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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(Cl)=C(C=C1)C(CN2C=CN=C2)OCC3=CC=C(SC4=CC=CC=C4)C=C3

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 ( + / - )

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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.
PubMed

PubMed

TitleDatePubMed
Irritation and toxicity studies with fenticonazole applied topically to the skin and mucous membranes.
1981
Toxicological and pharmacological properties of fenticonazole, a new topical antimycotic.
1981
Mutagenicity studies on fenticonazole, a new antifungal imidazole derivative.
1981
Antifungal activity of fenticonazole in experimental dermatomycosis and candidiasis.
1981
Fenticonazole, a new imidazole derivative with antibacterial and antifungal activity. In vitro study.
1981
New alpha-aryl-beta,N-imidzolylethyl benzyl and naphthylmethyl ethers with antimycotic and antibacterial activity.
1981
The Salmonella mutagenicity assay on fenticonazole, a new antifungal imidazole derivative.
1981
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
Patents

Patents

Sample Use Guides

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
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 Fri Dec 15 15:31:57 UTC 2023
Edited
by admin
on Fri Dec 15 15:31:57 UTC 2023
Record UNII
8V4JGC8YRF
Record Status Validated (UNII)
Record Version
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Name Type Language
FENTICONAZOLE NITRATE
EP   MART.   USAN   WHO-DD  
USAN  
Official 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
LOMEXIN
Brand Name English
FENTICONAZOLE MONONITRATE
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
Code System Code Type Description
MERCK INDEX
m5302
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
277-302-6
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
CHEBI
83606
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PRIMARY
EPA CompTox
DTXSID30993890
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
CAS
73151-29-8
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
EVMPD
SUB13831MIG
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
FDA UNII
8V4JGC8YRF
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
SMS_ID
100000091096
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
RXCUI
236229
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C81508
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL1651990
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
PUBCHEM
51754
Created by admin on Fri Dec 15 15:31:57 UTC 2023 , Edited by admin on Fri Dec 15 15:31:57 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY