical Property:

• Appearance/Colour: White powder.
• Vapor Pressure: 6.07E-13mmHg at 25°C
• Melting Point: 159-163 °C
• Refractive Index: 1.639
• Boiling Point: 555.1 °C at 760 mmHg
• PKA: pKa 6.91(H2O,t =25) (Uncertain)
• Flash Point: 289.5 °C
• PSA: 27.05000
• Density: 1.4 g/cm³
• LogP: 6.45480
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Solubility.: Very slightly soluble in water, freely soluble in methanol, soluble in ethanol (96 per cent).
• Water Solubility.: Freely soluble in alcohols or acetone. Also soluble in DMF or chloroform. Insoluble in water
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 415.983074
• Heavy Atom Count: 25
• Complexity: 417

Purity/Quality:

99% ^*data from raw suppliers

Miconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-36

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
• Recent ClinicalTrials: Glutamine With Topical Corticosteroids for Lichen Planus Treatment
• Recent EU Clinical Trials: Optagelse af svampemidlet miconazol og effekt p? ?strogenmetaboliserende enzymer i mennesker
• Uses: Miconazole, is used as an antifungal inhibitor of aromatase. Miconazole has been shown to promote remyelination of neurons in chronic progressive multiple sclerosis mouse models. Miconazole is mainly used externally for the treatment of athlete's foot, ringworm, and jock itch. Internal application is used for oral or vaginal thrush (yeast infection). The oral gel may also be used for the lip disorder angular cheilitis. It is also used in photography. Antifungal;Sterol 14-demethylase inhibitor. Miconazole (Monistat-Derm, Micatin, etc.) is a synthetic imidazole antifungal compound that acts by altering cell membrane permeability. It is effective against most dermatophyte species, P. orbiculare, and C. albicans. Miconazole is an antifungal agent of the imidazole type. It is used in topical and vaginal preparations to prevent growth of dermatophytes, yeast, and molds.
• Indications: Miconazole (Monistat) is a broad-spectrum imidazole antifungal agent used in the topical treatment of cutaneous dermatophyte infections and mucous membrane Candida infections, such as vaginitis. Minimal absorption occurs from skin or mucous membrane surfaces. Local irritation to skin and mucous membranes can occur with topical use; headaches, urticaria, and abdominal cramping have been reported with treatment for vaginitis.
• Therapeutic Function: Antifungal
• Clinical Use: Antifungal agent
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: effect of coumarins enhanced. Antidepressants: avoid concomitant use with reboxetine. Antidiabetics: enhances hypoglycaemic effect of gliclazide and glipizide; concentration of sulphonylureas increased. Antiepileptics: effect of fosphenytoin and phenytoin enhanced; possibly increased carbamazepine concentration. Antihistamines: avoid with mizolastine, risk of ventricular arrhythmias. Antimalarials: avoid with piperaquine with artenimol and artemether with lumefantrine. Antipsychotics: increased risk of ventricular arrhythmias with pimozide - avoid; possibly increased concentration of quetiapine - avoid. Antivirals: concentration of saquinavir possibly increased. Ciclosporin: possibly increased ciclosporin concentration. Ergot alkaloids: increased risk of ergotism with ergotamine and methysergide - avoid. Sirolimus: concentration increased by miconazole. Statins: possibly increased risk of myopathy with atorvastatin and simvastatin - avoid with simvastatin. Tacrolimus: possibly increased tacrolimus concentration

Technology Process of Miconazole

There total 8 articles about Miconazole 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: 73.0%

2,4-Dichlorobenzyl chloride (94-99-5) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → miconazole (22916-47-8,47447-52-9)

Guidance literature:

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol; With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

2,4-Dichlorobenzyl chloride; In tetrahydrofuran; at 45 ℃; for 16h;

Reference yield:

2,4-dichlorobenzyl methanesulfonate + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → miconazole (22916-47-8,47447-52-9)

Guidance literature:

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

2,4-dichlorobenzyl methanesulfonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1039/c8ob00897c

Reference yield:

2,4-dichlorobenzaldeyhde (874-42-0) → miconazole (22916-47-8,47447-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82 percent / aq. KOH / acetonitrile / 3 h / 60 °C

2.1: 63 percent / pyridine / ethanol / 12 h / Heating

3.1: NaH; HMPA / tetrahydrofuran / 0.5 h / 20 °C

3.2: 73 percent / tetrahydrofuran / 16 h / 45 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium hydride; In tetrahydrofuran; ethanol; acetonitrile; 1.1: epoxidation / 2.1: Ring cleavage / 3.1: Substitution / 3.2: Substitution;

upstream raw materials:

2,4-Dichlorobenzyl chloride

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

2,4-dichlorobenzaldeyhde

2-(2,4-dichlorophenyl)oxirane

Downstream raw materials:

1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-(m-methylbenzyl)imidazolium bromide

1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-octyl-1H-imidazol-3-ium bromide

(+)-Miconazole

(-)-Miconazole

Refernces

• 1、 -. "Use of miconazole and derivatives thereof as TGR5 agonists (by machine translation)". Paragraph 0031; 0036; 0037-0040. . Retrieved 2020/05/02.
• 2、 -. "METHOD FOR PRODUCING PULVERIZED ORGANIC COMPOUND PARTICLE". . . Retrieved 2015/12/19.