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Key Documents

SML0888

Sigma-Aldrich

Sertaconazole nitrate

≥98% (HPLC)

Synonym(s):

1-[2-[(7-Chlorobenzo[b]thien-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole nitrate

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About This Item

Empirical Formula (Hill Notation):
C20H15Cl3N2OS · HNO3
CAS Number:
99592-39-9
Molecular Weight:
500.78
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

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)

InChI key

HAAITRDZHUANGT-UHFFFAOYSA-N

Biochem/physiol Actions

Sertaconazole nitrate is an antifungal agent with anti-inflammatory and anti-itch activity. Topical administration of this drug reduces the releases of cytokines from activated T-cell enriched human lymphocytes. Sertaconazole nitrate has been used as a highly safe and effective therapeutic for treating tinea pedis interdigitalis. It is also used to treat contact hypersensitivity and irritant contact dermatitis.
Sertaconazole nitrate is an imidazole antifungal. Like other imidazole antifungals, sertaconazole blocks the synthesis of ergosterol, an essential component of the fungal cell membrane, by inhibiting the P450 enzyme 14α-demethylase that converts lanosterol to ergosterol.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Safety and efficacy of sertaconazole nitrate cream 2% in the treatment of tinea pedis interdigitalis: a subgroup analysis.
Borelli C, et al.
Cutis; Cutaneous Medicine for the Practitioner, 85(2), 107-111 (2010)
Anti-Inflammatory Activity of Sertaconazole Nitrate Is Mediated via Activation of a p38?COX-2?PGE2 Pathway.
Sur R, et al.
The Journal of Investigative Dermatology, 128(2), 336-344 (2008)
Frank Liebel et al.
Archives of dermatological research, 298(4), 191-199 (2006-07-27)
Cutaneous fungal infections are frequently associated with an inflammatory component including irritated skin, itching and stinging/burning. Therapeutic anti-fungal agents that have anti-inflammatory activity have the potential to provide clinical benefit beyond fungus eradication. Recently, certain anti-fungal agents have been shown

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