Ketoconazole

Alias: Ketoconazole; Nizoral, Kuric, Fungoral, Ketoderm; Xolegel, Extina

Cat No.:V0804 Purity: ≥98%

COA Product Data Instructions for use SDS

Ketoconazole Chemical Structure CAS No.: 65277-42-1
Product category: P450 (e.g. CYP)

This product is for research use only, not for human use. We do not sell to patients.

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Nature 2021, 597(7874):119-125.

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J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

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Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Ketoconazole (Ketoconazol; Fungoral, Nizoral, Kuric, Xolegel, Ketoderm; Extina; R-41400; R 41400), a CYP3A4 and 24A1 inhibitor and antifungal agent, is a potent and synthetic imidazole-based antifungal drug used primarily to treat fungal infections. Ketoconazole acts by inhibiting cyclosporine oxidase and testosterone 6 beta-hydroxylase with IC50 of 0.19 mM and 0.22 mM, respectively.

Biological Activity I Assay Protocols (From Reference)

ln Vitro

When males are treated for persistent mycotic infections, ketoconazole (R-41400), an imidazole anti-fungal medication, frequently causes signs of androgen shortage, such as decreased libido, gynecomastia, impotence, oligospermia, and lowered testosterone levels[1]. Moreover, ketoconazole (R-41400) inhibits cytochrome P450[2]. Ketoconazole (R-41400), on the parasitological, histological, and biochemical characteristics to assess these quinolines' antischistosomal ability against Schistosoma mansoni infection. The mice were divided into seven groups: untreated (I), uninfected (II), infected (III), treated (IV) with PZQ (1,000 mg/kg), QN (400 mg/kg), KTZ (10 mg/kg) + QN as group IV (V), HF (400 mg/kg) (VI), and KTZ (as group V) + HF (as group VI) (VII). Compared to those treated with QN or HF alone, KTZ + QN or HF produced greater inhibition (P<0.05) in hepatic CYP450 (85.7 % and 83.8%) and CYT b5 (75.5 % and 73.5%) activity. More decreases in the number of female (89.0% and 79.3%), total worms (81.4% and 70.3%), and eggs load (hepatic; 83.8%, 66.0%, and intestinal; 68%, 64.5%), respectively, were also observed in conjunction with this[3]. The activation of the caspase-independent apoptosis pathway is encouraged, systemic calcitriol exposure is increased, and antiproliferative actions are enhanced by CYP24A1 inhibitors. Additionally, ketoconazole is a strong inhibitor of exosome formation and/or secretion[4].

ln 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. 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.

Animal Protocol

Dissolved in 0saline; 25 mg/kg; i.p. injection

Male Wistar rats

References

[1]. Seif El-Din SH, et al. Effect of ketoconazole, a cytochrome P450 inhibitor, on the efficacy of quinine and halofantrine against Schistosoma mansoni in mice. Korean J Parasitol. 2013 Apr;51(2):165-75.
[2]. Eil C. Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70.
[3]. Muindi JR et al. CYP24A1 inhibition enhances the antitumor activity of calcitriol. Endocrinology. 2010 Sep;151(9):4301-12.
[4]. Amrita Datta, et al. High-throughput screening identified selective inhibitors of exosome biogenesis and secretion: A drug repurposing strategy for advanced cancer. Sci Rep. 2018 May 25;8(1):8161.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C26H28CL2N4O4
Molecular Weight	531.4309
CAS #	65277-42-1
Related CAS #	(+)-Ketoconazole;142128-59-4;(-)-Ketoconazole;142128-57-2;Ketoconazole-d8;1217706-96-1;Ketoconazole-d4;1398065-75-2
SMILES	CC(N1CCN(C2=CC=C(OC[C@@H]3O[C@@](CN4C=CN=C4)(C5=CC=C(Cl)C=C5Cl)OC3)C=C2)CC1)=O
InChi Key	XMAYWYJOQHXEEK-OZXSUGGESA-N
InChi Code	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-/m0/s1
Chemical Name	1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
Synonyms	Ketoconazole; Nizoral, Kuric, Fungoral, Ketoderm; Xolegel, Extina
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: 7 mg/mL (13.2 mM)

Water:<1 mg/mL

Ethanol: 5 mg/mL (9.4 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (4.70 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (4.70 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (4.70 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 4: 30% propylene glycol, 5% Tween 80, 65% D5W: 30mg/mL

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8817 mL	9.4086 mL	18.8172 mL
	5 mM	0.3763 mL	1.8817 mL	3.7634 mL
	10 mM	0.1882 mL	0.9409 mL	1.8817 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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Concentration (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

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g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT04869449	Recruiting	Drug: Ketoconazole	Glioblastoma Glioblastoma Multiforme	Milton S. Hershey Medical Center	May 12, 2022	Early Phase 1
NCT04212000	Completed	Drug: Levoketoconazole Drug: Ketoconazole	Healthy	Cortendo AB	December 16, 2019	Phase 1
NCT00830388	Completed Has Results	Drug: Ketoconazole 2% Foam	Tinea Versicolor	Boni Elewski, MD	November 2008	Phase 4
NCT01330563	Completed	Drug: CKD-501, Ketoconazole	Type 2 Diabetes Mellitus	Chong Kun Dang Pharmaceutical	March 2011	Phase 1

Biological Data

Ketoconazole (prototype imidazole) inhibits exosome biogenesis through ESCRT dependent and independent pathway.

Masson's trichrome stained liver sections of (A) S. mansoni-infected untreated mice showing irregularly outlined large fibrocellular granuloma formed of a central egg (with a living miracidium; arrow), surrounded mainly by lymphocytes, eosinophils, and extensive collagen depositions as concentric collagen fibers. (B) PZQ-treated group showing medium circumscribed fibrocellular granuloma (arrow) with eggs starting degeneration. (C, D) QN and KTZ+QN-treated groups, respectively, showing the smallest size and well-demarcated fibrocellular granuloma, formed of central degenerated egg (D; arrow), surrounded by lymphocytes, eosinophils, neutrophils, scattered macrophages, and fewer collagen depositions (C; arrow). (E, F) HF and KTZ+HF-treated groups, respectively, showing small fibrocellular granuloma formed of central degenerated egg (E; arrow), surrounded mainly by lymphocytes, eosinophils, neutrophils, and few concentric collagen fibers (F; arrow) (×200).

Effect of QN or HF alone and in addition to KTZ on percent inhibitions in hepatic CYP450 and CYT b5 relative to uninfected group in S. mansoni-infected mice at week 9 PI (i.e., week 2 post treatment). No. of animals in each group; 8 mice. Values are presented as the mean±SD. aSignificant difference from uninfected group at P<0.05. bSignificant difference from QN group at P<0.05. cSignificant difference from HF group at P<0.05.