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Atlas / Drug / Ketoconazole

Ketoconazole

drug
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Also known as Daktarin goldDaktarin intensivDandrazolDandridExtinaJ02AB02KetoconazolKetoconazole hraKetoconazolumKetopineKetozoleNizoralNizoral a-dNizoral anti-dandruffNizorelleNSC-317629R 41,400R-41400Xolegel

Summary

Ketoconazole (CHEMBL157101) is an approved small molecule (ATC D01AC08) targeting CYP3A4 and KCNA10; indicated across 44 conditions including tinea pedis and seborrheic dermatitis.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: D01AC08 (+3 more)
  • Targets: 2 (CYP3A4, KCNA10)
  • Indications: 44 conditions
  • Clinical trials: 151
  • Chemistry: 531.4 Da · C26H28Cl2N4O4

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL157101
NameKetoconazole
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID3823
ChEBICHEBI:48339
ATCD01AC08, G01AF11, H02CA03, J02AB02
Molecular formulaC26H28Cl2N4O4
Molecular weight531.4
InChIKeyXMAYWYJOQHXEEK-UHFFFAOYSA-N

SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl

IUPAC name: 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone

ChEBI definition: A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.

Also known as: Daktarin gold, Daktarin intensiv, Dandrazol, Dandrid, Extina, J02AB02, Ketoconazol, Ketoconazole, Ketoconazole hra, Ketoconazolum, Ketopine, Ketozole

Patent coverage: 21,188 distinct patent families (75,361 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 75,285 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CYP3A4CYP3A4Inhibition70%P08684
KCNA10Kv1.86.315.2%Q16322

Broader ChEMBL bioactivity targets: 96 (assay-derived). Sample: Sterol 14-alpha demethylase, Tyrosyl-DNA phosphodiesterase 1, UDP-glucuronosyltransferase 1A1, Microtubule-associated protein tau, Ubiquitin carboxyl-terminal hydrolase 2, Nuclear receptor ROR-gamma, Survival motor neuron protein, Prelamin-A/C, RecQ-like DNA helicase BLM, Thrombopoietin.

Bioactivity

ChEMBL activities: 397 potent at pChembl ≥ 5 of 490 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P309699.66Kd0.22nMCHEMBL_ACT_718830
P309699.43Kd0.38nMCHEMBL_ACT_718831
CYP3A49.05IC500.9nMCHEMBL_ACT_26190733
CYP3A49IC501nMCHEMBL_ACT_16621084
CYP3A49IC501nMCHEMBL_ACT_25460195
CYP2D68.73IC501.86nMCHEMBL_ACT_24736497
CYP3A48.62IC502.38nMCHEMBL_ACT_23256962
CYP3A48.4IC504nMCHEMBL_ACT_16621073
CYP3A48.4IC504nMCHEMBL_ACT_3011472
CYP3A48.15Ki7nMCHEMBL_ACT_15460854
CYP3A48.15IC507nMCHEMBL_ACT_23298970
CYP3A48.13IC507.4nMCHEMBL_ACT_16744597
CYP3A48.11IC507.8nMCHEMBL_ACT_5201913
CYP3A48.04IC509.1nMCHEMBL_ACT_16744595
CYP3A48.01IC509.8nMCHEMBL_ACT_15460856
CYP2D68IC5010nMCHEMBL_ACT_18383187
CYP3A48IC5010nMCHEMBL_ACT_24925864
CYP3A47.96Ki11nMCHEMBL_ACT_15460852
CYP3A47.96IC5011nMCHEMBL_ACT_22441267
CYP3A47.96IC5011nMCHEMBL_ACT_3299981
LMNA7.95Potency11.2nMCHEMBL_ACT_3643757
CYP3A47.93IC5011.7nMCHEMBL_ACT_23308590
CYP3A47.92IC5012nMCHEMBL_ACT_17692369
CYP3A47.92IC5012nMCHEMBL_ACT_17718294
CYP3A47.92IC5012nMCHEMBL_ACT_25692103
CYP3A47.9IC5012.5nMCHEMBL_ACT_23174373
CYP3A47.9IC5012.5nMCHEMBL_ACT_24776091
CYP3A47.89IC5013nMCHEMBL_ACT_1146602
CYP3A47.89IC5013nMCHEMBL_ACT_18295692
CYP3A47.89IC5013nMCHEMBL_ACT_25984592

Target pathways

Aggregated over 2 target gene(s): CYP3A4, KCNA10.

Top Reactome pathways

10 total, by targets touching each:

PathwayTargetsGenes
Neuronal System1KCNA10
Potassium Channels1KCNA10
Voltage gated Potassium channels1KCNA10
Phase I - Functionalization of compounds1CYP3A4
Xenobiotics1CYP3A4
Aflatoxin activation and detoxification1CYP3A4
Biosynthesis of maresin-like SPMs1CYP3A4
Aspirin ADME1CYP3A4
Atorvastatin ADME1CYP3A4
Prednisone ADME1CYP3A4

Dominant GO biological processes

GO termTargets
lipid hydroxylation1
lipid metabolic process1
steroid catabolic process1
xenobiotic metabolic process1
steroid metabolic process1
cholesterol metabolic process1
androgen metabolic process1
estrogen metabolic process1
alkaloid catabolic process1
monoterpenoid metabolic process1
xenobiotic catabolic process1
vitamin D metabolic process1
vitamin D catabolic process1
retinol metabolic process1
retinoic acid metabolic process1

Indications & clinical

Indications

44 indications (6 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
tinea pedis4MONDO:0005984EFO:0007512
seborrheic dermatitis4MONDO:0006608EFO:1000764
adrenal gland disorder4MONDO:0005495EFO:0005539
blastomycosis4MONDO:0005672EFO:0007174
tinea infection4MONDO:0005982EFO:0007510
Cushing syndrome4MONDO:0018912EFO:0003099
acne3MONDO:0011438EFO:0003894
vulvovaginal candidiasis3MONDO:0006014EFO:0007543
bacterial vaginosis3MONDO:0005316EFO:0003932
dermatitis3MONDO:0002406MONDO:0002406
adult acute respiratory distress syndrome3MONDO:0100130MONDO:0100130
neoplasm2MONDO:0005070EFO:0000616
prostate adenocarcinoma2MONDO:0005082EFO:0000673
prostate carcinoma2MONDO:0005159EFO:0001663
burn2MONDO:0043519EFO:0009516
psoriasis2MONDO:0005083EFO:1001494
hypogonadism2MONDO:0002146MONDO:0002146
breast neoplasm2MONDO:0021100MONDO:0007254
chronic myeloid leukemia2MONDO:0011996EFO:0000339
chronic obstructive pulmonary disease1MONDO:0005002EFO:0000341
immune system disorder1MONDO:0005046EFO:0000540
lymphoma1MONDO:0005062EFO:0000574
neuroblastoma1MONDO:0005072EFO:0000621
melanoma1MONDO:0005105EFO:0000756
osteoporosis1MONDO:0005298EFO:0003882
erectile dysfunction1MONDO:0005362EFO:0004234
non-Hodgkin lymphoma1MONDO:0018908EFO:0005952
gastroparesis1MONDO:0006769EFO:1000948
B-cell chronic lymphocytic leukemia1MONDO:0004948EFO:0000095
hepatitis C virus infection1MONDO:0005231EFO:0003047
essential hypertension1MONDO:0001134MONDO:0001134
Alzheimer disease1MONDO:0004975MONDO:0004975
asthma1MONDO:0004979MONDO:0004979
type 2 diabetes mellitus1MONDO:0005148MONDO:0005148
multiple sclerosis1MONDO:0005301MONDO:0005301
pityriasis versicolor1MONDO:0005915EFO:0007439
tinea unguium1MONDO:0001628MONDO:0001628
hematopoietic and lymphoid system neoplasm1MONDO:0002334MONDO:0044881
glioblastoma0MONDO:0018177EFO:0000519

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 151.

Phase distribution

PhaseTrials
PHASE188
PHASE226
PHASE311
Not specified8
PHASE47
EARLY_PHASE16
PHASE1/PHASE24
PHASE2/PHASE31

Top trials by phase / activity

NCTPhaseStatusTitle
NCT07333170PHASE4NOT_YET_RECRUITINGComparison of the Efficacy of Topical Luliconazole 2% Cream vs Topical Ketoconazole 1% Cream in the Treatment of Pityriasis Versicolor.
NCT07471178PHASE4NOT_YET_RECRUITINGMycological Efficacy and Safety of Ketoconazole 2% Shampoo With a Seven-Day Versus Three-Day Treatment Duration in Pityriasis Versicolor
NCT00703846PHASE4COMPLETEDSTUDY TO ASSESS THE LONG-TERM SAFETY OF EXTINA (KETOCONAZOLE) FOAM, 2%
NCT00824863PHASE4COMPLETEDSafety and Efficacy of Ketoconazole 2% Foam in the Treatment of Pityrosporum Folliculitis
NCT00830388PHASE4COMPLETEDKetoconazole Foam 2% for the Treatment of Versicolor
NCT01288521PHASE4COMPLETEDPharmacogenetics to Predict Drug Interactions in Kidney Transplant Recipients
NCT01378520PHASE4COMPLETEDEffect of Ketoconazole on Breathlessness
NCT00000579PHASE3COMPLETEDAcute Respiratory Distress Syndrome Clinical Network (ARDSNet)
NCT00002760PHASE3COMPLETEDAntiandrogen Withdrawal in Treating Patients With Hormone-Refractory Prostate Cancer
NCT00002855PHASE3COMPLETEDChemotherapy Plus Hormone Therapy Versus Androgen Suppression in Treating Patients With Metastatic or Unresectable Prostate Cancer
NCT00024167PHASE3TERMINATEDChemotherapy With or Without Strontium-89 in Treating Patients With Prostate Cancer
NCT00027859PHASE3COMPLETEDHormone Therapy Compared With Combination Chemotherapy in Treating Patients With Prostate Cancer
NCT00030654PHASE3COMPLETEDHormone Therapy Plus Chemotherapy in Treating Patients With Prostate Cancer
NCT00675714PHASE2/PHASE3TERMINATEDAssessment of the Treatment of Severely Burned With Anabolic Agents on Clinical Outcomes, Recovery and Rehabilitation
NCT01110330PHASE3TERMINATEDAn Efficacy Study of a New Formulation of Ketoconazole 2% Cream in Patients With Tinea Pedis, Commonly Known as Athlete’s Foot
NCT02606383PHASE3WITHDRAWNNon-inferiority Phase III Trial Comparing Dapaconazole Cream 2% With Ketoconazole Cream 2% in Patients With Tinea Pedis
NCT03320486PHASE3COMPLETEDNon-inferiority Trial of Dapaconazole Versus Ketoconazole
NCT03473418PHASE3UNKNOWNKetoconazole Gel Versus Terconazole Cream for Vaginal Candidiasis
NCT03845348PHASE3UNKNOWNTo Evaluate the Efficacy and Safety of Shampoo TD03 and TD07 in Scalp Diseases
NCT00859781PHASE2ACTIVE_NOT_RECRUITING177Lu Radiolabeled Monoclonal Antibody HuJ591 (177Lu-J591) and Ketoconazole in Patients With Prostate Cancer
NCT00003084PHASE2COMPLETEDCombination Chemotherapy With Ketoconazole in Treating Patients With Prostate Cancer
NCT00006371PHASE2TERMINATEDA Phase II Trial of Early Medical Adrenalectomy for D0.5 Prostate Cancer
NCT00014352PHASE2COMPLETEDCombination Chemotherapy Plus Warfarin in Treating Patients With Prostate Cancer
NCT00019695PHASE2TERMINATEDKetoconazole With or Without Alendronate Sodium in Treating Patients With Metastatic Prostate Cancer
NCT00211393PHASE2COMPLETEDA Pilot Study of the Treatment of Central Serous Chorioretinopathy With Ketoconazole
NCT00212095PHASE2COMPLETEDDocetaxel Combined With Ketoconazole in Treatment of Breast Cancer
NCT00298155PHASE2COMPLETEDMaximal Suppression of the Androgen Axis in Clinically Localized Prostate Cancer
NCT00309894PHASE2COMPLETEDKetoconazole, Hydrocortisone, and GM-CSF in Treating Patients With Progressive Prostate Cancer After Hormone Therapy
NCT00393848PHASE2COMPLETEDEffectiveness of Two Types of Treatment in Restoring Muscle After Hip or Knee Surgery
NCT00403559PHASE2COMPLETEDA 4 Week Study of Elidel (Pimecrolimus) for the Treatment of Seborrheic Dermatitis
NCT00447473PHASE2TERMINATEDTrial of GM-CSF Given in Combination With Ketoconazole and Mitoxantrone in Patients With Progressive Prostate Cancer
NCT00460031PHASE2COMPLETEDTreating Patients With Prostate Cancer That Did Not Respond to Hormone Therapy
NCT00536991PHASE1/PHASE2TERMINATEDCalcitriol in Combination With Ketoconazole and Therapeutic Hydrocortisone in Treating Patients With Prostate Cancer
NCT00586898PHASE2COMPLETEDRapid Hormonal Cycling as Treatment for Patients With Prostate Cancer: The Men’s Cycle
NCT00678756PHASE2UNKNOWNInvestigation of Antipsoriatic Effects of UVB-induced Synthesis of 1alpha, 25-Dihydroxyvitamin D3 (1alpha, 25(OH)2D3, Calcitriol)in Keratinocytes of Psoriatic Skin, Using Cytochrom-P(CYP)Inhibitor Ketokonazol
NCT00697437PHASE2COMPLETEDEffect of Ketoconazole Inhibition of CYP3A on Urinary Excretion of Docetaxel
NCT00895310PHASE2COMPLETEDUse of Low Dose Ketoconazole in Prostate Cancer That Does Not Respond to Hormone Therapy and Prior Chemotherapy
NCT00953576PHASE1/PHASE2TERMINATEDKetoconazole, Hydrocortisone, Dutasteride and Lapatinib (KHAD-L) in Prostate Cancer
NCT01036594PHASE2COMPLETEDKetoconazole and Dexamethasone in Prostate Cancer
NCT01215292PHASE1/PHASE2COMPLETEDITT4 Intratesticular Hormonal Milieu in Man (ITT4)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

583 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DIHYDROERGOTAMINEChEMBL + PubChemPhase 4 (approved)CYP3A4
ElagolixChEMBL + PubChemPhase 4 (approved)CYP3A4
SAXAGLIPTINChEMBL + PubChemPhase 4 (approved)CYP3A4
ABIRATERONEChEMBLPhase 4 (approved)CYP3A4
ACETAMINOPHENChEMBLPhase 4 (approved)CYP3A4
ACRISORCINChEMBLPhase 4 (approved)CYP3A4
ALOSETRONChEMBLPhase 4 (approved)CYP3A4
AMINOGLUTETHIMIDEChEMBLPhase 4 (approved)CYP3A4
AMIODARONEChEMBLPhase 4 (approved)CYP3A4
AMITRIPTYLINEChEMBLPhase 4 (approved)CYP3A4
AMLODIPINEChEMBLPhase 4 (approved)CYP3A4
AMOXAPINEChEMBLPhase 4 (approved)CYP3A4
AMPICILLINChEMBLPhase 4 (approved)CYP3A4
AMPRENAVIRChEMBLPhase 4 (approved)CYP3A4
AMSACRINEChEMBLPhase 4 (approved)CYP3A4
APOMORPHINEChEMBLPhase 4 (approved)CYP3A4
APREPITANTChEMBLPhase 4 (approved)CYP3A4
ASTEMIZOLEChEMBLPhase 4 (approved)CYP3A4
ATOMOXETINEChEMBLPhase 4 (approved)CYP3A4
ATORVASTATINChEMBLPhase 4 (approved)CYP3A4
AZATHIOPRINEChEMBLPhase 4 (approved)CYP3A4
AZELASTINEChEMBLPhase 4 (approved)CYP3A4
AZITHROMYCINChEMBLPhase 4 (approved)CYP3A4
BACLOFENChEMBLPhase 4 (approved)CYP3A4
BENDROFLUMETHIAZIDEChEMBLPhase 4 (approved)CYP3A4
BENZBROMARONEChEMBLPhase 4 (approved)CYP3A4
BENZNIDAZOLEChEMBLPhase 4 (approved)CYP3A4
BENZONATATEChEMBLPhase 4 (approved)CYP3A4
BENZTHIAZIDEChEMBLPhase 4 (approved)CYP3A4
BEPRIDILChEMBLPhase 4 (approved)CYP3A4
BERBERINEChEMBLPhase 4 (approved)CYP3A4
BIFONAZOLEChEMBLPhase 4 (approved)CYP3A4
BITHIONOLChEMBLPhase 4 (approved)CYP3A4
BITHIONOLATEChEMBLPhase 4 (approved)CYP3A4
BRETYLIUM TOSYLATEChEMBLPhase 4 (approved)CYP3A4
BROMHEXINEChEMBLPhase 4 (approved)CYP3A4
BROMOCRIPTINEChEMBLPhase 4 (approved)CYP3A4
BROMPERIDOLChEMBLPhase 4 (approved)CYP3A4
BUDESONIDEChEMBLPhase 4 (approved)CYP3A4
BUPIVACAINEChEMBLPhase 4 (approved)CYP3A4
BUSPIRONEChEMBLPhase 4 (approved)CYP3A4
BUTAMBENChEMBLPhase 4 (approved)CYP3A4
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)CYP3A4
CANNABIDIOLChEMBLPhase 4 (approved)CYP3A4
CAPSAICINChEMBLPhase 4 (approved)CYP3A4
CARBETAPENTANEChEMBLPhase 4 (approved)CYP3A4
CARBIDOPAChEMBLPhase 4 (approved)CYP3A4
CARFILZOMIBChEMBLPhase 4 (approved)CYP3A4
CARISOPRODOLChEMBLPhase 4 (approved)CYP3A4
CEFDITOREN PIVOXILChEMBLPhase 4 (approved)CYP3A4
CELECOXIBChEMBLPhase 4 (approved)CYP3A4
CHLORAMPHENICOLChEMBLPhase 4 (approved)CYP3A4
CHLOROXINEChEMBLPhase 4 (approved)CYP3A4
CHLORPROMAZINEChEMBLPhase 4 (approved)CYP3A4
CHLORPROPAMIDEChEMBLPhase 4 (approved)CYP3A4
CHOLECALCIFEROLChEMBLPhase 4 (approved)CYP3A4
CHOLIC ACIDChEMBLPhase 4 (approved)CYP3A4
CIMETIDINEChEMBLPhase 4 (approved)CYP3A4
CINNARIZINEChEMBLPhase 4 (approved)CYP3A4
CISAPRIDEChEMBLPhase 4 (approved)CYP3A4

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot