(Rac)-Ketoconazole (Synonyms: (Rac)-Ketoconazol; (Rac)-R 41400)

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(Rac)-Ketoconazole ((Rac)-R 41400) is an antifungal imidazole compound with oral activity. (Rac)-Ketoconazole interferes with ergosterol synthesis by inhibiting cytochrome P450-dependent 14α-sterol demethylase (CYP51), a key enzyme on the fungal cell membrane, leading to membrane dysfunction and ultimately inhibition of fungal growth and reproduction. (Rac)-Ketoconazole is indicated for studies of fungal infections.

For research use only. We do not sell to patients.

(Rac)-Ketoconazole Chemical Structure

CAS No. : 79156-75-5

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Other Forms of (Rac)-Ketoconazole:

Ketoconazole In-stock
(+)-Ketoconazole In-stock
(-)-Ketoconazole In-stock
(-)-Ketoconazole-d₃ Get quote
Ketoconazole-d₈ Get quote
Ketoconazole-d₄ Get quote

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•Related Small Molecules:

•Related Proteins:

View All Cytochrome P450 Isoform Specific Products:

View All Isoforms

CYP1 CYP2 CYP3 CYP4 CYP11 CYP17 Aromatase/CYP19A1 CYP26 CYP51 CYP1A2 CYP2D6 CYP2C9 CYP2C19 CYP3A4 CYP17A1

Biological Activity
Purity & Documentation
References
Customer Review

Description

Cellular Effect

Cell Line	Type	Value	Description	References
Caco-2	IC₅₀	2.36 μM Compound: KETOCONAZOLE	Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells after 48 hours by high content imaging Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells after 48 hours by high content imaging	10.21203/rs.3.rs-23951/v1
Caco-2	CC₅₀	28.62 μM Compound: KETOCONAZOLE	Toxicity against Caco-2 cells determined at 48 hours by intracellular ATP concentration using the CellTiter-Glo Luminescent Cell Viability Assay Toxicity against Caco-2 cells determined at 48 hours by intracellular ATP concentration using the CellTiter-Glo Luminescent Cell Viability Assay	10.21203/rs.3.rs-23951/v1
HEK293	IC₅₀	13 μM Compound: Ketoconazole	Inhibition of human recombinant UGT1A1 expressed in HEK293 cells assessed as reduction in estradiol 3-glucuronidation by LC-MS/MS method Inhibition of human recombinant UGT1A1 expressed in HEK293 cells assessed as reduction in estradiol 3-glucuronidation by LC-MS/MS method	[PMID: 21030469]
HEK293	IC₅₀	2.6 μM Compound: ketoconazole	Inhibition of human OCT1 expressed in HEK293 cells assessed as decrease in uptake of ASP+ after 2 mins by fluorescence assay Inhibition of human OCT1 expressed in HEK293 cells assessed as decrease in uptake of ASP+ after 2 mins by fluorescence assay	[PMID: 28230985]
HEK293	IC₅₀	27 μM Compound: Ketoconazole	Inhibition of human recombinant UGT1A1 expressed in HEK293 cells assessed as reduction in bilirubin glucuronidation by LC-MS/MS method Inhibition of human recombinant UGT1A1 expressed in HEK293 cells assessed as reduction in bilirubin glucuronidation by LC-MS/MS method	[PMID: 21030469]
HepG2	CC₅₀	51 μM Compound: ketoconazole	Cytotoxicity against human HepG2 cells by neutral red uptake assay Cytotoxicity against human HepG2 cells by neutral red uptake assay	[PMID: 17433670]
J774	IC₅₀	< 50 μM Compound: Ktz	Cytotoxicity against mouse J774 cells after 48 hrs by MTT assay Cytotoxicity against mouse J774 cells after 48 hrs by MTT assay	[PMID: 19110434]
J774	IC₅₀	< 50 μM Compound: KTZ	Cytotoxicity against mouse J774 cells after 48 hrs by MTT assay Cytotoxicity against mouse J774 cells after 48 hrs by MTT assay	[PMID: 18547811]
K562	CC₅₀	102 μM Compound: 1	Cytotoxicity against human K562 cells after assessed as reduction of cell viability 24 hrs by MTT assay Cytotoxicity against human K562 cells after assessed as reduction of cell viability 24 hrs by MTT assay	[PMID: 18529046]
