Tioconazole - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (2)Enzymes (8)

Targets (2)Enzymes (8)Biointeractions (10)

Identification

Name

Tioconazole

Accession Number

DB01007 (APRD01262)

Type

Small Molecule

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.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Tioconazol

Tioconazolum

Vagistat-1

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Tioconazole hydrochloride	T1QKM21KYB	61675-64-7	UKQXXGSDDSCAHA-UHFFFAOYSA-N	Details

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Careone Tioconazole 1	Ointment	6.5 g/100g	Vaginal	American Sales Company	2008-01-07	Not applicable	US
Equaline Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Supervalu	2016-03-08	Not applicable	US
Equate Tioconazole 1 Day	Ointment	6.5 g/100g	Vaginal	Walmart Stores	2007-11-01	Not applicable	US
Good Neighbor Pharmacy Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Amerisource Bergen	2008-02-20	Not applicable	US
Gynecure External Cream 1% (refill)	Cream	1 %	Topical	Pfizer Canada Inc., Consumer Healthcare Division	Not applicable	Not applicable	Canada
Gynecure Vaginal Ointment 6.5% W/w	Ointment	6.5 %	Vaginal	Pfizer Canada Inc., Consumer Healthcare Division	1995-12-31	2002-11-11	Canada
Gynecure Vaginal Ovule 300mg	Suppository	300 mg	Vaginal	Pfizer Canada Inc., Consumer Healthcare Division	1995-12-31	2002-08-06	Canada
Healthy Accents Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Dza Brands,	2008-04-06	Not applicable	US
Image Essentials Tioconazole Treatment	Ointment	6.5 g/100g	Vaginal	Kmart Corporation	2014-12-26	Not applicable	US
Leader Tioconastat 1 1 Dose Treatment	Ointment	6.5 g/100g	Vaginal	Cardinal Health	2008-04-03	Not applicable	US
Shoprite Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Wakfern Food Corporation	2013-09-17	Not applicable	US
Signature Care Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Safeway	2015-09-24	Not applicable	US
Smart Sense Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Kmart Corporation	2011-07-11	Not applicable	US
Smart Sense Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Kmart Corporation	2016-06-28	Not applicable	US
Sunmark Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Mc Kesson	2007-12-18	Not applicable	US
Tioconazole	Ointment	6.5 g/100g	Vaginal	Hyvee	2008-03-03	Not applicable	US
Tioconazole 1	Ointment	6.5 g/100g	Vaginal	H.E.B.	2016-05-09	Not applicable	US
Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Cvs Health	2015-11-12	Not applicable	US
Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Meijer Distribution	2008-01-09	Not applicable	US
Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Walgreen	2007-12-19	Not applicable	US
Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Western Family Foods	2016-06-01	Not applicable	US
Tioconazole 1 1 Dose Treatment	Ointment	6.5 g/100g	Vaginal	Rite Aid	2007-12-13	Not applicable	US
Tioconazole 1 Day	Ointment	300 mg/g	Topical	Insight Pharmaceuticals	2001-11-21	Not applicable	US
Tioconazole Ointment 6.5%	Ointment	65 mg/g	Vaginal	DPT Laboratories, Ltd.	2007-08-22	Not applicable	US
Topcare Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Topco Associates	2008-03-03	Not applicable	US
Trosyd AF Cream 1%	Cream	1 %	Topical	Pfizer Canada Inc., Consumer Healthcare Division	1987-12-31	2002-02-01	Canada
Trosyd J Cream 1% W/w	Cream	10 mg	Topical	Pfizer Canada Inc., Consumer Healthcare Division	1997-03-27	2002-08-06	Canada
Up and Up Tioconazole 1	Ointment	6.5 g/100g	Vaginal	Target Corporation.	2009-07-08	Not applicable	US
Vagistat-1	Ointment	300 mg/1	Vaginal	Novartis	1997-02-11	2016-12-07	US

Unapproved/Other Products

Not Available

International Brands

Name	Company
GyneCure	Not Available
Monistat 1	Not Available
Trosyd	Not Available
Trosyl	Not Available

