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Ketoconazole

CAT: 0804-HY-B0105-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-B0105-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Ketoconazole (R-41400) is an imidazole anti-fungal agent, a CYP3A4 and CYP24A1 inhibitor.
CAS Number
65277-42-1
Product Name Alternative
Ketoconazol; R 41400
UNSPSC
12352005
Hazard Statement
H301, H360
Target
Bacterial; Cytochrome P450; Fungal; Ras
Type
Reference compound
Related Pathways
Anti-infection; GPCR/G Protein; MAPK/ERK Pathway; Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/Ketoconazole.html
Concentration
10mM
Purity
99.57
Solubility
DMSO : 10 mg/mL (ultrasonic; warming; heat to 60°C)
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
Molecular Formula
C26H28Cl2N4O4
Molecular Weight
531.43
Precautions
H301, H360
References & Citations
[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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
CYP3; CYP4

Chemical Information

Ketoconazole

(2S,4R)-ketoconazole is a cis-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine which dioxolane moiety has (2S,4R)-configuration. It is an enantiomer of a (2R,4S)-ketoconazole.

CAS Number65277-42-1
PubChem CID47576
IUPAC Name1-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
Molecular FormulaC26H28Cl2N4O4
Molecular Weight531.4
XLogP4.3
Topological Polar Surface Area69.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Heavy Atom Count36
Formal Charge0
Complexity735
SMILES
CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@@H]3CO[C@@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
InChI
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-/m1/s1
InChIKey
XMAYWYJOQHXEEK-ZEQKJWHPSA-N
Chemical Structure
2D Structure
2D structure of Ketoconazole
CAS: 65277-42-1
CID: 47576
Formula: C26H28Cl2N4O4
MW: 531.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight531.4
XLogP34.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Exact Mass530.1487608
Monoisotopic Mass530.1487608
Topological Polar Surface Area69.1 Ų
Heavy Atom Count36
Formal Charge0
Complexity735
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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