Ketoconazole (CED0002023)

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:11 UTC

Update Date

2026-05-14 16:56:11 UTC

SynCED ID

CED0002023

Secondary Accession Numbers

CHEM002324
T3D2961

Identification

Common Name

Ketoconazole

Class

Small Molecule

Description

Ketoconazole is an exogenous solid with the chemical formula C26H28Cl2N4O4. Ketoconazole belongs to the piperazines, a subclass of diazinanes within the organic compounds. With an average molecular weight of 531.43 g/mol, Ketoconazole is a heavy molecule. It functions as an antifungal agent and is used industrially as an anti-dandruff agent. Recorded exposure routes include topical, oral, and inhalation. The compound is found in 26 recorded sources, including drinking water and water supply. It is present in healthcare, pharmaceuticals and veterinary products such as antibiotics, antimycotics, gynecologicals, antiadrenal preparations, and antifungals for dermatological use. Other sources include food preservation and meat processing, as well as household cleaning and consumer products such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. It is also found in electrical and electronic equipment, including antennas, communication cables or conductors, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices or electric hearing aids. Ketoconazole targets 23 recorded proteins. It interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol, which results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of purine uptake, inhibition of yeast transformation to mycelial forms, and impairment of triglyceride and/or phospholipid biosynthesis. Additionally, it is an inhibitor of the Androgen receptor (AR), Aromatase (CYP19A1), Steroid 21-hydroxylase (CYP21A2), Aryl hydrocarbon receptor (AHR), and 18 other proteins.

Contaminant Type

14-alpha Demethylase Inhibitor
Amide
Amine
Antifungal Agent
Cosmetic Toxin
Drug
Ether
Food Toxin
Household Toxin
Human Neurotoxin
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Janssen brand OF ketoconazole	MeSH
Ketoconazole janssen brand	MeSH
Nizoral	MeSH

Chemical Formula

C₂₆H₂₈Cl₂N₄O₄

Average Molecular Mass

531.431 g/mol

Monoisotopic Mass

530.149 g/mol

CAS Registry Number

65277-42-1

IUPAC Name

1-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

Traditional Name

ketoconazole

SMILES

CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1

InChI Identifier

InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3

InChI Key

XMAYWYJOQHXEEK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Phenylpiperazines

Alternative Parents

Substituents

Phenylpiperazine
N-arylpiperazine
Aminophenyl ether
1,3-dichlorobenzene
Phenol ether
Tertiary aliphatic/aromatic amine
Phenoxy compound
Dialkylarylamine
Aniline or substituted anilines
Alkyl aryl ether
Ketal
Halobenzene
Chlorobenzene
Monocyclic benzene moiety
Aryl chloride
Aryl halide
N-substituted imidazole
Benzenoid
Meta-dioxolane
Heteroaromatic compound
Tertiary carboxylic acid amide
Imidazole
Azole
Acetamide
Carboxamide group
Amino acid or derivatives
Tertiary amine
Acetal
Oxacycle
Azacycle
Carboxylic acid derivative
Ether
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Organonitrogen compound
Organochloride
Organopnictogen compound
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:48339 )
imidazoles (CHEBI:48339 )
ether (CHEBI:48339 )
dioxolane (CHEBI:48339 )
dichlorobenzene (CHEBI:48339 )
N-carbonylpiperazine (CHEBI:48339 )
a small molecule (CPD-4503 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

antifungal agent

Biological Roles

antifungal agent ?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	146°C
Boiling Point	Not Available
Solubility	0.0866 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0093 g/L	ALOGPS
logP	4.3	ALOGPS
logP	4.19	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	6.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.07 m³·mol⁻¹	ChemAxon
Polarizability	54.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0031490000-58a475e5974da2dfdc18	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ik9-5395740000-08c010ea5c947e1a62f5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9520100000-76672a88c60da8324f81	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00or-2090150000-e4d86d7a4af384399254	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9240000000-92849351dd004ec26239	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00or-5940000000-e2a0f55e6d356bbc9c0e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0000090000-081787cba0594aced901	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0011980000-f9fa0eaf2d1b6889e098	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-066v-3140900000-ae27808322ff5c503bcf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0010390000-0eb582e7b11176ec640c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9030210000-9ea18251d96dd5cc657e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00o0-4930100000-6819285e7904a4b66c66	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
44.0 mg/kg	Mouse	LD50	Intravenous	experimental	Not Available	9
702.0 mg/kg	Mouse	LD50	Oral	experimental	Not Available	9
231.0 Log mg/kg [130:410]	Rat	LD50	oral	predicted	Not Available	Not Available
100.0 mg/kg/org	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
30.0 mg/kg-day	Mouse	NOEC	oral	experimental	Not Available	ECOTOX - EPA ORD