Brand mixtures

Name	Labeller	Ingredients
Gynecure Com.pk.vag Ont6.5%vulvar Crm1% W/w	Pfizer Canada Inc., Consumer Healthcare Division	Tioconazole Tioconazole
Gynecure Com.pk.vag Ovule300mg Vulv.crm1%w/w	Pfizer Canada Inc., Consumer Healthcare Division	Tioconazole Tioconazole
Gynecure Tandempk.vag Ont6.5%/vulv.crm1%-w/w	Pfizer Canada Inc., Consumer Healthcare Division	Tioconazole Tioconazole
Gynecure Tandempk.vag Ov.300mg/vulv.crm1%w/w	Pfizer Canada Inc., Consumer Healthcare Division	Tioconazole Tioconazole

Categories

UNII

S57Y5X1117

CAS number

65899-73-2

Weight

Average: 387.711
Monoisotopic: 385.981416859

Chemical Formula

C₁₆H₁₃Cl₃N₂OS

InChI Key

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

Pharmacology

Indication

For the local treatment of vulvovaginal candidiasis (moniliasis).

Structured Indications

Vulvovaginal Candidiasis

Pharmacodynamics

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.

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Lanosterol 14-alpha demethylase	Protein	yes	antagonist	Yeast	P10613	details
Lanosterol 14-alpha demethylase	Protein	unknown	inhibitor	Human	Q16850	details

