Ketoconazole, (2S,4R)- (CED0017609)

Record Information

Version

1.0

Creation Date

2026-04-05 15:30:58 UTC

Update Date

2026-08-22 06:25:06 UTC

Accession Number

CHEM104343

Identification

Common Name

Ketoconazole, (2S,4R)-

Class

Small Molecule

Description

Ketoconazole, (2S,4R)- belongs to the piperazines, a subclass of diazinanes within the organic compounds. With an average molecular weight of 531.43 g/mol, Ketoconazole, (2S,4R)- is a heavy molecule with the formula C26H28Cl2N4O4. Biologically, it functions as an inhibitor (PMC5824109) and an antifungal agent (PMC10162950). It acts on five recorded protein targets, serving as an inhibitor of Lanosterol 14-alpha demethylase (CYP51A1), Steroid 17-alpha-hydroxylase/17,20 lyase (CYP17A1), Cytochrome P450 11B1, mitochondrial (CYP11B1), Cytochrome P450 11B2, mitochondrial (CYP11B2), and one other protein. This compound is found in or released from four recorded sources, including healthcare, pharmaceuticals & veterinary products such as antiadrenal preparations, and household cleaning & consumer products including bleaching agents. It is also associated with electrical & electronic equipment, specifically television systems and electric switches. The recorded route of exposure for this compound is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈Cl₂N₄O₄

Average Molecular Mass

531.430 g/mol

Monoisotopic Mass

530.149 g/mol

CAS Registry Number

142128-57-2

IUPAC Name

Not Available

Traditional Name

Not Available

SMILES

CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=C(Cl)C=C(Cl)C=C2)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/t23-,26-/m1/s1

InChI Key

XMAYWYJOQHXEEK-ZEQKJWHPSA-N

Chemical Taxonomy

Classification

Not classified

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001i-9345700000-032f45d476928c144063	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-3530190000-a2b05a2498270bcd4a7e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-3430090000-055d7bbaadb1e1716a8b	Not Available	View Spectrum
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	splash10-004i-0010390000-00106b8b890fdebbf036	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9030210000-22cee3cdcfef8b4b8068	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00o0-4930100000-6819285e7904a4b66c66	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

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
231.0	Log mg/kg	[130:410]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference
oral candidiasis	is_treatment_for	Not Available	PMC3935911

Exposure Sources

Source ID	Source	Sector	Reference
233	Brushes	Personal care & cosmetics	Not Available
331	Antiadrenal preparations	Healthcare, pharmaceuticals & veterinary products	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
555	Bleaching Agents	Household cleaning & consumer products	Not Available
604	Pest Attractants	Agriculture & land management	Not Available
607	Rodenticides(1)	Agriculture & land management	Not Available
608	Rodenticides	Agriculture & land management	Not Available
609	Aftershave	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
657	Surface Finishing Of Leather	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Steroid 21-hydroxylase	P08686	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q64654	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Cytochrome P450 11B1, mitochondrial	P15150	Bos taurus	Predicted (SEA)	0.0778492
Click to view 3D structure	25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial	O35084	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Cytochrome P450 11B1, mitochondrial	P15538	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Heme oxygenase 1	P06762	Rattus norvegicus	Predicted (SEA)	0.467095
Click to view 3D structure	Heme oxygenase 2	P23711	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q16850	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Lanosterol 14-alpha demethylase	P10613	Yeast	Predicted (SEA)	0.0778492
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	21.4085
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	7.00643
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	12.3002
Click to view 3D structure	7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase	Q9UNU6	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	5.68299
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Predicted (SEA)	5.44945
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	84.6221
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	65.0819
Click to view 3D structure	ATP-dependent translocase ABCB1	P21447	Mus musculus	Predicted (SEA)	0.622794
Click to view 3D structure	Cytochrome P450 2A2	P15149	Rat	Predicted (SEA)	0.155698
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q4PJW3	Bos taurus	Predicted (SEA)	0.0778492
Click to view 3D structure	Cholesterol side-chain cleavage enzyme, mitochondrial	P14137	Rattus norvegicus	Predicted (SEA)	0.155698
Click to view 3D structure	Cytochrome P450 7A1	P18125	Rattus norvegicus	Predicted (SEA)	0.155698