1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

• ChemBase ID: 880
• Molecular Formular: C16H13Cl3N2OS
• Molecular Mass: 387.71122
• Monoisotopic Mass: 385.98141709
• SMILES: Clc1c(C(OCc2ccsc2Cl)Cn2ccnc2)ccc(Cl)c1
• Canonical SMILES: Clc1ccc(c(c1)Cl)C(Cn1ccnc1)OCc1ccsc1Cl
• InChI: InChI=1S/C16H13Cl3N2OS/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
• InChIKey: QXHHHPZILQDDPS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
• IUPAC Traditional name: trosid; tioconazole
• Brand Name: Fungibacid; GyneCure; Gyno-trosyd; Monistat 1; Trosyd; Trosyd AF; Trosyd J; Trosyl; Tz-3; Vagistat; Vagistat-1; Zoniden
• Synonyms: (±)-Tioconazole; Fungibacid; Gyno-Trosyd; New Straitus U; Trosyd; Trosyl; Vagistat; Vagistat 1; Zoniden; Tioconazol [INN-Spanish]; Tioconazolum [INN-Latin]; Tioconazole; 1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole; Thioconazole; Tioconazole; 1-(2-((2-chlorothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)-ethyl)imidazole

Database IDs

• CAS Number: 65899-73-2
• EC Number: 265-973-8
• MDL Number: MFCD00057276
• PubChem SID: 46508604; 160964343
• PubChem CID: 5482

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.7685566
• LogD (pH = 7.4): 5.2330527
• Log P: 5.298762
• Molar Refractivity: 94.5285 cm^3
• Polarizability: 36.8694 Å^3
• Polar Surface Area: 27.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.86
• LOG S: -4.37
• Solubility (Water): 1.65e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4.4

Safety Information

• Storage Condition: -20°C
• RTECS: NI4480000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H413
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥96.5% (HPLC); 96.5-103.5% (NT); 97%; 98%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C16H13Cl3N2OS

DETAILS

DrugBank - DB01007

• Drug Groups: approved
• Description: Tioconazole 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, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability.
• Indication: For the local treatment of vulvovaginal candidiasis (moniliasis).
• 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.
• Toxicity: Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning,; and general irritation of the skin, and cramps.
• Affected Organisms: Yeast and other fungi
• Biotransformation: Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.
• Absorption: Systemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1910

Research Area: Infection
Biological Activity:

Sigma Aldrich - 03907

Application
Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by fungus and yeast. It is used to study the synergistic mechanisms of antifungals on Candida albicans 1 as well as significant drug-drug interactions in vivo2.
Biochem/physiol Actions
Tioconazole is an antifungal that is more active than fluconazole or voriconazole against Candida glabrata mutant strains.3 Its mechanism of action is through membrane disruption and loss of intracellular ATP.4

Toronto Research Chemicals - T444680

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

REFERENCES

• Jevons, S., et al.: Antimicrob. Agents Chemother., 15, 597 (1979)
• Clayton, Y.M., et al.: Clin. Exp. Dermatol., 7, 543 (1979)
• Marriott, M.S., et al.: Dermatologica, 166, 1 (1979)