ECONAZOLE NITRATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H15Cl3N2O.HNO3
Molecular Weight	444.696
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[N+]([O-])=O.ClC1=CC=C(COC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1

InChI

InChIKey=DDXORDQKGIZAME-UHFFFAOYSA-N

InChI=1S/C18H15Cl3N2O.HNO3/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;2-1(3)4/h1-9,12,18H,10-11H2;(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula	HNO3
Molecular Weight	63.0128
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/205175s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/98315

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
Cytochrome P450 51 28 Target ID: CHEMBL1780 Sources: https://www.drugbank.ca/drugs/DB01127 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/205175s000lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/20149798	Inhibitor 8297		17.9 nM [Kd]
Trichophyton rubrum 5 Target ID: CHEMBL612649 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2737705 \| https://www.ncbi.nlm.nih.gov/pubmed/400880	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tinea pedis 28 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=121446	Curative		Approved 8429	ECOZA Approved Use Ecoza (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 Date 1982

C_max

Value	Dose	Co-administered	Analyte	Population
417 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/205175s000lbl.pdf	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	Analyte	Population
3440 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/205175s000lbl.pdf	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

Doses

Dose	Population	Adverse events
150 mg 1 times / day multiple, vaginal Dose: 150 mg, 1 times / day Route: vaginal Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32410819	healthy, 18 - 55 years Health Status: healthy Age Group: 18 - 55 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/32410819	Sources: https://pubmed.ncbi.nlm.nih.gov/32410819

