A triazole antifungal agent
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Labeled Version(s)
10010656Ketoconazole-d3
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Ketoconazole

Item No. 15212

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-ethanone
CAS Number
65277-42-1
Synonyms
  • R 41400
Molecular Formula
C26H28Cl2N4O4
Formula Weight
531.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 2 mg/mlEthanol: 1 mg/ml
λmax
244, 297 nm
SMILES
CC(N1CCN(C2=CC=C(OC[C@@H]3O[C@](C4=CC=C(Cl)C=C4Cl)(CN5C=CN=C5)OC3)C=C2)CC1)=O
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
InChi Key
XMAYWYJOQHXEEK-OZXSUGGESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ketoconazole is a broad-spectrum triazole antifungal agent that has activity against C. albicans, C. krusei, C. tropicalis, C. glabrata, C. parapsilosis, C. neoformans, and A. fumigatus strains (IC50s = 0.031-8 µg/ml).1 It inhibits the fungal cytochrome P450 (CYP) isoform CYP51, also known as lanosterol 14α-demethylase, which arrests ergosterol (Item No. 19850) biosynthesis at the fungal membrane. Ketoconazole also inhibits human CYP3A4 (IC50 = 0.54 µM). Formulations containing ketoconazole have been used in the treatment of fungal infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dilmaghanian, S., Gerber, J.G., Filler, D.G., et al. Enantioselectivity of inhibition of cytochrome P450 3A4 (CYP3A4) by ketoconazole: Testosterone and methadone as substrates. Chirality 16(2), 79-85 (2004).