22916-47-8

Basic information

• Product Name: Miconazole
• Synonyms: 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-imidazol;1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)-imidazol;1-[2-[(2,4-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole;Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-;Imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)-;micronazol;Minostate;mjr1762
• CAS NO: 22916-47-8
• Molecular Formula: C₁₈H₁₄Cl₄N₂O
• Molecular Weight: 416.13
• EINECS: 245-324-5
• Product Categories: Monistat
• Mol File: 22916-47-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 159-163C
• Boiling Point: 555.1 °C at 760 mmHg
• Flash Point: 87°(189°F)
• Appearance: /
• Density: 1.5326 (rough estimate)
• Vapor Pressure: 6.07E-13mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Very slightly soluble in water, freely soluble in methanol, soluble in ethanol (96 per cent).
• PKA: pKa 6.91(H2O,t =25) (Uncertain)
• Water Solubility: Freely soluble in alcohols or acetone. Also soluble in DMF or chloroform. Insoluble in water
• Sensitive: Light Sensitive
• CAS DataBase Reference: Miconazole(CAS DataBase Reference)
• NIST Chemistry Reference: Miconazole(22916-47-8)
• EPA Substance Registry System: Miconazole(22916-47-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-36
• RIDADR: 3249
• WGK Germany: 3
• RTECS: NI4770000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 22916-47-8(Hazardous Substances Data)

Usage

Chemical Properties

White or almost white powder.

Uses

Different sources of media describe the Uses of 22916-47-8 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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

Synthesis

Miconazole, 1-[2,4-dichloro-β-[(2,4-dichlorobenzyl)oxy]phenethyl]-imidazole (35.2.7), like ketoconazol, is synthesized from 2,4-dichlorophenacylbromide, which is reacted with imidazole to make 1-(2,4-dichlorobenzoylmethyl)-imidazole[2,4-dichloro-ω-(1-imidazolyl)-acetophenone] (35.2.5). Reducing the carbonyl group in this molecule with sodium borohydride gives 1-(2,4-dichlorophenyl)-3-(1-imidazolyl)-ethanol (35.2.6), and the hydroxyl group is alkylated by 2,4-dichlorobenzylbromide using a powerful base such as sodium hydride to make miconazole (35.2.7).

Veterinary Drugs and Treatments

Different sources of media describe the Veterinary Drugs and Treatments of 22916-47-8 differently. You can refer to the following data:
1. Miconazole is a broad spectrum imidazole antifungal agent with some antibacterial activity. Miconazole will penetrate the intact corneal epithelium. Topical miconazole therapy has been a favorite first choice agent for treatment of fungal keratitis in the horse by veterinary ophthalmologists for several years. Miconazole may be delivered by subconjunctival route, but with some local irritation, and topical use is the most commonly employed treatment method.
2. Topical miconazole has activity against dermatophytes and yeasts; miconazole shampoos can be effective treatment for Malassezia dermatitis. Patients with severe, generalized infections may require systemic therapy. Lotions, sprays and creams are generally used for localized lesions associated with Malassezia or dermatophytes. See otic section for information on application for Malassezia otitis externa. Topical miconazole products are generally ineffective (or minimally effective) when used alone for dermatophytosis; adjunctive systemic treatment is usually required. Miconazole’s actions are a result of altering permeability of fungal cellular membranes and interfering with peroxisomal and mitochondrial enzymes, leading to intracellular necrosis. Miconazole products are fungicidal with repeated application.

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

Metabolism

Miconazole is metabolised in the liver to inactive metabolites; 10-20% of an oral dose is excreted in the urine as metabolites. About 50% of an oral dose may be excreted mainly unchanged in the faeces

InChI:InChI=1/C18H14Cl4N2O/c19-12-2-1-11(15(21)7-12)10-25-17(9-18-23-5-6-24-18)14-4-3-13(20)8-16(14)22/h1-8,17H,9-10H2,(H,23,24)

Synthetic route

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)

Conditions	Yield
Stage #1: 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; Substitution; Stage #2: 2,4-Dichlorobenzyl chloride In tetrahydrofuran at 45℃; for 16h; Substitution;	73%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 2,4-Dichlorobenzyl chloride In N,N-dimethyl-formamide at 20℃;

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

Conditions	Yield
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 View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / acetonitrile / 60 - 65 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere 3.2: 20 °C View Scheme

2-(2,4-dichlorophenyl)oxirane (13692-15-4) → miconazole (22916-47-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 63 percent / pyridine / ethanol / 12 h / Heating 2.1: NaH; HMPA / tetrahydrofuran / 0.5 h / 20 °C 2.2: 73 percent / tetrahydrofuran / 16 h / 45 °C View Scheme

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

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Stage #2: 2,4-dichlorobenzyl methanesulfonate In N,N-dimethyl-formamide at 20℃; for 12h;	118 mg

