Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C16H13Cl3N2OS.ClH |
| Molecular Weight | 424.172 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.ClC1=C(COC(CN2C=CN=C2)C3=CC=C(Cl)C=C3Cl)C=CS1
InChI
InChIKey=UKQXXGSDDSCAHA-UHFFFAOYSA-N
InChI=1S/C16H13Cl3N2OS.ClH/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19;/h1-7,10,15H,8-9H2;1H
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01007 | http://reference.medscape.com/drug/vagistat-1-tioconazole-topical-343494 | https://www.drugs.com/cdi/tioconazole.html
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01007 | http://reference.medscape.com/drug/vagistat-1-tioconazole-topical-343494 | https://www.drugs.com/cdi/tioconazole.html
Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by a fungus or yeast. Tioconazole is a broad-spectrum imidazole antifungal agent that inhibits the growth of human pathogenic yeasts. Tioconazole exhibits fungicidal activity in vitro against Candida albicans, other species of the genus Candida, and against Torulopsis glabrata. Tioconazole prevents the growth and function of some fungal organisms by interfering with the production of substances needed to preserve the cell membrane. This drug is effective only for infections caused by fungal organisms. Tioconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Tioconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel. Side effects (for the women's formulas) may include temporary burning/irritation of the vaginal area, moderate drowsiness, headache similar to a sinus headache, hives, and upper respiratory infection.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1780 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | TZ-3 Approved UseDirections before using this product read the enclosed brochure and instructions on foil packet for complete directions and information adults and children 12 years and over: 1.Open the foil packet just before use and remove purple cap. 2.Insert entire contents of applicator into the vagina at bedtime. Throw applicator away after use. children under 12 years of age: ask a doctor, Do not use if sealed foil packet torn, open, or incompletely sealed. 1-DOSE TREATMENT TIOCONAZOLE OINTMENT 6.5% VAGINAL ANTIFUNGAL DIRECTIONS FOR USE Tear open foil packet just before using. It is best to use at bedtime. Remove applicator and plunger from packet. Applicator is prefilled with vaginal ointment. While firmly holding the purple-capped end of the applicator, push the tip of the plunger into the base of applicator. REMOVE PURPLE CAP from top of applicator with a pull-twist action. Insert the applicator Lie on your back with your knees bent. Gently insert applicator into the vagina as far as it will go comfortably. Push the plunger into the applicator until it will go no farther. Withdraw the applicator and plunger and dispose of it in the wastebasket. Do not flush. DO NOT USE TAMPONS while using this medicine. Use sanitary napkins instead. PLEASE READ EDUCATIONAL BROCHURE FOR ADDITIONAL INFORMATION. 4260000 P6 DISTRIBUTED BY PERRIGO ALLEGAN, MI 48010 U.S.A. Tioconazole_oint_fig1-01 Tioconazole_oint_fig2-01 Tioconazole_oint_fig3-01 Launch Date1983 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6873743/ |
6 % single, vaginal dose: 6 % route of administration: Vaginal experiment type: SINGLE co-administered: |
TIOCONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
150 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6873743/ |
6 % single, vaginal dose: 6 % route of administration: Vaginal experiment type: SINGLE co-administered: |
TIOCONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
6.5 % 1 times / day multiple, topical Highest studied dose Dose: 6.5 %, 1 times / day Route: topical Route: multiple Dose: 6.5 %, 1 times / day Sources: |
unhealthy, adult n = 80 Health Status: unhealthy Condition: vulvovaginal candidiasis Age Group: adult Sex: unknown Population Size: 80 Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [Ki 0.02 uM] | ||||
| yes [Ki 0.4 uM] | ||||
| yes [Ki 0.4 uM] | ||||
| yes [Ki 0.4 uM] | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antifungal activity of tioconazole (UK-20,349), a new imidazole derivative. | 1979 Apr |
|
| Current and emerging azole antifungal agents. | 1999 Jan |
|
| Synthesis and antifungal activity of novel pyrano[2',3':4,5]thiazolo[2,3-b]quinazolines, pyrido[2',3':4,5]thiazolo[2,3-b]quinazolines and pyrazolo[2',3':4,5]thiazolo[2,3-b]quinazolines. | 2000 Apr |
|
| Ciclopiroxolamine: in vitro antifungal activity against clinical yeast isolates. | 2002 Nov |
|
| In vivo patterns of resistance to the HIV attachment inhibitor BMS-488043. | 2011 Feb |
Patents
Sample Use Guides
Insert 1 applicatorful (5 g of 6.5% ointment) intravaginally qHS once
Route of Administration:
Vaginal
The compounds were dissolved in dimethyl formamnide, and water was added to give a final Tioconazole concentration of 1 mg/ml in 10% dimethyl formamide-water. From this solution, serial twofold dilutions of the compounds in water were incorporated into diagnostic sensitivity test agar over an appropriate concentration range (normally 100 mkg/ml down to 0.0 1mkg/ml). Organisms were inoculated onto the surface of the agar, using a multipoint inoculator (Denley Instruments) which delivers approximately 1 id of the fungal inoculum. Candida spp., Torulopsis glabtata, and Cryptococcus neofomnans were grown overnight at 37 C in brain heart infusion broth (Difco Laboratories). The concentration of cells in the culture was determined in a hemocytometer and then appropriately diluted in broth to10 cells per ml. MICs were read after incubation at 37 C for 48 h.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
T1QKM21KYB
Created by
admin on Fri Dec 15 15:50:49 GMT 2023 , Edited by admin on Fri Dec 15 15:50:49 GMT 2023
|
PRIMARY | |||
|
DBSALT002308
Created by
admin on Fri Dec 15 15:50:49 GMT 2023 , Edited by admin on Fri Dec 15 15:50:49 GMT 2023
|
PRIMARY | |||
|
18615661
Created by
admin on Fri Dec 15 15:50:49 GMT 2023 , Edited by admin on Fri Dec 15 15:50:49 GMT 2023
|
PRIMARY | |||
|
61675-64-7
Created by
admin on Fri Dec 15 15:50:49 GMT 2023 , Edited by admin on Fri Dec 15 15:50:49 GMT 2023
|
PRIMARY | |||
|
m10878
Created by
admin on Fri Dec 15 15:50:49 GMT 2023 , Edited by admin on Fri Dec 15 15:50:49 GMT 2023
|
PRIMARY | Merck Index |
ACTIVE MOIETY
SUBSTANCE RECORD
