CH₃CH₃

Ketoconazole

Chemistry

64 atoms · Conformer computed and published by PubChem.
Formula
C26H28Cl2N4O4
Molar mass
531.4 g/mol
IUPAC name
1-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
InChIKey
XMAYWYJOQHXEEK-ZEQKJWHPSA-N

Chemistry from PubChem CID 47576.

Also known as

  • Nizoral
  • 65277-42-1
  • Panfungol
  • Ketoderm
  • Fungarest
  • Fungoral
  • Ketoisdin
  • Ketozole

Stereoisomers

4 distinct stereoisomers are registered for this structure.

  • Ketoconazole this area CID 47576
  • (2R,4S)-Ketoconazole CID 456201
  • (2S,4S)-ketoconazole CID 638701
  • trans-Ketoconazole CID 12854713
  • 1-(4-(4-((2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethanone mixture CID 3823

Attribution

  • Paul Janssen — first synthesis, 1976

    Janssen Pharmaceutica under his direction only — the chemistry paper (J Med Chem 1979) is Jan Heeres, Leo Backx, J.H. Mostmans and Jan Van Cutsem, without Janssen as an author. The first orally active broad-spectrum antifungal; patented 1977, US introduction 1981. Family name is invented.

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