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone. (2, 3, 4, 5) Hepatotoxicity, LD₅₀=86 mg/kg (orally in rat)

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Side effects of the potential hepatotoxicity of Ketoconazole include abdominal pain or tenderness, clay-colored stools, dark urine, decreased appetite, fever, headache, itching, loss of appetite, nausea and vomiting, skin rash, swelling of the feet or lower legs, unusual tiredness or weakness, and yellow eyes or skin. (6)

Treatment

In the event of accidental overdosage, supportive measures, including gastric lavage with sodium bicarbonate, should be employed. (7)

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000115	Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.	Drinking water & water supply	Not Available
CEDs000233	Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.	Personal care & cosmetics	PubChem
CEDs000299	Antifungals for dermatological use?Antifungals for dermatological use are synthetic chemicals developed to treat fungal infections affecting the skin, hair, and nails.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000306	Antibiotics?Antibiotics are synthetic or semi-synthetic compounds used to treat bacterial infections in humans and animals.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000316	Gynecologicals?Gynecologicals encompass a range of synthetic chemicals used in the treatment of various women's health issues, including hormonal therapies, contraceptives, and antifungal agents.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000331	Antiadrenal preparations?Antiadrenal preparations are synthetic chemicals designed to inhibit adrenal hormone production, primarily used in therapeutic settings to manage conditions such as Cushing's syndrome and certain cancers.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000348	Antimycotics?Antimycotics are synthetic chemicals used to prevent or treat fungal infections.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	PubChem
CEDs000510	Communication Cables Or Conductors?Communication cables or conductors are essential components in the transmission of data and signals in various applications, including telecommunications and networking.	Electrical & Electronic Equipment	PubChem
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000516	Electric Hearing Aids?Electric hearing aids are small electronic devices designed to amplify sound for individuals with hearing loss.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000519	Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.	Electrical & Electronic Equipment	PubChem
CEDs000524	Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.	Electrical & Electronic Equipment	PubChem
CEDs000527	Magnets?Magnets, commonly used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials used in their production.	Electrical & Electronic Equipment	PubChem
CEDs000529	Power Cables?Power cables are used to transmit electrical energy and are typically composed of conductive materials, insulation, and protective coatings.	Electrical & Electronic Equipment	PubChem
CEDs000531	Relays?Relays are electromechanical switches used to control circuits and manage electrical loads.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000552	Processing Meats?Processing meats can lead to synthetic chemical contamination primarily through the use of additives and preservatives.	Food, food processing & cookware	PubChem
CEDs000555	Bleaching Agents?Bleaching agents are chemical substances used to whiten or lighten materials, often employed in various cleaning products for their stain removal and disinfecting properties.	Household cleaning & consumer products	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000564	Soap Dispensers?Soap dispensers, commonly used for dispensing liquid soaps and sanitizers, can become a source of synthetic chemical contamination due to the materials used in their construction and the products they dispense.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	PubChem
CEDs000603	Nematocides?Nematocides are synthetic chemicals specifically designed to control nematodes, which are microscopic roundworms that can cause significant damage to crops and plants.	Agriculture & land management	PubChem
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	PubChem
CEDs000606	Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.	Agriculture & land management	PubChem
CEDs000607	Rodenticides(1)?Rodenticides are synthetic chemicals specifically formulated to control rodent populations, serving as a crucial tool in managing pests that can damage crops and spread diseases.	Agriculture & land management	PubChem
CEDs000608	Rodenticides?Rodenticides are chemical substances specifically designed to control rodent populations by causing death through various mechanisms, including anticoagulation or neurotoxicity.	Agriculture & land management	PubChem
CEDs000609	Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.	Personal care & cosmetics	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000612	Body Washing Or Cleaning Implements?Body washing or cleaning implements, such as synthetic sponges, loofahs, and washcloths, can be sources of synthetic chemical contamination due to the materials used in their production.	Personal care & cosmetics	PubChem
CEDs000613	Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000616	Face Mask Cosmetics?Face mask cosmetics often contain a variety of synthetic chemicals, including preservatives, emulsifiers, and fragrances, which can contribute to chemical contamination.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000619	Manicure Pedicure?Manicure and pedicure procedures often involve the use of various synthetic chemicals, including solvents, nail polishes, and nail adhesives.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000643	Headwear?Headwear made from synthetic materials often incorporates chemicals used in the manufacturing and finishing processes, such as dyes, flame retardants, and water repellents.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000652	Ropes?Ropes manufactured from synthetic fibers, such as polypropylene, nylon, and polyester, are widely used in various applications, including marine, construction, and outdoor activities.	Textiles, leather & furnishings	PubChem
CEDs000657	Surface Finishing Of Leather?Surface finishing of leather often involves the use of various synthetic chemicals, including dyes, resins, and finishing agents.	Textiles, leather & furnishings	PubChem
CEDs000662	Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.	Textiles, leather & furnishings	PubChem
CEDs000665	Fire Extinguishers?Fire extinguishers contain various synthetic chemicals designed to suppress flames and prevent the spread of fire.	Fire suppression systems & agents	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000673	Unmanned Aerial Vehicles?Unmanned Aerial Vehicles (UAVs), commonly known as drones, utilize various synthetic chemicals in their manufacturing, operation, and maintenance processes.	Aviation & Aerospace	PubChem
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000692	Silica Free Oxide Glass?Silica Free Oxide Glass is a type of glass that is produced using alternative materials to traditional silica-based formulations.	Building & Construction	PubChem
CEDs000693	Silica Glass?Silica glass, primarily composed of silicon dioxide (SiO2), is widely used in various applications, including windows, glass facades, and insulation materials.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000698	Jewellery?Jewellery production often involves the use of various synthetic chemicals during the extraction and processing of metals.	Mining & metal processing	PubChem
CEDs000727	Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.	Paper, pulp & fiber products	PubChem
CEDs000730	Contact Lens Cases?Contact lens cases are small containers designed to store contact lenses in a sterile environment, typically made from various synthetic materials including plastics such as polypropylene or polycarbonate.	Healthcare, pharmaceuticals & veterinary products	PubChem
CEDs000732	Spectacle Cases?Spectacle cases can serve as a source of synthetic chemical contamination due to the materials used in their production, such as polycarbonate, PVC, and various plastics, which may leach harmful substances over time.	Healthcare, pharmaceuticals & veterinary products	PubChem
CEDs000734	Coating Compositions?Coating compositions, which include paints, sealants, and varnishes, are formulated with a variety of synthetic chemicals such as solvents, resins, pigments, and additives.	Building & Construction	PubChem
CEDs000738	Cooling Circuit Water?Cooling circuit water is utilized in various industrial processes to absorb and dissipate heat generated during operations.	Industrial manufacturing & chemical processing	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000743	Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.	Wastewater, sanitation & biosolids	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

3 pathwaysPathway Source: PathBank

Ketoconazole Anti-fungal Action Pathway

Ketoconazole Drug Metabolism Action Pathway

Ketoconazole Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 2A2	P15149	Rat	Predicted (SEA)	Prediction Confidence Score 1.0 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 3 E-value 0.155698
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q4PJW3	Bos taurus	Predicted (SEA)	Prediction Confidence Score 1.0 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Cholesterol side-chain cleavage enzyme, mitochondrial	P14137	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 1.0 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 3 E-value 0.155698
Click to view 3D structure	Cytochrome P450 7A1	P18125	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 1.0 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 3 E-value 0.155698
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.871 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 1538 E-value 0.0778492
Click to view 3D structure	Steroid 21-hydroxylase	P08686	Humans	Predicted (SEA)	Prediction Confidence Score 0.83 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 26 E-value 0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q64654	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.739 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 7 E-value 0.0778492
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	Prediction Confidence Score 0.7 Applicability Domain 1.0 Statistical Significance 3.00e-05 Supporting Reference Compounds 127 E-value 0.233548
Click to view 3D structure	Cytochrome P450 11B1, mitochondrial	P15150	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.641 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 5 E-value 0.0778492
Click to view 3D structure	25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial	O35084	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.591 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 2 E-value 0.0778492
Click to view 3D structure	Cytochrome P450 11B1, mitochondrial	P15538	Humans	Predicted (SEA)	Prediction Confidence Score 0.588 Applicability Domain 1.0 Statistical Significance 6.00e-05 Supporting Reference Compounds 66 E-value 0.467095
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	Prediction Confidence Score 0.588 Applicability Domain 1.0 Statistical Significance 3.00e-05 Supporting Reference Compounds 69 E-value 0.233548
Click to view 3D structure	Heme oxygenase 1	P06762	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.565 Applicability Domain 1.0 Statistical Significance 6.00e-05 Supporting Reference Compounds 15 E-value 0.467095
Click to view 3D structure	Heme oxygenase 2	P23711	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.562 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 9 E-value 0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q16850	Humans	Predicted (SEA)	Prediction Confidence Score 0.56 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 12 E-value 0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	P10613	Yeast	Predicted (SEA)	Prediction Confidence Score 0.521 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 11 E-value 0.0778492
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.493 Applicability Domain 1.0 Statistical Significance 0.0027 Supporting Reference Compounds 593 E-value 21.4085
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.493 Applicability Domain 1.0 Statistical Significance 9.00e-04 Supporting Reference Compounds 340 E-value 7.00643
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.493 Applicability Domain 1.0 Statistical Significance 0.0016 Supporting Reference Compounds 487 E-value 12.3002
Click to view 3D structure	7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase	Q9UNU6	Humans	Predicted (SEA)	Prediction Confidence Score 0.487 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 8 E-value 0.0778492
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	Prediction Confidence Score 0.483 Applicability Domain 1.0 Statistical Significance 7.30e-04 Supporting Reference Compounds 373 E-value 5.68299
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Predicted (SEA)	Prediction Confidence Score 0.456 Applicability Domain 1.0 Statistical Significance 7.00e-04 Supporting Reference Compounds 139 E-value 5.44945
