Record Information
Version1.0
Creation date2011-09-21 01:46:45 UTC
Update date2015-07-21 06:59:34 UTC
Primary IDFDB028884
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKetoconazole
DescriptionKetoconazole (pronounced /ˌkiːtoʊˈkoʊnəzoʊl/) is a synthetic antifungal drug used to prevent and treat skin and fungal infections, especially in immunocompromised patients such as those with AIDS. Ketoconazole is sold commercially as an anti-dandruff shampoo. Ketoconazole is very lipophilic, which leads to accumulation in fatty tissues. The less toxic and more effective triazole compounds fluconazole and itraconazole have largely replaced ketoconazole for internal use. Ketoconazole is best absorbed at highly acidic levels, so antacids or other causes of decreased stomach acid levels will lower the drug's absorption when taken orally. -Wikipedia [HMDB]
CAS Number65277-42-1
Structure
Thumb
Synonyms
SynonymSource
(2S,4R)-1-Acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazineChEBI
1-ACETYL-4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazineChEBI
NizoralKegg
XolegelKegg
ABBR KTCKegg
(+-)-cis-1-Acetyl-4-(P-((2-(2,4-dichlorophenyl)-2-(imidazol-1- ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazineHMDB
cis-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H- imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-ketoconazolHMDB
FungarestHMDB
FungoralHMDB
KetodermHMDB
KetoisdinHMDB
Orifungal mHMDB
PanfungolHMDB
PiperazineHMDB
Janssen brand OF ketoconazoleMeSH, HMDB
Ketoconazole janssen brandMeSH, HMDB
KetoconazoleMeSH
(+-)-cis-1-acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1- ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazinehmdb
cis-1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H- imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-ketoconazolhmdb
fungaresthmdb
fungoralhmdb
ketodermhmdb
ketoisdinhmdb
nizoralhmdb
orifungal Mhmdb
panfungolhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0093 g/LALOGPS
logP4.3ALOGPS
logP4.19ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.06 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity138.07 m³·mol⁻¹ChemAxon
Polarizability54.67 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H28Cl2N4O4
IUPAC name1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
InChI IdentifierInChI=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-/m1/s1
InChI KeyXMAYWYJOQHXEEK-ZEQKJWHPSA-N
Isomeric SMILESCC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1
Average Molecular Weight531.431
Monoisotopic Molecular Weight530.148760818
Classification
Description Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Aminophenyl ether
  • 1,3-dichlorobenzene
  • Phenol ether
  • Tertiary aliphatic/aromatic amine
  • Phenoxy compound
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Ketal
  • Halobenzene
  • Chlorobenzene
  • Monocyclic benzene moiety
  • Aryl chloride
  • Aryl halide
  • N-substituted imidazole
  • Benzenoid
  • Meta-dioxolane
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Imidazole
  • Azole
  • Acetamide
  • Carboxamide group
  • Amino acid or derivatives
  • Tertiary amine
  • Acetal
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organonitrogen compound
  • Organochloride
  • Organopnictogen compound
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
  • cis-1-acetyl-4-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)piperazine (CHEBI:47518 )
Ontology
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSKetoconazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9345700000-032f45d476928c144063Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-3530190000-a2b05a2498270bcd4a7e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-3430090000-055d7bbaadb1e1716a8b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0031490000-58a475e5974da2dfdc182017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-5395740000-08c010ea5c947e1a62f52017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9520100000-76672a88c60da8324f812017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-2090150000-e4d86d7a4af3843992542017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9240000000-92849351dd004ec262392017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-5940000000-e2a0f55e6d356bbc9c0e2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0010390000-00106b8b890fdebbf0362021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9030210000-22cee3cdcfef8b4b80682021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-4930100000-6819285e7904a4b66c662021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-081787cba0594aced9012021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0011980000-f9fa0eaf2d1b6889e0982021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066v-3140900000-ae27808322ff5c503bcf2021-09-25View Spectrum
NMRNot Available
ChemSpider ID43284
ChEMBL IDCHEMBL295698
KEGG Compound IDNot Available
Pubchem Compound ID47576
Pubchem Substance IDNot Available
ChEBI ID47519
Phenol-Explorer IDNot Available
DrugBank IDDB01026
HMDB IDHMDB12242
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDKLN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference