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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
Structure of TIOCONAZOLE HYDROCHLORIDE

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

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TZ-3

Approved Use

Directions 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 Date

1983
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
150 ng × h/mL
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

Doses

DosePopulationAdverse 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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

Insert 1 applicatorful (5 g of 6.5% ointment) intravaginally qHS once
Route of Administration: Vaginal
In Vitro Use Guide
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
TIOCONAZOLE HYDROCHLORIDE
MI  
Common Name English
UK-20349 HCL
Common Name English
1-(2-((2-CHLORO-3-THIENYL)METHOXY)-2-(2,4-DICHLOROPHENYL)ETHYL)-1H-IMIDAZOLE MONOHYDROCHLORIDE
Systematic Name English
TIOCONAZOLE HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
FDA UNII
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
DRUG BANK
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
PUBCHEM
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
CAS
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
MERCK INDEX
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