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Sertaconazole (nitrate)

CAT: 0804-HY-B0736A-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B0736A-01Size:10 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Sertaconazole nitrate (FI7056) is a broad-spectrum topical antifungal agent, exhibits anti-inflammatory activity via activation of a p38-COX-2-PGE2 pathway. Sertaconazole nitrate is also a microtubule inhibitor, shows antiproliferative effect, induces apoptosis and autophagy, and can also inhibit the migration of cells[1][2][3][4].
CAS Number
99592-39-9
Product Name Alternative
FI7056
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Autophagy; Fungal; Microtubule/Tubulin; p38 MAPK
Type
Reference compound
Related Pathways
Anti-infection; Apoptosis; Autophagy; Cell Cycle/DNA Damage; Cytoskeleton; MAPK/ERK Pathway
Applications
COVID-19-immunoregulation
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/sertaconazole-nitrate.html
Concentration
10mM
Purity
99.58
Solubility
DMSO : ≥ 100 mg/mL
Smiles
ClC1=CC=C(C(OCC2=CSC3=C(Cl)C=CC=C32)CN4C=CN=C4)C(Cl)=C1.O[N+]([O-])=O
Molecular Formula
C20H16Cl3N3O4S
Molecular Weight
500.78
Precautions
H302, H315, H319, H335
References & Citations
[1]Carrillo-Muñoz AJ, et al. In-vitro antifungal activity of sertaconazole, econazole, and bifonazole against Candida spp. J Antimicrob Chemother. 1995 Oct;36 (4) :713-6.|[2]Sur R, et al. Anti-inflammatory activity of sertaconazole nitrate is mediated via activation of a p38-COX-2-PGE2 pathway. J Invest Dermatol. 2008 Feb;128 (2) :336-44.|[3]Sebastian J, et al. Sertaconazole induced toxicity in HeLa cells through mitotic arrest and inhibition of microtubule assembly. Naunyn Schmiedebergs Arch Pharmacol. 2021 Jun;394 (6) :1231-1249.|[4]Zhang W, et al. Sertaconazole provokes proapoptotic autophagy via stabilizing TRADD in nonsmall cell lung cancer cells. MedComm (2020) . 2021 Dec 16;2 (4) :821-837.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Sertaconazole Nitrate

Sertaconazole Nitrate is the nitrate salt form of sertaconazole, a synthetic imidazole derivative with antifungal property. Sertaconazole nitrate inhibits fungal cytochrome P-450 sterol C-14 alpha-demethylation, resulting in the accumulation of fungal 14 alpha-methyl sterols and the inhibition of ergosterol synthesis, an essential component of the cell membrane of fungi. This leads to a disruption of cell membrane permeability and leakage of adenine triphosphate (ATP) and other constituents from fugal cells.

CAS Number99592-39-9
PubChem CID200103
IUPAC Name1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid
Molecular FormulaC20H16Cl3N3O4S
Molecular Weight500.8
Topological Polar Surface Area121
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Heavy Atom Count31
Formal Charge0
Complexity513
SMILES
C1=CC2=C(C(=C1)Cl)SC=C2COC(CN3C=CN=C3)C4=C(C=C(C=C4)Cl)Cl.[N+](=O)(O)[O-]
InChI
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)
InChIKey
HAAITRDZHUANGT-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Sertaconazole Nitrate
CAS: 99592-39-9
CID: 200103
Formula: C20H16Cl3N3O4S
MW: 500.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight500.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass498.992710
Monoisotopic Mass498.992710
Topological Polar Surface Area121 Ų
Heavy Atom Count31
Formal Charge0
Complexity513
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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