Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H15Cl3N2O.C7H6O6S |
| Molecular Weight | 599.867 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC(=CC=C1O)S(O)(=O)=O.ClC2=CC=C(COC(CN3C=CN=C3)C4=C(Cl)C=C(Cl)C=C4)C=C2
InChI
InChIKey=WJRNYYWHDHVDCF-UHFFFAOYSA-N
InChI=1S/C18H15Cl3N2O.C7H6O6S/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21;8-6-2-1-4(14(11,12)13)3-5(6)7(9)10/h1-9,12,18H,10-11H2;1-3,8H,(H,9,10)(H,11,12,13)
| Molecular Formula | C18H15Cl3N2O |
| Molecular Weight | 381.684 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | C7H6O6S |
| Molecular Weight | 218.184 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Econazole (commonly used as the nitrate salt) is an antifungal medication of the imidazole class. It is a broad spectrum antimycotic with some action against Gram positive bacteria. It is used topically in dermatomycoses also orally and parenterally. Sold under the brand name Ecoza among others, it is indicated for the treatment of interdigital tinea
pedis caused by Trichophyton rubrum, Trichophyton mentagrophytes, and
Epidermophyton floccosum in patients 12 years of age and older. Econazole 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. Econazole 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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 17.9 nM [Kd] | |||
Target ID: CHEMBL612649 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | ECOZA Approved UseEcoza (econazole nitrate) topical foam, 1%, is indicated for the treatment of interdigital tinea
pedis caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton
floccosum in patients 12 years of age and older. Launch Date1982 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
417 pg/mL |
24 mg 1 times / day steady-state, topical dose: 24 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
ECONAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3440 pg × h/mL |
24 mg 1 times / day steady-state, topical dose: 24 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
ECONAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
53 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32410819 |
150 mg single, vaginal dose: 150 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
ECONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
81.77 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32410819 |
150 mg 1 times / day multiple, vaginal dose: 150 mg route of administration: Vaginal experiment type: MULTIPLE co-administered: |
ECONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Antifungal drug susceptibility of Candida causing oropharyngeal candidiasis in HIV infected patients]. | 2001 |
|
| Effect of epidermal growth factor on phosphate uptake in renal proximal tubule cells: involvement of PKC, MAPK, and cPLA2. | 2003 |
|
| The role of calcium channels in substance P-induced contractile response in the rat iris. | 2003 Dec |
|
| Experimental evaluation of antifungal and antiseptic agents against Rhodotorula spp. | 2003 Dec |
|
| Inhibition of heme crystal growth by antimalarials and other compounds: implications for drug discovery. | 2003 Dec 1 |
|
| Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. | 2004 Apr 15 |
|
| Thapsigargin-stimulated MAP kinase phosphorylation via CRAC channels and PLD activation: inhibitory action of docosahexaenoic acid. | 2004 Apr 23 |
|
| In vitro antifungal activity of sertaconazole compared with nine other drugs against 250 clinical isolates of dermatophytes and Scopulariopsis brevicaulis. | 2004 Dec |
|
| Poliosis associated with treatment of fungal endophthalmitis. | 2004 Dec |
|
| Co-isolation of Trichosporon inkin and Candida parapsilosis from a scalp white piedra case. | 2004 Feb |
|
| Dermatophyte-related granular parakeratosis. | 2004 Feb |
|
| Increased calcium influx and ribosomal content correlate with resistance to endoplasmic reticulum stress-induced cell death in mutant leukemia cell lines. | 2004 Feb 20 |
|
| Characteristics and a functional implication of Ca(2+)-activated K(+) current in mouse aortic endothelial cells. | 2004 Jan |
|
| Imidazole analogues of fluoxetine, a novel class of anti-Candida agents. | 2004 Jul 29 |
|
| Usage of antifungal drugs for therapy of genital Candida infections, purchased as over-the-counter products or by prescription: I. Analyses of a unique database. | 2004 Jun |
|
| Antioxidative natural product protect against econazole-induced liver injuries. | 2004 Mar 1 |
|
| Epidermal growth factor inhibits 14C-alpha-methyl-D-glucopyranoside uptake in renal proximal tubule cells: involvement of PLC/PKC, p44/42 MAPK, and cPLA2. | 2004 May |
|
