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03907

Sigma-Aldrich

Tioconazole

97%

Synonym(s):

1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole, Thioconazole

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About This Item

Empirical Formula (Hill Notation):
C16H13Cl3N2OS
CAS Number:
65899-73-2
Molecular Weight:
387.71
EC Number:
265-973-8
MDL number:
MFCD00057276
UNSPSC Code:
51302325
PubChem Substance ID:
329747834
NACRES:
NA.85

assay

≥96.5% (HPLC)
96.5-103.5% (NT)
97%

form

powder

color

white to off-white

antibiotic activity spectrum

fungi
yeast

mode of action

cell membrane | interferes

SMILES string

Clc1ccc(C(Cn2ccnc2)OCc3ccsc3Cl)c(Cl)c1

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

InChI key

QXHHHPZILQDDPS-UHFFFAOYSA-N

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General description

Chemical structure: pyrimidine

Application

Tioconazole was used to study the synergistic mechanisms of antifungals on Candida albicans as well as significant drug-drug interactions in vivo.

Biochem/physiol Actions

Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by fungus and yeast.It is more active than fluconazole or voriconazole against Candida glabrata mutant strains. It acts by membrane disruption and loss of intracellular ATP.

Packaging

10G

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wenjiang Zhang et al.
Drug metabolism and disposition: the biological fate of chemicals, 30(3), 314-318 (2002-02-21)
The interactions of a panel of antifungal agents with cytochromes P450 (P450s), as a means of predicting potential drug-drug interactions, have not yet been investigated. The objective of this study was to evaluate the specificity and selectivity of five antifungal
Synergistic action of nikkomycin X/Z with azole antifungals on Candida albicans.
Slawomir Milewski, Fiorenzo Mignini, et. Al
Microbiology, 137, 2155-2161 (1991)
C Nolting et al.
Mycoses, 40 Suppl 1, 73-75 (1997-01-01)
We report on a 75 year old patient with a bronchial asthma treated at least for 15 years with low dose prednisolone. Under this treatment he developed a tinea follicularis and was demonstrated in our clinic with papulopustular skin lesions
Allergic contact dermatitis from tioconazole.
A Faria et al.
Contact dermatitis, 35(4), 250-252 (1996-10-01)
Karine Bourcier et al.
Drug metabolism and disposition: the biological fate of chemicals, 38(6), 923-929 (2010-03-23)
Imidazoles and triazoles represent major classes of antifungal azole derivatives. With respect to UDP-glucuronosyltransferase (UGT) enzymes, the drug metabolism focus has mainly concentrated on their inhibitory effects with little known about azoles as substrates for UGTs. N-Glucuronide metabolites of the
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