Sertaconazole Nitrate | CAS#99592-39-9 | Antifungal

MedKoo Cat#: 318689 | Name: Sertaconazole nitrate

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Description:

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

Sertaconazole nitrate is a topical broad-spectrum antifungal that is developed to provide an additional agent for the treatment of superficial cutaneous and mucosal infections. Sertaconazole nitrate 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

Sertaconazole nitrate

CAS#99592-39-9 (nitrate)

Theoretical Analysis

MedKoo Cat#: 318689

Name: Sertaconazole nitrate

CAS#: 99592-39-9 (nitrate)

Chemical Formula: C20H16Cl3N3O4S

Exact Mass: 0.0000

Molecular Weight: 500.78

Elemental Analysis: C, 47.97; H, 3.22; Cl, 21.24; N, 8.39; O, 12.78; S, 6.40

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 350.00
100mg	USD 650.00
200mg	USD 1,050.00

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Related CAS #

99592-32-2 (free base) 99592-39-9 (nitrate)

Synonym

Sertaconazole Nitrate; Dermofix; Ertaczo; Zalain; Sertaconazole (nitrate); Dermoseptic; Ginedermofix; Mykosert; sertaconazole; sertaconazole nitrate; Zalain;

IUPAC/Chemical Name

1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid

InChi Key

HAAITRDZHUANGT-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H15Cl3N2OS.HNO3/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22;2-1(3)4/h1-8,11-12,19H,9-10H2;(H,2,3,4)

SMILES Code

C1=CC2=C(C(=C1)Cl)SC=C2COC(CN3C=CN=C3)C4=C(C=C(C=C4)Cl)Cl.[N+](=O)(O)[O-]

Appearance

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, DMF, and ethanol

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sertaconazole is a broad spectrum antifungal agent that is both fungistatic and fungicidal in vitro (MICs = 0.35 to 5.04 and 0.5 to 16 μg/ml, respectively). It inhibits ergosterol synthesis (IC50 = 115 nM) and decreases intracellular ATP levels in C. albicans. Topical application of sertaconazole (0.03 ml of a 2% formulation) reduced C. albicans cell numbers by 97.9% in a murine model of vaginal candidiasis.

In vitro activity:

Sertaconazole has potential as a topical chemotherapy agent for skin cancers, possibly in combination with systemic anticancer agents. Sertaconazole bound to goat brain tubulin with dissociation constant of 9 μM, inhibited HeLa cell proliferation with IC50 value of 28, and induced a mitotic block. Sertaconazole inhibited tubulin polymerization and activated apoptosis in A549 cells. Additionally, sertaconazole inhibited cell migration and showed synergistic antiproliferative potential with vinblastine. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2021 Jun;394(6):1231-1249. https://pubmed.ncbi.nlm.nih.gov/33620548/

In vivo activity:

Sertaconazole nitrate suppressed tumor growth in an HCT116 nude mouse xenograft tumor model without causing evident cytotoxicity. Sertaconazole nitrate induces antitumor effects in colorectal cancer by inhibiting IDO1-modulated autophagy and apoptosis, providing a clue for repurposing Sertaconazole nitrate as a novel and potentially effective candidate medication for the future treatment of colorectal cancer. Reference: Eur J Pharmacol. 2023 Mar 5;942:175515. https://pubmed.ncbi.nlm.nih.gov/36669614/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	49.92
	DMSO	25.0	49.92
	Ethanol	0.1	0.20

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 500.78 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. Zhang W, Zhou L, Qin S, Jiang J, Huang Z, Zhang Z, Zhang X, Shi Z, Lin J. Sertaconazole provokes proapoptotic autophagy via stabilizing TRADD in nonsmall cell lung cancer cells. MedComm (2020). 2021 Dec 16;2(4):821-837. doi: 10.1002/mco2.102. PMID: 34977879; PMCID: PMC8706745. 2. Sebastian J, Rathinasamy K. Sertaconazole induced toxicity in HeLa cells through mitotic arrest and inhibition of microtubule assembly. Naunyn Schmiedebergs Arch Pharmacol. 2021 Jun;394(6):1231-1249. doi: 10.1007/s00210-021-02059-5. Epub 2021 Feb 23. PMID: 33620548. 3. Liu R, Li Q, Qin S, Qiao L, Yang M, Liu S, Nice EC, Zhang W, Huang C, Zheng S, Gao W. Sertaconazole-repurposed nanoplatform enhances lung cancer therapy via CD44-targeted drug delivery. J Exp Clin Cancer Res. 2023 Jul 29;42(1):188. doi: 10.1186/s13046-023-02766-2. PMID: 37507782; PMCID: PMC10385912. 4. Yang Y, Jin Y, Yin L, Liu P, Zhu L, Gao H. Sertaconazole nitrate targets IDO1 and regulates the MAPK signaling pathway to induce autophagy and apoptosis in CRC cells. Eur J Pharmacol. 2023 Mar 5;942:175515. doi: 10.1016/j.ejphar.2023.175515. Epub 2023 Jan 18. PMID: 36669614.

In vitro protocol:

In vivo protocol:

1. Liu R, Li Q, Qin S, Qiao L, Yang M, Liu S, Nice EC, Zhang W, Huang C, Zheng S, Gao W. Sertaconazole-repurposed nanoplatform enhances lung cancer therapy via CD44-targeted drug delivery. J Exp Clin Cancer Res. 2023 Jul 29;42(1):188. doi: 10.1186/s13046-023-02766-2. PMID: 37507782; PMCID: PMC10385912. 2. Yang Y, Jin Y, Yin L, Liu P, Zhu L, Gao H. Sertaconazole nitrate targets IDO1 and regulates the MAPK signaling pathway to induce autophagy and apoptosis in CRC cells. Eur J Pharmacol. 2023 Mar 5;942:175515. doi: 10.1016/j.ejphar.2023.175515. Epub 2023 Jan 18. PMID: 36669614.

1: Yang Y, Jin Y, Yin L, Liu P, Zhu L, Gao H. Sertaconazole nitrate targets IDO1 and regulates the MAPK signaling pathway to induce autophagy and apoptosis in CRC cells. Eur J Pharmacol. 2023 Mar 5;942:175515. doi: 10.1016/j.ejphar.2023.175515. Epub 2023 Jan 18. PMID: 36669614. 2: Abdellatif MM, Josef M, El-Nabarawi MA, Teaima M. Sertaconazole-Nitrate- Loaded Leciplex for Treating Keratomycosis: Optimization Using D-Optimal Design and In Vitro, Ex Vivo, and In Vivo Studies. Pharmaceutics. 2022 Oct 18;14(10):2215. doi: 10.3390/pharmaceutics14102215. PMID: 36297650; PMCID: PMC9611087. 3: Tarsitano M, Mancuso A, Cristiano MC, Paolino D, Fresta M. In Situ Swelling Formulation of Glycerol-Monooleate-Derived Lyotropic Liquid Crystals Proposed for Local Vaginal Application. Molecules. 2022 Sep 23;27(19):6295. doi: 10.3390/molecules27196295. PMID: 36234833; PMCID: PMC9571072. 4: Georgescu SR, Mitran CI, Mitran MI, Amuzescu A, Matei C, Tampa M. A Meta- Analysis on the Effectiveness of Sertaconazole 2% Cream Compared with Other Topical Therapies for Seborrheic Dermatitis. J Pers Med. 2022 Sep 19;12(9):1540. doi: 10.3390/jpm12091540. PMID: 36143325; PMCID: PMC9501484. 5: Fink S, Burmester A, Hipler UC, Neumeister C, Götz MR, Wiegand C. Efficacy of antifungal agents against fungal spores: An in vitro study using microplate laser nephelometry and an artificially infected 3D skin model. Microbiologyopen. 2022 Feb;11(1):e1257. doi: 10.1002/mbo3.1257. PMID: 35212482; PMCID: PMC8756736. 6: Bubić Pajić N, Vucen S, Ilić T, O'Mahony C, Dobričić V, Savić S. Comparative efficacy evaluation of different penetration enhancement strategies for dermal delivery of poorly soluble drugs - A case with sertaconazole nitrate. Eur J Pharm Sci. 2021 Sep 1;164:105895. doi: 10.1016/j.ejps.2021.105895. Epub 2021 Jun 1. PMID: 34087357. 7: Ansari S, Ahmadi B, Tabatabaeifar SN, Hedayati MT, Javidnia J, Taghizadeh Armaki M, Shokoohi GR, Rezaei-Matehkolaei A. Familial Cases of Trichophyton benhamiae Infection Transmitted from a Guinea Pig in Iran. Mycopathologia. 2021 Mar;186(1):119-125. doi: 10.1007/s11046-020-00513-1. Epub 2021 Jan 4. PMID: 33394270. 8: Abdellatif MM, Khalil IA, Elakkad YE, Eliwa HA, Samir TM, Al-Mokaddem AK. Formulation and Characterization of Sertaconazole Nitrate Mucoadhesive Liposomes for Vaginal Candidiasis. Int J Nanomedicine. 2020 Jun 11;15:4079-4090. doi: 10.2147/IJN.S250960. PMID: 32606665; PMCID: PMC7295534. 9: Kracht T, Müller-Goymann CC. Antifungal efficacy of liquid poloxamer 407-based emulsions loaded with sertaconazole nitrate. Int J Pharm. 2020 Jul 30;585:119400. doi: 10.1016/j.ijpharm.2020.119400. Epub 2020 Jun 5. PMID: 32512222. 10: Tan J, Liu X, Gao Z, Yang H, Yang L, Wen H. A case of Tinea Faciei caused by Trichophyton benhamiae: first report in China. BMC Infect Dis. 2020 Feb 22;20(1):171. doi: 10.1186/s12879-020-4897-z. PMID: 32087692; PMCID: PMC7036192. 11: Shah R, Verma PK. Therapeutic importance of synthetic thiophene. Chem Cent J. 2018 Dec 19;12(1):137. doi: 10.1186/s13065-018-0511-5. PMID: 30564984; PMCID: PMC6768136. 12: Younes NF, Abdel-Halim SA, Elassasy AI. Solutol HS15 based binary mixed micelles with penetration enhancers for augmented corneal delivery of sertaconazole nitrate: optimization, in vitro, ex vivo and in vivo characterization. Drug Deliv. 2018 Nov;25(1):1706-1717. doi: 10.1080/10717544.2018.1497107. PMID: 30442039; PMCID: PMC6249589. 13: Younes NF, Abdel-Halim SA, Elassasy AI. Corneal targeted Sertaconazole nitrate loaded cubosomes: Preparation, statistical optimization, in vitro characterization, ex vivo permeation and in vivo studies. Int J Pharm. 2018 Dec 20;553(1-2):386-397. doi: 10.1016/j.ijpharm.2018.10.057. Epub 2018 Oct 26. PMID: 30393167. 14: Pajić NZB, Todosijević MN, Vuleta GM, Cekić ND, Dobričić VD, Vučen SR, Čalija BR, Lukić MŽ, Ilić TM, Savić SD. Alkyl polyglucoside vs. ethoxylated surfactant-based microemulsions as vehicles for two poorly water-soluble drugs: physicochemical characterization and in vivo skin performance. Acta Pharm. 2017 Dec 20;67(4):415-439. doi: 10.1515/acph-2017-0036. PMID: 29337676. 15: Mandlik SK, Siras SS, Birajdar KR. Optimization and characterization of sertaconazole nitrate flexisomes embedded in hydrogel for improved antifungal activity. J Liposome Res. 2019 Mar;29(1):10-20. doi: 10.1080/08982104.2017.1402926. Epub 2017 Dec 4. PMID: 29160732. 16: Abdellatif MM, Khalil IA, Khalil MAF. Sertaconazole nitrate loaded nanovesicular systems for targeting skin fungal infection: In-vitro, ex-vivo and in-vivo evaluation. Int J Pharm. 2017 Jul 15;527(1-2):1-11. doi: 10.1016/j.ijpharm.2017.05.029. Epub 2017 May 15. PMID: 28522423. 17: Manian M, Madrasi K, Chaturvedula A, Banga AK. Investigation of the Dermal Absorption and Irritation Potential of Sertaconazole Nitrate Anhydrous Gel. Pharmaceutics. 2016 Jul 7;8(3):21. doi: 10.3390/pharmaceutics8030021. PMID: 27399763; PMCID: PMC5039440. 18: Pande VV, Kadnor NA, Kadam RN, Upadhye SA. Fabrication and Characterization of Sertaconazole Nitrate Microsponge as a Topical Drug Delivery System. Indian J Pharm Sci. 2015 Nov-Dec;77(6):675-80. doi: 10.4103/0250-474x.174986. PMID: 26997694; PMCID: PMC4778226. 19: Soliman GM, Attia MA, Mohamed RA. Poly(ethylene glycol)-block- poly(ε-caprolactone) nanomicelles for the solubilization and enhancement of antifungal activity of sertaconazole. Curr Drug Deliv. 2014;11(6):753-62. doi: 10.2174/1567201811666140605151923. PMID: 24909149. 20: Pande V, Patel S, Patil V, Sonawane R. Design expert assisted formulation of topical bioadhesive gel of sertaconazole nitrate. Adv Pharm Bull. 2014;4(2):121-30. doi: 10.5681/apb.2014.019. Epub 2013 Dec 24. PMID: 24511475; PMCID: PMC3915811.