Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H14Cl4N2O |
Molecular Weight | 416.129 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1
InChI
InChIKey=BYBLEWFAAKGYCD-UHFFFAOYSA-N
InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2
Molecular Formula | C18H14Cl4N2O |
Molecular Weight | 416.129 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Miconazole is a synthetic imidazole derivative, a topical antifungal agent for use in the local treatment of vaginal, and skin and nail infections due to yeasts and dermatophytes. It is particularly active against Candida spp., Trichophyton spp., Epidermophyton spp., Microsporum spp. and Pityrosporon orbiculare (Malassezia furfur), but also possesses some activity against Gram-positive bacteria. It binds to the heme moiety of the fungal cytochrome P-450 dependent enzyme lanosterol 14-alpha-demethlyase. Inhibits 14-alpha-demethlyase, blocks formation of ergosterol and leads to the buildup of toxic methylated 14-a-sterols. Miconazole also affects the synthesis of triglycerides and fatty acids and inhibits oxidative and peroxidative enzymes, increasing the amount of active oxygen species within the cell.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1780 |
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Target ID: CHEMBL3286061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28930429 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | ORAVIG Approved UseORAVIG is an azole antifungal indicated for the local treatment of oropharyngeal candidiasis in adults Launch Date1.26144004E11 |
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Curative | MONISTAT 1 COMBINATION PACK Approved UseUsed to treats vaginal yeast infections, relieves external itching and irritation due to a vaginal yeast infection Launch Date9.9368639E11 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
39.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MICONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
136.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MICONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MICONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg single, vaginal Recommended Dose: 1200 mg Route: vaginal Route: single Dose: 1200 mg Sources: |
unhealthy, 18 - 60 years n = 50 Health Status: unhealthy Condition: vaginal candidosis Age Group: 18 - 60 years Sex: F Population Size: 50 Sources: |
|
200 mg 1 times / day multiple, intravenous Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Co-administed with:: amphotericin B Sources: itraconazole |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: |
Disc. AE: Fibrillation ventricular... AEs leading to discontinuation/dose reduction: Fibrillation ventricular (grade 5, 11.1%) Sources: |
800 mg single, intravenous Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Co-administed with:: amphotericin B Sources: itraconazole |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: |
Disc. AE: Bradyarrhythmia... AEs leading to discontinuation/dose reduction: Bradyarrhythmia (5.2%) Sources: |
0.25 % 7 times / day steady, topical Recommended Dose: 0.25 %, 7 times / day Route: topical Route: steady Dose: 0.25 %, 7 times / day Sources: |
unhealthy, newborns n = 330 Health Status: unhealthy Condition: Diaper dermatitis complicated by candidiasis Age Group: newborns Sex: M+F Population Size: 330 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fibrillation ventricular | grade 5, 11.1% Disc. AE |
200 mg 1 times / day multiple, intravenous Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Co-administed with:: amphotericin B Sources: itraconazole |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: |
Bradyarrhythmia | 5.2% Disc. AE |
800 mg single, intravenous Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Co-administed with:: amphotericin B Sources: itraconazole |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: M Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes [IC50 0.175 uM] | |||
Page: - |
yes [Ki 0.01 uM] | |||
Page: - |
yes [Ki 0.028 uM] | |||
Page: - |
yes [Ki 0.05 uM] | |||
Page: - |
yes [Ki 0.7 uM] | |||
Page: - |
yes [Ki 1.2 uM] | |||
Page: - |
yes [Ki 2.2 uM] | |||
Page: - |
yes [Ki 3.2 uM] | |||
Page: - |
yes [Ki 7.3 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/ Page: - |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
Antituberculosis activity of certain antifungal and antihelmintic drugs. | 1999 |
|
Triorganotin compounds as antimicrobial agents. | 1999 Apr 30 |
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Gold(I) complexes as antimicrobial agents. | 1999 Apr 30 |
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Sesquiterpene lactones from Centaurea thessala and Centaurea attica. Antifungal activity. | 2000 Dec |
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Synthesis and antimicrobial activity of new 3-(1-R-3(5)-methyl-4-nitroso-1H-5(3)-pyrazolyl)-5-methylisoxazoles. | 2000 Dec |
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Antifungal activity of a new triazole, voriconazole (UK-109496), against clinical isolates of Aspergillus spp. | 2000 Jun |
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Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis. | 2000 Nov 15 |
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In vitro antifungal activity of a novel lipopeptide antifungal agent, FK463, against various fungal pathogens. | 2000 Oct |
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[Klion D - possibilities of prophylaxis and treatment during pregnancy]. | 2001 |
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[Current problems in etiotropic therapy of mycoses]. | 2001 |
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Spectrophotometric resolution of metronidazole and miconazole nitrate in ovules using ratio spectra derivative spectrophotometry and RP-LC. | 2001 Apr |
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Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels. | 2001 Apr 17 |