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	Prediction Confidence Score 0.434 Applicability Domain 1.0 Statistical Significance 0.0109 Supporting Reference Compounds 1245 E-value 84.6221
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.43 Applicability Domain 1.0 Statistical Significance 0.0084 Supporting Reference Compounds 1130 E-value 65.0819
Click to view 3D structure	ATP-dependent translocase ABCB1	P21447	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.43 Applicability Domain 1.0 Statistical Significance 8.00e-05 Supporting Reference Compounds 23 E-value 0.622794
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Known	Not Available
Click to view 3D structure	Aromatase	P11511	Humans	Known	Not Available
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q16850	Humans	Known	Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone. (A365)
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Known	Not Available
Click to view 3D structure	1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial	Q07973	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 11B2, mitochondrial	P19099	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 11B1, mitochondrial	P15538	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Known	Not Available
Click to view 3D structure	Steroid 21-hydroxylase	P08686	Humans	Known	Not Available
Click to view 3D structure	25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial	O15528	Humans	Known	Not Available
Click to view 3D structure	Androgen receptor	P10275	Humans	Known	Not Available
Click to view 3D structure	Bile salt export pump	O95342	Humans	Known	Not Available
Click to view 3D structure	Malate dehydrogenase, cytoplasmic	P40925	Humans	Known	Not Available
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 3	Q14994	Humans	Known	Not Available
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Known	Not Available
Click to view 3D structure	Hepatic sodium/bile acid cotransporter	Q14973	Humans	Known	Not Available
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Known	Not Available
Click to view 3D structure	Aryl hydrocarbon receptor	P35869	Humans	Known	Not Available
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Known	Not Available
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Known	Not Available
Click to view 3D structure	Vitamin D3 receptor	P11473	Humans	Known	Not Available
Click to view 3D structure	Sterol regulatory element-binding protein 1	P36956	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

3691

ChEBI ID

48339

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

U.S. Patent 4,144,346.

MSDS

Link

General References

Kojima T, Matsumoto M, Togashi H, Tachibana K, Kemmotsu O, Yoshioka M: Fluvoxamine suppresses the long-term potentiation in the hippocampal CA1 field of anesthetized rats: an effect mediated via 5-HT1A receptors. Brain Res. 2003 Jan 3;959(1):165-8. [PubMed: 12480170]
Goeders NE, Peltier RL, Guerin GF: Ketoconazole reduces low dose cocaine self-administration in rats. Drug Alcohol Depend. 1998 Dec 1;53(1):67-77. [PubMed: 10933341]
Berwaerts J, Verhelst J, Mahler C, Abs R: Cushing's syndrome in pregnancy treated by ketoconazole: case report and review of the literature. Gynecol Endocrinol. 1999 Jun;13(3):175-82. [PubMed: 10451809]
Kazy Z, Puho E, Czeizel AE: Population-based case-control study of oral ketoconazole treatment for birth outcomes. Congenit Anom (Kyoto). 2005 Mar;45(1):5-8. [PubMed: 15737124]
Pierard-Franchimont C, Goffin V, Decroix J, Pierard GE: A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis. Skin Pharmacol Appl Skin Physiol. 2002 Nov-Dec;15(6):434-41. [PubMed: 12476017]
Drugs.com - http://www.drugs.com/cons/Ketoconazole.html
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/
Wikipedia. Ketoconazole. Last Updated 7 December 2009. - http://en.wikipedia.org/wiki/Ketoconazole
O'Neil MJ (ed) (2001). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc.
McEvoy GK (ed) (2006). American Hospital Formulary Service - Drug Information 2006. Bethesda, MD: American Society of Health-System Pharmacists.

Ketoconazole (CED0002023)

Structure for CHEM002324: Ketoconazole

Structure