QuickView for Miconazole (compound)

Summary
General Info

PubChem

PubChem Compound 4189

Name:	Miconazole
PubChem Compound ID:	4189
Description:	An imidazole antifungal agent that is used topically and by intravenous infusion.
Molecular formula:	C₁₈H₁₄Cl₄N₂O
Molecular weight:	416.127 g/mol
Synonyms:	75319-47-0; Miconazol [INN-Spanish]; Miconazole [USAN:BAN:INN:JAN]; Daktarin IV; NINDS_000156; MCZ; 5-23-04-00320 (Beilstein Handbook Reference); AIDS-007318; Aflorix(nitrate); Epi-Monistat(nitrate). show more » 75319-47-0; Miconazol [INN-Spanish]; Miconazole [USAN:BAN:INN:JAN]; Daktarin IV; NINDS_000156; MCZ; 5-23-04-00320 (Beilstein Handbook Reference); AIDS-007318; Aflorix(nitrate); Epi-Monistat(nitrate); Spectrum2_001048; Monistat; Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)- (9CI); Monistat IV; Florid(nitrate); KBio2_001445; 1-(2,4-Dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole; Monista (nitrate); Prestwick_335; KBio1_000156; BRN 0965511; NCI60_001353; Miconazole; KBioSS_001445; Albistat(nitrate); NCI60_001380; 22832-87-7; EINECS 245-324-5; CPD-4501; 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole; Spectrum3_000507; Monistat (TN); Andergin(nitrate); 1H-Imidazole, 1-[2- (2,4-dichlorophenyl)-2-[(2, 4-dichlorophenyl)methoxy]ethyl]-; NSC 170986; Lotrimin AF(nitrate); 1H-imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl) methoxy)ethyl)-; NSC169434; Spectrum_000965; Miconazolum [INN-Latin]; SPBio_000976; KBio2_006581; Monistat IV (TN); AIDS007318; MJR 1762; 1-[2-(2,4-Dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole; Prestwick1_000067; Micantin (nitrate); Prestwick0_000067; Spectrum4_000061; Imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)-; 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl) imidazole; 1H-Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-; R 14889; Conofite(nitrate); CCRIS 7924; D00416; Miconazole (JP15/USP); Imidazole, 1-[2,4-dichloro-.beta.-[ (2, 4-dichlorobenzyl)oxy]phenethyl]-; NSC170986; KBio2_004013; 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-; R 18134; 22916-47-8; imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy) phenethyl)-; Minostate; DivK1c_000156; KBio3_001533; Miconazolo [DCIT]; KBioGR_000581; CHEBI:6923; SPBio_002174; imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl) methoxy)ethyl)- (9CI); Gyno-Daktar(nitrate) show less «

DrugBank

Identification

Name:	Miconazole
Name (isomeric):	DB01110
Drug Type:	small molecule
Description:	An imidazole antifungal agent that is used topically and by intravenous infusion.
Synonyms:	MCZ
Brand:	Monistat IV, Miconazole 7 Combination Pack, Monistat 3 Dual-Pak, M-zole 7 Dual Pack, Monistat 1 Combination Pack, Monistat 7 Vaginal Suppositories, Miconazole 3 Combination Pack, Miconazole Nitrate Combination Pack, Monistat, Vusion, Monazole 7, Miconazole Nitrate, Monistat 7 Combination Pack, Monistat 3 Combination Pack, Miconazole-7, Monistat-Derm, Zimycan, Minostate, Miconazole 7, Miconazole 3, Femizol-M, Monistat 5 Tampon, Monistat 7 Dual-Pak, M-zole 3 Combination Pack, Monistat 7, Novo-Miconazole Vaginal Ovules, Monistat 3, Monistat-3 Combination Pack, Monistat Dual- PAK, Micatin, Monistat 3 Vaginal Ovules, Monistat 5, Daktarin, Micozole
Category:	Antifungal Agents
CAS number:	22916-47-8