(2,4-dichlorophenyl)methanol (1777-82-8) → miconazole (22916-47-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 2 h / 0 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C 2.2: 12 h / 20 °C View Scheme

2,2',4'-trichloroacetophenone (4252-78-2) → miconazole (22916-47-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dichloromethane / 12 h / 0 - 20 °C 2.1: sodium tetrahydroborate; methanol / dichloromethane / 2 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C 3.2: 12 h / 20 °C View Scheme

1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone (46503-52-0) → miconazole (22916-47-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol / dichloromethane / 2 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C 2.2: 12 h / 20 °C View Scheme

4-((1,3-bis(dodecanoyloxy)propan-2-yl)oxy)-4-oxobutanoic acid (150994-84-6) + miconazole (22916-47-8) → 4-((1,3-bis(dodecanoyloxy)propan-2-yl)oxy)-4-oxobutanoate 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazol-1-ium

Conditions	Yield
In acetonitrile at 50℃; for 6h;	100%

hexadecanyl bromide (112-82-3) + miconazole (22916-47-8) → 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-hexadecyl-1H-imidazol-3-ium bromide

Conditions	Yield
In acetonitrile at 70℃; for 12h;	95%

1-bromo-octane (111-83-1) + miconazole (22916-47-8) → 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-octyl-1H-imidazol-3-ium bromide (57264-59-2)

Conditions	Yield
In acetonitrile at 70℃; for 12h;	93%
In acetonitrile for 2h; Reflux;	93%

silver perchlorate + miconazole (22916-47-8) → [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2ClO4]

Conditions	Yield
In ethanol at 20℃; for 24h;	92%
In ethanol; water at 20℃; for 24h;	82%

1-bromo-hexane (111-25-1) + miconazole (22916-47-8) → 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-hexyl-1H-imidazol-3-ium bromide

Conditions	Yield
In acetonitrile at 70℃; for 12h;	90%

1-dodecylbromide (143-15-7) + miconazole (22916-47-8) → 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-dodecyl-1H-imidazol-3-ium bromide

Conditions	Yield
In acetonitrile at 70℃; for 12h;	90%

chromium(III) nitrate nonahydrate + miconazole (22916-47-8) → C18H14Cl4CrN5O10

Conditions	Yield
In methanol for 3h; Reflux;	86.96%

1-bromomethyl-3,5-difluoro-benzene (141776-91-2) + miconazole (22916-47-8) → 3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1-(3,5-difluoro-benzyl)-3H-imidazol-1-ium; bromide

Conditions	Yield
In ethyl acetate for 48h; Heating;	86%

1-bromo dodecane (112-29-8) + miconazole (22916-47-8) → 3-decyl-1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazol-3-ium bromide (57264-60-5)

Conditions	Yield
In acetonitrile at 70℃; for 12h;	85%

copper(II) choride dihydrate + miconazole (22916-47-8) → [Cu(II)Cl2(miconazol)2(water)2]*2water

Conditions	Yield
In ethanol; water addn. of hot soln. of copper compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	85%

1-Bromotetradecane (112-71-0) + miconazole (22916-47-8) → 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-tetradecyl-1H-imidazol-3-ium bromide

Conditions	Yield
In acetonitrile at 70℃; for 12h;	85%

silver(I) hexafluorophosphate (26042-63-7) + [RhCl2(p-cymene)]2 + miconazole (22916-47-8) → [(η6-p-cymene)Ru(miconazole)3](PF6)2

Conditions	Yield
In methanol; chloroform for 3h; Reflux;	83%

silver nitrate + miconazole (22916-47-8) → [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2NO3]

Conditions	Yield
In ethanol; water at 20℃; for 24h;	82%

silver tetrafluoroborate (14104-20-2) + miconazole (22916-47-8) → [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2BF4]

Conditions	Yield
In ethanol; water at 20℃; for 24h;	82%

zinc(II) chloride dihydrate + miconazole (22916-47-8) → [Zn(II)Cl2(miconazol)2(water)2]*3water

Conditions	Yield
In ethanol; water addn. of hot soln. of zinc compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	80%

silver nitrate + miconazole (22916-47-8) → [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2NO3]

Conditions	Yield
In ethanol at 20℃; for 24h;	80%

[RhCl2(p-cymene)]2 + miconazole (22916-47-8) → [(η6-p-cymene)RuCl(miconazole)2]Cl (1581279-28-8)

Conditions	Yield
In methanol; chloroform for 5h; Reflux;	77%

manganese(II) chloride dihydrate + miconazole (22916-47-8) → [Mn(II)Cl2(miconazol)2(water)2]*water (1410795-51-5)

Conditions	Yield
In ethanol; water addn. of hot soln. of manganese compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	75%

