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Tioconazole

Tioconazole structure

CAS No:
65899-73-2
Formula:
C16H13Cl3N2OS
Chemical Name:
Tioconazole
Synonyms:
1H-Imidazole,1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-;1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole;Tioconazole;(±)-Tioconazole;Trosyd;Trosyl;Gyno-Trosyd;Vagistat 1;Zoniden;Vagistat;Fungibacid;New Straitus U;1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl) ethyl]-1H-imidazole;1-[2-[(2-Chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;144025-07-0
Categories:
Cosmetic Ingredient > Antimicrobials

Description

Tioconazole is an antifungal medication.Target: AntifungalTioconazole is an antifungal medication of the Imidazole class used to treat infections caused by a fungus or yeast. Tioconazole topical (skin) preparations are also available for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus". Tioconazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioco

Solid

1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2. It is an ether, a member of imidazoles, a member of thiophenes and a dichlorobenzene.|Tioconazole is an imidazole antifungal used to treat fungal and yeast infections. Topical formulations are used for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus". Tioconazole interacts with 14-alpha 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 Basic Attributes

Molecular Weight：

387.71

Exact Mass：

387.71

EC Number：

265-973-8

NSC Number：

759169

DSSTox ID：

DTXSID3046619

ATC Code：

D - Dermatologicals|G - Genito urinary system and sex hormones

HScode：

2934990002

Characteristics

PSA：

55.3

XLogP3：

5.3

Appearance：

white to off-white

Density：

1.4±0.1 g/cm3

Boiling Point：

534.5ºC at 760 mmHg

Flash Point：

277.0±30.1 °C

Refractive Index：

1.654

Water Solubility：

1.65e-02 g/L

Collision Cross Section：

180.7 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

RTECS Number：

NI4480000

Marks：

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P333+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 227 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.

Drug Information

Drug Indication：

For the local treatment of vulvovaginal candidiasis (moniliasis).|FDA Label

Pharmacology：

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. It will not work for bacterial or viral infections.

MeSH：

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism. (See all compounds classified as 14-alpha Demethylase Inhibitors.)

Absorption：

Systemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.

Metabolism/Metabolites：

Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.

Mechanism of Action：

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.

MeSH Entry Terms：

Gyno-Trosyd

Tioconazole Use and Manufacturing

Uses

Tioconazole is an antifungal that is more active than Fluconazole (F421000) or Voriconazole (V760000) against Candida glabrata mutant strains. Antifungal (topical).

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:387.7
XLogP3:5.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:385.981417
Monoisotopic Mass:385.981417
Topological Polar Surface Area:55.3
Heavy Atom Count:23
Complexity:379
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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