Econazole nitrate | CAS#27220-47-9 | Antifungal

MedKoo Cat#: 317765 | Name: Econazole nitrate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Econazole is a broad spectrum ketoconazole-like azole based antifungal agent which is also potent against Gram positive bacteria. It is used topically in dermatomycoses as well as orally and parenterally. Econazole kills or prevents the growth of fungus or yeast by inhibiting the production of substances vital for their growth and function. 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.

Chemical Structure

Econazole nitrate

CAS#24169-02-6 (nitrate)

Theoretical Analysis

MedKoo Cat#: 317765

Name: Econazole nitrate

CAS#: 24169-02-6 (nitrate)

Chemical Formula: C18H16Cl3N3O4

Exact Mass: 0.0000

Molecular Weight: 444.69

Elemental Analysis: C, 48.62; H, 3.63; Cl, 23.92; N, 9.45; O, 14.39

Price and Availability

Size	Price	Availability	Quantity
5g	USD 350.00	2 Weeks
25g	USD 550.00	2 Weeks

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Related CAS #

24169-02-6 (nitrate) 27220-47-9 (free base)

Synonym

Econazole nitrate; Ifenec; Epi-pevaryl; R 14827; R14827; R-14827; Spectazole; SQ 13050; SQ13050; SQ-13050; Ecoza; Gyno-pevaryl; NSC 243115; NSC243115; NSC-243115

IUPAC/Chemical Name

1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid

InChi Key

DDXORDQKGIZAME-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

C1=CC(=CC=C1COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl)Cl.[N+](=O)(O)[O-]

Appearance

White to off-white solid powder.

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Related CAS# 24169-02-6 (Econazole Nitrate ) 27220-47-9 (Econazole free base)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Econazole nitrate is an imidazole class antifungal medication.

In vitro activity:

A significant dose-dependent increase in the number of AGS and SNU1 cells at the sub-G1 phase were observed following econazole treatments (Fig. 1C). Apoptotic death and PARP cleavage in response to econazole treatment were assessed in AGS and SNU1 cells using Annexin V/PI staining (Fig. 1D) and western blot analysis (Fig. 1E). The cells treated with econazole showed positive staining for Annexin V and PI. This study also found that exposure of gastric cancer cell lines to econazole resulted in a dose-dependent increase in the cleavage of PARP compared to untreated cells. These results indicate that econazole induced death via apoptosis of gastric cancer cells. Reference: Biomol Ther (Seoul). 2020 Jul 1; 28(4): 370–379. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7327138/

In vivo activity:

As shown in Fig. 5A, econazole significantly suppressed tumor growth compared to the vehicle control. The tumor weight from the econzaole treatment group was also significantly lighter than the negative control group while it did not affect mouse bodyweight. These results suggested that econazole is a candidate anti-cancer drug for human lung adenocarcinoma. Reference: Sci Rep. 2017; 7: 17987. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5740072/

	Solvent	mg/mL	mM
Solubility
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.67
	DMF	25.0	56.22
	Ethanol	2.5	5.64
	Water	0.7	1.51

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 444.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Choi EK, Park EJ, Phan TT, Kim HD, Hoe KL, Kim DU. Econazole Induces p53-Dependent Apoptosis and Decreases Metastasis Ability in Gastric Cancer Cells. Biomol Ther (Seoul). 2020 Jul 1;28(4):370-379. doi: 10.4062/biomolther.2019.201. PMID: 32209732; PMCID: PMC7327138. 2. Sun J, Yu CH, Zhao XL, Wang Y, Jiang SG, Gong XF. Econazole Nitrate Induces Apoptosis in MCF-7 Cells via Mitochondrial and Caspase Pathways. Iran J Pharm Res. 2014 Fall;13(4):1327-34. PMID: 25587322; PMCID: PMC4232799. 3. Dong C, Chen Y, Ma J, Yang R, Li H, Liu R, You D, Luo C, Li H, Yang S, Ke K, Lin MC, Chen C. Econazole nitrate reversed the resistance of breast cancer cells to Adriamycin through inhibiting the PI3K/AKT signaling pathway. Am J Cancer Res. 2020 Jan 1;10(1):263-274. PMID: 32064166; PMCID: PMC7017736. 4. Dong C, Yang R, Li H, Ke K, Luo C, Yang F, Shi XN, Zhu Y, Liu X, Wong MH, Lin G, Wang X, Leung KS, Kung HF, Chen C, Lin MC. Econazole nitrate inhibits PI3K activity and promotes apoptosis in lung cancer cells. Sci Rep. 2017 Dec 21;7(1):17987. doi: 10.1038/s41598-017-18178-0. PMID: 29269744; PMCID: PMC5740072.