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Characterization of glassy itraconazole: a comparative study of its molecular mobility below T(g) with that of structural analogues using MTDSC. | 2001 Feb 1 |
|
Regulation of phosphatidylserine transbilayer redistribution by store-operated Ca2+ entry: role of actin cytoskeleton. | 2001 Feb 16 |
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Corneal co-infection with Scedosporium apiospermum and Acanthamoeba after sewage-contaminated ocular injury. | 2001 Jan |
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Reduced glutathione, dithiothreitol and cytochrome P-450 inhibitors do not influence hypoxic chemosensory responses in the rat carotid body. | 2001 Jan 19 |
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In vitro comparison of the antimycotic activity of a miconazole-HP-beta-cyclodextrin solution with a miconazole surfactant solution. | 2001 Jul |
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Miconazole-warfarin interaction: increased INR. | 2001 Jul 10 |
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Endothelium-dependent desensitization to angiotensin II in rabbit aorta: the mechanisms involved. | 2001 Jun |
|
A neuronal isoform of nitric oxide synthase expressed in pancreatic beta-cells controls insulin secretion. | 2001 Jun |
|
Androgen metabolism in oyster Crassostrea gigas: evidence for 17beta-HSD activities and characterization of an aromatase-like activity inhibited by pharmacological compounds and a marine pollutant. | 2001 Oct |
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Inhibition of sarcoplasmic reticulum Ca2+-ATPase by miconazole. | 2002 Jul |
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Comparison of dermatopharmacokinetic vs. clinicial efficacy methods for bioequivalence assessment of miconazole nitrate vaginal cream, 2% in humans. | 2002 Mar |
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Enhancement of skin permeation of miconazole by phospholipid and dodecyl 2-(N,N-dimethyl amino)propionate (DDAIP). | 2002 Mar 2 |
|
Pityriasis versicolor rubra. | 2002 Mar-Apr |
Sample Use Guides
Application of one ORAVIG 50 mg buccal tablet to the gum region once daily for 14 consecutive days.
External miconazole nitrate vulvar cream (2%): twice daily, for up to 7 days as needed.
Miconazole nitrate vaginal insert (1200mg): with the applicator place the vaginal insert into the vagina.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15825399
The antifungal drug, miconazole nitrate, inhibits the growth of several species of Candida. Candida albicans, one of the pathogenic species, was totally inhibited at a concentration of approximately 10 mug/ml.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:41:52 UTC 2023
by
admin
on
Wed Jul 05 22:41:52 UTC 2023
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Record UNII |
7NNO0D7S5M
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QD01AC02
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WHO-ATC |
J02AB01
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WHO-ATC |
G01AF04
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NDF-RT |
N0000008217
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WHO-VATC |
QA01AB09
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CFR |
21 CFR 524.1445
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WHO-VATC |
QA07AC01
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FDA ORPHAN DRUG |
406413
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NDF-RT |
N0000175487
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WHO-ATC |
S02AA13
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WHO-ATC |
D01AC02
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CFR |
21 CFR 524.1443
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WHO-ATC |
A01AB09
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WHO-VATC |
QS02AA13
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WHO-VATC |
QG01AF04
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WHO-VATC |
QD01AC52
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WHO-ATC |
D01AC52
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WHO-ATC |
A07AC01
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NCI_THESAURUS |
C514
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WHO-ESSENTIAL MEDICINES LIST |
13.1
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WHO-VATC |
QJ02AB01
Created by
admin on Wed Jul 05 22:41:52 UTC 2023 , Edited by admin on Wed Jul 05 22:41:52 UTC 2023
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CFR |
21 CFR 524.1132
Created by
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Code System | Code | Type | Description | ||
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245-324-5
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4189
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22916-47-8
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2728
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DTXSID6023319
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C62048
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7NNO0D7S5M
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1800
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100000090369
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SUB08944MIG
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6932
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D008825
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6923
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MICONAZOLE
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Miconazole
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7NNO0D7S5M
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DB01110
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CHEMBL91
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M7527
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2449
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1443409
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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METABOLIC ENZYME -> INHIBITOR |
IC50
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |