WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H317765
CAS#: 24169-02-6 (nitrate)
Description: Econazole nitrate 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. In studies, econazole nitrate is used on processes such as platelet serotonin uptake, prostanoid biosynthesis, EDHF-mediated relaxation, and Ca2+ transport pathways in thymic lymphocytes1.
Hodoodo Cat#: H317765
Name: Econazole Nitrate
CAS#: 24169-02-6 (nitrate)
Chemical Formula: C18H16Cl3N3O4
Exact Mass: 0.00
Molecular Weight: 444.690
Elemental Analysis: C, 48.62; H, 3.63; Cl, 23.92; N, 9.45; O, 14.39
Related CAS #: 27220-47-9 (free base) 24169-02-6 (nitrate)
Synonym: Econazole Nitrate; R 14,827; R 14827; Spectazole; SQ 13050; SQ13050; SQ-13050; Ecoza; epi-Pevaryl; Gyno-pevaryl; Ifenec.
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)
| 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 | Max Conc. mg/mL | Max Conc. 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 |
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: | 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. |
| 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: Kraus CL, Trivedi RH, Wilson ME. Intraocular pressure control with
echothiophate iodide in children's eyes with glaucoma after cataract extraction.
J AAPOS. 2015 Apr;19(2):116-8.e1. doi: 10.1016/j.jaapos.2014.11.006. Epub 2015
Mar 26. PubMed PMID: 25818282.
2: Schmidt KG, Horowitz Y, Buckman G, Segev E, Levinger E, Geyer O. Lowering of
IOP by echothiophate iodide in pseudophakic eyes with glaucoma. Curr Eye Res.
2010 Aug;35(8):698-702. doi: 10.3109/02713681003794076. PubMed PMID: 20673046.
3: Mezer E, Krivoy N, Scharf J, Miller B. Echothiophate iodide induced transient
hyper- and hypothyroidism. J Glaucoma. 1996 Jun;5(3):191-2. PubMed PMID: 8795758.
4: Raab EL. Cycloplegic refraction after echothiophate iodide. J Pediatr
Ophthalmol Strabismus. 1983 Jul-Aug;20(4):141-4. PubMed PMID: 6886952.
5: Kaufman PL, Erickson KA, Neider MW. Echothiophate iodide cataracts in monkeys.
Occurrence despite loss of accommodation induced by retrodisplacement of ciliary
muscle. Arch Ophthalmol. 1983 Jan;101(1):125-8. PubMed PMID: 6849646.
6: Friberg TR, Thomas JV, Dressel TD. Serum cholinesterase, serum lipase, and
serum amylase levels during long-term echothiophate iodide therapy. Am J
Ophthalmol. 1981 Apr;91(4):530-3. PubMed PMID: 6164295.
7: Bito LZ, Merritt SQ. Paradoxical ocular hypertensive effect of pilocarpine on
echothiophate iodide--treated primate eyes. Invest Ophthalmol Vis Sci. 1980
Apr;19(4):371-7. PubMed PMID: 6766911.
8: Mathias CG, Mailbach HI, Irvine A, Adler W. Allergic contact dermatitis to
echothiophate iodide and phenylephrine. Arch Ophthalmol. 1979 Feb;97(2):286-7.
PubMed PMID: 550798.
9: Rothkoff L, Biedner B, Blumenthal M. Echothiophate iodide for flat anterior
chamber following cataract extraction. Ophthalmic Surg. 1977 Dec;8(6):62-4.
PubMed PMID: 600492.
10: Hallett M, Cullen RF Jr. Intoxication with echothiophate iodide. An acute
cholinergic crisis. JAMA. 1972 Dec 11;222(11):1414-5. PubMed PMID: 4678321.
11: Harris LS. Dose-response analysis of echothiophate iodide. Arch Ophthalmol.
1971 Nov;86(5):503-5. PubMed PMID: 5114443.
12: Morton WR, Drance SM, Fairclough M. Effect of echothiophate iodide on the
lens. Am J Ophthalmol. 1969 Dec;68(6):1003-10. PubMed PMID: 5362877.
13: Lipson ML, Holmes JH, Ellis PP. Oral administration of pralidoxime chloride
in echothiophate iodide therapy. Arch Ophthalmol. 1969 Dec;82(6):830-5. PubMed
PMID: 5355272.
14: Gorin G. Echothiophate iodide for glaucoma or flat anterior chamber following
cataract extraction. Am J Ophthalmol. 1969 Mar;67(3):392-5. PubMed PMID: 5774254.
15: Hussain A, Schurman P, Peter V, Milosovich G. Kinetics and mechanism of
degradation of echothiophate iodide in aqueous solution. J Pharm Sci. 1968
Mar;57(3):411-8. PubMed PMID: 5655578.
16: Wilensky JG, Dettbarn WD, Rosenberg P, De Roetth A Jr. Effect of ocular
instillation of echothiophate iodide and isoflurophate on cholinesterase activity
of various rabbit tissues. Am J Ophthalmol. 1967 Sep;64(3):398-404. PubMed PMID:
6036299.
17: Ellis PP, Esterdahl M. Echothiophate iodide therapy in children. Effect upon
blood cholinesterase levels. Arch Ophthalmol. 1967 May;77(5):598-601. PubMed
PMID: 6022729.
18: Hiscox PE, McCulloch C. The effect of echothiophate iodide on systemic
cholinesterase. Can J Ophthalmol. 1966 Oct;1(4):274-82. PubMed PMID: 5977437.
19: Kellerman L, King AD. Preliminary observations on the use of new
concentrations of echothiophate iodide in the treatment of glaucoma. Am J
Ophthalmol. 1966 Aug;62(2):278-81. PubMed PMID: 5944743.
20: Hiscox PE, McCulloch C. Cardiac arrest occurring in a patient on
echothiophate iodide therapy. Am J Ophthalmol. 1965 Sep;60(3):425-7. PubMed PMID:
5825146.