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP 111	CYP51 3	CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/205175s003lbl.pdf Page: 5.0	no
CYP 147	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/20637317/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP51 3	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21114623/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY545729	https://www.001chemical.com/chem/27220-47-9
3B Scientific (Wuhan) Corp	3B2-1071	http://www.3bsc.com/index/pro_info.php?id=48135
AHH Chemical co.,ltd	MT-50766	http://www.ahhchemical.com/product/MT-50766.html
AK Scientific, Inc. (AKSCI)	J10460	http://www.aksci.com/item_detail.php?cat=J10460
AK Scientific, Inc. (AKSCI)	M369	http://www.aksci.com/item_detail.php?cat=M369
Achemtek	0104-009378	http://www.achemtek.com/27220-47-9
Acorn PharmaTech	ACN-037051	http://www.acornpharmatech.com/
Acros Organics	AC458630050	https://www.fishersci.com/shop/products/econazole-99-acros-organics-1/AC458630050
Acros Organics	AC458630250	https://www.fishersci.com/shop/products/econazole-99-acros-organics/AC458630250
Angel Pharmatech	AG153817	http://www.angelpharmatech.com/27220-47-9.html
Angene	AGN-PC-0JK6HF	http://www.angenechemical.com/productshow/AGN-PC-0JK6HF.html
Ark Pharm	AK174005	http://www.arkpharminc.com/products/27220-47-9.html
AvaChem Scientific	2679B	http://www.avachem.com/productSearch.asp?2679B
BLD Pharm	BD16828	http://www.bldpharm.com/products/27220-47-9.html
BioSynth	W-107123	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-107123.html
CSNpharm	CSN12439	https://www.csnpharm.com/products/econazole.html
Chem Scene	CS-4348	http://www.chemscene.com/27220-47-9.html
Chemspace	CSSB00000043504	https://chem-space.com/CSSB00000043504
Debye Scientific	DB-047186	http://www.debyesci.com/cas_27220-47-9.html
Finetech	FT-0630530	http://www.finetechnology-ind.com/prod/detail/pub/27220-47-9.html
Glentham Life Sciences	GA7153	http://www.glentham.com/products/product/GA7153/
Hairui	HR122661	http://www.hairuichem.com/en/product/27220-47-9.html
LGC Standards	LGCFOR3432.00	https://www.lgcstandards.com/US/en/p/LGCFOR3432.00
LGC Standards	MM3432.00	https://www.lgcstandards.com/US/en/p/MM3432.00
Lab Network	LN00244250	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00244250
MedChem Express	HY-B0885	https://www.medchemexpress.com/Econazole.html
Molcore	MC545729	https://www.molcore.com/product/27220-47-9
MuseChem	I002936	https://www.musechem.com/product/I002936.html
OChem	8326	http://www.ocheminc.com/index.php?act=psearch&pid=220E479
Parchem	28805	http://www.parchem.com/chemical-supplier-distributor/Econazole-Nitrate-018805.aspx
Shanghai Send Pharmaceutical Technology Co., Ltd	send35664	http://shsendpharm.com/
Smolecule	S591883	https://www.smolecule.com/products/s591883
THE BioTek	bt-315148	https://www.thebiotek.com/product/others/bt-315148
Vitas-M Laboratory	STL483402	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL483402&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
abcr GmbH	AB437715	http://www.abcr.com/shop/en/AB437715
eNovation Chemicals	D405419	https://www.enovationchem.com/ProductDetails.asp?ProductID=D405419
iChemical	EBD15324	http://www.ichemical.com/products/27220-47-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
In vitro activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp.	1992 Apr	1406898
[Antifungal drug susceptibility of Candida causing oropharyngeal candidiasis in HIV infected patients].	2001	15773146
Cellular mechanism of calcification and its prevention in glutaraldehyde treated vascular tissue.	2001	11374041
Systemic Candida infection in University hospital 1997-1999: the distribution of Candida biotypes and antifungal susceptibility patterns.	2001	11307597
Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs.	2001 Aug	11569882
[New developments in medical mycology].	2001 Feb	11244898
Antifungal and immunomodulating activities of 1,4-benzothiazine azole derivatives: review.	2001 Feb	11233807
[Invasive rhinocerebral aspergillosis occurred during myelosuppressive phase after chemotherapy: a case report and literature review].	2001 Jul	11877100
Fatty acids inhibit anion secretion in rat colon: apical and basolateral action sites.	2001 Jul	11510894
Mechanisms and modulation of formyl-methionyl-leucyl-phenylalanine (fMLP)-induced Ca2+ mobilization in human neutrophils.	2001 Jul	11460314
Effect of angiotensin II on calcium reabsorption by the luminal membranes of the nephron.	2001 Jun	11350774
Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis.	2001 Jun 15	11377375
Comparison of in vitro activities of amphotericin, clotrimazole, econazole, miconazole, and nystatin against Fusarium oxysporum.	2001 May	11411855
Sertaconazole: in-vitro antifungal activity against vaginal and other superficial yeast isolates.	2001 Oct	11760221
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens.	2001 Oct	11744942
Pharmacological modulation of monovalent cation currents through the epithelial Ca2+ channel ECaC1.	2001 Oct	11588099
Fendiline mobilizes intracellular Ca2+ in Chang liver cells.	2001 Sep	11553031
Purging of contaminating breast cancer cells from hematopoietic progenitor cell preparations using activation enhanced cell death.	2002 Apr	12058968
Assessing pregnancy risks of azole antifungals using a high throughput aromatase inhibition assay.	2002 Aug	12489563
Ascorbyl free radical and dehydroascorbate formation in rat liver endoplasmic reticulum.	2002 Aug	12392195
Comparative study of the enantiomeric resolution of chiral antifungal drugs econazole, miconazole and sulconazole by HPLC on various cellulose chiral columns in normal phase mode.	2002 Jan 15	11755745
Involvement of oxidative stress in bee venom-induced inhibition of Na+/glucose cotransporter in renal proximal tubule cells.	2002 Jul	12060098
Hepatoprotective and therapeutic effects of tetramethylpyrazine on acute econazole-induced liver injury.	2002 Jun	12094293
(2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species.	2002 Mar	11900868
Ciclopiroxolamine: in vitro antifungal activity against clinical yeast isolates.	2002 Nov	12431873
Sensitivity of myeloid leukemia cells to calcium influx blockade: application to bone marrow purging.	2002 Oct	12384154
Azole antifungals are potent inhibitors of cytochrome P450 mono-oxygenases and bacterial growth in mycobacteria and streptomycetes.	2002 Oct	12368427
Pituitary adenylate cyclase-activating polypeptide induces a sustained increase in intracellular free Ca(2+) concentration and catechol amine release by activating Ca(2+) influx via receptor-stimulated Ca(2+) entry, independent of store-operated Ca(2+) channels, and voltage-dependent Ca(2+) channels in bovine adrenal medullary chromaffin cells.	2002 Sep	12183654
Effects of Toona sinensis leaf extract on lipolysis in differentiated 3T3-L1 adipocytes.	2003 Aug	12962425
Enhanced econazole penetration into human nail by 2-n-nonyl-1,3-dioxolane.	2003 Jan	12486690
A randomised clinical trial comparing 2% econazole and 5% natamycin for the treatment of fungal keratitis.	2003 Oct	14507756
Identification and prediction of promiscuous aggregating inhibitors among known drugs.	2003 Oct 9	14521410
Evaluation of in vitro activity of ciclopirox olamine, butenafine HCl and econazole nitrate against dermatophytes, yeasts and bacteria.	2003 Sep	12895182
Intracellular mediators of granulysin-induced cell death.	2003 Sep 1	12928406
Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors.	2004 Apr 15	15135088
Increased calcium influx and ribosomal content correlate with resistance to endoplasmic reticulum stress-induced cell death in mutant leukemia cell lines.	2004 Feb 20	14660643
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	15739823
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	15040003
Athlete's foot.	2005 Dec	16620478
[Congenital cutaneous candidiasis: a case report and review].	2005 Dec	16425712
Cytochrome P450 products and arachidonic acid-induced, non-store-operated, Ca2+ entry in cultured bovine endothelial cells.	2005 Jul-Aug	16162437
[Experimental study on apoptosis in leukemia cells induced by econazole].	2005 Jun	15972127
Altered expression profile of mycobacterial surface glycopeptidolipids following treatment with the antifungal azole inhibitors econazole and clotrimazole.	2005 Jun	15942015
The role of TRPM channels in cell death.	2005 Oct	16025303
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	15919146
In vitro and ex vivo antimycobacterial potential of azole drugs against Mycobacterium tuberculosis H37Rv.	2005 Oct 1	16143463
Nano-encapsulation of azole antifungals: potential applications to improve oral drug delivery.	2005 Sep 14	16023808
What's your diagnosis? Nine-year-old girl with a pubic rash gone incognito.	2006 Aug	16873039
What is the best way to treat tinea cruris?	2006 Mar	16510062
Inhibition of Ca2+ influx is required for mitochondrial reactive oxygen species-induced endoplasmic reticulum Ca2+ depletion and cell death in leukemia cells.	2006 Oct	16849592

