ContaminantDB: Tioconazole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:09 UTC

Update Date

2016-11-09 01:08:44 UTC

Accession Number

CHEM002319

Identification

Common Name

Tioconazole

Class

Small Molecule

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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

14-alpha Demethylase Inhibitor
Amine
Antifungal Agent
Drug
Ether
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Vagistat-1	Kegg
Monistat 1-day	HMDB
Trosyl	HMDB
Gyno-trosyd	HMDB
Trosyd	HMDB
Mykontral	HMDB
Trosderm	HMDB
Trosid	HMDB
Vagistat	HMDB
Tioconazole	MeSH

Chemical Formula

C₁₆H₁₃Cl₃N₂OS

Average Molecular Mass

387.711 g/mol

Monoisotopic Mass

385.981 g/mol

CAS Registry Number

65899-73-2

IUPAC Name

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

Traditional Name

tioconazole

SMILES

ClC1=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=CS1

InChI Identifier

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
N-substituted imidazole
Azole
Heteroaromatic compound
Thiophene
Imidazole
Azacycle
Dialkyl ether
Organoheterocyclic compound
Ether
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:77898 )
thiophenes (CHEBI:77898 )
ether (CHEBI:77898 )
dichlorobenzene (CHEBI:77898 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.65e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	4.86	ALOGPS
logP	5.3	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	6.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	94.53 m³·mol⁻¹	ChemAxon
Polarizability	36.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9322000000-f6f11c3dd1abefdb5472	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0009000000-2827a77fbda828e7453e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0009000000-27b855fca59ed08acb85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0903000000-30ef91f27453208dd584	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-2ed7f788cac071d871e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-94a2a2533441e3179663	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-001i-0900000000-fa59d0317db7f93d6c2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0019-1619000000-7bfbe2de2c4aa4e6cd39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0019000000-9710e360ac903a19e761	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4059000000-11184eccc1c4190d1d56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9220000000-92260c4a2b938613c391	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2009000000-694e0b1bbedf8c9a518a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9002000000-892ee7d55153e17c3fb5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9110000000-a6e3b216a6c36e5201db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-46e7ef27c173cdeac926	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0009000000-55ff8b5cd7b6cb6c4a94	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9620000000-6425beede3614c6e9d8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-2089000000-ebf536df5e672f10ce98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9420000000-122db257637508515ef4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00lr-9010000000-fb107803b0fd9576864e	Spectrum

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

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.

Metabolism

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

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the local treatment of vulvovaginal candidiasis (moniliasis).

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

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

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01007

HMDB ID

HMDB0015142

FooDB ID

Not Available

Phenol Explorer ID