Absorption

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

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

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

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

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

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Amlodipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Amlodipine.	Approved
Amodiaquine	The serum concentration of Amodiaquine can be increased when it is combined with Tioconazole.	Approved
Amphotericin B	The therapeutic efficacy of Amphotericin B can be decreased when used in combination with Tioconazole.	Approved, Investigational
Amrinone	The risk or severity of adverse effects can be increased when Tioconazole is combined with Amrinone.	Approved
Aripiprazole	The serum concentration of Aripiprazole can be increased when it is combined with Tioconazole.	Approved, Investigational
Azelnidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Azelnidipine.	Approved
Azimilide	The risk or severity of adverse effects can be increased when Tioconazole is combined with Azimilide.	Investigational
Barnidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Barnidipine.	Approved
Benidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Benidipine.	Approved
Bepridil	The risk or severity of adverse effects can be increased when Tioconazole is combined with Bepridil.	Approved, Withdrawn
Buspirone	The metabolism of Buspirone can be decreased when combined with Tioconazole.	Approved, Investigational
Busulfan	The serum concentration of Busulfan can be increased when it is combined with Tioconazole.	Approved, Investigational
Carboxyamidotriazole	The risk or severity of adverse effects can be increased when Tioconazole is combined with Cai.	Investigational
Cilnidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Cilnidipine.	Approved
Cilostazol	The serum concentration of Cilostazol can be increased when it is combined with Tioconazole.	Approved
Cinnarizine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Cinnarizine.	Approved
Cisapride	The serum concentration of Cisapride can be increased when it is combined with Tioconazole.	Approved, Investigational, Withdrawn
Clevidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Clevidipine.	Approved
Conivaptan	The metabolism of Conivaptan can be decreased when combined with Tioconazole.	Approved, Investigational
Cyclosporine	The metabolism of Cyclosporine can be decreased when combined with Tioconazole.	Approved, Investigational, Vet Approved
Darodipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Darodipine.	Experimental
Didanosine	Didanosine can cause a decrease in the absorption of Tioconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Diltiazem	The risk or severity of adverse effects can be increased when Tioconazole is combined with Diltiazem.	Approved
Docetaxel	The metabolism of Docetaxel can be decreased when combined with Tioconazole.	Approved, Investigational
Dofetilide	The metabolism of Dofetilide can be decreased when combined with Tioconazole.	Approved
Efonidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Efonidipine.	Approved
Eperisone	The risk or severity of adverse effects can be increased when Tioconazole is combined with Eperisone.	Approved, Investigational
Etravirine	The serum concentration of Etravirine can be increased when it is combined with Tioconazole.	Approved
Felodipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Felodipine.	Approved, Investigational
Fendiline	The risk or severity of adverse effects can be increased when Tioconazole is combined with Fendiline.	Withdrawn
Flunarizine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Flunarizine.	Approved
Fosphenytoin	The serum concentration of Tioconazole can be decreased when it is combined with Fosphenytoin.	Approved
Gabapentin	The risk or severity of adverse effects can be increased when Tioconazole is combined with Gabapentin.	Approved, Investigational
Gallopamil	The risk or severity of adverse effects can be increased when Tioconazole is combined with Gallopamil.	Investigational
Isradipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Isradipine.	Approved
Lacidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Lacidipine.	Approved
Lamotrigine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Lamotrigine.	Approved, Investigational
Lercanidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Lercanidipine.	Approved, Investigational
Losartan	The metabolism of Losartan can be decreased when combined with Tioconazole.	Approved
Magnesium Sulfate	The risk or severity of adverse effects can be increased when Tioconazole is combined with Magnesium Sulfate.	Approved, Vet Approved
Manidipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Manidipine.	Approved
Mibefradil	The risk or severity of adverse effects can be increased when Tioconazole is combined with Mibefradil.	Withdrawn
Naftopidil	The risk or severity of adverse effects can be increased when Tioconazole is combined with Naftopidil.	Investigational
Nicardipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Nicardipine.	Approved
Nifedipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Nifedipine.	Approved
Niguldipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Niguldipine.	Experimental
Niludipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Niludipine.	Experimental
Nilvadipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Nilvadipine.	Approved
Nimesulide	The risk or severity of adverse effects can be increased when Tioconazole is combined with Nimesulide.	Approved, Withdrawn
Nimodipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Nimodipine.	Approved
Nisoldipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Nisoldipine.	Approved
Nitrendipine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Nitrendipine.	Approved
Perhexiline	The risk or severity of adverse effects can be increased when Tioconazole is combined with Perhexiline.	Approved
Phenytoin	The serum concentration of Phenytoin can be increased when it is combined with Tioconazole.	Approved, Vet Approved
Pimozide	Tioconazole may increase the arrhythmogenic activities of Pimozide.	Approved
Pinaverium	The risk or severity of adverse effects can be increased when Tioconazole is combined with Pinaverium.	Approved
Pregabalin	The risk or severity of adverse effects can be increased when Tioconazole is combined with Pregabalin.	Approved, Illicit, Investigational
Prenylamine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Prenylamine.	Withdrawn
Progesterone	The therapeutic efficacy of Progesterone can be decreased when used in combination with Tioconazole.	Approved, Vet Approved
Quinidine	The metabolism of Quinidine can be decreased when combined with Tioconazole.	Approved
Ranolazine	The metabolism of Ranolazine can be decreased when combined with Tioconazole.	Approved, Investigational
Rifabutin	The serum concentration of Rifabutin can be increased when it is combined with Tioconazole.	Approved
Rifampicin	The serum concentration of Rifampicin can be increased when it is combined with Tioconazole.	Approved
Rifapentine	The serum concentration of Rifapentine can be increased when it is combined with Tioconazole.	Approved
Risedronate	The risk or severity of adverse effects can be increased when Tioconazole is combined with Risedronate.	Approved, Investigational
Solifenacin	The metabolism of Solifenacin can be decreased when combined with Tioconazole.	Approved
Sucralfate	Sucralfate can cause a decrease in the absorption of Tioconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Sunitinib	The metabolism of Sunitinib can be decreased when combined with Tioconazole.	Approved, Investigational
Tacrolimus	The metabolism of Tacrolimus can be decreased when combined with Tioconazole.	Approved, Investigational
Tizanidine	The serum concentration of Tizanidine can be increased when it is combined with Tioconazole.	Approved
Tolfenamic Acid	The risk or severity of adverse effects can be increased when Tioconazole is combined with Tolfenamic Acid.	Approved
Tranilast	The risk or severity of adverse effects can be increased when Tioconazole is combined with Tranilast.	Approved, Investigational
Verapamil	The risk or severity of adverse effects can be increased when Tioconazole is combined with Verapamil.	Approved
Vinpocetine	The risk or severity of adverse effects can be increased when Tioconazole is combined with Vinpocetine.	Investigational
Xylometazoline	The risk or severity of adverse effects can be increased when Tioconazole is combined with Xylometazoline.	Approved
Ziconotide	The risk or severity of adverse effects can be increased when Tioconazole is combined with Ziconotide.	Approved
Zolpidem	The serum concentration of Zolpidem can be increased when it is combined with Tioconazole.	Approved

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15142
KEGG Drug	D00890
KEGG Compound	C08082
PubChem Compound	5482
PubChem Substance	46508604
ChemSpider	5282
BindingDB	50370218
ChEBI	77898
ChEMBL	CHEMBL1200438
Therapeutic Targets Database	DAP001268
PharmGKB	PA164746156
Drug Product Database	1808
RxList	http://www.rxlist.com/cgi/generic3/tioconaz.htm
Drugs.com	http://www.drugs.com/cdi/tioconazole.html
Wikipedia	Tioconazole

ATC Codes

G01AF08 — Tioconazole

D01AC07 — Tioconazole

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Download (784 KB)

MSDS

Not Available

Clinical Trials

Not Available

Pharmacoeconomics

Manufacturers

Pfizer laboratories div pfizer inc
L perrigo co
Novartis consumer health inc

Packagers

Dosage forms

Form	Route	Strength
Cream; ointment	Topical; Vaginal
Cream; suppository	Topical; Vaginal
Ointment	Vaginal	6.5 %
Suppository	Vaginal	300 mg
Ointment	Vaginal	6.5 g/100g
Ointment	Topical	300 mg/g
Ointment	Vaginal	65 mg/g
Cream	Topical	1 %
Cream	Topical	10 mg
Ointment	Vaginal	300 mg/1

Prices

Unit description	Cost	Unit
Monistat-Derm 2% Cream 28.35 gm Tube	41.99USD	tube
Monistat-Derm 2% Cream 15 gm Tube	32.0USD	tube
Monistat 1 combination pack	16.81USD	each
Monistat 1 6.5% ointment	3.6USD	g
Vagistat-1 6.5% ointment	3.6USD	g
Tioconazole 1 6.5% ointment	1.75USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	4.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0165 mg/mL	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

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.966
Blood Brain Barrier	+	0.9814
Caco-2 permeable	+	0.5812
P-glycoprotein substrate	Non-substrate	0.5819
P-glycoprotein inhibitor I	Non-inhibitor	0.911
P-glycoprotein inhibitor II	Non-inhibitor	0.5295
Renal organic cation transporter	Inhibitor	0.5164
CYP450 2C9 substrate	Non-substrate	0.8248
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.7558
CYP450 1A2 substrate	Inhibitor	0.946
CYP450 2C9 inhibitor	Inhibitor	0.8757
CYP450 2D6 inhibitor	Inhibitor	0.9032
CYP450 2C19 inhibitor	Inhibitor	0.926
CYP450 3A4 inhibitor	Inhibitor	0.8406
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.9934
Ames test	Non AMES toxic	0.8092
Carcinogenicity	Non-carcinogens	0.8543
Biodegradation	Not ready biodegradable	0.9869
Rat acute toxicity	2.7335 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7187
hERG inhibition (predictor II)	Inhibitor	0.6506

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0009000000-2827a77fbda828e7453e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0009000000-27b855fca59ed08acb85	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-001i-0903000000-30ef91f27453208dd584	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-001i-0900000000-2ed7f788cac071d871e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-001i-0900000000-94a2a2533441e3179663	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-fa59d0317db7f93d6c2a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0019-1619000000-7bfbe2de2c4aa4e6cd39	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

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

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

Direct Parent

Benzylethers

Alternative Parents

Dichlorobenzenes / N-substituted imidazoles / Aryl chlorides / Thiophenes / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides

Substituents

Benzylether / 1,3-dichlorobenzene / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / N-substituted imidazole / Azole / Heteroaromatic compound / Thiophene

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

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

Targets

Details

1. Lanosterol 14-alpha demethylase

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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Details

2. Lanosterol 14-alpha demethylase

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

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 ]
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 ]
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 ]
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

Details

1. Aromatase

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

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 ]

Details

2. Cytochrome P450 1A2

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

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 ]

Details

3. Cytochrome P450 2C19

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

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 ]

Details

4. Cytochrome P450 2C8

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

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 ]

Details

5. Cytochrome P450 2C9

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

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 ]

Details

6. Cytochrome P450 2E1

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

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 ]

Details

7. Cytochrome P450 3A4

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

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 ]

Details

8. Cytochrome P450 2D6

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular Weight:: 55768.94 Da

Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:55

Get DrugBank to go!

Structure for DB01007 (Tioconazole)

Targets

References

References

Enzymes

References

References

References

References

References

References

References