Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H20Cl2N2OS |
Molecular Weight | 455.399 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC(Cl)=C(C=C1)C(CN2C=CN=C2)OCC3=CC=C(SC4=CC=CC=C4)C=C3
InChI
InChIKey=ZCJYUTQZBAIHBS-UHFFFAOYSA-N
InChI=1S/C24H20Cl2N2OS/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/h1-14,17,24H,15-16H2
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1780 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25204341 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | LOMEXIN Approved UseLomexin is used to treat a common vaginal infection known as vaginal candidiasis (vaginal thrush) in adolescents more than 16 years and adults. |
PubMed
Title | Date | PubMed |
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Irritation and toxicity studies with fenticonazole applied topically to the skin and mucous membranes. | 1981 |
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Toxicological and pharmacological properties of fenticonazole, a new topical antimycotic. | 1981 |
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Mutagenicity studies on fenticonazole, a new antifungal imidazole derivative. | 1981 |
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Antifungal activity of fenticonazole in experimental dermatomycosis and candidiasis. | 1981 |
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Fenticonazole, a new imidazole derivative with antibacterial and antifungal activity. In vitro study. | 1981 |
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The Salmonella mutagenicity assay on fenticonazole, a new antifungal imidazole derivative. | 1981 |
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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
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19223627
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
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admin
on
Edited
Fri Dec 15 15:42:12 GMT 2023
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Record UNII |
QG05NRB077
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
D01AC12
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WHO-ATC |
G01AF12
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WHO-VATC |
QG01AF12
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NCI_THESAURUS |
C514
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WHO-VATC |
QD01AC12
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24876
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72479-26-6
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m5302
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100000092574
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Fenticonazole
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1166
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CHEMBL1651990
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C033486
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DB13434
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QG05NRB077
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82863
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SUB07600MIG
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C72963
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51755
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DTXSID7057812
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |