Miconazole
A01A - Stomatological preparations
ATC G01AF04
Small molecule
approved 1974
Parenteral
Topical
Natural product
JFDA label: Gyno-Candizol
Mechanism of Action
Inhibitor of Lanosterol 14-alpha demethylase — Cytochrome P450 51 inhibitor
| Target | Action | Gene / class |
|---|---|---|
| Lanosterol 14-alpha demethylase efficacy | INHIBITOR | ERG11 |
Indications
Approved
- Infections — infection
- Mycoses — fungal infectious disease
- Pruritus — Pruritus
- Tinea — tinea
- Tinea Pedis — tinea pedis
Off-label
- HIV Infections
- Otomycosis
- Stomatitis
Class profile
| antifungalClass | Azole (topical/mucosal) |
|---|---|
| targetMolecule | Lanosterol 14-alpha-demethylase (CYP51) |
| isFungicidal | 0 |
| spectrumCandida | S |
| spectrumAspergillus | Limited topical |
| spectrumCryptococcus | Limited |
| spectrumDermatophytes | S |
| resistanceMechanisms | ERG11 mutations,Efflux pumps |
| source | Pappas2016/Lass-Florl2011 |
Adverse Reactions
Very Common >10%Common 1–10%Uncommon 0.1–1%
Rare 0.01–0.1%Very Rare <0.01%Not Known
Nervous system disorders (1)
Common Headache
Blood and lymphatic system disorders (3)
Common Anaemia · Lymphopenia · Neutropenia
Gastrointestinal disorders (9)
Very Common Gastrointestinal disorder
Common Abdominal pain · Abdominal pain upper · Diarrhoea · Dry mouth · Gastroenteritis · Gastrointestinal pain · Nausea · Vomiting
Skin and subcutaneous tissue disorders (1)
Common Pruritus
Musculoskeletal and connective tissue disorders (1)
Common Muscle spasms
Infections and infestations (2)
Very Common Infection
Common Upper respiratory tract infection
Investigations (1)
Common Gamma-glutamyltransferase increased
General disorders and administration site conditions (10)
Very Common Infestation · Nervous system disorder
Common Ageusia · Asthenia · Blood disorder · Dysgeusia · Fatigue · Glossodynia · Oral discomfort · Pain
Respiratory, thoracic and mediastinal disorders (1)
Common Cough
Dosing
Source: openFDA
Directions Clean the affected area and dry thoroughly • Apply a thin layer of the product over affected area twice daily (morning and night) or as directed by a healthcare professional • Supervise children in the use of this product. For athlete's foot: • Use daily for 4 weeks. If condition persists, consult a healthcare professional. • Pay special attention to the spaces between the toes • Wear well fitting, ventilated shoes • Change socks atleast once daily. For ringworm: Use daily for 4 weeks. If condition persists, consult a healthcare professional. For jock itch: Use daily for 2 weeks. If condition persists longer, consult a healthcare professional. This product is not effective on the scalp or nails.
Warnings & Precautions
Source: openFDA
Warnings & Precautions
Warnings For external use only
Pregnancy & Lactation
Pregnancy
Lactation
Caution
Hale L3
Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.
Monitoring
| Efficacy | Fungal culture and species identification; minimum inhibitory concentration (MIC) where available; clinical response (temperature, imaging for invasive fungal disease) |
|---|---|
| Toxicity | LFTs (hepatotoxicity — azoles in particular); renal function; ECG for QT prolongation (azoles); drug levels if available (itraconazole, voriconazole) |
| Clinical pearl | Voriconazole levels are highly variable due to CYP2C19 polymorphism — TDM recommended (target trough 2–5 mg/L). Check for drug interactions with CYP3A4 substrates. |
| Counseling | Report visual disturbances (voriconazole), jaundice, or rash. Take azoles with food or as directed to optimise absorption. |
Chemistry & Properties
| Formula | C18H14Cl4N2O |
|---|---|
| Molecular weight | 416.13 g/mol |
| IUPAC name | 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole |
| CAS | 22916-47-8 |
| PubChem CID | 4189 |
| InChIKey | BYBLEWFAAKGYCD-UHFFFAOYSA-N |
| logP | 6.45 (XLogP 5.3) |
| Polar surface area | 27.05 Ų |
| H-bond acceptors / donors | 3 / 0 |
| Drug-likeness (QED) | 0.46 |
| Lipinski violations | 1 |
SMILES
Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)c(Cl)c1Biology & Pharmacokinetics
Pharmacokinetics predicted
| Bioavailability | 35.0% |
|---|---|
| Half-life | 1.222 h |
| Volume of distribution | 5.099 L/kg |
| Protein binding | 95.3% |
| BBB penetrant | No |
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP1A2 | Inhibitor | IC₅₀ 3.4526801184007745 µM |
| CYP1A2 | Substrate | — |
| CYP2B6 | Inhibitor | — |
| CYP2C19 | Inhibitor | IC₅₀ 0.09143941539177035 µM |
| CYP2C8 | Inhibitor | — |
| CYP2C9 | Inhibitor | IC₅₀ 0.956101084646861 µM |
| CYP2D6 | Inhibitor | IC₅₀ 1.1279347245227418 µM |
| CYP3A4 | Inhibitor | IC₅₀ 0.3706107091093686 µM |
| CYP3A4 | Substrate | — |
Receptor binding (top 2)
| Target | Action | Affinity |
|---|---|---|
| CYP8B1 (CYP8B1) | Inhibitor | pKd 7.0 |
| CYP8B1 (CYP8B1) | Inhibitor | pIC50 6.3 |
Transporters
BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MDR1 (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)MRP3 (Inhibitor)MRP4 (Inhibitor)OATP1B1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)
Drug–drug interactions (100+, DDInter)
| Interacting drug | Severity | Management |
|---|---|---|
| Acetohexamide | major | |
| Anisindione | major | |
| Astemizole | major | |
| Chlorpropamide | major | |
| Dicoumarol | major | |
| Eliglustat | major | |
| Glimepiride | major | |
| Glipizide | major | |
| Glyburide | major | |
| Pexidartinib | major | |
| Terfenadine | major | |
| Tolazamide | major | |
| Tolbutamide | major | |
| Warfarin | major | |
| Acalabrutinib | moderate | |
| Alfentanil | moderate | |
| Alfuzosin | moderate | |
| Aliskiren | moderate | |
| Alosetron | moderate | |
| Alprazolam | moderate | |
| Amiodarone | moderate | |
| Amitriptyline | moderate | |
| Amlodipine | moderate | |
| Apixaban | moderate | |
| Aprepitant | moderate | |
| Aripiprazole | moderate | |
| Artemether | moderate | |
| Atazanavir | moderate | |
| Atorvastatin | moderate | |
| Avapritinib | moderate | |
| Axitinib | moderate | |
| Benzhydrocodone | moderate | |
| Bepridil | moderate | |
| Boceprevir | moderate | |
| Bosentan | moderate | |
| Bosutinib | moderate | |
| Brigatinib | moderate | |
| Budesonide | moderate | |
| Budesonide (nasal) | moderate | |
| Buprenorphine | moderate |
Showing 40 of 100+.
Registered Products (39)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| Cyprozol Cream | Cream 2 % | 15 g tube | Reda Jardaneh Drug Store | 0.890 |
| Candizol Cream | Cream 2 % | 15 g tube pack varies | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 1.000 |
| Mycoderm Cream | Cream 2 % | 15 g tube pack varies | Amman Pharmaceutical Indusries | 1.050 |
| candicort cream | Cream 1 %, 2 % | 15 g tube | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 1.460 |
| meconazol cream | Cream 2 % | 15 g tube pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 1.480 |
| MYCOHEAL-HC CREAM | Cream 1 %, 2 % | 15 g tube | Dar Al Dawa Development and Investment Co Ltd/Jordan | 1.740 |
| Daktacort cream | Cream 10 mg/g, 20 mg/g | 15 g tube | Al-Amad Drug Store | 1.810 |
| Daktarin cream | Cream 20 mg/1 g | 15 g tube | Telegraph Drug Store | 1.850 |
| Mikozal Cream | Cream 2 % | 30 g tube | Professional Drug Store | 1.940 |
| Ticozal | Cream Miconazole 2 %WW | (30 GM) / | PELLA PHARMACEUTICALS CO.LTD/JORDAN | 1.970 |
| meconazol powder | Powder 2 % | 15 g pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 1.970 |
| Candizol Cream | Cream 2 % | 30 g tube pack varies | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 2.000 |
| MYCOHEAL CREAM | Cream 20 mg | 30 g tube | Dar Al Dawa Development and Investment Co Ltd/Jordan | 2.000 |
| Mycoderm Cream | Cream 2 % | 30 g tube pack varies | Amman Pharmaceutical Indusries | 2.000 |
| ticozal | Cream Miconazole Nitrate 2 %WW | (30 GM) / TUB | PELLA PHARMACEUTICALS CO.LTD/JORDAN | 2.000 |
| meconazol cream. | Cream 2 % | 30 g tube pack varies | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 2.160 |
| Mycoderm-V Vaginal Cream | Cream 2 % | 40gm | Amman Pharmaceutical Indusries | 2.330 |
| Candizol Oral Gel | Gel 2 % | 40 g tube | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 2.580 |
| Mycogel Oral Gel | Gel 2 % | 40 gm | Amman Pharmaceutical Industries Co | 2.580 |
| MYCOHEAL 400 VAG.SUPP. | Vaginal 400 mg | 3 | Dar Al Dawa Development and Investment Co Ltd/Jordan | 2.700 |
| Meconazol Oral Gel | Gel 2 % | 40 g tube | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 2.760 |
| Micozole Gel | Gel 20 mg/g | 40 g tube | JERASH PHARMACEUTICALS LTD.CO/JORDAN | 2.760 |
| MYCOHEAL 200 VAG.SUPP. | Vaginal 200 mg | 7 | Dar Al Dawa Development and Investment Co Ltd/Jordan | 2.800 |
| Micover 200mg ovules | Vaginal 200 mg | 7 Vag.Ovules pack varies | JORDAN RIVER PHARMA.IND(JORIVER)/JORDAN | 2.800 |
| Micover Ovules | Ovule 400 mg | 3 pack varies | JORDAN RIVER PHARMA.IND(JORIVER)/JORDAN | 2.800 |
| Gyno-Meconazol V Cream | Cream 20 mg/g | 40 g tube | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 2.810 |
| Gyno-Meconazol Vag. Ovules | Vaginal 400 mg | 3 Ovules | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 2.810 |
| MYCOHEAL ORAL GEL | Gel 20 mg | 40 g tube | Dar Al Dawa Development and Investment Co Ltd/Jordan | 2.980 |
| MICOZEN ORAL GEL | Gel Miconazole 20 mg/1000 mg | (40 GM) / TUB | AlGadeed Pharmaceutical Industries | 3.050 |
| gyno-meconazol vag. Ovules | Vaginal 200 mg | 7 Ovules | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 3.130 |
| Gyno-Candizol | Tablet 400 mg | 3 tab | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 3.200 |
| Daktarin Oral gel | Gel 2 % | 40 g tube | Al-Amad Drug Store | 3.280 |
| Gyno-Candizol | Vaginal 200 mg | 7 S.G Vaginal Ovules | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 3.750 |
| MYCOHEAL Vag. Cream | Cream 20 mg/g | 50 g tube | Dar Al Dawa Development and Investment Co Ltd/Jordan | 3.780 |
| gyno-meconazol vaginal cream | Cream 20 mg/g | 78 g tube | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 5.470 |
| Meconasol Aerosol | Cream 0.3 g/150 g | 150 g tube | MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN | 6.620 |
| Micover 200mg ovules | Vaginal 200 mg | 120 Vag.Ovules pack varies | JORDAN RIVER PHARMA.IND(JORIVER)/JORDAN | 43.200 |
| Micover Ovules | Vaginal 400 mg | 120 Vag Ovules pack varies | JORDAN RIVER PHARMA.IND(JORIVER)/JORDAN | 89.600 |
| Micover Ovules | Vaginal 400 mg | 240 Ovules pack varies | JORDAN RIVER PHARMA.IND(JORIVER)/JORDAN | 150.000 |