LLC-PK1	IC₅₀	3.8 μM Compound: Ketoconazole	Inhibition of P-glycoprotein, mouse L-mdr1a expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay Inhibition of P-glycoprotein, mouse L-mdr1a expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay	[PMID: 12699389]
LLC-PK1	IC₅₀	4.8 μM Compound: Ketoconazole	Inhibition of P-glycoprotein, human L-MDR1 expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay Inhibition of P-glycoprotein, human L-MDR1 expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay	[PMID: 12699389]
LLC-PK1	IC₅₀	6.7 μM Compound: Ketoconazole	Inhibition of P-glycoprotein, mouse L-mdr1b expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay Inhibition of P-glycoprotein, mouse L-mdr1b expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay	[PMID: 12699389]
THP-1	IC₅₀	44 μM Compound: KTZ	Cytotoxicity against human THP1 cells after 48 hrs Cytotoxicity against human THP1 cells after 48 hrs	[PMID: 17960923]
THP-1	IC₅₀	44 μM Compound: KTZ	Cytotoxicity against human THP1 cells assessed as reduction of cell viability after 48 hrs Cytotoxicity against human THP1 cells assessed as reduction of cell viability after 48 hrs	[PMID: 17287123]
U-937	CC₅₀	125 μM Compound: 1	Cytotoxicity against human U937 cells assessed as reduction of cell viability after 24 hrs by MTT assay Cytotoxicity against human U937 cells assessed as reduction of cell viability after 24 hrs by MTT assay	[PMID: 18529046]
V79	IC₅₀	0.52 μM Compound: ketoconazole	Inhibition of human recombinant CYP24A1 expressed in chinese hamster V79 cells using [3H-1-beta]calcitriol after 60 mins by scintillation counting Inhibition of human recombinant CYP24A1 expressed in chinese hamster V79 cells using [3H-1-beta]calcitriol after 60 mins by scintillation counting	[PMID: 20594862]
V79	IC₅₀	127 nM Compound: KTZ	Inhibition of human CYP11B1 expressed in hamster V79 MZ cells using [3H] 11 deoxycorticosterone as substrate by HPLC radioflow detector Inhibition of human CYP11B1 expressed in hamster V79 MZ cells using [3H] 11 deoxycorticosterone as substrate by HPLC radioflow detector	[PMID: 24900349]
V79	IC₅₀	67 nM Compound: KTZ	Inhibition of human CYP11B2 expressed in hamster V79 MZ cells using [3H] 11 deoxycorticosterone as substrate by HPLC radioflow detector Inhibition of human CYP11B2 expressed in hamster V79 MZ cells using [3H] 11 deoxycorticosterone as substrate by HPLC radioflow detector	[PMID: 24900349]

Molecular Weight

531.43

Formula

C₂₆H₂₈Cl₂N₄O₄

CAS No.

79156-75-5

SMILES

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

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Chenge J T, et al. Structural characterization and ligand/inhibitor identification provide functional insights into the Mycobacterium tuberculosis cytochrome P450 CYP126A1[J]. Journal of Biological Chemistry, 2017, 292(4): 1310-1329. [Content Brief]

(Rac)-Ketoconazole Related Classifications

Infection

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The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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The dilution calculator equation

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)	×	Volume _(start)	=	Concentration _(final)	×	Volume _(final)
	×		=		×
C1		V1		C2		V2

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

(Rac)-Ketoconazole79156-75-5(Rac)-Ketoconazol (Rac)-R 41400FungalCytochrome P450CYPsAntifungal activitycytochrome P450methylation enzymemembrane functionInhibitorinhibitorinhibit

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