Patents

Sample Use Guides

In Vivo Use Guide

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

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 by `admin` on `Fri Dec 15 15:19:13 GMT 2023` Edited by `admin` on `Fri Dec 15 15:19:13 GMT 2023`
Record UNII	H438WYN10E
Record Status	`Validated (UNII)`
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Name

Type

Language

ECONAZOLE NITRATE

Official Name

English

R-14827

Code

English

SQ13050

Code

English

ECONAZOLE NITRATE [USP-RS]

Common Name

English

ECONAZOLE NITRATE [EP IMPURITY]

Common Name

English

(±)-1-(2,4-DICHLORO-.BETA.-((P-CHLOROBENZYL)OXY)PHENETHYL)-IMIDAZOLE MONONITRATE

Common Name

English

SPECTAZOLE

Brand Name

English

1H-IMIDAZOLE, 1-(2-((4-CHLOROPHENYL)METHOXY)-2-(2,4-DICHLOROPHENYL)ETHYL)-, MONONITRATE, (±)-

Systematic Name

English

ECONAZOLE NITRATE [MART.]

Common Name

English

Econazole nitrate [WHO-DD]

Common Name

English

ECONAZOLE NITRATE [ORANGE BOOK]

Common Name

English

ECONAZOLE NITRATE [USP MONOGRAPH]

Common Name

English

ECONAZOLE NITRATE [MI]

Common Name

English

ECONAZOLE NITRATE [VANDF]

Common Name

English

SQ-13050

Code

English

ECONAZOLE NITRATE [JAN]

Common Name

English

ECONAZOLE NITRATE [USAN]

Common Name

English

ECONAZOLE NITRATE [EP MONOGRAPH]

Common Name

English

R14827

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C514