In vitro protocol:

In vivo protocol:

1. Dong C, Chen Y, Ma J, Yang R, Li H, Liu R, You D, Luo C, Li H, Yang S, Ke K, Lin MC, Chen C. Econazole nitrate reversed the resistance of breast cancer cells to Adriamycin through inhibiting the PI3K/AKT signaling pathway. Am J Cancer Res. 2020 Jan 1;10(1):263-274. PMID: 32064166; PMCID: PMC7017736. 2. Dong C, Yang R, Li H, Ke K, Luo C, Yang F, Shi XN, Zhu Y, Liu X, Wong MH, Lin G, Wang X, Leung KS, Kung HF, Chen C, Lin MC. Econazole nitrate inhibits PI3K activity and promotes apoptosis in lung cancer cells. Sci Rep. 2017 Dec 21;7(1):17987. doi: 10.1038/s41598-017-18178-0. PMID: 29269744; PMCID: PMC5740072.

1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Econazole. 2024 Nov 15. PMID: 30000511. 2: Kasuya K, Takahashi K, Hashimoto M, Ohta T. Nociceptive transient receptor potential ankyrin 1 (TRPA1) in sensory neurons are targets of the antifungal drug econazole. BMC Pharmacol Toxicol. 2024 Aug 21;25(1):53. doi: 10.1186/s40360-024-00779-x. PMID: 39169383; PMCID: PMC11337588. 3: De Jesús-Pérez JJ, Gabrielle M, Raheem S, Fluck EC, Rohacs T, Moiseenkova- Bell VY. Structural mechanism of TRPV5 inhibition by econazole. Structure. 2024 Feb 1;32(2):148-156.e5. doi: 10.1016/j.str.2023.11.012. Epub 2023 Dec 22. PMID: 38141613; PMCID: PMC10872542. 4: Bayan MF, Chandrasekaran B, Alyami MH. Development and Characterization of Econazole Topical Gel. Gels. 2023 Nov 25;9(12):929. doi: 10.3390/gels9120929. PMID: 38131915; PMCID: PMC10743284. 5: Lakes YB, Moye SL, Mo J, Tegtmeyer M, Nehme R, Charlton M, Salinas G, McKay RM, Eggan K, Le LQ. Econazole selectively induces cell death in NF1-homozygous mutant tumor cells. Cell Rep Med. 2023 Dec 19;4(12):101309. doi: 10.1016/j.xcrm.2023.101309. Epub 2023 Dec 11. PMID: 38086379; PMCID: PMC10772348. 6: Wang JL, Jan CR, Chen MH. Action of econazole on Ca2+ levels and cytotoxicity in OC2 human oral cancer cells. J Dent Sci. 2023 Jul;18(3):1280-1287. doi: 10.1016/j.jds.2023.02.013. Epub 2023 Mar 6. PMID: 37404653; PMCID: PMC10316490. 7: Liang Z, Zhang Z, Lu P, Yang J, Han L, Liu S, Zhou T, Li J, Zhang J. The effect of charges on the corneal penetration of solid lipid nanoparticles loaded Econazole after topical administration in rabbits. Eur J Pharm Sci. 2023 Aug 1;187:106494. doi: 10.1016/j.ejps.2023.106494. Epub 2023 Jun 12. PMID: 37315870. 8: Li Q, Qin S, Tian H, Liu R, Qiao L, Liu S, Li B, Yang M, Shi J, Nice EC, Li J, Lang T, Huang C. Nano-Econazole Enhanced PD-L1 Checkpoint Blockade for Synergistic Antitumor Immunotherapy against Pancreatic Ductal Adenocarcinoma. Small. 2023 Jun;19(23):e2207201. doi: 10.1002/smll.202207201. Epub 2023 Mar 10. PMID: 36899444. 9: Puri V, Savla R, Chen K, Robinson K, Virani A, Michniak-Kohn B. Antifungal Nail Lacquer for Enhanced Transungual Delivery of Econazole Nitrate. Pharmaceutics. 2022 Oct 16;14(10):2204. doi: 10.3390/pharmaceutics14102204. PMID: 36297639; PMCID: PMC9607990. 10: Wong A, Fallon M, Celiksoy V, Ferla S, Varricchio C, Whitaker D, Quantock AJ, Heard CM. A Composite System Based upon Hydroxypropyl Cyclodextrins and Soft Hydrogel Contact Lenses for the Delivery of Therapeutic Doses of Econazole to the Cornea, In Vitro. Pharmaceutics. 2022 Aug 4;14(8):1631. doi: 10.3390/pharmaceutics14081631. PMID: 36015257; PMCID: PMC9412546. 