Ketoconazole
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Category | Bioactive by-products |
Catalog number | BBF-04031 |
CAS | 65277-42-1 |
Molecular Weight | 531.43 |
Molecular Formula | C26H28Cl2N4O4 |
Purity | >98% |
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Description
Ketoconazole inhibits cyclosporine oxidase and testosterone 6 beta-hydroxylase with IC50 of 0.19 mM and 0.22 mM, respectively. It is used primarily to treat fungal infections.
Specification
Synonyms | Kuric; Nizoral; (2R,4S)-ketoconazole; Fungarest |
Storage | Store at 2-8°C |
IUPAC 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 |
Canonical SMILES | CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(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-/m0/s1 |
InChI Key | XMAYWYJOQHXEEK-OZXSUGGESA-N |
Source | Synthetic |
Properties
Appearance | White to Off-white Solid |
Application | For the treatment of fungal infections. |
Antibiotic Activity Spectrum | fungi |
Boiling Point | 753.4°C at 760 mmHg |
Melting Point | 148-150°C |
Density | 1.38 g/cm3 |
Solubility | Soluble in DMSO |
LogP | 4.35 |
Toxicity
Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Mechanism Of Toxicity | Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone. |
Toxicity | Hepatotoxicity, LD50: 86 mg/kg (orally in rat); LD50 = 44 mg/kg (Intravenous, Mouse); LD50: 702 mg/kg (Oral, Mouse). |
Reference Reading
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2