Pharmacology

Indication:	For topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by <i>Trichophyton rubrum</i>, <i>Trichophyton mentagrophytes</i>, and <i>Epidermophyton floccosum</i>, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor.
Pharmacology:	Miconazole is an anti-fungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). It is used either on the skin or in the vagina for fungal infections. Miconazole was approved by the FDA in 1974. Miconazole prevents fungal organisms from producing vital substances requi... show more » Miconazole is an anti-fungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). It is used either on the skin or in the vagina for fungal infections. Miconazole was approved by the FDA in 1974. Miconazole prevents fungal organisms from producing vital substances required for growth and function. This medication is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections. show less «
Mechanism of Action:	Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiratio... show more » Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis. show less «
Toxicity:	Oral, mouse: LD₅₀ = 3800 mg/kg; Oral, rat: LD₅₀ = 3 gm/kg. Ingestion of the amounts of the components contained in a tube of cream are unlikely to produce overdosage and toxic effects.
Affected organisms:	Fungi, yeast and protozoans

Interactions

Drug interaction:

Telithromycin	Miconazole may increase the plasma concentration of Telithromycin. Consider alternate therapy or monitor therapeutic/adverse effects.
Vardenafil	Miconazole, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
Tacrolimus	The strong CYP3A4 inhibitor, Miconazole, may decrease the metabolism and clearance of Tacrolimus, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Tacrolimus if Miconazole is initiated, discontinued or dose changed.
Tacrine	The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by Miconazole, a CYP1A2 inhibitors. Monitor the efficacy and toxicity of Tacrine if Miconazole is initiated, discontinued or if the dose is changed.
Acenocoumarol	Miconazole may increase the serum concentration of acenocoumarol by decreasing its metabolism.

Telithromycin	Miconazole may increase the plasma concentration of Telithromycin. Consider alternate therapy or monitor therapeutic/adverse effects.
Vardenafil	Miconazole, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
Tacrolimus	The strong CYP3A4 inhibitor, Miconazole, may decrease the metabolism and clearance of Tacrolimus, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Tacrolimus if Miconazole is initiated, discontinued or dose changed.
Tacrine	The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by Miconazole, a CYP1A2 inhibitors. Monitor the efficacy and toxicity of Tacrine if Miconazole is initiated, discontinued or if the dose is changed.
Acenocoumarol	Miconazole may increase the serum concentration of acenocoumarol by decreasing its metabolism.
Trazodone	The CYP3A4 inhibitor, Miconazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Consider alternate therapy or monitor for changes in Trazodone efficacy/toxicity if Miconazole is initiated, discontinued or dose changed.
Venlafaxine	Miconazole, a CYP2D6 and CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 and CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Miconazole is initiated, discontinued, or dose changed.
Vinblastine	Miconazole, a strong CYP3A4 inhibitor, may decrease the metabolism of Vinblastine. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Miconazole is initiated, discontinued or dose changed.
Tiagabine	The strong CYP3A4 inhibitor, Miconazole, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Miconazole is initiated, discontinued or dose changed.
Tramadol	Miconazole may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Miconazole may decrease the effect of Tramadol by decreasing active metabolite production.
Vincristine	Miconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of Vincristine by decreasing its metabolism. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Miconazole is initiated, discontinued or dose changed.
Teniposide	The strong CYP3A4 inhibitor, Miconazole, may decrease the metabolism and clearance of Teniposide, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Teniposide if Miconazole is initiated, discontinued or dose changed.
Tolterodine	Miconazole may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Trimipramine	The strong CYP3A4/2D6/2C19 inhibitor, Miconazole, may decrease the metabolism and clearance of Trimipramine, a CYP3A4/2D6/2C19 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Miconazole is initiated, discontinued or dose changed.
Vinorelbine	Miconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of Vinorelbine by decreasing its metabolism. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Miconazole is initiated, discontinued or dose changed.
Torasemide	Miconazole, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Miconazole is initiated, discontinued or dose changed.
Tizanidine	Miconazole may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
Temsirolimus	Miconazole may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
Tolbutamide	Miconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Miconazole is initiated, discontinued or dose changed.
Dicumarol	Miconazole may increase the serum concentration of dicumarol by decreasing its metabolism.
Tamsulosin	Miconazole, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Miconazole is initiated, discontinued, or dose changed.
Tamoxifen	Miconazole may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
Tadalafil	Miconazole may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
Verapamil	Miconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Miconazole is initiated, discontinued or dose changed.
Warfarin	Miconazole, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if miconazole is initiated, discontinued or dose changed.
Voriconazole	Miconazole, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if miconazole is initiated, discontinued or dose changed.
Anisindione	Miconazole may increase the serum concentration of anisindione by decreasing its metabolism.
Trimethoprim	The strong CYP2C9 inhibitor, Miconazole, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Miconazole is initiated, discontinued or dose changed.