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Identification
NameTioconazole
Accession NumberDB01007  (APRD01262)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
Tioconazol
Tioconazolum
Vagistat-1
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Careone Tioconazole 1ointment6.5 g/100gvaginalAmerican Sales Company2008-01-07Not applicableUs
Equaline Tioconazole 1ointment6.5 g/100gvaginalSupervalu Inc2016-03-08Not applicableUs
Equate Tioconazole 1 Dayointment6.5 g/100gvaginalWal Mart Stores Inc2007-11-01Not applicableUs
Good Neighbor Pharmacy Tioconazole 1ointment6.5 g/100gvaginalAmerisource Bergen2008-02-20Not applicableUs
Gynecure External Cream 1% (refill)cream1 %topicalPfizer Canada Inc., Consumer Healthcare DivisionNot applicableNot applicableCanada
Gynecure Vaginal Ointment 6.5% W/wointment6.5 %vaginalPfizer Canada Inc., Consumer Healthcare Division1995-12-312002-11-11Canada
Gynecure Vaginal Ovule 300mgsuppository300 mgvaginalPfizer Canada Inc., Consumer Healthcare Division1995-12-312002-08-06Canada
Healthy Accents Tioconazole 1ointment6.5 g/100gvaginalDZA Brands LLC2008-04-06Not applicableUs
Image Essentials Tioconazole Treatmentointment6.5 g/100gvaginalKmart Corporation2014-12-26Not applicableUs
Leader Tioconastat 1 1 Dose Treatmentointment6.5 g/100gvaginalCardinal Health2008-04-03Not applicableUs
Shoprite Tioconazole 1ointment6.5 g/100gvaginalWakefern Food Corporation2013-09-17Not applicableUs
Signature Care Tioconazole 1ointment6.5 g/100gvaginalSafeway2015-09-24Not applicableUs
Smart Sense Tioconazole 1ointment6.5 g/100gvaginalKmart Corporation2011-07-11Not applicableUs
Sunmark Tioconazole 1ointment6.5 g/100gvaginalMc Kesson2007-12-18Not applicableUs
Tioconazoleointment6.5 g/100gvaginalHy Vee Inc2008-03-03Not applicableUs
Tioconazole 1ointment6.5 g/100gvaginalCVS Pharmacy2015-11-12Not applicableUs
Tioconazole 1ointment6.5 g/100gvaginalMeijer Distribution Inc2008-01-09Not applicableUs
Tioconazole 1ointment6.5 g/100gvaginalWalgreen Company2007-12-19Not applicableUs
Tioconazole 1 1 Dose Treatmentointment6.5 g/100gvaginalRite Aid Corporation2007-12-13Not applicableUs
Tioconazole 1 Dayointment300 mg/gtopicalInsight Pharmaceuticals LLC2001-11-21Not applicableUs
Tioconazole Ointment 6.5%ointment65 mg/gvaginalDPT Laboratories, Ltd.2007-08-22Not applicableUs
Topcare Tioconazole 1ointment6.5 g/100gvaginalTopco Associates LLC2008-03-03Not applicableUs
Trosyd AF Cream 1%cream1 %topicalPfizer Canada Inc., Consumer Healthcare Division1987-12-312002-02-01Canada
Trosyd J Cream 1% W/wcream10 mgtopicalPfizer Canada Inc., Consumer Healthcare Division1997-03-272002-08-06Canada
Up and Up Tioconazole 1ointment6.5 g/100gvaginalTarget Corporation2009-07-08Not applicableUs
Vagistat-1ointment300 mg/1vaginalNovartis Consumer Health, Inc1997-02-11Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
GyneCureNot Available
Monistat 1Not Available
TrosydNot Available
TrosylNot Available
Brand mixtures
NameLabellerIngredients
Gynecure Com.pk.vag Ont6.5%vulvar Crm1% W/wPfizer Canada Inc., Consumer Healthcare Division
Gynecure Com.pk.vag Ovule300mg Vulv.crm1%w/wPfizer Canada Inc., Consumer Healthcare Division
Gynecure Tandempk.vag Ont6.5%/vulv.crm1%-w/wPfizer Canada Inc., Consumer Healthcare Division
Gynecure Tandempk.vag Ov.300mg/vulv.crm1%w/wPfizer Canada Inc., Consumer Healthcare Division
SaltsNot Available
Categories
UNIIS57Y5X1117
CAS number65899-73-2
WeightAverage: 387.711
Monoisotopic: 385.981416859
Chemical FormulaC16H13Cl3N2OS
InChI KeyInChIKey=QXHHHPZILQDDPS-UHFFFAOYSA-N
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
IUPAC Name
1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
SMILES
ClC1=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=CS1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzylethers
Direct ParentBenzylethers
Alternative Parents
Substituents
  • Benzylether
  • 1,3-dichlorobenzene
  • Halobenzene
  • Chlorobenzene
  • N-substituted imidazole
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Thiophene
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the local treatment of vulvovaginal candidiasis (moniliasis).
PharmacodynamicsTioconazole 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.
Mechanism of actionTioconazole 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.
Related Articles
AbsorptionSystemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.966
Blood Brain Barrier+0.9814
Caco-2 permeable+0.5812
P-glycoprotein substrateNon-substrate0.5819
P-glycoprotein inhibitor INon-inhibitor0.911
P-glycoprotein inhibitor IINon-inhibitor0.5295
Renal organic cation transporterInhibitor0.5164
CYP450 2C9 substrateNon-substrate0.8248
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateInhibitor0.946
CYP450 2C9 inhibitorInhibitor0.8757
CYP450 2D6 inhibitorInhibitor0.9032
CYP450 2C19 inhibitorInhibitor0.926
CYP450 3A4 inhibitorInhibitor0.8406
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9934
Ames testNon AMES toxic0.8092
CarcinogenicityNon-carcinogens0.8543
BiodegradationNot ready biodegradable0.9869
Rat acute toxicity2.7335 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7187
hERG inhibition (predictor II)Inhibitor0.6506
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pfizer laboratories div pfizer inc
  • L perrigo co
  • Novartis consumer health inc
Packagers
Dosage forms
FormRouteStrength
Ointment; creamtopical; vaginal
Suppository; creamtopical; vaginal
Ointmentvaginal6.5 %
Suppositoryvaginal300 mg
Ointmentvaginal6.5 g/100g
Ointmenttopical300 mg/g
Ointmentvaginal65 mg/g
Creamtopical1 %
Creamtopical10 mg
Ointmentvaginal300 mg/1
Prices
Unit descriptionCostUnit
Monistat-Derm 2% Cream 28.35 gm Tube41.99USD tube
Monistat-Derm 2% Cream 15 gm Tube32.0USD tube
Monistat 1 combination pack16.81USD each
Monistat 1 6.5% ointment3.6USD g
Vagistat-1 6.5% ointment3.6USD g
Tioconazole 1 6.5% ointment1.75USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP4.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0165 mg/mLALOGPS
logP4.86ALOGPS
logP5.3ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.05 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.53 m3·mol-1ChemAxon
Polarizability36.84 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesD01AC07G01AF08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (784 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Tioconazole.
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Tioconazole.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Tioconazole.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
yes
Actions
antagonist
General Function:
Sterol 14-demethylase activity
Specific Function:
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
ERG11
Uniprot ID:
P10613
Molecular Weight:
60674.965 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Ballard SA, Lodola A, Tarbit MH: A comparative study of 1-substituted imidazole and 1,2,4-triazole antifungal compounds as inhibitors of testosterone hydroxylations catalysed by mouse hepatic microsomal cytochromes P-450. Biochem Pharmacol. 1988 Dec 15;37(24):4643-51. [PubMed:3202901 ]
  3. Fliri AF, Loging WT, Thadeio PF, Volkmann RA: Biological spectra analysis: Linking biological activity profiles to molecular structure. Proc Natl Acad Sci U S A. 2005 Jan 11;102(2):261-6. Epub 2004 Dec 29. [PubMed:15625110 ]
  4. Bellamine A, Lepesheva GI, Waterman MR: Fluconazole binding and sterol demethylation in three CYP51 isoforms indicate differences in active site topology. J Lipid Res. 2004 Nov;45(11):2000-7. Epub 2004 Aug 16. [PubMed:15314102 ]
  5. Guinea J, Sanchez-Somolinos M, Cuevas O, Pelaez T, Bouza E: Fluconazole resistance mechanisms in Candida krusei: the contribution of efflux-pumps. Med Mycol. 2006 Sep;44(6):575-8. [PubMed:16966178 ]
  6. Chau AS, Chen G, McNicholas PM, Mann PA: Molecular basis for enhanced activity of posaconazole against Absidia corymbifera and Rhizopus oryzae. Antimicrob Agents Chemother. 2006 Nov;50(11):3917-9. Epub 2006 Sep 11. [PubMed:16966400 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sterol 14-demethylase activity
Specific Function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular Weight:
56805.26 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Fliri AF, Loging WT, Thadeio PF, Volkmann RA: Biological spectra analysis: Linking biological activity profiles to molecular structure. Proc Natl Acad Sci U S A. 2005 Jan 11;102(2):261-6. Epub 2004 Dec 29. [PubMed:15625110 ]
  4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12