structure of Sertaconazole nitrate

Sertaconazole nitrate

CAS No.: 99592-39-9
M. Wt: 500.783
M. Fa: C20H16Cl3N3O4S
InChI Key: HAAITRDZHUANGT-UHFFFAOYSA-N
Appearance: White To Beige Powder

Names and Identifiers of Sertaconazole nitrate

CAS Number

99592-39-9

MDL Number

MFCD00918063

IUPAC Name

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

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

Canonical SMILES

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

UNII

1DV05410M5

UNSPSC Code

12352100

Physical and chemical properties of Sertaconazole nitrate

Acidity coefficient

pKb: 7.26(at 25℃)

Boiling Point

614.1ºC at 760mmHg

Exact Mass

498.992706

Flash Point

325.2ºC

H Bond Acceptors

2

H Bond Donors

0

LogP

7.19160

Melting Point

158-160°

Molecular Formula

C20H16Cl3N3O4S

Molecular Weight

500.783

PSA

121.34000

Solubility

DMSO: soluble20mg/mL, clear

Storage condition

?20°C

Water Solubility

DMSO: soluble20mg/mL, clear

Safety Information of Sertaconazole nitrate

Pictograms

Signal Word

 Warning

Safety Data Sheet
Supports customized editing of SDS information and downloading in PDF documents.

Applications of Sertaconazole nitrate

Sertaconazole nitrate is primarily used in dermatology for treating superficial fungal infections. Its applications include:

  • Topical treatment: Cream formulations are used for skin infections like athlete's foot and ringworm.
  • Vaginal formulations: Available as vaginal tablets for treating candidiasis.
  • Potential antibacterial applications: Ongoing research explores its use against bacterial infections due to its antibacterial properties .

Interaction Studies of Sertaconazole nitrate

Studies on sertaconazole nitrate indicate that it interacts with various biological targets:

  • Cytochrome P-450 enzymes: Its primary mechanism involves inhibition of specific P-450 enzymes crucial for ergosterol biosynthesis .
  • Membrane interactions: Sertaconazole's ability to form pores in fungal membranes suggests potential interactions with lipid components, affecting membrane fluidity and integrity .
  • Cytokine modulation: Research suggests that sertaconazole can modulate immune responses by inhibiting pro-inflammatory cytokine release from activated immune cells .

Biological Activity of Sertaconazole nitrate

Sertaconazole exhibits several biological activities:

  • Antifungal: It effectively inhibits the growth of fungi by disrupting ergosterol synthesis.
  • Antibacterial: Sertaconazole has shown activity against certain bacteria, likely through similar mechanisms that affect membrane integrity.
  • Antiinflammatory: The compound can inhibit the release of pro-inflammatory cytokines, reducing inflammation associated with infections.
  • Antitrichomonal: It has demonstrated efficacy against Trichomonas vaginalis in vitro .

The compound's unique mechanism involving pore formation in fungal membranes sets it apart from other antifungal agents, leading to rapid cell death within hours of application .

Physical sample testing spectrum (NMR) of Sertaconazole nitrate

Physical sample testing spectrum (NMR) of Sertaconazole nitrate