(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.

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(Rac)-Ketoconazole Chemical Structure

CAS No. : 79156-75-5

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Other Forms of (Rac)-Ketoconazole:

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View All Isoforms

CYP1 CYP2 CYP3 CYP4 CYP11 CYP17 Aromatase/CYP19A1 CYP26 CYP51 CYP1A2 CYP2D6 CYP2C9 CYP2C19 CYP3A CYP3A4 CYP17A1

Biological Activity
Purity & Documentation
References
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Description

Cellular Effect

Cell Line	Type	Value	Description	References
ASPC1	IC₅₀	0.117 μM Compound: Keto	Inhibition of CYP3A4 in CRISPR/Cas9-mediated CYP3A5 knock-out and doxycycline-induced CYP3A4 overexpressing human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate pretreated with doxycycline for 24 hrs followed by incubation with compound for 24 hrs by LC-MS/MS analysis Inhibition of CYP3A4 in CRISPR/Cas9-mediated CYP3A5 knock-out and doxycycline-induced CYP3A4 overexpressing human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate pretreated with doxycycline for 24 hrs followed by incubation with compound for 24 hrs by LC-MS/MS analysis	[PMID: 31965799]
ASPC1	IC₅₀	0.141 μM Compound: Keto	Inhibition of CYP3A5 in doxycycline-induced CYP3A5 overexpressing wild type human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate pretreated with doxycycline for 24 hrs followed by incubation with compound for 24 hrs by LC-MS/MS analysis Inhibition of CYP3A5 in doxycycline-induced CYP3A5 overexpressing wild type human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate pretreated with doxycycline for 24 hrs followed by incubation with compound for 24 hrs by LC-MS/MS analysis	[PMID: 31965799]
ASPC1	IC₅₀	0.162 μM Compound: Keto	Inhibition of CYP3A5 in CRISPR/Cas9-mediated CYP3A5 knock-out and doxycycline-induced CYP3A5 overexpressing human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate pretreated with doxycycline for 24 hrs followed by incubation with compound for 24 hrs by LC-MS/MS analysis Inhibition of CYP3A5 in CRISPR/Cas9-mediated CYP3A5 knock-out and doxycycline-induced CYP3A5 overexpressing human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate pretreated with doxycycline for 24 hrs followed by incubation with compound for 24 hrs by LC-MS/MS analysis	[PMID: 31965799]
ASPC1	IC₅₀	0.439 μM Compound: Keto	Inhibition of CYP3A5 in lentiviral pLVX-TRE3G-ZsGreen1-CYP3A5 transduced wild type human AsPC1 cells overexpressing CYP3A5 assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate after 24 hrs by LC-MS/MS analysis Inhibition of CYP3A5 in lentiviral pLVX-TRE3G-ZsGreen1-CYP3A5 transduced wild type human AsPC1 cells overexpressing CYP3A5 assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate after 24 hrs by LC-MS/MS analysis	[PMID: 31965799]
ASPC1	IC₅₀	0.513 μM Compound: Keto	Inhibition of CYP3A5 in wild type human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate after 24 hrs by LC-MS/MS analysis Inhibition of CYP3A5 in wild type human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate after 24 hrs by LC-MS/MS analysis	[PMID: 31965799]
CHO	IC₅₀	0.52 μM Compound: ketoconazole	Inhibition of CYP24A1 expressed in CHO cells Inhibition of CYP24A1 expressed in CHO cells	[PMID: 20655626]
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
Caco-2	IC₅₀	1.2 μM Compound: Ketoconazole	TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical) (Digoxin: 5 uM) in Caco-2 cells TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical) (Digoxin: 5 uM) in Caco-2 cells	[PMID: 10820137]
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
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]
HeLa	IC₅₀	264 μM Compound: Ketoconazole	TP_TRANSPORTER: inhibition of Taurocholate uptake in NTCP-expressing HeLa cells TP_TRANSPORTER: inhibition of Taurocholate uptake in NTCP-expressing HeLa cells	[PMID: 10565843]
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: 18547811]
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]
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]
K562	CC₅₀	61.7 μM Compound: 1	Cytotoxicity to reduce chronic myeloid leukemia K 562 cells Cytotoxicity to reduce chronic myeloid leukemia K 562 cells	[PMID: 15267229]
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	3.8 μM Compound: Ketoconazole	TP_TRANSPORTER: inhibition of Calcein-AM efflux in Mdr1a-expressing LLC-PK1 cells TP_TRANSPORTER: inhibition of Calcein-AM efflux in Mdr1a-expressing LLC-PK1 cells	[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	4.8 μM Compound: Ketoconazole	TP_TRANSPORTER: inhibition of Calcein-AM efflux in MDR1-expressing LLC-PK1 cells TP_TRANSPORTER: inhibition of Calcein-AM efflux in MDR1-expressing LLC-PK1 cells	[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]
LLC-PK1	IC₅₀	6.7 μM Compound: Ketoconazole	TP_TRANSPORTER: inhibition of Calcein-AM efflux in Mdr1b-expressing LLC-PK1 cells TP_TRANSPORTER: inhibition of Calcein-AM efflux in Mdr1b-expressing LLC-PK1 cells	[PMID: 12699389]
LNCaP	GI₅₀	25 μM Compound: Ketoconazole	Growth inhibition of androgen-sensitive human LNCAP cells incubated for 48 hrs by sulforhodamine B assay Growth inhibition of androgen-sensitive human LNCAP cells incubated for 48 hrs by sulforhodamine B assay	[PMID: 27423983]
M109	IC₅₀	17 μg/mL Compound: ketoconazole	Cytotoxicity against mouse M109 cells Cytotoxicity against mouse M109 cells	[PMID: 9784152]
MCF7	IC₅₀	12 μM Compound: ketoconazole	Inhibition of CYP26A1 in human MCF7 cells assessed as all-trans retinoic acid metabolism Inhibition of CYP26A1 in human MCF7 cells assessed as all-trans retinoic acid metabolism	[PMID: 16279770]
NCI-H295R	IC₅₀	0.34 μM Compound: ketoconazole	Inhibition of testosterone synthesis in human NCI-H295R cells by Enzyme immunoassay Inhibition of testosterone synthesis in human NCI-H295R cells by Enzyme immunoassay	[PMID: 34387987]
NCI-H295R	IC₅₀	0.44 μM Compound: ketoconazole	Inhibition of cortisol synthesis in human NCI-H295R cells by Enzyme immunoassay Inhibition of cortisol synthesis in human NCI-H295R cells by Enzyme immunoassay	[PMID: 34387987]
NCI-H295R	IC₅₀	1.4 μM Compound: ketoconazole	Inhibition of aldosterone synthesis in human NCI-H295R cells by Enzyme immunoassay Inhibition of aldosterone synthesis in human NCI-H295R cells by Enzyme immunoassay	[PMID: 34387987]
NCI-H295R	IC₅₀	2.5 μM Compound: ketoconazole	Inhibition of corticosterone synthesis in human NCI-H295R cells by Enzyme immunoassay Inhibition of corticosterone synthesis in human NCI-H295R cells by Enzyme immunoassay	[PMID: 34387987]
NIH-3T3-G185	IC₅₀	23.4 μM Compound: Ketoconazole	TP_TRANSPORTER: inhibition of LDS-751 efflux in NIH-3T3-G185 cells TP_TRANSPORTER: inhibition of LDS-751 efflux in NIH-3T3-G185 cells	[PMID: 11716514]
NIH-3T3-G185	IC₅₀	5.6 μM Compound: Ketoconazole	TP_TRANSPORTER: inhibition of Daunorubicin efflux in NIH-3T3-G185 cells TP_TRANSPORTER: inhibition of Daunorubicin efflux in NIH-3T3-G185 cells	[PMID: 11716514]
NIH-3T3-G185	IC₅₀	53.4 μM Compound: Ketoconazole	TP_TRANSPORTER: inhibition of Rhodamine 123 efflux in NIH-3T3-G185 cells TP_TRANSPORTER: inhibition of Rhodamine 123 efflux in NIH-3T3-G185 cells	[PMID: 11716514]
NIH3T3	IC₅₀	396 μg/mL Compound: Ketoconazole	Cytotoxicity against mouse NIH/3T3 cells assessed as reduction in cell viability after 24 hrs by MTT assay Cytotoxicity against mouse NIH/3T3 cells assessed as reduction in cell viability after 24 hrs by MTT assay	[PMID: 29274492]
PC-3	GI₅₀	11.7 μM Compound: Ketoconazole	Growth inhibition of androgen-insensitive human PC3 cells incubated for 48 hrs by sulforhodamine B assay Growth inhibition of androgen-insensitive human PC3 cells incubated for 48 hrs by sulforhodamine B assay	[PMID: 27423983]
RBL-1	IC₅₀	> 25 μM Compound: Ketoconazole	Inhibitory activity against 5-lipoxygenase of RBL-1 cell line Inhibitory activity against 5-lipoxygenase of RBL-1 cell line	[PMID: 1507204]
Sf21	IC₅₀	15.6 μM Compound: Ketoconazole	Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake	[PMID: 21965623]
Sf21	IC₅₀	2.9 μM Compound: Ketoconazole	Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake	[PMID: 21965623]
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]
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]
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]
U-937	CC₅₀	70 μM Compound: 1	Cytotoxicity to reduce human histolytic lymphoma U937 cells Cytotoxicity to reduce human histolytic lymphoma U937 cells	[PMID: 15267229]
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	224 nM Compound: ketoconazole	Inhibition of human CYP11B1 expressed in V79 11B1 cells Inhibition of human CYP11B1 expressed in V79 11B1 cells	[PMID: 16570918]
V79	IC₅₀	312 nM Compound: ketoconazole	Inhibition of human CYP24 hydroxylase expressed in V79 cells Inhibition of human CYP24 hydroxylase expressed in V79 cells	[PMID: 15615534]
V79	IC₅₀	312 nM Compound: ketoconazole	Inhibition of human CYP24A1 expressed in chinese hamster V79 cells Inhibition of human CYP24A1 expressed in chinese hamster V79 cells	[PMID: 20594862]
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]
V79	IC₅₀	81 nM Compound: ketoconazole	Inhibition of human CYP11B2 expressed in V79 11B2 cells Inhibition of human CYP11B2 expressed in V79 11B2 cells	[PMID: 16570918]

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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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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