Arasertaconazole | CAS#583057-48-1 | 583057-49-2 | sterol-14-alpha demethylation inhibitor

MedKoo Cat#: 328022 | Name: Arasertaconazole

Description:

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

Arasertaconazole is a sterol-14-alpha demethylation inhibitor potentially for treatment of vulvovaginal candcanidiasis and provokes proapoptotic autophagy via stabilizing TRADD in nonsmall cell lung cancer cells.

Chemical Structure

Arasertaconazole

CAS#583057-48-1

Theoretical Analysis

MedKoo Cat#: 328022

Name: Arasertaconazole

CAS#: 583057-48-1

Chemical Formula: C20H15Cl3N2OS

Exact Mass: 435.9971

Molecular Weight: 437.76

Elemental Analysis: C, 54.87; H, 3.45; Cl, 24.29; N, 6.40; O, 3.65; S, 7.32

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Related CAS #

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Synonym

Arasertaconazole

IUPAC/Chemical Name

1-((2R)-2-((7-Chloro-1-benzothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

InChi Key

JLGKQTAYUIMGRK-IBGZPJMESA-N

InChi Code

InChI=1S/C20H15Cl3N2OS/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/h1-8,11-12,19H,9-10H2/t19-/m0/s1

SMILES Code

ClC1=CC=C([C@@H](OCC2=CSC3=C(Cl)C=CC=C23)CN4C=CN=C4)C(Cl)=C1

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

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# 583057-48-1 (Arasertaconazole) 583057-49-2 (Arasertaconazole Nitrate)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 437.76 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

1: Carrillo-Muñoz AJ, Tur-Tur C, Giusiano G, Marcos-Arias C, Eraso E, Jauregizar N, Quindós G. Sertaconazole: an antifungal agent for the topical treatment of superficial candidiasis. Expert Rev Anti Infect Ther. 2013 Apr;11(4):347-58. doi: 10.1586/eri.13.17. PMID: 23566144. 2: Croxtall JD, Plosker GL. Sertaconazole: a review of its use in the management of superficial mycoses in dermatology and gynaecology. Drugs. 2009;69(3):339-59. doi: 10.2165/00003495-200969030-00009. PMID: 19275277. 3: Torres J, Márquez M, Camps F. Sertaconazole in the treatment of mycoses: from dermatology to gynecology. Int J Gynaecol Obstet. 2000 Dec;71 Suppl 1:S3-20. doi: 10.1016/s0020-7292(00)00349-0. PMID: 11118560. 4: 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. 5: Araujo M, Hurault-Delarue C, Sommet A, Damase-Michel C, Lacroix I. Topical sertaconazole during pregnancy and risk of adverse pregnancy outcome and major congenital anomalies: Comparative study in the EFEMERIS database. Mycoses. 2022 Apr;65(4):481-489. doi: 10.1111/myc.13422. Epub 2022 Feb 8. PMID: 35067990. 6: 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. 7: Carrillo-Muñoz AJ, Giusiano G, Ezkurra PA, Quindós G. Sertaconazole: updated review of a topical antifungal agent. Expert Rev Anti Infect Ther. 2005 Jun;3(3):333-42. doi: 10.1586/14787210.3.3.333. PMID: 15954850. 8: Palacín C, Tarragó C, Ortiz JA. Sertaconazole: pharmacology of a gynecological antifungal agent. Int J Gynaecol Obstet. 2000 Dec;71 Suppl 1:S37-46. doi: 10.1016/s0020-7292(00)00351-9. PMID: 11118563. 9: Nemati S, Gerami H, Faghih Habibi A, Kazemnejad E, Shabani N, Aghsaghloo V, Montazeri S. Sertaconazole versus Clotrimazole and Miconazole Creams in the Treatment of Otomycosis: A Placebo-Controlled Clinical Trial. Iran J Otorhinolaryngol. 2022 Jan;34(120):27-34. doi: 10.22038/IJORL.2021.54805.2872. PMID: 35145933; PMCID: PMC8801007. 10: 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. 11: 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. 12: Goldust M, Ranjkesh MR, Amirinia M, Golforoushan F, Rezaee E, Rezazadeh Saatlou MA. Sertaconazole 2% cream versus hydrocortisone 1% cream in the treatment of seborrheic dermatitis. J Dermatolog Treat. 2013 Feb 24. doi: 10.3109/09546634.2012.755251. Epub ahead of print. PMID: 23210976. 13: Pfaller MA, Sutton DA. Review of in vitro activity of sertaconazole nitrate in the treatment of superficial fungal infections. Diagn Microbiol Infect Dis. 2006 Oct;56(2):147-52. doi: 10.1016/j.diagmicrobio.2006.04.006. Epub 2006 Jul 5. PMID: 16822638. 14: 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. 15: Tavakoli N, Taymouri S, Saeidi A, Akbari V. Thermosensitive hydrogel containing sertaconazole loaded nanostructured lipid carriers for potential treatment of fungal keratitis. Pharm Dev Technol. 2019 Sep;24(7):891-901. doi: 10.1080/10837450.2019.1616755. Epub 2019 Jun 4. PMID: 31062987. 16: Ghaninejad H, Gholami K, Hashemi P, Hajibabai M, Rahbar Z, Farivar MS, Mastani F, Rashidi A. Sertaconazole 2% cream vs. miconazole 2% cream for cutaneous mycoses: a double-blind clinical trial. Clin Exp Dermatol. 2009 Dec;34(8):e837-9. doi: 10.1111/j.1365-2230.2009.03579.x. Epub 2009 Sep 28. PMID: 19793095. 17: Behnam M, Zarrinfar H, Najafzadeh MJ, Naseri A, Jarahi L, Babič MN. Low in vitro activity of sertaconazole against clinical isolates of dermatophyte. Curr Med Mycol. 2020;6(1):36-41. doi: 10.18502/cmm.6.1.2507. PMID: 32420506; PMCID: PMC7217247. 18: Gupta AK, Foley KA, Versteeg SG. New Antifungal Agents and New Formulations Against Dermatophytes. Mycopathologia. 2017 Feb;182(1-2):127-141. doi: 10.1007/s11046-016-0045-0. Epub 2016 Aug 8. PMID: 27502503. 19: Susilo R, Korting HC, Greb W, Strauss UP. Nail penetration of sertaconazole with a sertaconazole-containing nail patch formulation. Am J Clin Dermatol. 2006;7(4):259-62. doi: 10.2165/00128071-200607040-00007. PMID: 16901186. 20: Azizzadeh M, Pahlevan D, Bagheri B. The efficacy and safety of pimecrolimus 1% cream vs. sertaconazole 2% cream in the treatment of patients with facial seborrhoeic dermatitis: a randomized blinded trial. Clin Exp Dermatol. 2022 May;47(5):926-931. doi: 10.1111/ced.15067. Epub 2022 Jan 25. PMID: 34910320.