| Concurrent use of 5% natamycin and 2% econazole for the management of fungal keratitis. | 2004 Nov |
|
| Inhibition of TRPM2 channels by the antifungal agents clotrimazole and econazole. | 2004 Oct |
|
| Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles. | 2004 Oct 15 |
|
| The calcium influx pathway in rat olfactory ensheathing cells shows TRPC channel pharmacology. | 2004 Oct 8 |
|
| P2Y2-receptor-mediated activation of a contralateral, lanthanide-sensitive calcium entry pathway in the human airway epithelium. | 2004 Sep |
|
| Athlete's foot. | 2005 Dec |
|
| [Congenital cutaneous candidiasis: a case report and review]. | 2005 Dec |
|
| [Diagnosis at a glance. Leisure athlete with itchy back]. | 2005 Dec 8 |
|
| Cytochrome P450 products and arachidonic acid-induced, non-store-operated, Ca2+ entry in cultured bovine endothelial cells. | 2005 Jul-Aug |
|
| [Experimental study on apoptosis in leukemia cells induced by econazole]. | 2005 Jun |
|
| Altered expression profile of mycobacterial surface glycopeptidolipids following treatment with the antifungal azole inhibitors econazole and clotrimazole. | 2005 Jun |
|
| Signaling pathways in the biphasic effect of ANG II on Na+/H+ exchanger in T84 cells. | 2005 May |
|
| The role of TRPM channels in cell death. | 2005 Oct |
|
| Molecular mechanisms of econazole-induced toxicity on human colon cancer cells: G0/G1 cell cycle arrest and caspase 8-independent apoptotic signaling pathways. | 2005 Oct |
|
| In vitro and ex vivo antimycobacterial potential of azole drugs against Mycobacterium tuberculosis H37Rv. | 2005 Oct 1 |
|
| Econazole induces increases in free intracellular Ca2+ concentrations in human osteosarcoma cells. | 2005 Sep |
|
| Effects of econazole on Ca2+ levels in and the growth of human prostate cancer PC3 cells. | 2005 Sep |
|
| Nano-encapsulation of azole antifungals: potential applications to improve oral drug delivery. | 2005 Sep 14 |
|
| Signaling pathways influencing SLF and c-kit-mediated survival and proliferation. | 2006 |
|
| Near-infrared spectrometry for the quantification of dermal absorption of econazole nitrate and 4-cyanophenol. | 2006 Apr |
|
| Azole antifungals as novel chemotherapeutic agents against murine tuberculosis. | 2006 Aug |
|
| What's your diagnosis? Nine-year-old girl with a pubic rash gone incognito. | 2006 Aug |
|
| Cloning and characterization of CYP51 from Mycobacterium avium. | 2006 Aug |
|
| Effects of Ca2+ channel blockers on store-operated Ca2+ channel currents of Kupffer cells after hepatic ischemia/reperfusion injury in rats. | 2006 Aug 7 |
|
| TRPV6 potentiates calcium-dependent cell proliferation. | 2006 Feb |
|
| A screening method for chiral selectors that does not require covalent attachment. | 2006 Feb 22 |
|
| Single-dose sertaconazole vaginal tablet treatment of vulvovaginal candidiasis. | 2006 Jun |
|
| What is the best way to treat tinea cruris? | 2006 Mar |
|
| Antimycotic influence of beta-cyclodextrin complexes--in vitro measurements using laser nephelometry in microtiter plates. | 2006 Mar 27 |
|
| The potential of azole antifungals against latent/persistent tuberculosis. | 2006 May |
|
| Econazole attenuates cytotoxicity of 1-methyl-4-phenylpyridinium by suppressing mitochondrial membrane permeability transition. | 2006 May 31 |
|
| Increase in anticoagulant effect of warfarin in a patient using econazole cream. | 2006 Nov |
|
| Inhibition of Ca2+ influx is required for mitochondrial reactive oxygen species-induced endoplasmic reticulum Ca2+ depletion and cell death in leukemia cells. | 2006 Oct |
Patents
Sample Use Guides
Topical foam, 1% is for topical use only. Ecoza topical foam, 1% is not for oral,
ophthalmic, or intravaginal use.
Ecoza topical foam, 1% should be applied to cover affected areas once daily for 4 weeks.
Route of Administration:
Topical
In Vitro Use Guide
Curator's Comment: Econazole inhibited the growth of all isolates of Trichophyton species in low concentrations of 2-4 micrograms/ml except one isolate of T. rubrum which was inhibited by a concentration ug/ml. https://www.ncbi.nlm.nih.gov/pubmed/2737705
Minimum inhibitory concentrations (MIC) of econazole against Mycobacterium avium complex (MAC) and and a minimum bacteriocidal concentration was 4 ug/ml.
| Substance Class |
Chemical
Created
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admin
on
Edited
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| Record UNII |
JCB50IOD4Y
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| Record Status |
Validated (UNII)
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| Record Version |
|
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