C14H20B9(1-)*C4H12N(1+) + miconazole (22916-47-8) → C32H33B9Cl4N2O

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dimethoxyethane at 20℃; for 5h; Inert atmosphere; Schlenk technique;	73%

miconazole (22916-47-8) + methyl iodide (74-88-4) → 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-methyl-1H-imidazol-3-ium iodide

Conditions	Yield
In acetonitrile at 70℃; for 12h;	71%
In ethyl acetate at 20℃; for 48h;	69%
Heating; Yield given;

[RhCl2(p-cymene)]2 + miconazole (22916-47-8) → [(η6-p-cymene)RuCl2(miconazole)]

Conditions	Yield
In methanol; chloroform at 20℃; for 0.075h; Reflux;	71%

chromium chloride hexahydrate + miconazole (22916-47-8) → [Cr(III)Cl2(miconazol)2(water)2]Cl*3water

Conditions	Yield
In ethanol; water addn. of hot soln. of chromium compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	70%

cobalt(II) chloride hexahydrate + miconazole (22916-47-8) → [Co(II)Cl2(miconazol)2(water)2]*2water

Conditions	Yield
In ethanol; water addn. of hot soln. of cobalt compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	68%

iron(III) chloride hexahydrate + miconazole (22916-47-8) → [Fe(III)Cl2(miconazol)2(water)2]Cl*3water

Conditions	Yield
In ethanol; water addn. of hot soln. of iron compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	65%

[Ru(p-cymene)Cl2]2 + miconazole (22916-47-8) → [(η6-p-cymene)RuCl2(miconazole)]

Conditions	Yield
In acetone for 20h; Inert atmosphere; Schlenk technique;	65%

silver hexafluoroantimonate + miconazole (22916-47-8) → [Ag(1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole)2SbF6]

Conditions	Yield
In ethanol; water at 20℃; for 24h;	65%

nickel(II) chloride hexahydrate + miconazole (22916-47-8) → [Ni(II)Cl2(miconazol)2(water)2]*3water

Conditions	Yield
In ethanol; water addn. of hot soln. of nickel compd. in ethanol/water (1:1) to hot ethanolic soln. of miconazol at 60°C, stirring at reflux for 1 h; filtration, washing with ethanol/water and petroleum ether, elem. anal.;	60%

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) + miconazole (22916-47-8) → 3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-3H-imidazol-1-ium; iodide

Conditions	Yield
In tetrahydrofuran Heating;	52%

ammonium hexafluorophosphate + MnBr(bpyCOOCH3,COOCH3)(CO)3 + miconazole (22916-47-8) → [Mn(bpyCOOCH3,COOCH3)(CO)3(miconazole)]PF6

Conditions	Yield
Stage #1: MnBr(bpyCOOCH3,COOCH3)(CO)3 With silver trifluoromethanesulfonate In acetone at 20℃; for 3h; Darkness; Inert atmosphere; Schlenk technique; Stage #2: miconazole at 20℃; for 20h; Schlenk technique; Inert atmosphere; Darkness; Stage #3: ammonium hexafluorophosphate In methanol; water Schlenk technique; Inert atmosphere; Darkness;	49%

Upstream product

• 94-99-5 2,4-Dichlorobenzyl chloride 
• 24155-42-8 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol 
• 46503-52-0 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 1777-82-8 (2,4-dichlorophenyl)methanol 
• 13692-15-4 2-(2,4-dichlorophenyl)oxirane 
• 874-42-0 2,4-dichlorobenzaldeyhde 

Downstream Products

• 57265-38-0 1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-methylbenzyl)imidazolium bromide 
• 57265-33-5 1-(2,4-dichlorobenzyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazolium chloride 
• 57265-37-9 1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-(m-methylbenzyl)imidazolium bromide 
• 57264-60-5 3-decyl-1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazol-3-ium bromide 
• 57265-28-8 1-[2-(p-Bromobenzoyl)ethyl]-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium chloride 
• 57265-17-5 1-(p-bromobenzoylmethyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium chloride 
• 57265-35-7 1-(p-chlorobenzyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium iodide 
• 57265-34-6 1-(2-cyano-4-nitrobenzyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]imidazolium bromide 
• 57264-71-8 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,5-xylyl)carbamoylmethyl]imidazolium chloride 
• 57264-99-0 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-{1-[N-(p-methylbenzyl)carbamoyl]ethyl}-imidazolium bromide 
• 57265-02-8 1-{1-[N-(p-Chlorobenzyl)carbamoyl]ethyl}-3-[2,4-dichloroβ-(2,4-dichlorobenzyloxy)phenethyl]imidazolium bromide 
• 57304-29-7 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,5-dichlorophenyl)carbamoylmethyl]imidazolium chloride 
• 57265-00-6 1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-{1-[N-(p-methoxybenzyl)carbamoyl]ethyl]imidazolium bromide 
• 57265-36-8 1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-fluorobenzyl)-imidazolium iodide 

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