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
c1cc(cc(c1COC(Cn2ccnc2)c3ccc(cc3Cl)Cl)Cl)Cl
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 |
---|---|---|
In vitro synergism between nyasol, an active compound isolated from Anemarrhena asphodeloides, and azole agents against Candida albicans. | 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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Systemic Candida infection in University hospital 1997-1999: the distribution of Candida biotypes and antifungal susceptibility patterns. | 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 |
|
Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels. | 2001 Apr 17 |
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The importance of reassessment to chronic wound care. | 2001 Aug |
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Suppression of transient outward potassium currents in mouse ventricular myocytes by imidazole antimycotics and by glybenclamide. | 2001 Aug |
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Primary culture system of adrenocortical cells from dogs to evaluate direct effects of chemicals on steroidogenesis. | 2001 Aug 28 |
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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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Chronic sino-naso-orbital fungal infection due to Pseudallescheria boydii in a nonimmunocompromised host--a case report. | 2001 Jul |
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Systemic antifungal agents. | 2001 Jul |
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Characterization of endothelium-derived hyperpolarizing factor in the human forearm microcirculation. | 2001 Jun |
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Gender-specific compensation for the lack of NO in the mediation of flow-induced arteriolar dilation. | 2001 Jun |
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Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis. | 2001 Jun 15 |
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Influence of the roll compactor parameter settings and the compression pressure on the buccal bio-adhesive tablet properties. | 2001 Jun 4 |
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A novel bovine lactoferrin peptide, FKCRRWQWRM, suppresses Candida cell growth and activates neutrophils. | 2001 Mar |
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Progestins block cholesterol synthesis to produce meiosis-activating sterols. | 2001 Mar |
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Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions. | 2001 May 15 |
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Chronic estrogen depletion alters adenosine diphosphate-induced pial arteriolar dilation in female rats. | 2001 Nov |
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In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens. | 2001 Oct |
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Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria. | 2001 Oct |
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Signaling pathway and chronotropic action of parathyroid hormone in isolated perfused rat heart. | 2001 Oct |
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Involvement of cytochrome P450 metabolites in the vascular action of angiotensin II on the afferent arterioles. | 2001 Sep |
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The role of endothelium-derived hyperpolarizing factor in the regulation of the uterine circulation in pregnant rats. | 2001 Sep |
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Reversal effects of antifungal drugs on multidrug resistance in MDR1-overexpressing HeLa cells. | 2001 Sep |
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Crystallization and preliminary crystallographic analysis of a novel cytochrome P450 from Mycobacterium tuberculosis. | 2002 Apr |
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N-methyl-D-aspartate-induced vasodilation is mediated by endothelium-independent nitric oxide release in piglets. | 2002 Apr |
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Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts. | 2002 Feb |
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Fungal keratitis caused by Scedosporium apiospermum: report of two cases and review of treatment. | 2002 Jul |
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Severe keratomycosis secondary to Scedosporium apiospermum. | 2002 Jul |
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7-Benzyloxyquinoline oxidation by P450eryF A245T: finding of a new fluorescent substrate probe. | 2002 Jun |
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Antifungal prophylaxis for severely neutropenic chemotherapy recipients: a meta analysis of randomized-controlled clinical trials. | 2002 Jun 15 |
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Inhibition of cytochromes P450 by antifungal imidazole derivatives. | 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 |
|
[A case of abrupt pulmonary infection by Rhizopus microsporus var. rhizopodiformis during treatment for bronchial asthma]. | 2002 May |
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
Fri Jun 25 20:52:46 UTC 2021
by
admin
on
Fri Jun 25 20:52:46 UTC 2021
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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
Created by
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CFR |
21 CFR 524.1443
Created by
admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
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WHO-ATC |
A01AB09
Created by
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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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admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
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WHO-ATC |
A07AC01
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admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
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NCI_THESAURUS |
C514
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WHO-ESSENTIAL MEDICINES LIST |
13.1
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WHO-VATC |
QJ02AB01
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admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
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CFR |
21 CFR 524.1132
Created by
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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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22916-47-8
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C62048
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1800
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SUB08944MIG
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6932
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PRIMARY | RxNorm | ||
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D008825
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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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PRIMARY | Merck Index | ||
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2449
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1443409
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PRIMARY | USP-RS |
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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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |