Home Metabolism P450 (e.g. CYP17) inhibitor - Androgen Receptor inhibitor - Fungal inhibitor Ketoconazole For research use only.

Ketoconazole

Synonyms: R 41400

Ketoconazole inhibits cyclosporine oxidase and testosterone 6 beta-hydroxylase with IC50 of 0.19 mM and 0.22 mM, respectively. Ketoconazole is an androgen biosynthesis inhibitor.

Ketoconazole Chemical Structure

Ketoconazole Chemical Structure

CAS No. 65277-42-1

Purity & Quality Control

Ketoconazole Related Products

Signaling Pathway

P450 (e.g. CYP17) Signaling Pathways

P450 (e.g. CYP17) Signaling Pathway

Cell Data

Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
LLC-PK1 epithelial cells Function assay Inhibition of P-glycoprotein, human L-MDR1 expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay, IC50=4.8 μM 12699389
MCF7 cells Function assay Inhibition of CYP26A1 in human MCF7 cells assessed as all-trans retinoic acid metabolism, IC50=12 μM 16279770
human THP1 cells Cytotoxicity assay 48 h Cytotoxicity against human THP1 cells after 48 hrs, IC50=44 μM 17960923
CHO cells Function assay Inhibition of CYP24A1 expressed in CHO cells, IC50=0.52 μM 20655626
P815B cells Cytotoxicity assay 24 h Cytotoxicity against mouse P815B cells after 24 hrs by MTS/PMS assay, LD50=25 μM 25036789
V79 11B2 cells Function assay Inhibition of human CYP11B2 expressed in V79 11B2 cells, IC50=0.081 μM 16570918
V79 cells Function assay Inhibition of human CYP24 hydroxylase expressed in V79 cells, IC50=0.312 μM 15615534
hamster V79MZh11B1 cells Function assay Inhibition of human CYP11B1 expressed in hamster V79MZh11B1 cells, IC50=0.127 μM 18672868
hamster V79MZh11B2 cells Function assay Inhibition of human CYP11B2 expressed in hamster V79MZh11B2 cells, IC50=0.067 μM 18672868
CHO cells Function assay Inhibition of human ERG expressed in CHO cells by whole cell patch clamp technique, IC50=1.90546 μM 18448342
V79 11B1 cells Function assay Inhibition of human CYP11B1 expressed in V79 11B1 cells, IC50=0.224 μM 16570918
Topp 3 cells Function assay Inhibition of human CYP51 expressed in Topp 3 cells by lanosterol demethylase assay, IC50=0.19 μM 17194716
V79 cells Function assay Inhibition of human CYP24A1 expressed in chinese hamster V79 cells, IC50=0.312 μM 20594862
V79MZ cells Function assay Inhibition of human CYP11B2 expressed in hamster V79MZ cells using 11-deoxycorticosterone substrate, IC50=0.067 μM 24900247
V79MZh cells Function assay Inhibition of human CYP11B2 expressed in hamster V79MZh cells, IC50=0.067 μM 20550118
human epidermal keratinocytes Function assay Inhibition of CYP24A1 in human epidermal keratinocytes, IC50=0.126 μM 20594862
V79MZh cells Function assay Inhibition of human CYP11B1 expressed in hamster V79MZh cells, IC50=0.127 μM 20550118
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Biological Activity

Description Ketoconazole inhibits cyclosporine oxidase and testosterone 6 beta-hydroxylase with IC50 of 0.19 mM and 0.22 mM, respectively. Ketoconazole is an androgen biosynthesis inhibitor.
Features More active than both Econazole and Miconazole against Malassezia species.
Targets
Cyclosporine oxidase [1] Testosterone 6 beta-hydroxylase [1]
0.19 mM 0.22 mM
In vitro
In vitro Ketoconazole interacts with androgen receptors in a competitive fashion in intact human foreskin fibroblasts. Ketoconazole competes for [3H]dexamethasone binding to fibroblast glucocorticoid receptors with IC50 of 0.3 mM. [2] Ketoconazole reduces cell proliferation and [3H]thymidine incorporation with IC50 of 2.5 mM in the serum independent HT29-S-B6 colon cell clone. Ketoconazole inhibits the incorporation of [3H]thymidine with IC50 of 2 μM and 13 μM in the Evsa-T cell line and MDA-MB-231 cell line, respectively. Ketoconazole induces a decrease of the number of cells in S phase and a corresponding increase of the percentage of cells in Go-G1 in HT29-S-B6 cells. [3] Ketoconazole is susceptable to several Malassezia species with minimum inhibitory concentrations (MICs) of 0.03 µg/mL. [4]
Kinase Assay Whole Cell [3H]R1881 Binding Assay
Fibroblasts are grown to confluence in five or six 150 cm2 tissue culture flasks for routine assay. This usually requires 4-6 weeks from the time of the initial seeding of the cell line. All studies are performed between passages 3-20. Two days before assay, the medium is changed to one lacking fetal calf serum. This is repeated again 24 hours before assay. Competition assays are performed with 0.5-1.0 nM [3H]R1881 and increasing amounts of the nonradioactive compounds. Binding to low affinity sites is determined in the presence of 5 × 10-7 M R1881 and is subtracted from whole cell binding of [3H]R 1881 obtained in the absence of any inhibitor to assess binding to 5 high affinity site
Cell Research Cell lines HT29-S-B6 colon cell
Concentrations 25 μM
Incubation Time 72 hours
Method HT29-S-B6 cells (5×105) are plated in 35-mm Petri dishes. The next day, the medium is changed and effectors are added in a small volume (10-20 μL). The incubation medium is renewed every day during the experiments. The same triplicate dishes are used for cell counts, [3H]thymidine incorporation, and flow cytometry. [3H]Thymidine (0.5 μCi) is allowed to incorporate for 24 hours; at the end of incubation, cells are rinsed with 1 mL of medium, detached with 1 mL of trypsin-EDTA, and diluted (1:3) with the culture medium. An aliquot (0.5-1 mL) is used for cell count with a Coulter Counter.
In Vivo
In vivo Ketoconazole (25 mg/kg, i.p.) significantly decreases plasma corticosterone and reduces low dose cocaine self-administration without affecting food-reinforced responding in rats. [5] Ketoconazole raises the AUC of orally administered digoxin from 63 mg x h/L to 411 mg x h/L in rats. Ketoconazole raises the AUC of intravenously administered digoxin from 93 mg × h/L to 486 mg × h/L in rats. Ketoconazole increases digoxin bioavailability from 0.68 to 0.84 in rats, while mean absorption time is reduced from 1.1 hours to 0.3 hour. [6]
Animal Research Animal Models male Wistar rats
Dosages 25 mg/kg
Administration Intraperitoneal injection
NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT04869449 Recruiting
Glioblastoma|Glioblastoma Multiforme|Glioblastoma Multiforme of Brain|Glioblastoma Multiforme Adult
Milton S. Hershey Medical Center
 May 12 2022 Early Phase 1
NCT04212000 Completed
Healthy
Cortendo AB
 December 16 2019 Phase 1
NCT03796273 Recruiting
Anatomic Stage IV Breast Cancer AJCC v8|Astrocytoma|Breast Carcinoma Metastatic in the Brain|Glioma|Invasive Breast Carcinoma|Oligodendroglioma|Prognostic Stage IV Breast Cancer AJCC v8|Recurrent Glioma
Wake Forest University Health Sciences|National Cancer Institute (NCI)
 March 13 2019 Early Phase 1
NCT04872920 Recruiting
Cushing Syndrome
HRA Pharma
 December 20 2018 --
NCT03473418 Unknown status
Vaginal Candidiasis
Assiut University
 April 1 2018 Phase 3

Chemical Information & Solubility

Molecular Weight 531.43 Formula

C26H28Cl2N4O4
CAS No. 65277-42-1 SDF Download Ketoconazole SDF
Smiles CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
Storage (From the date of receipt)

In vitro
Batch:

Ethanol : 7 mg/mL

DMSO : 3 mg/mL ( (5.64 mM) Moisture-absorbing DMSO reduces solubility. Please use fresh DMSO.)

Water : Insoluble


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In vivo
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