Ketoconazole
Athanor · official
C26H28Cl2N4O4 · 531.4 g/mol
IUPAC name: 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
Also called Nizoral, imidazole antifungal
Names and identifiers
- IUPAC name
- 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
- Synonyms
- Nizoral, imidazole antifungal, DTXSID20273956
+ 39 more
1-(4-(4-((2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethanone, 1-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethanone, RefChem:935033, DTXCID90196446, (Rac)-Ketoconazole, KW-1414, 1-(4-(4-((2-((1H-Imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethanone, 1-[4-(4-{[2-(2,4-dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one, NSC 317629, C26H28Cl2N4O4, MFCD00058579, (+/-)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine, cis-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-1M-idazol-1-ylmethyl)-1,3-dioxolan-4-yl) methoxy) phenyl)-piperazine, (+/-)-ketoconazole, Conazoles, Ketoconazole hra, 1-{4-[4-({2-(2,4-Dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl}methoxy)phenyl]piperazin-1-yl}ethan-1-one, SCHEMBL8408, Oprea1_683648, US8987315, Ketoconazole, CHEMBL157101, GTPL2568, orb3134478, SCHEMBL18258319, CHEBI:48339, BDBM151585, HMS3267K04, HMS5087I15, 1-(4-(4-(((2R,4S)-2-((1H-IMIDAZOL-1-YL)METHYL)-2-(2,4-DICHLOROPHENYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZIN-1-YL)ETHANONE, Piperazine, (+/-)-1-acetyl-4-(4-(((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, rel-, SYB70696, EBC-27285, s1353, AKOS015918262, DB01026, HY-W422288, KW 1414, NCI60_002728, DB-054790
- Molecular formula
- C26H28Cl2N4O4
- Empirical formula
- C13H14ClN2O2
- Molecular weight
- 531.4 g/mol
- Exact mass
- 530.14876
- CAS number
- 65277-42-1
- PubChem CID
- 3823
- Canonical SMILES
- CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
- Isomeric 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
- InChIKey
- XMAYWYJOQHXEEK-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 36
- Rings
- 5
- Aromatic rings
- 3
- Fraction sp³ carbons (Fsp3)
- 0.38
- H-bond donors
- 0
- H-bond acceptors
- 6
- Rotatable bonds
- 7
- TPSA (Ų)
- 69.1
- Formal charge
- 0
- XLogP3
- 4.3 PubChem
- Complexity
- 735 PubChem
- Stereocenters
- 0 defined, 2 undefinedCIP: C14: undefined · C17: undefined
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C58.76%
- H5.31%
- Cl13.34%
- N10.54%
- O12.04%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 4.21 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -5.67 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.44 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 531.44
- log P ≤ 5 (Crippen): 4.21
- H-bond donors ≤ 5: 0
- H-bond acceptors ≤ 10: 6
Breaks 1 of the four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: AbaChemScene, Molport, MP Biomedicals.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 13C NMRSpectraBase
- GC-MSSpectraBase (DI)
- LC-MSMassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.