FENTICONAZOLE NITRATE

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 Search

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

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

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18840006 | https://mri.cts-mrp.eu/Human/Downloads/DK_H_2567_002_FinalPL.pdf

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 Target	Pharmacology	Condition	Potency
Cytochrome P450 51 28 Target ID: CHEMBL1780 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25204341	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vaginal candidiasis 8 Sources: https://mri.cts-mrp.eu/Human/Downloads/DK_H_2567_002_FinalPL.pdf	Curative		Approved 8583	LOMEXIN Approved Use Lomexin is used to treat a common vaginal infection known as vaginal candidiasis (vaginal thrush) in adolescents more than 16 years and adults.

C_max

Value	Dose	Co-administered	Analyte	Population
0.499 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29404019/	0.1 g single, topical dose: 0.1 g route of administration: Topical experiment type: SINGLE co-administered:		FENTICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.957 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29404019/	0.1 g single, vaginal dose: 0.1 g route of administration: Vaginal experiment type: SINGLE co-administered:		FENTICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
12.914 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29404019/	0.1 g single, topical dose: 0.1 g route of administration: Topical experiment type: SINGLE co-administered:		FENTICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
159.22 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29404019/	0.1 g single, vaginal dose: 0.1 g route of administration: Vaginal experiment type: SINGLE co-administered:		FENTICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
27.883 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29404019/	0.1 g single, topical dose: 0.1 g route of administration: Topical experiment type: SINGLE co-administered:		FENTICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
26.51 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29404019/	0.1 g single, vaginal dose: 0.1 g route of administration: Vaginal experiment type: SINGLE co-administered:		FENTICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Doses

Dose	Population	Adverse events
5 g 1 times / day multiple, vaginal Studied dose Dose: 5 g, 1 times / day Route: vaginal Route: multiple Dose: 5 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3542628/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3542628/	Sources: https://pubmed.ncbi.nlm.nih.gov/3542628/
200 mg 1 times / day multiple, vaginal Studied dose Dose: 200 mg, 1 times / day Route: vaginal Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12017948/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12017948/	Sources: https://pubmed.ncbi.nlm.nih.gov/12017948/
600 mg single, vaginal Studied dose Dose: 600 mg Route: vaginal Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2202548/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2202548/	Sources: https://pubmed.ncbi.nlm.nih.gov/2202548/
1000 mg single, vaginal Highest studied dose Dose: 1000 mg Route: vaginal Route: single Dose: 1000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3315778/	unhealthy Health Status: unhealthy Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3315778/	Sources: https://pubmed.ncbi.nlm.nih.gov/3315778/

PubMed

Title	Date	PubMed
Irritation and toxicity studies with fenticonazole applied topically to the skin and mucous membranes.	1981	7199317
In vitro activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp.	1992 Apr	1406898

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 Created by `admin` on `Mon Mar 31 18:00:15 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:15 GMT 2025`
Record UNII	8V4JGC8YRF
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FENTICONAZOLE NITRATE

Official Name

English

LOMEXIN

Preferred Name

English

Fenticonazole nitrate [WHO-DD]

Common Name

English

FENTICONAZOLE MONONITRATE [MI]

Common Name

English

REC-15/1476

Code

English

REC 15/1476

Code

English

FENTICONAZOLE NITRATE [EP MONOGRAPH]

Common Name

English

1H-IMIDAZOLE, 1-(2-(2,4-DICHLOROPHENYL)-2-((4-(PHENYLTHIO)PHENYL)METHOXY)ETHYL)-, (±)-, MONONITRATE

Systematic Name

English

FENTICONAZOLE NITRATE [MART.]

Common Name

English

FENTICONAZOLE NITRATE [USAN]

Common Name

English

(±)-1-(2,4-DICHLORO-.BETA.-((P-(PHENYLTHIO)BENZYL)OXY)PHENETHYL)IMIDAZOLE MONONITRATE

Common Name

English

FENTICONAZOLE MONONITRATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514