ChemSpider 2D Image | (+)-Ketoconazole | C26H28Cl2N4O4

(+)-Ketoconazole

  • Molecular FormulaC26H28Cl2N4O4
  • Average mass531.431 Da
  • Monoisotopic mass530.148743 Da
  • ChemSpider ID401695
  • defined stereocentres - 2 of 2 defined stereocentres


More details:



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(+)-Ketoconazole
(2R,4S)-ketoconazole
1-[4-(4-{[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]ethanone [ACD/IUPAC Name]
1-[4-(4-{[(2R,4S)-2-(2,4-Dichlorophényl)-2-(1H-imidazol-1-ylméthyl)-1,3-dioxolan-4-yl]méthoxy}phényl)-1-pipérazinyl]éthanone [French] [ACD/IUPAC Name]
1-[4-(4-{[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethanone
1-[4-(4-{[(2R,4S)-2-(2,4-Dichlorphenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]ethanon [German] [ACD/IUPAC Name]
1-[4-(4-{[(4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethanone
1-acétyl-4-(4-{[(2R,4S)-2-(2,4-dichlorophényl)-2-(1H-imidazol-1-ylméthyl)-1,3-dioxolan-4-yl]méthoxy}phényl)pipérazine [French]
1-Acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorphenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin
265-667-4 [EINECS]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS007337 [DBID]
AIDS-007337 [DBID]
AIDS112209 [DBID]
AIDS-112209 [DBID]
AIDS112210 [DBID]
AIDS-112210 [DBID]
BRN 4303081 [DBID]
CORT-001 [DBID]
D00351 [DBID]
DRG-0073 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Danger Biosynth Q-201267
      GHS06; GHS08; GHS09 Biosynth Q-201267
      H301; H360; H373; H410 Biosynth Q-201267
      P201; P273; P301+P310; P308+P313; P501 Biosynth Q-201267
    • Chemical Class:

      A <stereo>cis</stereo>-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1<element>H</element>-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine which dioxolane moiety has (2<stereo>R</stereo>, 4<stereo>S</stereo>)-configuration. ChEBI CHEBI:48336
    • Drug Status:

      approved BIONET-Key Organics KS-1205
    • Bio Activity:

      (+)-Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 inhibitor. MedChem Express
      (+)-Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 inhibitor.; Target: CYP3A4 ; (+)-Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1]. MedChem Express HY-B0105A, HY-B0105
      (+)-Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 inhibitor.;Target: CYP3A4 (+)-Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1]. (+)-Ketoconazole also is a cytochrome P450 inhibitor [2].(+)-Ketoconazole (KTZ), on the antischistosomal potential of these quinolines against Schistosoma mansoni infection by evaluating parasitological, histopathological, and biochemical parameters. Mice were classified into 7 groups: uninfected untreated (I), infected untreated (II), infected treated orally with PZQ (1,000 mg/kg) (III), QN (400 mg/kg) (IV), KTZ (10 mg/kg)+QN as group IV (V), HF (400 mg/kg) (VI), and KTZ (as group V)+HF (as group VI) (VII). KTZ plus QN or HF produced more inhibition (P<0.05) in hepatic CYP450 (85.7% and 83.8%) and CYT b5 (75.5% and 73.5%) activities, resp MedChem Express HY-B0105A, HY-B0105
      Antifungal MedChem Express HY-B0105A, HY-B0105
      Antifungal agent; potent inhibitor of cytochrome P450c17. Tocris Bioscience 1103
      Anti-infection MedChem Express HY-B0105A, HY-B0105
      Anti-infection; MedChem Express HY-B0105A, HY-B0105
      Cytochrome P450 Tocris Bioscience 1103
      Cytochrome P450c17 inhibitor Tocris Bioscience 1103
      Enzymes Tocris Bioscience 1103
      Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 inhibitor. MedChem Express
      Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 inhibitor.; Target: CYP3A4 ; Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1]. MedChem Express HY-B0105A, HY-B0105
      Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 inhibitor.;Target: CYP3A4 Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1]. Ketoconazole also is a cytochrome P450 inhibitor [2].Ketoconazole (KTZ), on the antischistosomal potential of these quinolines against Schistosoma mansoni infection by evaluating parasitological, histopathological, and biochemical parameters. Mice were classified into 7 groups: uninfected untreated (I), infected untreated (II), infected treated orally with PZQ (1,000 mg/kg) (III), QN (400 mg/kg) (IV), KTZ (10 mg/kg)+QN as group IV (V), HF (400 mg/kg) (VI), and KTZ (as group V)+HF (as group VI) (VII). KTZ plus QN or HF produced more inhibition (P<0.05) in hepatic CYP450 (85.7% and 83.8%) and CYT b5 (75.5% and 73.5%) activities, respectively, than i MedChem Express HY-B0105A, HY-B0105

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.4±0.1 g/cm3
Boiling Point: 753.4±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.5 mmHg at 25°C
Enthalpy of Vaporization: 109.8±3.0 kJ/mol
Flash Point: 409.4±32.9 °C
Index of Refraction: 1.642
Molar Refractivity: 139.1±0.5 cm3
#H bond acceptors: 8
#H bond donors: 0
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 1
ACD/LogP: 3.55
ACD/LogD (pH 5.5): 2.23
ACD/BCF (pH 5.5): 13.55
ACD/KOC (pH 5.5): 91.12
ACD/LogD (pH 7.4): 3.49
ACD/BCF (pH 7.4): 249.50
ACD/KOC (pH 7.4): 1677.54
Polar Surface Area: 69 Å2
Polarizability: 55.2±0.5 10-24cm3
Surface Tension: 52.2±7.0 dyne/cm
Molar Volume: 385.0±7.0 cm3

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