11: Dong C, Chen Y, Ma J, Yang R, Li H, Liu R, You D, Luo C, Li H, Yang S, Ke K, Lin MC, Chen C. Erratum: Econazole nitrate reversed the resistance of breast cancer cells to Adriamycin through inhibiting the PI3K/AKT signaling pathway. Am J Cancer Res. 2022 Jul 15;12(7):3486-3490. Erratum for: Am J Cancer Res. 2020 Jan 01;10(1):263-274. PMID: 35968323; PMCID: PMC9360247. 12: Weng N, Qin S, Liu J, Huang X, Jiang J, Zhou L, Zhang Z, Xie N, Wang K, Jin P, Luo M, Peng L, Nice EC, Goel A, Han S, Huang C, Zhu Q. Repurposing econazole as a pharmacological autophagy inhibitor to treat pancreatic ductal adenocarcinoma. Acta Pharm Sin B. 2022 Jul;12(7):3085-3102. doi: 10.1016/j.apsb.2022.01.018. Epub 2022 Feb 4. PMID: 35865101; PMCID: PMC9293665. 13: Maheen S, Younis H, Khan HU, Salman Shafqat S, Ali S, Rehman AU, Ilyas S, Zafar MN, Shafqat SR, Kalam A, Al-Ghamdi AA. Enhanced Antifungal and Wound Healing Efficacy of Statistically Optimized, Physicochemically Evaluated Econazole-Triamcinolone Loaded Silica Nanoparticles. Front Chem. 2022 May 3;10:836678. doi: 10.3389/fchem.2022.836678. PMID: 35592306; PMCID: PMC9112326. 14: Xie M, Chen K, Chan EW, Chen S. Synergistic Antimicrobial Effect of Colistin in Combination with Econazole against Multidrug-Resistant Acinetobacter baumannii and Its Persisters. Microbiol Spectr. 2022 Jun 29;10(3):e0093722. doi: 10.1128/spectrum.00937-22. Epub 2022 Apr 25. PMID: 35467374; PMCID: PMC9241926. 15: Gou S, Monod M, Salomon D, Kalia YN. Simultaneous Delivery of Econazole, Terbinafine and Amorolfine with Improved Cutaneous Bioavailability: A Novel Micelle-Based Antifungal "Tri-Therapy". Pharmaceutics. 2022 Jan 24;14(2):271. doi: 10.3390/pharmaceutics14020271. PMID: 35214004; PMCID: PMC8880516. 16: Verma S, Utreja P. Corrigendum to: Oleic Acid Vesicles as a New Approach for Transdermal Delivery of Econazole Nitrate: Development, Characterization, and In-vivo Evaluation in Wistar Rats. Recent Adv Antiinfect Drug Discov. 2021;16(2):174. doi: 10.2174/277243441602211018160649. PMID: 34961436. 17: Khera H, Pandey AK, Shafiq N, Khuller GK, Kondel Bhandari R, Panditrao A, Gamad N, Rohilla R, Bhattacharjee S, Murali N, Cvn H, Belavagi D, Mothsara C, Singh M, Sharma N, Behera D, Malhotra S. Single ascending dose safety, tolerability, and pharmacokinetic study of econazole in healthy volunteers. Expert Rev Anti Infect Ther. 2022 Jun;20(6):955-961. doi: 10.1080/14787210.2022.2016392. Epub 2022 Jan 2. PMID: 34913825. 18: Wang M, Chan EWC, Xu C, Chen K, Yang C, Chen S. Econazole as adjuvant to conventional antibiotics is able to eradicate starvation-induced tolerant bacteria by causing proton motive force dissipation. J Antimicrob Chemother. 2022 Feb 2;77(2):425-432. doi: 10.1093/jac/dkab384. PMID: 34747463. 19: Neuberger A, Nadezhdin KD, Sobolevsky AI. Structural mechanisms of TRPV6 inhibition by ruthenium red and econazole. Nat Commun. 2021 Nov 1;12(1):6284. doi: 10.1038/s41467-021-26608-x. PMID: 34725357; PMCID: PMC8560856. 20: Verma S, Utreja P. Corrigendum to: Transethosomes of Econazole Nitrate for Transdermal Delivery: Development, In-vitro Characterization, and Ex-vivo Assessment. Pharm Nanotechnol. 2021;9(3):245. doi: 10.2174/221173850903210813100519. PMID: 34433400.