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Details

Stereochemistry RACEMIC
Molecular Formula C24H20Cl2N2OS.HNO3
Molecular Weight 518.412
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENTICONAZOLE NITRATE

SMILES

O[N+]([O-])=O.ClC1=CC=C(C(CN2C=CN=C2)OCC3=CC=C(SC4=CC=CC=C4)C=C3)C(Cl)=C1

InChI

InChIKey=FJNRUWDGCVDXLU-UHFFFAOYSA-N
InChI=1S/C24H20Cl2N2OS.HNO3/c25-19-8-11-22(23(26)14-19)24(15-28-13-12-27-17-28)29-16-18-6-9-21(10-7-18)30-20-4-2-1-3-5-20;2-1(3)4/h1-14,17,24H,15-16H2;(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula HNO3
Molecular Weight 63.0128
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H20Cl2N2OS
Molecular Weight 455.399
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Fenticonazole is an imidazole derivative with a broad spectrum of antimycotic activity. It is used as a nitrate salt under different trade names (Lomexin, Gynoxin, Fentizol, etc) for the treatment of vaginal candidiasis. Fenticonazole inhibits the synthesis of ergosterol, an important step in the formation of the wall of fungi and blocks the oxidizing enzymes with the corresponding accumulation of peroxides and necrosis of the fungal cell. In vitro studies have shown a broad fungistatic and fungicidal activity. Like other azole agents, the spectrum of action of Fenticonazole also extends to some gram-positive bacteria such as Staphylococcus aureus. In vivo studies have also shown activity against Trichomonas Vaginalis.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
LOMEXIN

Cmax

ValueDoseCo-administeredAnalytePopulation
0.499 ng/mL
0.1 g single, topical
FENTICONAZOLE plasma
Homo sapiens
5.957 ng/mL
0.1 g single, vaginal
FENTICONAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
12.914 ng × h/mL
0.1 g single, topical
FENTICONAZOLE plasma
Homo sapiens
159.22 ng × h/mL
0.1 g single, vaginal
FENTICONAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
27.883 h
0.1 g single, topical
FENTICONAZOLE plasma
Homo sapiens
26.51 h
0.1 g single, vaginal
FENTICONAZOLE plasma
Homo sapiens

Doses

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose is 1 soft vaginal capsule of 200 mg for three consecutive days or 1 soft vaginal capsule of 600 mg (single administration).
Route of Administration: Vaginal
In Vitro Use Guide
Candida strains were treated with fenticonazole at a final concentration range of 0.0312 ug/ml to 32 ug/ml. MIC50 values were 0.03-0.5 ug/ml for C. albicans, 0.03-1 ug/ml for C. glabrata, 0.03-1 ug/ml for C. parapsilosis and 0.06-2 ug/ml for C. krusei.
Substance Class Chemical
Record UNII
8V4JGC8YRF
Record Status Validated (UNII)
Record Version