Miconazole

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Miconazole
Systematic (IUPAC) name
1-[2-(2,4-dichlorophenyl)-2- [(2,4-dichlorophenyl) methoxy]ethyl]imidazole
Identifiers
CAS number	22916-47-8
ATC code	D01AC02 A01AB09 A07AC01 G01AF04
PubChem	4189
DrugBank	APRD01115
Chemical data
Formula	C18H14Cl4N2O
Mol. mass	416.127 g/mol
Pharmacokinetic data
Bioavailability	n/a
Metabolism	n/a
Half life	n/a
Excretion	n/a
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	topical

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Miconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, and commonly applied topically (to the skin) or mucus membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes. It can also be used against certain species of Leishmania protozoa (which are a type of unicellular parasite), as these also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, it also has some limited antibacterial properties.

United States Patent 5461068 lists the solubilities of Miconazole nitrate powder in water at 0.03%, in ethanol at 0.76%; and in their novel method of using acetic acid to achieve solubilities of up to 4%.

Miconazole is also used in Ektachrome film developing (along with surfactants such as Photo-Flo) in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde. Fuji Hunt also includes Miconazole as a final rinse additive in their formulation of the process C-41RA rapid access color negative developing process.

Indications

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). In addition the oral gel may also be used for the lip disorder angular cheilitis.

It has an advantage over Nystatin in the treatment of neonatal oral thrush in that the latter is only licensed in the UK for those over the age of one month; but note the possibility for drug interactions.

Side effects

Unlike nystatin, some miconazole is absorbed by the intestinal tract when used orally (and possibly if used vaginally^[1]) which may lead to drug interactions.

Of note may be interactions with anticoagulants, phenytoin, terbinafine, some newer atypical antipsychotics, cyclosporin and some statins used to treat hypercholesterolemia.

Formulations

Oral treatment: (brands: Daktarin in UK)

• Oral gel 24mg/ml (20mg/g)

External skin treatment: (brands: Micatin, Monistat-Derm, Daktarin in UK)

• Topical cream: 2%.
• Combination: 2% cream with 1% hydrocortisone (Daktacort in UK)

Vaginal treatment: (brands: Monistat, Femizol or Gyno-Daktariin in UK)

• Pessaries: 200 mg or 100 mg
• Vaginal cream: 2%
• Combination: 2% cream with either 100mg or 200 mg pessaries.

See also

• Antifungal drugs
• Cremophor EL
• Castor oil
• E-6 process
• Ektachrome

References

External links

Medical

• Miconazole (www.meds-help.com)
• Miconazole (National Institutes of Health)
• United States Patent 5461068 Imidazole derivative tincture and method of manufacture

Photographic

• Kodak process E6 Ektachrome (color transparency) processing manual Z-119

• Kodak process E6 Q-LAB processing manual Z-6 (more details than processing manual Z119 above)

v • d • e Stomatological preparations (A01)
Caries prophylactic agents	Sodium fluoride - Sodium monofluorophosphate - Olaflur - Stannous fluoride
Anti-infectives and antiseptics	Hydrogen peroxide - Chlorhexidine - Amphotericin B - Polynoxylin - Domiphen - Oxyquinoline - Neomycin - Miconazole - Natamycin - Hexetidine - Tetracycline - Benzoxonium chloride - Tibezonium iodide - Mepartricin - Metronidazole - Clotrimazole - Sodium perborate - Chlortetracycline - Doxycycline - Minocycline - Eugenol
Corticosteroids	Triamcinolone - Dexamethasone - Hydrocortisone
Other	Epinephrine/Adrenalone - Benzydamine - Acetylsalicylic acid - Amlexanox

v • d • e Antidiarrheals, intestinal anti-inflammatory/anti-infective agents (A07)
Intestinal anti-infectives	Antibiotics (Neomycin, Nystatin, Natamycin, Streptomycin, Polymyxin B, Paromomycin, Amphotericin B, Kanamycin, Vancomycin, Colistin, Rifaximin) Sulfonamides (Phthalylsulfathiazole, Sulfaguanidine, Succinylsulfathiazole) other (Miconazole, Broxyquinoline, Acetarsol, Nifuroxazide, Nifurzide)
Intestinal adsorbents	Charcoal - Bismuth - Pectin - Kaolin - Crospovidone - Attapulgite - Diosmectite
Antipropulsives	Diphenoxylate - Opium - Loperamide - Difenoxin
Intestinal anti-inflammatory agents	corticosteroids acting locally (Prednisolone, Hydrocortisone, Prednisone, Betamethasone, Tixocortol, Budesonide, Beclometasone) antiallergic agents, excluding corticosteroids (Cromoglicic acid) aminosalicylic acid and similar agents (Sulfasalazine, Mesalazine, Olsalazine, Balsalazide)
Antidiarrheal micro-organisms	Saccharomyces boulardii
Other antidiarrheals	Albumin tannate - Ceratonia - Racecadotril

v • d • e Antifungals (D01 and J02)
Antibiotics	Griseofulvin • polyene antimycotics (Natamycin, Nystatin)
Topical azoles	imidazoles (Bifonazole, Clomidazole, Clotrimazole, Econazole, Fenticonazole, Ketoconazole, Isoconazole, Miconazole, Oxiconazole, Sertaconazole, Sulconazole, Tioconazole) • triazoles (Fluconazole) • benzimidazole (Thiabendazole)
Other topicals	Ciclopirox • Ethylparaben • Flucytosine • Salicylic acid • Selenium sulfide • Tolnaftate • Undecylenic acid • allylamines (Amorolfine, Butenafine, Naftifine, Terbinafine)
For systemic use	Griseofulvin • allylamine (Terbinafine) • polyene antimycotic (Amphotericin B) • triazoles (Itraconazole, Posaconazole, Voriconazole) • echinocandins (Anidulafungin, Caspofungin, Micafungin)
Other	Tea tree oil • citronella oil • lemon grass • orange oil • patchouli • lemon myrtle

v • d • e Gynecological anti-infectives and antiseptics (G01)
Antibiotics	polyene antimycotic (Nystatin, Natamycin, Amphotericin B) - Candicidin - Chloramphenicol - Hachimycin - Oxytetracycline - Carfecillin - Mepartricin - Clindamycin - Pentamycin
Arsenic compounds	Acetarsol
Quinoline derivatives	Diiodohydroxyquinoline - Clioquinol - Chlorquinaldol - Dequalinium - Broxyquinoline - Oxyquinoline
Organic acids	Lactic acid - Acetic acid - Ascorbic acid
Sulfonamides	Sulfatolamide
Imidazole derivatives	Metronidazole - Clotrimazole - Miconazole - Econazole - Ornidazole - Isoconazole - Tioconazole - Ketoconazole - Fenticonazole - Azanidazole - Propenidazole - Butoconazole - Omoconazole - Oxiconazole - Flutrimazole
Triazole derivatives	Terconazole
Other	Clodantoin - Inosine - Policresulen - Nifuratel - Furazolidone - Methylrosaniline - Povidone-iodine - Ciclopirox - Protiofate - Lactobacillus fermentum - Copper usnate

v • d • e Otologicals (S02)
Anti-infectives	Chloramphenicol - Nitrofural - Boric acid - Aluminium acetotartrate - Clioquinol - Hydrogen peroxide - Neomycin - Tetracycline - Chlorhexidine - Acetic acid - Polymyxin B - Rifamycin - Miconazole - Gentamicin
Corticosteroids	Hydrocortisone - Prednisolone - Dexamethasone - Betamethasone
Other otologicals	Lidocaine - Cocaine

hu:Mikonazol nl:Miconazol