22916-47-8 Usage
Uses
Used in Pharmaceutical Industry:
Miconazole is used as an antifungal agent for the treatment of various skin conditions caused by dermatophytes, yeast, and molds. It is particularly effective against most dermatophyte species, P. orbiculare, and C. albicans. Miconazole is used in topical and vaginal preparations to prevent the growth of these fungi.
Used in Treatment of Fungal Infections:
Miconazole is used as an external treatment for athlete's foot, ringworm, and jock itch. It is also used internally for oral or vaginal thrush (yeast infection). The oral gel form of Miconazole may also be used for the lip disorder angular cheilitis.
Used in Neurological Applications:
Miconazole has been shown to promote remyelination of neurons in chronic progressive multiple sclerosis mouse models, indicating its potential use in neurological applications.
Used in Photography Industry:
Miconazole is also utilized in the photography industry, although the specific application is not detailed in the provided materials.
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
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.
Veterinary Drugs and Treatments
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
Check Digit Verification of cas no
The CAS Registry Mumber 22916-47-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,9,1 and 6 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 22916-47:
(7*2)+(6*2)+(5*9)+(4*1)+(3*6)+(2*4)+(1*7)=108
108 % 10 = 8
So 22916-47-8 is a valid CAS Registry Number.
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)
22916-47-8Relevant articles and documents
SMALL MOLECULE STIMULATORS OF THE CORE PARTICLE OF THE PROTEASOME
-
, (2021/02/26)
This present disclosure relates to series compounds and methods of use for the treatment of a disease caused by abnormal regulation of the ubiquitin-proteasome system (UPS), and wherein said compound is an effective stimulator of the 20S core particle (CP) of the UPS. Composition matters and methods of uses are within the scope of this disclosure.
Use of miconazole and derivatives thereof as TGR5 agonists (by machine translation)
-
Paragraph 0031; 0036; 0037-0040, (2020/05/02)
The invention belongs to the technical field of medicines, and relates to novel application TGR5 of miconazole and derivatives thereof in treatment, of diseases and conditions of a biological pathologic process involved in treatment, and. The miconazole and the analogues thereof can activate TGR5 active, for use TGR5 in the treatment or prevention of diseases associated with, activity modulation. (by machine translation)
Anti-staphylococcal biofilm activity of miconazoctylium bromide
Tessier, Jérémie,Golmohamadi, Mahmood,Wilkinson, Kevin J.,Schmitzer, Andreea R.
, p. 4288 - 4294 (2018/06/22)
We designed and synthesized miconazole analogues containing a substituted imidazolium moiety. The structural modification of the miconazole led to a compound with high potency to prevent the formation and disrupt bacterial biofilms, as a result of accumulation in the biofilm matrix, permeabilization of the bacterial membrane and generation of reactive oxygen species in the cytoplasm.
METHOD FOR PRODUCING PULVERIZED ORGANIC COMPOUND PARTICLE
-
, (2015/12/19)
Disclosed is a method for producing pulverized particles of a crystalline organic compound which is poorly water-soluble. Also disclosed is a pulverized organic compound particle produced by such a method. Specifically disclosed is a method for producing a poorly water-soluble organic compound particle for medical use, which is characterized in that a poorly water-soluble organic compound for medical use is mixed with a physiologically acceptable salt and a physiologically acceptable polyol, and subjected to wet milling. Also specifically disclosed is a poorly water-soluble organic compound particle for medical use, which is produced by such a production method.
